---
title: "Sell to the Blocker, Not the Champion"
episode: 81
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Leigh Gross"
guest_title: "Chief Revenue Officer, Synctera"
date_published: 2026-05-27
date_modified: 2026-07-22
duration: 00:48:44
word_count: 9448
topics: ["enterprise-sales", "revenue-operations", "sales-leadership", "forecasting", "ai-in-gtm", "gtm-strategy"]
canonical_url: https://leanscale-knowledge-hub.netlify.app/podcast/leigh-gross-compliance-killed-my-deal/
source: "LeanScale Podcast Knowledge Hub — https://leanscale-knowledge-hub.netlify.app"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# Sell to the Blocker, Not the Champion

_Leigh Gross (CRO, Synctera) on 20-person fintech deals, why RevOps is your first GTM hire, and the mid-funnel AI use case nobody talks about_

**Episode 81 · The LeanScale Podcast**  
Leigh Gross, Chief Revenue Officer, Synctera · Hosted by Anthony Enrico  
Published May 27, 2026 · Updated July 22, 2026 · 00:48:44  
Canonical: https://leanscale-knowledge-hub.netlify.app/podcast/leigh-gross-compliance-killed-my-deal/

**Topics:** Enterprise & Public-Sector Sales · Revenue Operations · Sales Leadership · Forecasting · AI in GTM · GTM Strategy


## Executive summary

Leigh Gross runs one of the most complicated enterprise sales motions you will ever hear described. As CRO at Synctera, the banking-as-a-service platform behind embedded banking and card products for companies like Bolt, Zenoti, and BTG Pactual, his team coordinates deals with roughly ten people on Synctera's side, ten on the customer's side, and a sponsor bank in the middle — across cycles that can stretch past a year. His vantage point is unusual: before fintech he was a commercial attorney, and he has spent twelve years selling in heavily regulated, incredibly complex markets (student loans, SMB lending, credit data) where compliance can quietly kill a deal from a room you're never invited into.

The spine of the conversation with LeanScale co-founder Anthony Enrico is what it takes to sell when a deal has to satisfy two organizations that don't speak the same language plus a regulator behind them. Synctera runs a tripartite motion — one process to win the fintech, a second to sign a sponsor bank, and a third to marry them under a tri-party agreement — and Leigh walks through how each specialized role slots in. His biggest structural lesson: the sales engineer is the most underrated specialized hire in complex deals, because the solution document they produce doubles as the single source of truth that holds both the fintech and the bank accountable to what was actually approved. That discipline is how Synctera turned banking-as-a-service launches from years into a three-month average — and made speed its moat.

The middle of the episode is a clinic on GTM build order. Leigh's hard-won view, from having done it the other way and 'felt the pain,' is that RevOps is effectively your first go-to-market hire — before you scale AEs, before you spin up a BDR team. Without it you can't answer the one question every board and investor will ask: what's your weighted pipeline, your sales velocity, your stage-to-stage conversion? He tells the CommonBond story of re-engineering a BDR motion on the fly, over pizzas, because the system wasn't built first; and he makes the case that bad early data costs real money — tens of millions in valuation — when you can't articulate and forecast performance at fundraise. Anthony adds the LeanScale lens: a lean team of high performers with a strong supporting cast beats hiring twenty AEs and letting eighteen go.

They also dig into segment-based planning (treat enterprise, mid-market, and SMB as separate lines of business, each with its own ACV, conversion rate, and cycle), how to hire that first ambiguity-tolerant enterprise rep, and the mid-funnel AI use case Leigh thinks is wildly underrated: not list-building or outbound, but AI-generated handoff documents that move a deal cleanly from phase to phase, plus trend analysis that lets a single leader see objections, competition, and pricing timing across every call the team is having.

The closing idea is the one that reframes the whole episode: sell to the blocker, not the champion. Deals rarely die to competitors — they die from someone you've never met, and in a regulated business that someone is usually compliance or a bank's board. Since you often can't get in the room, the job is to control the process early, map every party who has to sign off, prepare your champion to carry the pitch you can't deliver yourself, and surface the 'no' before it hardens — because it takes a lot of capital to overturn a no. Who should listen: founders and CROs building a complex or regulated GTM motion, RevOps leaders arguing for early investment, and any seller who has ever watched a deal die from a room they were never invited into.


## Key takeaways

1. **Complex marketplace deals mean running several sales processes in parallel** — Synctera doesn't run one sale; it runs three at once — winning the fintech that wants a banking or card product, signing a sponsor bank willing to back the program, and then marrying two parties who don't share a language or mindset under a tri-party agreement. Every program has to have a bank, so the fintech interest is almost the easy part.
   _Why it matters:_ If your product is a two-sided or multi-party motion, design your stages, staffing, and forecasting around all the processes simultaneously — not just the buyer who's easiest to excite. The constraint is usually the party you don't control.
   _For:_ Sales Leaders, Revenue Executives, Founders

2. **Make forecasting part of the sales process, not an afterthought** — Asking a customer late for projections gets weak, deprioritized answers. Instead Synctera bakes it into qualification as a 'give and get': the fintech shares customer counts and average spend, and in return gets a professionally built deal model they can use internally to sell the program to their own executives — one document both sides work from.
   _Why it matters:_ Trade something of value for the projection data you need. Framing forecasting as a mutual planning artifact gets you better inputs earlier and gives your champion a tool to sell up their own chain.
   _For:_ Sales Leaders, RevOps Leaders, Revenue Executives

3. **Generic BANT/MEDDPICC didn't fit — qualify on whether you can actually deliver** — Leigh never subscribed to a named methodology. In his motion the decisive qualifier isn't just budget and urgency; it's whether, given the bank network's appetite, a sponsor can even be found. If not, the smart move is to say so early — 'our banks want 24 months of runway and $5M raised; come back when you're there' — rather than waste everyone's time.
   _Why it matters:_ Build qualification around your specific structural constraints, not a borrowed acronym. Disqualifying honestly and early preserves the relationship; many of those companies come back a year later ready.
   _For:_ Sales Leaders, RevOps Leaders

4. **The sales engineer is the most underrated specialized role — and it's an implementation tool too** — In a regulated pairing, a fintech will happily change scope at the 11th hour ('we said debit card, can we do credit?') while the bank 'will lose their minds' at unapproved tweaks. The SE's solution document — almost a statement of work — becomes the single source of truth that holds the fintech to what was agreed and the bank to what it approved.
   _Why it matters:_ Bring sales engineering in early in any complex, multi-party deal. Beyond showing the customer an organized solution, its documentation is what stops deals from dying in the implementation and signing phases.
   _For:_ Sales Leaders, Founders

5. **Turn compliance complexity into a moat** — Understanding what banks need and translating it into fintech language so it actually happens is Synctera's biggest competitive advantage. In banking-as-a-service, time-to-launch is often measured in years; Synctera reduced its average to about three months by getting into the bank's mindset and making the process repeatable and scientific.
   _Why it matters:_ In regulated markets, the muscle to navigate compliance is defensible. Make speed-to-launch a headline selling point — tell prospects to ask any alternative how long it will take.
   _For:_ Founders, Revenue Executives

6. **The most underrated AI use case is mid-funnel, not top-of-funnel** — Most CROs reach for AI to build lists, automate outbound, and route leads. Leigh's highest-value use is different: AI-generated handoff documents that carry consistent, complete context from one phase (and one specialist) to the next without slowing the deal down, plus trend analysis that lets one leader see objections, competition, and pricing timing across every call the team runs.
   _Why it matters:_ Point AI at the handoffs and the cross-deal patterns, not just prospecting. In long, multi-stakeholder cycles this preserves quality, speeds cycles, and gives leaders visibility they can't get by watching a fraction of calls.
   _For:_ RevOps Leaders, Sales Leaders

7. **RevOps is effectively your first GTM hire — that's the build order** — Leigh's thinking evolved from 'get out there, start selling, build the system when things break' to putting RevOps first. Right after your first salesperson, you'd better have a RevOps person, unless your market is literally twenty companies. Without it you create internal confusion and lose the value of the information you should be capturing.
   _Why it matters:_ Stand up RevOps before scaling headcount so you know your target market, get data into your systems cleanly, and can measure what's breaking. It reshapes even how you hire.
   _For:_ Founders, RevOps Leaders

8. **Don't hire 20 AEs before the process works** — Blowing out a 20-person BDR team and 25 AEs before the funnel and process are proven wastes money and turns off prospects — you end up letting 18 of them go. A lean team of high performers with a strong supporting cast that helps navigate every deal is the stronger recipe; then the only bottleneck is the rep's calendar.
   _Why it matters:_ Get the motion right a couple of times, standardize it, then scale. Reps would rather have a mechanized system feeding them tiered ICP accounts than an unbounded 'call anyone' territory — which usually means the company doesn't know what it's doing.
   _For:_ Founders, Sales Leaders

