---
title: "The Hidden Problem Killing Workplace Culture"
episode: 70
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Tom Witte"
guest_title: "Chief Revenue Officer, Upflex"
date_published: 2026-05-15
date_modified: 2026-07-22
duration: 00:53:22
word_count: 8036
topics: ["sales-leadership", "ai-in-gtm", "sales-enablement", "revenue-operations"]
canonical_url: https://leanscale-knowledge-hub.netlify.app/podcast/tom-witte-workplace-culture/
source: "LeanScale Podcast Knowledge Hub — https://leanscale-knowledge-hub.netlify.app"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# The Hidden Problem Killing Workplace Culture

_Tom Witte (CRO, Upflex) on hybrid work, AI-orchestrated culture, and becoming an AI-first revenue leader_

**Episode 70 · The LeanScale Podcast**  
Tom Witte, Chief Revenue Officer, Upflex · Hosted by Anthony Enrico  
Published May 15, 2026 · Updated July 22, 2026 · 00:53:22  
Canonical: https://leanscale-knowledge-hub.netlify.app/podcast/tom-witte-workplace-culture/

**Topics:** Sales Leadership · AI in GTM · Sales Enablement · Revenue Operations


## Executive summary

The remote-vs-office war is the wrong war. That's the argument Tom Witte — Chief Revenue Officer at Upflex and a 15-year veteran of employee experience across benefits, well-being, and now workplace and workspace optimization — brings to this conversation with LeanScale co-founder Anthony Enrico. Witte's throughline across every job has been a single mission: making work better. And in his view, most leaders are fighting over a false binary (butts-in-seats five days a week versus everyone isolated at home) while ignoring the variable that actually produces culture, energy, and retention — how intentionally you bring the right people together.

The reframe is deceptively simple: it's not the building, it's who you're doing it with. Companies have poured money into amenity-rich offices as a magnet, but the far more powerful magnet is orchestration — making sure that when people show up, the right people are there for the right reason. Witte names the failure mode directly: the 'Swiss cheese effect,' where scattered pockets of two or three people leave a building that's technically occupied but feels dead. Most leaders misread that as proof that hybrid is broken and mandate a full return; the real fix is to densify and organize, not recall. Getting there is a 'Rubik's cube' problem — honoring every person's flexibility, team adjacencies, and the actual work being done — that long ago exceeded human coordination and is exactly what AI is now good at solving autonomously, so employees never have to book a desk or self-organize.

The episode widens into how distributed work scales — from a single hub, to a distributed org, to localized clusters that each need their own intentional cadence — and into Witte's most human idea: the reciprocal-care loop. When a company demonstrably cares for employees, most of all by respecting their time (which he calls the most valuable asset in the world), they reciprocate with dividends: discretionary effort, loyalty, and a willingness to stay even for lower compensation. Anthony threads LeanScale's own story through it — starting remote with a co-founder in Brazil, an early 'have and have-nots' problem that pushed the company fully remote, a first office that was a sewage-smelling 'dumpster fire' yet magical because the right people were in it, and quarterly all-company offsites that gave way to local meetups as the team scaled.

The back half turns to Witte as an AI-first revenue leader running a lean, scrappy team. His operating principle: take every process the business hates and ask whether AI can do it better, faster, cheaper — but only after connecting the tools into the company's whole data and workflow ecosystem. He's watched AI first-draft quality jump from 75–80% to roughly 95% in a matter of months and expects purpose-built 'agent armies' next. Anthony matches it with LeanScale's fleet-wide agent deployment on Claude Code, where a meeting transcript becomes a project plan pushed straight to the PM system. Both land on the same underrated frontier: AI as a democratized self-coach — Anthony's podcast-coaching agent that grades his questions, cadence, and talk-time is the example — putting elite, specific training in reach of someone at a two-person company.

It closes on the harder questions. AI hasn't reduced work; the people leveraging it most are working more, because a growth-hungry appetite (backed by a Harvard study pinning happiness on achievement) always finds new work to fill the new capacity. That's why Witte rejects the layoff logic: give him a tool that makes someone 10x more productive and he wants to find a few more of them, not cut two. But both worry about cognitive atrophy — the 'mental gym' you may need to keep critical thinking sharp — and what education and even the notion of work look like for their kids. The through-note is grit: Witte's story of launching a wealth-management practice into the 2008 crash and losing half of it in months, Anthony's of banking with SVB through its 2021 collapse, and the shared conviction that adaptability and resilience are the two traits that decide who comes out ahead. Who should listen: founders, CROs, and team leaders trying to build high-performing culture in a hybrid, AI-shaped world — and anyone who wants a concrete operating model for intentional collaboration instead of a mandate.