9. **Weighted pipeline is the currency of fundraising — and it has to be real** — At some point, six months in at most, the board and every investor in the data room will ask for weighted pipeline, sales velocity, and stage-to-stage timing. You can't assign random percentages to stages; the number has to be grounded in reality. Being unable to articulate and forecast performance can cost tens of millions in valuation.
   _Why it matters:_ Invest early in the data and process behind a defensible weighted pipeline. CROs effectively get one grace board meeting — after that you'd better be fully buttoned up.
   _For:_ Founders, Revenue Executives, RevOps Leaders

10. **Plan by segment — treat each one like its own line of business** — Leigh's most useful planning lesson (from running five or six verticals at Array) is to break the business into distinct segments, each with its own product needs, marketing plan, ACV/LTV, conversion rate, and sales cycle. Enterprise might be ten deals a year at ~$1M ACV; SMB might be three times the volume at ~$100K — different motions, different staffing, different quotas.
   _Why it matters:_ Give each segment its own plan and instrumentation, and don't assume lead-gen tactics transfer. In one Array vertical BDRs produced ~27 leads per rep; in the bank sector, outbound didn't work at all and required a partner-and-conference strategy instead.
   _For:_ RevOps Leaders, Sales Leaders

11. **The first enterprise rep is a different hire — profile and comp both shift** — Leigh calls it the hardest hire; the best option is often someone you already know. Before the process is dialed in, you need a curious, ambiguity-tolerant rep who can digest information and help build the motion — someone who will take losses they shouldn't have and learn why. That may mean a comp plan skewed slightly more qualitative than the standard ~80%-revenue-driven design.
   _Why it matters:_ Hire for process-building and learning, not just closing, until the motion is repeatable. Screen for motivation — many strong early reps are aiming at a future leadership role and will help you build.
   _For:_ Sales Leaders, Founders

12. **Sell to the blocker, not the champion — and control the process to surface it early** — Deals rarely die to competitors; they die from someone you've never met who has to approve them — in a regulated business, usually compliance or a bank's board you can't address directly. Compliance doesn't decide to do the deal, but it can say no. The job is to control the process upfront: map every party who must sign off, prepare your champion to carry the pitch you can't deliver, and get ahead of the no.
   _Why it matters:_ Arm the champion, then go find and sell the blockers. Once a compliance 'no' hardens you may not get another shot, and it takes a lot of capital for a champion to overturn one — so alleviate the concern before it's ever raised.
   _For:_ Sales Leaders, Revenue Executives


## Frameworks

### The Tripartite Sales Motion (01:24)

**Definition:** Three sales processes run in parallel and then fused: win the fintech that wants a banking/card product, sign a sponsor bank willing to back the program, and marry the two under a single tri-party agreement.

Because every program must have a bank, exciting the fintech is the easy part; the constraint is the party you don't control. Stages, staffing, and forecasting all have to account for two organizations plus a regulator, not one buyer.

### The Give-and-Get Deal Model (03:24)

**Definition:** Bake forecasting into qualification as a trade: the customer shares projections (customer counts, average spend) and in return receives a professionally built deal model showing how the program becomes profitable — one shared document both sides work from.

Asking for projections late gets weak, deprioritized answers. Framing it as mutual planning gets better inputs earlier, arms the champion to sell internally, and gives Synctera the volume story it needs to interest a sponsor bank.

### Sales Engineering as the Single Source of Truth (07:44)

**Definition:** Use the sales engineer's solution document — effectively a statement of work — as the artifact that holds every party accountable to exactly what was scoped and approved.

In a regulated pairing, fintechs change scope late and banks revolt at unapproved tweaks. Clear SE documentation stops deals from dying in implementation and signing by making late changes visible and holding both the fintech and the bank to the agreed program.

### The Build Order of GTM (RevOps First) (20:14)

**Definition:** The sequence in which a founder should lay down go-to-market foundations — with RevOps placed effectively first, right after the first salesperson, before scaled AE or BDR headcount.

Without RevOps you can't define your target market, get clean data into your systems, measure what's breaking, or answer the board's velocity and pipeline questions. Skipping it creates confusion and forfeits the value of information you should be capturing.

### Segment-Based Planning (31:50)

**Definition:** Treat each go-to-market segment (enterprise, mid-market, SMB, and their international variants) as its own line of business, with distinct product needs, marketing plan, ACV/LTV, conversion rate, sales cycle, and quotas.

Segments look fundamentally different, so they warrant different motions, staffing, and investment. Modeling each separately is what lets you set credible goals, allocate reps, and know the pipeline you need to hit next year's number.

### Selling to the Blocker, Not the Champion (42:20)

**Definition:** Identify and win over the people who can kill a deal — often someone you never meet, like compliance or a bank's board — rather than over-investing only in the enthusiastic champion.

Deals die from the person you don't know. The tactics: control the process early, map every required sign-off, prepare the champion to carry the pitch you can't deliver, and surface the 'no' before it hardens — because overturning a no costs your champion scarce political capital.


## Quotes

_Speakers inferred from an undiarized transcript — verify before attributing._

> "We're taking a fintech that wants to offer some sort of banking or card product, we're giving them the technology to do that, and we're matching them with a sponsor bank in our network. Every program has to have a bank."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (01:24)

> "You really have to make forecasting a part of your sales process. If you just treat it haphazardly and ask the customer, 'Would you mind sharing some projections?' — it doesn't get you the response you want."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (03:02)

> "It's a little bit of give and get. We want to walk through your projections, and what we're going to give you back is a deal model you can use internally to sell this to your executives. We work off the same document."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (03:24)

> "In a regulated space, the bank will lose their minds if you do that. You can't make tweaks you feel like making, even if from a technical perspective it's not a big deal."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (10:15)

> "The time to launch for these programs oftentimes could be years. We've been able to reduce that significantly — our average launch time is about three months. And that becomes a huge selling point."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (12:10)

> "You run the risk of losing a lot in these handoffs. AI has really helped us in our meeting tools — creating summaries and being able to hand these things off quickly. That's been the biggest thing we're seeing."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (14:46)

> "What I really like is the ability to look at the last 10 deals in this vertical — here are the objections we got, how did we try to overcome them, was that the right thing to do, did it work?"
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (19:01)

> "The most important thing that I would start with is RevOps. Right after you give a salesperson, you better have a RevOps person — unless your market is just 20 companies and you don't need to do anything."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (20:54)

> "Would you rather share your territory with a bunch of other reps, or have a complete mechanized system that feeds you leads and helps you navigate the deal? Then the bottleneck really just becomes your calendar."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 81 (23:20)

> "You're going to be letting 18 of them go. Just saying to a rep, 'call anybody you want, your territory is whatever you can find' — it sounds good, but that typically means we don't know what we're doing."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (24:42)

> "I told my team, we're going to have to spend a couple of days re-engineering this, it's going to suck and you're not going to be selling anything. We treated it like a project, ordered in some pizzas, and did it — but it was painful."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (28:24)

> "I think CROs get one board meeting. The first one's great — welcome, everyone's excited you're there. On the next one, you better be fully buttoned up."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 81 (30:10)

> "Weighted pipeline is the currency of when you're out there trying to raise money. It has to be based in some reality — you can't just assign random percentages to your stages."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (29:39)

> "It's helpful to break out these distinct segments and treat each one like it's its own almost line of business — its own product needs, its own marketing plan, its own expectations."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (32:06)

> "The deal dies from someone that you don't know. Your champion likes the deal — but what you really need to figure out is who can kill this, the person I probably haven't met who's going to have to approve it."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (42:05)

> "In a regulated space, compliance can kill these deals. Compliance doesn't make the decision to do it, but compliance can say we're not doing it."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (43:26)

> "It's easy to talk to people who want to do what you're telling them — that's fun. But you really need to get in front of the person who doesn't want to do it and can say no."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (44:37)

> "You have to control the sales process early. If you wait too long, it's already too late — your champion doesn't want to burn their political capital when they've already heard a no. It takes a lot of capital to overturn a no."
>
> — Leigh Gross, The LeanScale Podcast Ep. 81 (46:30)


## Practical advice by role

### Founders

- Treat RevOps as effectively your first GTM hire, right after your first salesperson — define your target market and get clean data into your systems before you scale AEs or BDRs.
- Don't blow out a 20-person BDR team and 25 AEs before the process is proven; get it right a couple of times, standardize, then scale, or you'll waste money and turn off prospects.
- In a regulated or complex market, invest early in the muscle to navigate compliance — speed-to-launch (Synctera's ~3 months vs. years) can become your moat and your headline selling point.

### RevOps Leaders

- Bake forecasting into the sales process as a 'give and get' — trade a professionally built deal model for the customer's projections so you get better inputs earlier.
- Build a defensible weighted pipeline grounded in real stage-to-stage timing and velocity; it's the currency of fundraising and the first thing every board and data room will demand.
- Model each segment separately (ACV, conversion rate, sales cycle) as its own line of business — and watch that CRM stage/parking-lot changes don't silently corrupt your metrics and timing.

### Sales Leaders

- Bring a sales engineer in early on complex, multi-party deals; their solution document is both a sales asset and the statement-of-truth that keeps deals from dying in implementation.
- Point AI at the middle of the funnel — consistent AI-built handoff documents between phases and cross-call trend analysis on objections, competition, and pricing timing — not just outbound.
- Sell to the blocker, not the champion: control the process upfront, map every required sign-off, and surface compliance or approval risk before a 'no' hardens.
- For the first enterprise rep, hire for curiosity and ambiguity-tolerance (ideally someone you already know), and accept a slightly more qualitative comp plan while they help you build the motion.

### Revenue Executives

- Design qualification around your real structural constraint (for Synctera, whether a sponsor bank can even be found), not a borrowed BANT/MEDDPICC acronym — and disqualify honestly and early.
- Assume you get roughly one grace board meeting; after that you must articulate and forecast performance, because an inability to tell the story can cost tens of millions in valuation.
- Prepare champions to carry the pitch into rooms you can't enter (a bank's board), and give non-sellers everything they need to succeed on your behalf.


## AI takeaways

**Thesis:** In long, multi-stakeholder sales, the highest-leverage AI is mid-funnel, not top-of-funnel: it preserves context across handoffs and gives leaders cross-deal visibility they otherwise can't get. Point AI at the messy middle before the hyped prospecting use cases.

- **Handoffs are where deals leak** — In a motion with many specialists (qualify, sales engineering, compliance/due diligence, bank matching), AI-built summaries and handoff documents carry consistent, complete context from phase to phase without slowing the deal to re-teach each new owner.
- **Trend analysis across every call** — A single leader can only sit in on a fraction of conversations. AI that cuts across all calls surfaces objections, competitive mentions, and when pricing comes up (too soon? right time?), turning the whole team's calls into learnable signal.
- **An AI layer can beat the CRM itself** — Leigh gets limited value from Salesforce directly but 'lives' in an AI overlay on top of it to manage pipeline and interrogate deals — a reminder that the intelligence layer, not the system of record, is often where reps actually work.
- **Recording isn't reviewing** — Even with Gong installed, no leader realistically watches every call on a weekend. AI that reads and synthesizes calls delivers the value the old 'we have the recordings' promise never did.
- **Build with agentic tooling** — Anthony notes LeanScale built custom agents and proprietary apps with Claude Code to deliver its service — evidence operators are building GTM software, not just buying it.

**Agent & automation ideas**

- A deal-handoff agent that generates a standardized, phase-specific brief (requirements, decisions, open items, key clips) each time an opportunity moves to the next specialist or stage.
- A cross-call trend agent that mines every rep conversation for objections, competitor mentions, and pricing-timing patterns by vertical, then recommends which rebuttals actually worked.
- A requirements-extraction agent that reads discovery/sales-engineering transcripts and drafts the single-source-of-truth solution document (the statement of work) that keeps fintech and bank aligned.
- A CRM-connected GTM diagnostic agent that ingests a prospect's pipeline and generates a full go-to-market assessment and project roadmap in minutes.


## Operations takeaways

### Revenue operations

- **RevOps is the build-order priority.** Place RevOps effectively first — right after the first salesperson — so you have target-market definition, clean data, and measurability before you scale headcount.
- **Instrument velocity and stage timing.** Track sales velocity and stage-to-stage conversion from day one; you can bluff it for maybe six months before the board demands real numbers.
- **Protect your metrics from process changes.** Moving deals between pipeline and a 'parking lot' scrambled Synctera's metrics and timing — model CRM state changes carefully so cleanup doesn't corrupt reporting.
- **Segment-level modeling.** Give every segment its own conversion rate, cycle, and ACV; it's the only way to set credible goals, allocate reps, and size the pipeline you need.
- **Feed the deal model.** Operationalize the give-and-get so projection inputs are captured in qualification, not begged for later.

### Pipeline & marketing ops

- **Weighted pipeline is fundraising currency.** A grounded, non-arbitrary weighted pipeline is what boards and investors ask for repeatedly; an inability to defend it can cost tens of millions in valuation.
- **Qualify on deliverability.** The decisive qualifier is structural (can a sponsor bank be found?), not a generic BANT/MEDDPICC checklist — disqualify early and honestly.
- **Control the process to protect the funnel.** Map every required sign-off upfront and surface blockers (compliance, a bank's board) before a 'no' hardens and kills the deal from a room you can't enter.
- **Lean team over headcount blitz.** A small, high-performing team with strong support closes more than a 20-AE hiring spree that ends in layoffs; make the rep's calendar the only bottleneck.


## Metrics mentioned

| Value | Metric | Context |
| --- | --- | --- |
| ~20 people (10 Synctera + 10 customer) | Deal stakeholders | A single Synctera deal coordinates roughly ten people on each side, plus a sponsor bank — a quadratically complex, multi-party motion. |
| Can stretch past a year | Sales cycle length | The regulated, two-sided BaaS motion produces long cycles, which is what makes early forecasting and process control so critical. |
| ~3 months (vs. years) | Average launch time | Synctera compressed BaaS program launches from the industry norm of years to about three months — its core competitive moat and selling point. |
| 24 months runway, $5M+ raised | Bank qualification thresholds | Rough bar the sponsor-bank network wants to see in a fintech before backing a program; below it, Synctera disqualifies early and invites them back later. |
| Enterprise ~10 deals/yr at ~$1M ACV vs. SMB ~$100K ACV at ~3x volume | Segment economics example | Illustrates why segments are planned as separate lines of business with different motions, staffing, and quotas. |
| ~27 leads per rep (some verticals) | Vertical lead yield | At Array, proven verticals produced ~27 leads per rep via BDRs, while the bank sector yielded none that way and required a partner/conference strategy. |
| 2–3 weeks to minutes | GTM diagnostic time | Anthony's example of mid-funnel AI value: LeanScale's CRM-connected GTM diagnostic dropped from a 2–3 week process to minutes, speeding sales cycles and raising quality. |


## Entities mentioned

- **Synctera** (company) — Leigh's employer, where he is CRO; a banking-as-a-service platform that pairs fintechs with sponsor banks (customers include Bolt, Zenoti, and BTG Pactual). Its tripartite motion, ~3-month launch moat, and compliance-as-a-blocker dynamics are the episode's central case. · https://leanscale-knowledge-hub.netlify.app/company/synctera/
- **CommonBond** (company) — Student-loan refinancing company where Leigh previously led sales; his example of feeling the pain of skipping RevOps — being unable to provide projections/velocity, and re-engineering a BDR motion on the fly (the 'pizzas' story). · https://leanscale-knowledge-hub.netlify.app/company/commonbond/
- **Array** (company) — Fintech (credit/data) where Leigh ran five or six distinct sales verticals; his source case for segment-based planning and for vertical-specific lead strategies (~27 leads/rep in some verticals; partner-and-conference motion for the bank sector). · https://leanscale-knowledge-hub.netlify.app/company/array/
- **Leigh Gross** (person, guest) — CRO of Synctera (banking-as-a-service); a former commercial attorney with 12+ years selling in heavily regulated fintech (CommonBond, Array). · https://leanscale-knowledge-hub.netlify.app/guest/leigh-gross/
- **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://leanscale-knowledge-hub.netlify.app/guest/anthony-enrico/
- **Salesforce** (tool, CRM) — Synctera's CRM of record; Leigh notes he gets limited value from Salesforce itself and lives in an AI overlay on top of it, and recounts a pipeline-to-'parking-lot' change that scrambled his metrics and timing.
- **Gong** (tool, Revenue Intelligence) — Cited as the prior generation of call recording — even with Gong installed, a leader can't realistically watch every call, which is why AI cross-call trend analysis is more valuable than raw recordings.
- **Claude Code** (tool, AI Dev Tool) — Referenced by Anthony (as 'cloud code') as what LeanScale used to build custom agents, proprietary apps, and platforms that deliver its service.


## FAQ

**Q: What does it mean to sell to the blocker instead of the champion?**

A: It means proactively identifying and winning over the people who can kill a deal — often someone you never meet, like a compliance team or a bank's board — rather than over-investing only in the enthusiastic champion. Leigh Gross's point is that deals rarely die to competitors; they die from someone you don't know who has to approve them. The job is to control the process early, map every required sign-off, prepare your champion to carry the pitch into rooms you can't enter, and surface the 'no' before it hardens.

**Q: Why does compliance kill so many enterprise and fintech deals?**

A: In regulated markets, compliance doesn't decide to do a deal, but it can veto one — and it often sits in a room the seller can't access, such as a sponsor bank's approval board. Because a hardened compliance 'no' can be nearly impossible to reverse (and burns your champion's political capital to try), the winning move is to identify the compliance stakeholders early, get in front of them or arm your champion to represent the deal accurately, and alleviate concerns before they're ever formally raised.

**Q: When should a startup hire its first RevOps person?**

A: According to Leigh Gross, effectively right after the first salesperson — before scaling AEs or BDRs. Unless your market is only about 20 companies, standing up RevOps early lets you define your target market, get clean data into your systems, measure what's breaking, and answer the pipeline and velocity questions every board will ask. Skipping it creates internal confusion and forfeits the value of information you should be capturing, and re-engineering the motion later is painful.