## Key takeaways

1. **Remote vs. office is a false binary — orchestration is the real lever** — Witte is disappointed that the conversation collapsed into 'in office' versus 'remote.' People isolated at home five days a week is just as wrong as forcing 40 hours in a building where everyone ends up on Zoom with someone elsewhere anyway. The magic of connection is real, but it can be engineered intentionally — it doesn't require co-location all the time.
   _Why it matters:_ Stop debating where people work and start designing when and with whom they come together. The intentional-orchestration frame dissolves a fight that has no winner.
   _For:_ Founders, Revenue Executives, Sales Leaders

2. **It's not the building, it's who you're doing it with** — Companies chase amenity-rich offices as the draw, but the bigger piece of the pie is the interactions you get there that you couldn't have gotten from home — shoulder-to-shoulder work with the right people. Anthony's first LeanScale office (a sewage-smelling, dust-covered 'dumpster fire') proves the point: no amenities, but magical because everyone they cared about working with was in it.
   _Why it matters:_ Invest in who is in the room and why, not just in the room. Great space helps at the margin; the people and the reason for being together are the actual product.
   _For:_ Founders, Sales Leaders, RevOps Leaders

3. **Orchestration beats amenities as the magnet** — How you orchestrate people day-to-day within a space is a more powerful magnet than how nice the space is. Done well, employees are guided to the right day, place, and people to have high-value in-person moments — without having to book a desk, indicate when they're coming in, or coordinate the friction themselves.
   _Why it matters:_ Shift budget and attention from real-estate niceties to the operating system that groups the right people together. Remove the self-organization burden and attendance stops being a mandate.
   _For:_ Sales Leaders, RevOps Leaders, Revenue Executives

4. **The Swiss cheese effect signals a design problem, not a hybrid failure** — When a building holds a couple of people here and a couple there with gaps in between, the energy feels dead — and leaders misread it as 'hybrid isn't working, get everyone back five days.' In reality the company usually has too much space; densifying and grouping the right teams on the right days would raise vibrancy dramatically.
   _Why it matters:_ Diagnose low office energy as an occupancy-orchestration problem before mandating a return. The fix is often to organize and densify, not to recall the whole company.
   _For:_ Founders, Sales Leaders, RevOps Leaders

5. **The warning sign is that you've put the onus on employees to self-organize** — The tell that org design needs attention is when 'flexibility' has really just offloaded coordination onto employees — creating burden and friction. It shows up as low adoption of booking systems and people not doing what they indicated, and humans are simply inefficient at self-organizing at scale and complexity.
   _Why it matters:_ If your flexibility policy creates work for employees, it's incomplete. Own the coordination centrally (increasingly with AI) rather than telling people to 'figure it out.'
   _For:_ RevOps Leaders, Sales Leaders, Founders

6. **Every team is different — raise your hand and engineer around each cohort** — A finance company, a tech company, and a food-and-beverage manufacturer work differently, and inside a company the engineering team and the sales team have different needs. The first step is admitting there's variability in what's optimal, then listening to each cohort and engineering their cadence around how they actually do their best work.
   _Why it matters:_ Reject one-size-fits-all workplace policy. Segment by team and function, and expect the right answer to keep evolving as you scale.
   _For:_ Founders, Sales Leaders, RevOps Leaders

7. **Distributed work scales in stages, and the cadence must evolve with it** — Companies move from a single hub where everyone's together, to a distributed org with people everywhere, to localized clusters in different pockets of the country or world. Each stage needs different mechanics: quality time for local clusters, occasional whole-company gatherings, and day-to-day team self-organization. LeanScale lived this — in-person hub, then fully remote, then quarterly all-company offsites that became unmanageable and gave way to local meetups.
   _Why it matters:_ Plan for connection to be a moving target. What works at one hub breaks at 200 people distributed across time zones — build the next stage before the current one cracks.
   _For:_ Founders, RevOps Leaders, Revenue Executives