**Q: Why is weighted pipeline called the currency of fundraising?**

A: Because when a company raises capital, the board and every investor in the data room repeatedly ask for weighted pipeline, sales velocity, and stage-to-stage conversion timing. The number must be grounded in reality — you can't assign arbitrary percentages to stages. Being unable to articulate and forecast performance credibly can cost tens of millions of dollars in valuation, which is why the data and process behind a defensible weighted pipeline need to exist early.

**Q: What is the most underrated way to use AI in a complex sales process?**

A: Leigh Gross argues it's mid-funnel, not top-of-funnel. The highest-value uses are AI-generated handoff documents that carry consistent, complete context from one phase and specialist to the next without slowing the deal, and trend analysis that cuts across every call the team runs to surface objections, competitive mentions, and pricing timing. This gives a single leader visibility they can't get by watching a fraction of calls, and preserves quality in long, multi-stakeholder cycles.

**Q: How should you plan go-to-market across different segments?**

A: Treat each segment — enterprise, mid-market, SMB, and their international variants — as its own line of business, with distinct product needs, marketing plan, ACV/LTV, conversion rate, and sales cycle. Enterprise might be around ten deals a year at roughly $1M ACV while SMB might be three times the volume at about $100K, warranting different motions, staffing, and quotas. Lead-generation tactics don't transfer between segments: what produced ~27 leads per rep in one Array vertical produced none in the bank sector, which needed a partner-and-conference strategy instead.

**Q: Why is the sales engineer such an important role in complex deals?**

A: In a multi-party, regulated sale, the sales engineer's solution document functions as both a sales asset and an implementation statement of work — a single source of truth. It stops deals from dying in the implementation and signing phases by holding the fintech to what was agreed and the bank to what it approved, so a last-minute scope change (like switching from a debit to a credit card program) is surfaced and controlled rather than silently derailing the launch.

**Q: How do you hire your first enterprise sales rep?**

A: Leigh Gross calls it the hardest hire, and says the best option is often someone you already know. Before the process is dialed in, you need a curious, ambiguity-tolerant rep who can quickly digest information and help build the motion — someone willing to take losses they arguably shouldn't and learn why. That may justify a comp plan skewed slightly more qualitative than the standard roughly 80%-revenue-driven design, because you're paying them to help define a repeatable process, not just to close.


## Timeline

- **00:00** — Intro: from commercial attorney to CRO of a BaaS platform
- **01:24** — The 20-person deal: what a Synctera sales motion actually looks like
- **03:02** — Forecasting long cycles: the deal model give-and-get
- **05:04** — Why BANT/MEDDPICC didn't fit and what replaced it
- **07:12** — The cast of characters and why sales engineering is non-negotiable
- **11:56** — How compliance complexity became Synctera's moat
- **14:07** — The most underrated AI use case: mid-funnel handoffs and trend analysis
- **18:22** — The AI overlay, Salesforce, and how Leigh actually uses AI as a sales leader
- **20:30** — The build order of GTM: why RevOps comes first
- **26:00** — The painful re-engineering project (and pizzas)
- **29:47** — Why weighted pipeline is the currency of fundraising
- **31:50** — Planning nightmares and segment-based GTM
- **37:43** — Hiring the first enterprise rep: curiosity, ambiguity, and comp design
- **42:20** — Selling to the blocker: why deals die from people you've never met
- **47:07** — Controlling the sales process upfront to surface compliance early


## Related episodes

- **Ep. 86: Why the Best CROs Don't Come From Sales** (Jerry Brooner) — Leigh went from commercial attorney to CRO — a direct companion to the argument that the best revenue leaders come from outside pure sales. · https://leanscale-knowledge-hub.netlify.app/podcast/jerry-brooner-best-cros-dont-come-from-sales/
- **Ep. 94: Why Only 500 Apps Can Sell to the U.S. Government** (Irina Denisenko (Knox)) — Both make compliance a moat: the hard gate that few clear becomes the durable advantage in regulated and public-sector markets. · https://leanscale-knowledge-hub.netlify.app/podcast/irina-denisenko-knox-selling-to-government/
- **Ep. 66: How Tyler Molinaro Scales SaaS in Government** (Tyler Molinaro) — Another complex, compliance-heavy enterprise motion — long cycles and approval gates that reward the vendors who navigate them. · https://leanscale-knowledge-hub.netlify.app/podcast/tyler-molinaro-saas-government/
- **Ep. 88: Why AI Won't Close Your Biggest Deals** (Michael Kiernan (Nextdoor)) — Pairs with Leigh's mid-funnel view of AI: it accelerates complex enterprise deals but doesn't replace the human work of winning the blocker. · https://leanscale-knowledge-hub.netlify.app/podcast/michael-kiernan-nextdoor-ai-wont-close-deals/
- **Ep. 95: Why AI Means More RevOps Hires, Not Fewer** (Jimmy O'Halloran (New Relic)) — The operator's case for RevOps and forecasting rigor — the same 'build the operating layer first' argument Leigh makes about build order. · https://leanscale-knowledge-hub.netlify.app/podcast/jimmy-ohalloran-new-relic-revops-consumption-revenue/
- **Ep. 35: Operate Like You're Already Public** (Stephanie Ucko) — Board-ready forecasting and weighted pipeline discipline — the 'you get one grace board meeting' pressure Leigh describes at fundraise. · https://leanscale-knowledge-hub.netlify.app/podcast/stephanie-ucko-revops-through-ipo/
- **Ep. 15: Where Should RevOps Report?** (Cameron Legge (LeanScale)) — Org-design companion to the build-order thesis about when and where RevOps should sit in a scaling GTM organization. · https://leanscale-knowledge-hub.netlify.app/podcast/cameron-legge-where-revops-report/


## Full transcript

_Machine-transcribed and not diarized; speaker attribution is inferred._  
_Transcript only, as a separate file: https://leanscale-knowledge-hub.netlify.app/podcast/leigh-gross-compliance-killed-my-deal/transcript.md_

### 00:00 — Intro: from commercial attorney to CRO of a BaaS platform

**[0:00]** (logo whooshing) Today, I'm sitting down with Lee Gross, who's the CRO at Sinctera. They're a banking-as-a-service platform helping companies like Bolt, Sunodi, and BTGPactual build embedded banking and card products. Before this, Lee spent 12 years in fintech sales across student loans, SMB lending, and credit data. All heavily regulated, all incredibly complex. What makes his perspective interesting is that Lee came from law. He was a commercial attorney before making the jump to sales. And now, he's running one of the most complex enterprise sales motions I've ever heard of. We're talking 10 people on Sinctera side of the deal,

**[0:43]** 10 people on the customer side, cycles that can stretch past a year, but value and deal size that make it all worthwhile. We're going to get into what it actually takes to sell when compliance can kill your deal, why you should sell to the blocker instead of the champion, and what he learned the hard way about setting up your GTM foundation before you go to market. Lee, you told me Sinctera sales motion involves 10 people on your side, 10 people on the customer side. That's 20 people involved in coordinating a deal. Walk me through what that actually looks like and what it takes to pull off that kind of deal. - Yeah, thanks, Anthony.

### 01:24 — The 20-person deal: what a Synctera sales motion actually looks like

**[1:24]** Yeah, so what we're doing at Sinctera is we're actually taking a FinTech that wants to offer some sort of a banking or card product. We're giving them technology to do that, and we're also then matching them with a sponsor bank in our network who's going to be the bank behind that program. So every program has to have a bank. So we actually have multiple sales processes that we're running through kind of all at the same time. So if you think of it, we've got to go to market function where we're looking for FinTechs that would offer this type of product. We're speaking to them, we're selling to them. Think about a normal enterprise sales process.

**[2:03]** At that point, we're then also finding a bank in our network that would want to bank that program. We have to then sell that bank on the process and on the program. Then we have to bring them together and make sure that two types of people who generally don't speak the same language and come from the same mindset are able to work together. We have to bring all that together into one deal. We paper a tri-party agreement, and then we go to market. So it really does get fairly complicated, and it involves a number of different people in our organization. And we're selling to a number of different people across two different organizations, FinTech and a bank.

**[2:43]** - So in this type of scenario, something that comes to mind right off the bat is how are you communicating forecast and potential future performance as you're going through the process? I'm thinking things like your executive meetings with your CEO, board meetings, potential fundraising conversations. How do you forecast when it's so far out and there's so many moving parts? - Yeah, and that's always been a challenge here. One of the things that we started to do more recently is to make forecasting, you really have to make forecasting a part of your sales process. If you wait until, if you just kind of try to treat it haphazardly or just ask the customer,

### 03:02 — Forecasting long cycles: the deal model give-and-get

**[3:24]** hey, could you, would you mind sharing some projections? I need to talk to my board. It doesn't really get you the response that you want, and it doesn't usually get the prioritization that you want. One of the things that we started to do that I think's been really helpful is we started to say in the almost part of qualifying the deal, which is very early stage, it's a little bit of give and get. And so what we say is we want to walk through a little bit of about your projections. And what we're gonna give you back is a deal model that will show you if this program and how this program will be profitable and beneficial to you.

**[3:59]** So if you're able to give us a little bit of, okay, how many customers do you think you'll have? What's the average spend? Let's talk about these things. And what I'm gonna give you is a nicely built out deal model that you FinTech can use internally to sell this to your executives. We can work off of the same document. And so when you start doing it that way, you get a better handle on what the size of a potential program is. We also need that to present to our banks to get the banks interested in the program. They don't wanna do, they don't wanna bank a program that has no volume. So it allows us to, yeah, I think by approaching it earlier

**[4:34]** in the sales process, it allows us to get what we need, but also bring value to our customer so that they're willing to have that conversation and share that information with us. - I'm guessing the typical Bant Med Pick style qualification probably isn't gonna cut it in this type of sale process. Did you build out a custom qualification methodology as you're flowing these deals through? - Yeah, and I never really like, you know, subscribe to a particular method like that. Obviously, if you're gonna run any sales process, qualifying is certainly the most important part of it. But yes, we have a certain, because there's so much complexity

### 05:04 — Why BANT/MEDDPICC didn't fit and what replaced it

**[5:12]** and we wanna avoid wasting time on deals that, you know, because it's interesting, right? We can get a FinTech interested. That's almost the easy part. We've got a really good product. But if there isn't gonna be a bank to sponsor it, we're not selling anything then, right? We're kind of wasting everyone's time. So a lot of our qualifying is around the usual stuff about like, you know, who's your buyer, what's the urgency and all that. But it's also about, is this the type of program based on what we know about our bank network and their appetite? Are we going to be able to find a sponsor? And if in the early stage, we identify for whatever reason

**[5:49]** that we don't think we will be able to, the smart thing to do is to identify that, let the FinTech know. You know, for example, maybe they're early stage and we might say, look, you know, our banks are typically looking for companies that have 24 months of runway. They like to have seen at least $5 million raised. You know, you're not there yet. Let's stay in touch. You know, let's talk about when you've raised that money, maybe you come back. And we just see that a lot. We see a lot of companies that just weren't ready. And then in a year later, they come back to us. - Makes a ton of sense. I'm curious on the cast of characters. So 10 people on your side,

**[6:26]** little bit of a two-part question. One, what are the resources look like on your side? And two, I'm curious, when did you know you needed to involve specialized roles in order to win the deal? And how did you start to justify that on your side too? - That's a good question. Yeah, so yeah, I'll give you a sense of the cast of characters. So like any enterprise sales organization, you have your go-to-market team. So you have people who are focused on, whether it's outreach, it's a little bit of marketing. How are we getting our message out? Who are we targeting? And how are we getting those initial conversations? We're pretty fortunate also,

**[7:07]** in that a lot of our leads come inbound too. And we've built a, I think a pretty good reputation. And so that's your best friend if you're a sales leader. You can't get too lazy and rely on it, but it is nice when you have it and we do have that luxury. So the deals are coming in and we're doing that initial qualifying. Then it moves into our enterprise sales team. And that's the part where you're really taking it through and starting to understand and starting to sell the FinTech on what it is that we can do once we've qualified it. Then we get into what you mentioned around specialized roles and the most important specialized role

### 07:12 — The cast of characters and why sales engineering is non-negotiable

**[7:44]** that we realized we needed was a sales engineer, especially in this and I'll explain why in a minute. But our sales engineer then starts to map out the particular solution. What is the banking product that you're looking to launch? And we start to really put that down. And it's more than, it's both a sales exercise because it shows our value to the customer, but it also is an important implementation exercise. In that it starts to create that single source of truth that we need. And I'll get back to that in a minute. Then as we move forward, we start to get into compliance and due diligence. So we have to, and more importantly,

**[8:25]** our banks will ultimately have to complete due diligence on any of these programs. And so for us, we take the lead on that and we get started on that. So now we have a due diligence and a compliance team at Sintera that comes in and starts to do a little bit of their work. And this is all progressing and we've had to learn essentially over time, how to get this into sales stages and how to do this in an organized way. Then when you get past all of that, you start to get into what we call bank matching. So now you're trying to find a bank in our network that might be interested. And if we're lucky, hopefully we have multiple banks

**[8:58]** that could be interested in this. And so it moved into our bank matching team who then starts sharing this information with banks. And then it moves over more of the bank team. So, as you can see, it really starts to get more and more complex. One of the things that you mentioned is about specialized roles. And I think sales engineering is one of those roles that we realized was going to be extremely important. And it's something that I would take with me probably to any role in a complex sales process. What I think a sales engineer can serve so many different functions, there's certainly just a flat out sales focus to it

**[9:38]** where it's a good thing to show your customer that you have an organized way of coming up with a solution. But for us in a regulated market where you're trying to pair a bank and a FinTech, I think a FinTech tends to move more quickly. They'll tend to want to make changes. And we're a technology company. If you said to me at the last minute, "Hey, can we do this?" Generally, I'd probably say yes. I have a team, we'll go back to our product, we'll bug them and we'll ask them if they can do it. And generally, they'll say they can do it. And that's great. The problem is in a regulated space, the bank will lose their minds if you do that.

**[10:15]** And so you just can't make tweaks that you just feel like making, even if from a technical perspective, it's not a big deal. So what I was finding when I first got here was a lot of deals were getting stuck in the implementation phase. And even in that deal signing phase, because it wasn't clear exactly what was gonna be built. And every time the FinTech at the last minute comes back and says, "Actually, you know what? "I know we said debit card. "Can we do a credit card?" It's like, yes, we can. But that is a huge change in the entire program. And it's gonna cause a tremendous amount of delay if you introduce that at the 11th hour.

**[10:51]** So by having this sales engineering function and being really clear with our documentation, and it's almost like a statement of work at some point, we're able to hold both parties accountable to it. So not only the FinTech to say like, "Stop changing this, we've agreed." But also to the bank to say like, "This is what you approved. "If we stick to this, I'm like, "my expectation is this is gonna go through." So that was a really important learning. And I think something that I would probably take with me no matter what, it's a, that kind of organization and consistency, especially when you're dealing with multiple parties is really important.

**[11:23]** - So I wanna make sure I heard everything right, because this seems like a quadratically increasing level of complexity. We have a two-sided marketplace where you're matching the banks with the FinTechs. It's an enterprise deal. These are high ACV long-term deals. There's technology involved and layer on everybody's favorite thing, compliance. So with all of those factors there, do you feel like one of Sinctera's competitive advantages is building the muscle to navigate this complexity? And does that become a moat for you that makes it really difficult for people to come in? - Yeah, and I think that's right. Our ability to understand the compliance function

### 11:56 — How compliance complexity became Synctera's moat

**[12:10]** and what our banks are looking for and communicate that in sort of FinTech language so that it actually happens, I think is one of our biggest competitive advantages. You hear a lot about, especially in the banking as a service space, there's a lot of deals in play and there's a lot of things that are happening. But the time to launch for these programs oftentimes could be years. We've been able to reduce that significantly. Like our average launch time is about three months. And the reason that we're able to do that, and that becomes a huge selling point now, which is if you were thinking about doing something this year,

**[12:47]** if you're gonna try to do this yourself or perhaps go with another provider, ask them how long it's going to take and consider that. So I think that's become a big competitive advantage for us. You have to, in our space, you have to take the position and understand and get into the mindset of the bank. And if you can do that and you can have a good relationship with your bank network and understand what they really need, you can try to, as best you can, turn that into something that's repeatable and a little bit more scientific. And that's what we've been able to, I mean, it's always a work in progress, but that's what we've been able to do by and large.

**[13:23]** And that's how we get programs live within a reasonable amount of time. - I'm curious, a lot of times when I'm interviewing CROs and they're maybe more mid-market, high-velocity type of product, when they're thinking about how they're leveraging AI, typically they're thinking, oh, how am I automating lists, automating outbound, automating lead routing internally, getting leads to the right person? I'm curious and we have maybe a similar, it's not as complex, but a similar type of sales cycle. Have you been leveraging AI in the middle of funnel to help speed these processes along and maintain consistency? And is there anything that you're leveraging

### 14:07 — The most underrated AI use case: mid-funnel handoffs and trend analysis

**[14:08]** that you feel like has given you a competitive advantage in that area of the business as well? - Yeah, you know, I think, yeah, to your point on like the list building and all of that, we don't, we're not, there aren't, you know, a hundred, it's not one of those markets where there's hundreds of thousands of potential customers and we need to like, you know, I could see the value of that though. We don't really need that. We have started leveraging it mid funnel, just as you said. And I think the biggest value that we have from it is the ability to, we have a complex sales process and there's numerous people that have to play a role in it.