8. **Reciprocal care: respect people's time and they pay it back with dividends** — Drawing on his well-being days, Witte describes a loop: when a company's care for employees is felt and tangible — especially care for their time, the most valuable asset there is — employees reciprocate. They fight for the business, go the extra mile, stay, and statistically will even keep the job for lower compensation because they value what they're getting.
   _Why it matters:_ Treat flexibility and time as a retention and performance strategy, not a perk. The care compounds into productivity, satisfaction, and recruitment advantages.
   _For:_ Founders, Revenue Executives, Sales Leaders

9. **Run every process through the 'better, faster, cheaper with AI?' test** — Witte's AI adoption didn't start with 'here's an LLM, use it for anything.' It started with 'here's a process we hate that sucks — can AI do it, or do it better, faster, cheaper?' Applied to everything, that habit offloads time-consuming, non-human work to AI. The prerequisite is upfront plumbing: connecting the tools into the company's data sources and work systems (email, calendar) so they have what they need.
   _Why it matters:_ Adopt AI process by process against real pain, and invest first in the data and tool integrations. Value shows up only when the agent can actually reach your ecosystem.
   _For:_ RevOps Leaders, Revenue Executives, Founders

10. **AI democratizes elite coaching — build a self-improvement agent for any role** — Beyond executing workflows, the underused frontier is self-analysis and self-critique in a safe, personalized environment. Anthony runs an agent purpose-built as his podcast coach, grading every episode on question quality, cadence, talk-time, and pushback. It surfaces suggestions no human coach on the market would have given — and the same specificity is now available to someone young at a two-person company who once would have needed a big employer's formal training program.
   _Why it matters:_ Stand up personal coaching agents with the exact context of the job. Whoever leans into AI-driven self-improvement becomes a disproportionate weapon in the workforce.
   _For:_ Sales Leaders, RevOps Leaders, Revenue Executives

11. **AI grows work and headcount, not shrinks it** — AI hasn't reduced work — the people leveraging it most are working more, because new capability just means more becomes possible and gets put on the plate. A Harvard study pins happiness on achievement (including micro-achievements), and driven people feed on that output. So the instinct isn't to cut: give a leader a tool that makes someone 10x productive and they want to find a few more of those people and go faster.
   _Why it matters:_ Frame AI as a throughput multiplier against an unbounded appetite to produce, not a headcount-reduction lever. The rational move on a productivity gain is usually to add capacity.
   _For:_ Founders, Revenue Executives, RevOps Leaders

12. **Guard critical thinking — you may need a 'mental gym'** — Both worry that heavy, unintentional AI use is degrading cognitive ability. Anthony catches himself struggling to write a simple two-sentence email after leaning on agents to do everything, and predicts people will need a 'mental gym' — or to work in 'manual mode' on purpose — to keep critical thinking, adaptability, and resilience sharp. It reframes education too: foundational human skills first, then deep, specific, tool-assisted training on demand.
   _Why it matters:_ Preserve deliberate practice of core skills even as AI handles execution. Critical thinking is the durable edge; atrophy is a real risk if you never turn the tools off.
   _For:_ Founders, Revenue Executives, Sales Leaders

13. **Grit and adaptability are the two traits that decide who comes out ahead** — Witte launched a wealth-management practice straight out of college and into the 2008 crash, losing roughly half the business in a couple of months before rebuilding to his best years — his first real test and the source of his conviction that adaptability and resilience are the two most important characteristics for any businessperson. Anthony's version: starting LeanScale at the top of the 2021 tech high, then straight into tech winter with payroll and capital locked up at SVB. The lesson both carry: it's a knife fight, you'll want to quit, and you just keep choosing to keep going.
   _Why it matters:_ Expect peaks and valleys and treat crises as character-building. In a world changing this fast, the operators who adapt and endure beat the ones with the better original playbook.
   _For:_ Founders, Revenue Executives, Sales Leaders


## Frameworks

### The False Binary of Work (Orchestration, Not Location) (02:50)

**Definition:** The remote-vs-office debate is a false binary. The real variable isn't where people work but how intentionally the right people are brought together — connection can be engineered without full-time co-location.

Isolation at home is as flawed as forced in-office (where people end up on Zoom anyway). The 'X factor' of in-person magic is real but can be harvested deliberately rather than hoped for by chance, so the design question is when and with whom, not simply how many days in a building.