**[14:46]** And I think you run the risk of losing a lot in these handoffs, you know, what you don't wanna do is slow the process down by having to bring, okay, now it's time for bank matching. Do we really wanna spend two hours, you know, teaching something, like we wanna be able to do this in a smooth way. And AI has really helped us in our like meeting tools and just creating summaries and being able to hand these things off quickly. That's really helped us a lot. We've been able to create some like really good prompts that allow us to create these like handoff documents that are consistent. And so every time we bring it from one phase to the next phase,

**[15:25]** that particular person gets the information that they need. They can also go back, of course, and they can watch any meeting they want to, but they shouldn't have to because they're getting the key bits of information. That's been, to me, that like breakthrough in tools has been the biggest thing that we're seeing for us. - I think it's one of the most underrated aspects of leveraging AI, and I meant that in the beginning of, yes, there's so much buzz about those other aspects of using AI, which is fine and go to market, but I think these middle of funnel use cases to get documents put together,

**[15:59]** make sure you're getting requirements out of the transcripts, moving things along. We have a process at LeanScale, we call it the GTM diagnostic, where we leverage AI to connect to potential customers, CRM, and we can run an entire diagnostic on their entire go to market just by doing that, and then develop a roadmap of projects. And that for us, it was usually a two to three week process to get that done, now we can get it done in minutes, and it's helped us speed those sales cycles along, and increase quality, because now we have an even better idea of what's going on, very clear requirements and documentation that we can hand off.

**[16:38]** I think these middle of funnel use cases, they're just so underrated, but can add so much value. - As a sales leader, I love it. I mean, 'cause you can go in now and you can, I mean, you can really get granular on it and look at a particular reps halls and actually use it to determine if they're doing a good job, which is one way to use it. But I love just being able to find trends across all of your conversations to say like, who are we, what competition are we seeing in our deals? What are our customers saying? I like to use it to see like, when do we start talking about pricing? Are we, 'cause maybe we're talking about it too soon,

**[17:14]** or are we speaking about it at the right time? So there's just, there's so much that you can learn from, you know, 'cause you've got a team out there having, you know, multiple conversations every day. As a sales leader, you're not gonna, you know, you're not obviously gonna be on all of those, and you're gonna be on a fraction of those. So the ability to kind of really get a feel for like what's happening, they're invaluable for that. I really enjoy using the tool for that. - Yeah, are there any specific tools that you're using? On our side, we've developed a ton with cloud code. We've built a few of our own custom agents

**[17:49]** and our own proprietary apps and platforms to help us deliver the service that we have. But we've been huge fans of cloud code. I'm just curious, are there any specific tools that you're using or specific models that you're finding a lot of value in? - So the tool that we started using that I love is called Ada, and it's an overlay, you know, it sits on top of sales. We use Salesforce as our CRM, and that, I don't know, it was there when I got here, and I just didn't have the energy to try to make a change. But I'm not getting all that much value out of it, I would say, but this Ada tool that sits on top of it is basically where we all live,

### 18:22 — The AI overlay, Salesforce, and how Leigh actually uses AI as a sales leader

**[18:27]** and that's how we manage our pipeline. And that's the tool that I was referring to where I can, you know, obviously I can ask any question about any deal and it will pull, but I actually, you know, you can use it more for trends and it cuts across all calls. It's great, and there's the basic blocking and tackling, but I don't really, you know, if I have a call and it was an interesting call, I'll use it to create a summary. I'll use it to validate maybe the action items that I wrote down and I thought we have just to make sure I didn't miss anything. Yeah, that to me is neither here nor there. What I really like about it is the ability

**[19:01]** to look at like the last 10 deals in this vertical, here are the objections we got. And I can, you can actually look at that and you can, number one, you can see how did we try to overcome it? Was that the right thing to do? Did it work? So you can really like go deep and really learn a lot about what you're seeing in the market. And then when you're a single person as a leader, you're not, you know, in those conversations. So it's a great way to stay up to date. Yeah, and even the old way of, oh, if you had Gong installed, that doesn't mean you can spend your entire Saturday and Sunday reviewing every single call too and going through everything.

**[19:34]** Hey, you say you have the calls, but like, are you really, might be really gonna, I always, yeah, I had, you know, I'm excited that I can watch a call, but am I gonna actually watch it? No, probably not. One of the things I find interesting, I just wrote a post about this too. I call it the build order of GTM. So starting with the founder, what are the first GTM pieces you start to put in place as you're building out the organization? And then when do you start to layer in certain roles? I'm curious, since you've built these type of organizations from scratch, especially in this case where it's a very complex sales cycle,

**[20:14]** what did the build order look like for you? What are you looking for when you're creating this organization for the first time? Yeah, and I've, my thinking on this has evolved like over time as well. So I think when I first started doing this stuff, I was more of a let's get out there, let's get out there and start selling. Let's learn, let's figure out what's going on and then we'll like build a system around it. And, you know, we'll start getting the organization like when things start to break. So let's like create a problem first. And sometimes that makes sense, right? It's like, let's create the problem and then we'll fix it. It's a good problem.

### 20:30 — The build order of GTM: why RevOps comes first

**[20:54]** It's better than having no customers and no opportunities. But my thinking on that is change. And I would say like, to me, the most important thing that I would start with is RevOps, right? And is, we need to understand like, what is our target market? How are we going to get the information into our systems about who we're targeting? I would say that, you know, and that to me changes the way I think about even hiring. I would look at like a good RevOps person as one of the first probably right after, like give a salesperson, you better have a RevOps person. You know, unless your market is just 20 companies and you don't need to do anything, you know,

**[21:33]** that's a tough business. But, you know, to me, you start with that. And I like to have that, you know, you want to have like a system in place because you will very quickly, not only will you create confusion within your own organization, but you're going to lose the value of the information that you should be gathering. So I think that's really important. If it's, when I got here, it wasn't, you know, it was a small organization that we were building out. We did have deals and opportunities. So it wasn't like I was starting from completely zero to one. But like one of the first things we started to realize was the importance of sales engineering.

**[22:09]** And then we, after a few months, I started to say, okay, like what is our ideal sales process? Let's start to map that out. Like what do we want? How do we want deals to flow through? And let's see if we can actually make that happen. And then as you realize, okay, well, you know, maybe that didn't go, it's not going the way we thought exactly, we need to make some tweaks. That's how you try to do it. So, you know, to me, you need a couple of really good, your early sales reps have to be, of course you always want people who are good at selling, but they also have to be good at almost digesting information and being able to come back and say,

**[22:45]** listen, I know we said we want to do, we want to qualify it, then we want to do this, this and this, you know, it doesn't seem to be working because everyone's asking like this question. So you need people who are capable of doing that in the early stage so that you can start to build out the best possible process. I wouldn't want to go and start like rolling out like, you know, 20 person BDR teams and 25 AEs without having all of this in place first. I think you're wasting your money and you're actually going to turn off prospects too. So having a, you know, a really effective inbound funnel with no one to close it or with a really,

**[23:20]** with a lousy process that your prospects don't like, you know, that's not good for your company. You're much better off, get it right a couple of times, figure out something that's standardized and then you can blow it out. - Yeah, and you could take this opinion with a bit of great assault, three time, head of RevOps starting a RevOps company. But I think one of the biggest perspective changes is, if you're a sales rep, would you rather share your territory with a bunch of other reps or just have a complete mechanized system to feed you leads, help you navigate the deal, give you the tools to manage as many prospects as possible.

**[23:59]** And then the bottleneck really just becomes your calendar. And I think any rep ever would like to have more prospects on their plate, close more deals, make more money. And I think if you have a lean team of very high performing salespeople with a really strong supporting cast that is helping them navigate every bit of those deals, I think that's a strong recipe for success. And I've seen, I'm sure you have too, the let's go hire 20 AEs this quarter. I've seen that playbook a million times and I've never seen it work. So- - You're gonna be letting 18 of them go, right? And it's gonna just be uncomfortable. And you know, to your point,

**[24:42]** I think just saying to a rep, like you would think maybe if I just said to you, call anybody you want, your territory is whatever you can find. That actually isn't what you want. It sounds good, but ultimately that's just, you're gonna waste a ton of time. You would much, I think, if I were joining an organization, I would much rather have you tell me, this is your territory. Here's where your leads come from. If you're doing full sales cycle, here's where you're gonna be focused. That is much better than just saying, call anybody you want any time. That's just not, that typically means we don't know what we're doing. - Totally. Yeah, here's your tiered list.

**[25:19]** We have a, we know the accounts that have the highest propensity to buy. These are the tier one accounts. These are the personas that you should be targeting. Here's content that we've built for you. Here's all of the things that you need to go get in front of them. We have an event schedule that lines you up to meet them. Like very, very, very focused on those tier one ICP persona accounts. And then yes, giving them that and then saying, and just making sure it's healthy. It's like, hey, this is a big list of accounts. And they're all tier one and really good. - Right. And then you can actually track, the other thing is, right, how can you tell,

**[25:58]** if you don't give someone a territory, it's hard to tell you if they're being effective. You can always say, well, the bottom line is, are you closing any deals? But if you haven't really given them a construct and you're just saying, just get out there, it's really hard to tell what's breaking. And so that's why, again, that's why I go back to, and I guess we're aligned on this as a RevOps company. RevOps to me is like, right, something that you need to address much more sooner than later, that's for sure. And I have done it the other way and felt the pain of that. - Are there any specifics on that pain, things where,

### 26:00 — The painful re-engineering project (and pizzas)

**[26:37]** 'cause I think sometimes people who haven't, hit those potholes or roadblocks yet, but maybe they're coming, are there times where you felt like, man, we just hit a wall and we would have missed this if we would have had RevOps in sooner? - Yeah, I mean, there's two things about it. Let's say even in a good case, and I've gone through this where, we didn't really have it together, but we had good reps, we had figured out a pretty good process and they were selling. And this reminds me of my time at Common Bond, where student loan refinancing, the market was good. We were doing well. But at a certain point, you find yourself unable to,

**[27:17]** one, just from an internal, like if you're in the head of sales seat or the CRO seat, you need to at some point be able to provide projections. You need to provide sales velocity. You need to be able to do those things and you can get away with it probably for six months to say like we're working on it. But at some point, you've got to be able to answer that question and you're either gonna be in front of the board or your CEO and they're gonna say, what's gonna happen next quarter? Or what are you signing up for? And if you don't have this together, it's gonna be very difficult to do. You won't understand your sales velocity at all.

**[27:51]** So that's one of the things that I felt right off the bat. Second thing that happened was we were doing, we were making a switch from kind of being end to end sales to, okay, at the time we were targeting employers for this student loan benefit. And we said, okay, this is pre COVID. So you could actually like cold call people. And we were in an office and things like that. And so I said, all right, we're gonna build out a BDR team. And we were just completely unprepared to like how, what are we gonna give these people to do and how are we gonna measure them? And so I had to on the fly days and go back.

**[28:24]** And I can remember my team who was very cooperative with me. I was like, unfortunately, we're gonna have to come in and like spend a couple of days just re-engineering this and it's gonna suck and you're not gonna be selling anything. We're just gonna be doing this. And we treated it like a project, ordered it in some pizzas and we did it, but it was painful. And so I think that's the result of like not addressing it upfront. - To your point, sometimes catastrophe could happen or you just miss opportunities. And I think even if things are going well but you can't articulate that performance, especially for these companies

**[28:58]** that are looking to do another fundraise, they're working an exit process right now. It's one thing to have the performance but to be able to articulate it and forecast what future performance is based on data that you have, that could mean tens of millions of dollars in your valuation if you can get that performance story tight. - Oh yeah, I mean, weighted pipeline is like, that's the currency of like, when you're out there trying to raise money, your weighted sales pipeline is extremely important and it has to be based in some reality, meaning you can't just assign random percentages to each of your stages and say, here's some ridiculous number of,

**[29:39]** we're gonna do $18 billion, you have to base it. And so that's one of the things like, I'm constantly asked for, what's the latest weighted pipeline? What are we closing in the next quarter? How long is it taking to get from this stage to that stage? And so these are all things that you just have to have. And like I said, you can probably get away with it for six months or so as you come in and you're learning. If you're building out an organization, maybe you get a little bit longer, but very quickly, that's the question that you're gonna get asked. And you're gonna get asked that question for every board meeting.

### 29:47 — Why weighted pipeline is the currency of fundraising

**[30:10]** Anytime any investor wants to get into the data room and see anything, like you're gonna be updating it. So you better have a processor, you're gonna spend all your time just doing this manually, which I have also done, and that's not fun. - I think CROs get one board meeting. - Yeah, first one's fun. - Yep, first one's great, welcome, everyone's excited you're there. And then on the next one, you better be fully buttoned up. - Yeah, it's like when you bring in a new chief technology officer, the first one they tell you how everything's broken and everything they're gonna fix. And then you get one more meeting

**[30:39]** and then you better have, you better affix something. So it's very similar. - I think something, a big process that I've seen a lot of companies really, really struggle with, especially if they don't have a RevOps function that's performing well, is the planning process. And typically a lot of companies will do the annual planning process, but I think the planning process should really be a muscle that you can set all of your targets, bookings, create a pipe, wait a pipe, conversion cycle, split them by your segments, and then you should be able to monitor all of that data weekly, monthly, and then make adjustments quarterly if you need to.

**[31:22]** How has your experience been? Do you have any good planning stories? Any planning nightmares that you can maybe help somebody avoid in the future? How's your experience with planning been in general? - Yeah, I have a lot of nightmares probably. Yeah, I mean, it's funny, like when I was at Array, we had like five or six distinct sales verticals, which you might think it was complicated, but it also helped in a lot of ways because we had, and so we treated each one with its own go-to-market and we did its own sort of planning. And in a lot of ways, what I learned from that is that it's actually helpful to think of it that way,

### 31:50 — Planning nightmares and segment-based GTM

**[32:06]** to really break out and have these distinct segments of what you're doing so that you can treat each one like it's its own almost line of business. Everything from what specific product needs do we have to capture this vertical? What's our marketing plan for this vertical? What are our expectations? And I think where you get a lot of credit is if you can start to show what's the average contract value or the lifetime value of a customer in each one of these. And that allows you to create goals and set expectations. So, you know, if I, yeah, one of the things I would say is to the extent that you can do that

**[32:39]** and create your segments, it really does help you. It helps you think through it. So you might have a segment where, I mean, the most simple example would be we have an, we have a large, we have an enterprise segment and we have the sort of, you know, midsize and we have small deals. And we're gonna set up something where our average value of a small deal is gonna be $100,000 a year. We expect to sign, you know, three times as many deals in this segment. And as a result, we've created a very fast and simple sales process all the way up to the enterprise where we may only sign 10 deals this year, maybe less,

**[33:12]** but the average contract value is gonna be, you know, it's a million dollars a year. And therefore we understand what we're doing. And when we allocate reps to it, we can create the right quotas. So I think that's been something for planning purposes that that's really helped, you know, RevOps helps in that because you have to really have a clear, you have to clear understanding of what we're going after in each one of those verticals and what the expected performance is going to be. And again, like I said, if you wait too long to do that, then you're starting from zero. You're really not, you might think you can't record anything

**[33:43]** if you're not, you know, you just don't have it. I've tried to recreate it, it's very difficult. And even when I've, you know, even if you're using, let's say a regular, like a CRM using Salesforce, I just had this problem recently, you know, I created a parking lot for deals. What I wanted to do is keep my team focused on deals that are active. So we said, you know, but if, you know, if for some reason, if it goes a certain amount of time, get it out of there, I want it in the parking lot. I don't wanna talk about it. I also don't wanna forget about it. I wanna try to re-engage that. So we set up systems to do that.

**[34:18]** But then in the movement of the deals from pipeline to parking lot and out of pipeline, I screwed up all of our metrics and timing. So just one of those things, again, where you need to have these things in place and thought through in advance. - Yeah, sometimes I wish Salesforce had the command Z button. - Yeah. - But no, I think that's, I really, really like that. Even the way we approach planning, and we have a platform built out to do this. The first thing you do is you create a segment and it gets its own conversion rate, sales cycle, average contract value, because they look fundamentally different and you'll make totally different decisions.

**[34:56]** You'll staff it totally differently. The amount you're willing to invest in a sales process will look different. And I don't think having up to six segments is crazy. We've worked with quite a few where you have your enterprise, mid market, SMB, and then you may have an international version of those as well. So they all look a little different. You'll have different sales teams on them. So, oh, I was just gonna say, and to your point, if it takes time to get that data, especially in a long, complex cycle. I mean, if you're not tracking what the sales cycle and conversion rate is now, then you won't know what your creative pipeline needs to be

**[35:36]** in order to hit whatever your goal is for the next year. - Yeah, and one of the things like, some of the verticals, I'll give you an exact, some of the verticals where we needed, we said we're gonna get SDRs or BDRs because it's more of a, you know, it works. It's proven that it works. And I could tell you we're gonna get, you know, 27 leads per rep. Other verticals, like we had a bank sector when I was at array, it doesn't work at all, which we quickly learned. And like, you don't get meetings that way. You're not gonna, that's not worth it. So we don't have, so we said, all right, move that team out of there, put them on something that they can do.

**[36:12]** And so it said, all right, well, how are we gonna get leads in the bank sector? And we determined in this case, well, it's gonna have to be a partner strategy and also a conference strategy. Because when banks go to conferences, they are ready to talk, you have to be there. So each vertical though, you know, has its own, I think nuances and it's important that you treat them that way. - Absolutely. I'm curious, I'd like to go back to when you were talking about building out the GTM org and we started going into the RevOps build, but that first enterprise seller role, the person that you said, they need to be curious, they need to be able to understand

**[36:51]** and ingest information really quickly, probably be agile as well. How do you hire this person? What are you looking for? Where do you find them? How do you interview them? How do you make sure they're the right fit before they join? - That's the hardest hire. And to be honest, the best option is someone you already know, if you can, which you sometimes can do. But I'll say, yeah, the initial rep is gonna be different. What you, obviously in an ideal world, what you'd have is such a good process, such a good territory that you could look for the best possible seller that could come in and you could say to them, this is what we're selling.

**[37:30]** Here's the guidelines that you have, like go do it. And there are people who are great at that. You know, the difference, I think in an early role, an early stage role is you need someone who can help you build that and who can, I'll call it a little bit, like it's almost, I don't know if it's a maturity, but you have to almost be willing to like, you're gonna take losses that you probably shouldn't have taken, or you'll feel like you did everything right and you still didn't win. And the goal is to learn from that and figure out why, because it's something new to us and we didn't see it coming. And so the idea is that should never happen again.

### 37:43 — Hiring the first enterprise rep: curiosity, ambiguity, and comp design

**[38:04]** And so I think that's why a lot of times that first rep and even your comp plan for that first rep maybe is a little bit different and it has to be maybe slightly more qualitative versus quantitative where you really want, you know, 80% of your sales rep comp to just be revenue driven. You may have to make some allowances because what you really want is someone who's gonna help you define that process moving forward. And so, you know, if they're gonna live or die by every deal that they may not get because we're learning and you couldn't give them the right process, you have to have someone who's willing to live with that.

**[38:35]** So it's just a certain type of person. It's a little bit more creative and your goal is to get to a point where you're hiring gets easier because you've got the process like hammered out and you can find people who know how to do that. So if you, you know, and that's easier to interview before than that first role. - Whenever I'm hiring, I'm always looking for what's motivating them to be interested in this role and what are they using this experience to tee up for next? And I think if you have a great process, you have a great comp plan, you have a marketing engine that's working and you're, you know, things are going well,

**[39:14]** I think it's easy to find that seller that's, hey, I wanna, I wanna make money. I wanna join a winning team. Yeah, that's exactly what you want. I wanna join a winning team and I wanna win for you. And in this earlier hire, it feels like they may have a few different motivators and be seeing value in this experience. Are there certain tracks you see these people are trying to go towards that seem to fit this profile really well? - Oftentimes it's someone, not always, but oftentimes it's someone who wants to move into a leadership role. You know, you might look for someone who like, you know, maybe in three years you want my job. That's, and that's fine.

**[39:52]** And they'll help them, you know, you wanna help them get there. So I think it's generally someone who's a little bit more of thinking about getting to that level. And there are some people who, right, like you said before, some people are like, I'm here to make money. I'll work my ass off, but give me, you know, give me the instruction so that I can do this. And they're not gonna be tolerant of this uncertainty. So, you know, that's kind of the, living in that ambiguity is important. And so, yeah, that's the big thing that you look for, I think. - It makes a lot of sense. And I think if people are, yes, if you, if you have the person that you already know,

**[40:28]** go grab them, do what you can to make it happen. - Those have been my best hires too. But if you don't have that luxury, I think peeling back the layers of the onion to figure out, okay, what are you actually looking for? And if they are interested in leadership, then it sounds like that would be a good role for them. - Yeah, I think so. You have to enjoy, which I do, you know, you have to enjoy figuring out the process and that some people find that very tedious. Other people enjoy that. - One other thing that we talked about, and I'm hoping we can dive into this as our last topic, 'cause I think this is a big perspective shift

**[41:07]** for probably a lot of sellers. It was a big perspective shift for me when you were sharing it this way, is selling to the blocker, not the champion.

**[41:19]** I'm curious exactly what you mean by that, how you go about doing that, and really what it takes to make that happen. - Yeah, and again, one of the things that we saw here is you start to look at why are deals either dying, why are we losing deals or, so you lose deals for a couple of reasons, and we never really had a problem of losing deals, necessarily, to competitors. That's a small piece, and there's more than enough to go around. So then you look at, all right, why don't certain deals close? Why do they die? And what I have found, generally, is the deal dies from someone that you don't know. So your champion, you have to make a champion, of course,

**[42:05]** and your champion likes the deal, they wanna do this. They're trying, and if you're doing it right, they're helping you navigate. But you have to use that champion properly, and what you really need to figure out is, who can kill this? Who's the person that I probably haven't met, who's going to have to approve this, and who can kill this deal? And in our particular business, in our particular business, there's an added level of complexity, because oftentimes, it is someone at a bank who we will never meet, and you can't actually meet them in most cases. An example, banks oftentimes bring these deals to their board for approval.

### 42:20 — Selling to the blocker: why deals die from people you've never met

**[42:48]** I am not allowed to go speak to their board. So that means that someone at the bank is gonna pitch this deal to the board, and I need that board to say yes, but I'm not gonna get to go in there and do it. So that's one example. And so your goal there is, because you can't, that's an example where you're never gonna get to them, you can't speak to them. So you have to then think through, how do I best prepare this person for success? This person is not a salesperson, most likely. They're, you know, and may not do the best job at this, or this is not their core competency. So how am I going to give them everything they need to be successful in that position?

**[43:26]** So that's one example. The other I think is where the salesperson can impact it, which is making sure that you're figuring out who are the people that need to buy into this deal and who could possibly kill it. And a lot of cases in a heavily regulatory space, in a regulated space, it's going to be someone like compliance can kill these deals. Compliance doesn't make the decision that they want to do this, but compliance can say we're not doing it. And that was, you know, something that we knew in the space that we're in now, we were going to face. And so it is the job to me of the salesperson to identify that and get out in front of that

**[44:02]** and make sure that we are speaking to compliance. We should be able to, if we can't, we should be able to speak to them directly. You know, at Sinterra, we're lucky because we have a really strong compliance team. And I would oftentimes, one of my first things in an early call is to just figure out, we're going to have to take two or three paths to win this deal. Obviously product has to want to do it. You may have a, you know, a business person who wants to do it. And compliance needs to at least sign off. If not, they may not want to do anything, but they have to sign off. So you need to address that. And that's what we mean, I think, when we say like,

**[44:37]** you know, selling to the blocker. If you, it's easy to talk to people who want to do what you're telling them. And that's fun. And it's nice to hear everyone nodding their head and having, you know, saying, let's do it. But, you know, you really need to make sure that you get in front of the person who doesn't want to do it and can say no. - Yeah, and I've definitely fallen into that trap as well, where I'm working with the champion. It feels like they're so passionate about getting this done. I can't even imagine them not being able to sell this. And then the deal dies out of nowhere. I think I've learned that painful lesson before.

**[45:11]** And I think seeing, okay, great, we have a champion. Fantastic, let's arm them. Job is just getting started. We need to go find those blockers and then we need to go sell them next. Do you have any artful ways or tactics, things that have worked to help you get in front of those potential blockers or figure out who they are? - I think the biggest thing that I would, yeah, the biggest thing I think is that you have to control, you have to control the sales process early. And if you get control of it, and by controlling it, I think I mean, you have to be able to, generally in our, you're speaking to your champion probably in the beginning, right?

**[45:51]** The person who is gonna be excited about doing, they wanna do embedded finance, they're excited about it. That's great. You need to then show them how they're gonna buy the product and what's gonna have to happen to get this thing up and running. And I think if you lay that out upfront, and you can do that more systematically once you figure out what it is, and you say to them, we're gonna have to have these conversations. So I'm gonna need you to tell me who in your organization handles this, who handles this and who handles this. And I'm gonna make sure that each one of those three channels gets executed. And we're gonna get each one of those people

**[46:30]** to check the box and say, yeah, I've seen what I need to see, I'm good. So if you do that early and you show them, then usually you can get their buy-in to like make those introductions. If you wait too long, then it's already too late, right? They've already gotten the no. Sometimes like in the compliance case, if they say no, you don't always get a chance to even go back, they're done. And your champion doesn't wanna necessarily burn their political capital within their company when they've already heard a no. Takes a lot of capital to overturn a no. If you got out in front of it in the beginning and you had just alleviated whatever the concern was,

### 47:07 — Controlling the sales process upfront to surface compliance early

**[47:08]** which probably got miscommunicated anyway, that's how you would have gotten through that. So I think controlling the process from the beginning is really important in this case. - I love that, I love that. And I think it's a lesson anybody who's in sales can get a lot of value from. Lee, this has been really, really incredible. Thank you so much for sharing everything you have, going through navigating the level of complexity that has all the layers that you have at Singterra. The marketplace side, enterprise deals, heavy, heavy compliance, and then needing to navigate all kinds of stakeholders. I think when you can operate a sales process like that,

**[47:47]** you just learn so much and you have so much to share. I think your advice on getting RevOps in early, so you can make your early reps as efficient as possible, make sure you have the data to make really good decisions moving forward, and then segmenting your GTM planning. I love how you're leveraging AI in the middle of the funnel. I think there's so many top of funnel use cases that are so hyped up and really, really underestimated value in that middle of funnel with AI, I think is really helpful. And then I love your advice on how to get that first enterprise rep in and then selling to the blockers, not just the champions. So I learned a ton.

**[48:32]** I know everyone in our audience is gonna learn a lot. I appreciate you sharing everything you did today. And I can't wait to see what you and Syngterra do next. Yeah, thank you for having me on. It was great.


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