### It's Who You're Doing It With, Not the Building (08:04)

**Definition:** The magnet that makes an office worth showing up for is the interactions with the right people, not the space or its amenities.

Companies over-focus on the building as the draw; the bigger piece of the pie is the shoulder-to-shoulder work you couldn't have done from home. Amenities enrich the experience at the margin, but the people and the reason to be together are the actual value.

### The Orchestration Rubik's Cube (12:30)

**Definition:** Coordinating people day-to-day in space — honoring individual flexibility, team adjacencies, and the actual work being done — is a Rubik's cube problem that exceeds human capability and is well suited to AI.

Post-COVID hybrid variability at the person and team level made occupancy planning exponentially harder. An autonomous AI layer can read enterprise signals, infer groupings that transcend the org chart, and allocate the right people to the right place at the right time continuously — so employees never have to book desks or self-organize.

### The Swiss Cheese Effect (14:43)

**Definition:** A workplace failure mode where a building holds scattered pockets of two or three people with gaps in between, so it's technically occupied but feels low-energy and dead.

Leaders misread it as evidence hybrid is broken and mandate a full return. The real cause is usually too much space plus poor orchestration; densifying and grouping the right teams on the right days restores vibrancy far more effectively than a five-day recall.

### The Scaling Stages of Distributed Work (18:06)

**Definition:** Distributed organizations progress through stages — a single co-located hub, a fully distributed org, then localized clusters — each requiring a different connection cadence.

Early on a hub works; then people are everywhere; then natural clusters form in different regions. Each stage needs its own mechanics: local clusters get quality time together, the whole company gathers occasionally, and teams self-organize day-to-day. LeanScale's arc (in-person hub, fully remote, quarterly offsites, then local meetups) illustrates the evolution.

### The Reciprocal Care Loop (26:24)

**Definition:** When a company demonstrates tangible care for employees — above all, respect for their time — employees reciprocate that care back into the business with dividends.

From Witte's well-being background: time is the most valuable asset, and giving it back earns discretionary effort, loyalty, and retention, with employees statistically willing to stay even for lower compensation. It reframes flexibility as a performance-and-retention strategy rather than a perk.

### The Better/Faster/Cheaper AI Test (28:57)

**Definition:** Adopt AI by targeting real, painful processes and asking whether AI can do each one — or do it better, faster, or cheaper — rather than handing everyone an open-ended LLM.

The habit of catching yourself before a task and asking 'can I do this better, faster, cheaper with AI?' offloads non-human work. It only works after connecting the tools into the company's data sources and systems (email, calendar), which is the upfront investment that makes the outputs usable.


## Quotes

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

> "I'm somewhat disappointed in how much of a binary conversation it's become — that your organization is either in office or remote."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (02:50)

> "We don't necessarily have to be co-located in the same space all the time to get the benefit and sort of wring the juice out of connection, collaboration, and culture."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (04:27)

> "It's not the building that you're doing it in. It's who you're doing it with."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (08:04)

> "How we orchestrate folks day to day within space is actually the much more powerful magnet than how nice the space is itself."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (09:36)

> "The first LeanScale office was an absolute dumpster fire. There was a constant smell of sewage throughout the entire building, inches of dust around everything — but it was dirt cheap. And everybody that we cared about working with was there. Those moments were magical."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 70 (10:25)

> "That Rubik's cube problem of orchestrating people on a day-to-day basis quickly exceeded the capabilities of humans. And that's where we've really latched onto AI."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (12:30)

> "We sometimes refer to it as the Swiss cheese effect — two or three people over here and two or three people over there, with a lot of gaps in between. You may have a bunch of people in your building, but the energy feels really low."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (14:43)

> "The ability to give them time back, which I would argue is the most valuable asset in the world."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (20:48)

> "If the company really demonstrated care for the employee, and that was felt and tangible, the employees will reciprocate that care back into the business, probably with dividends."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (26:24)

> "It was: here's a process that we have as a business that sucks, that we hate doing. Can we get AI to do this for us? Or can we use it to complete that process better, faster, cheaper?"
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (28:57)

> "The initial output used to be our V1 that's maybe 75, 80% of the way there. Now the initial V1 outputs are coming out like 95% good — and that's just over the last few months."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (31:12)

> "I have an agent purpose-built to be my podcast coach. Every single episode is reviewed and I get a report card on quality of questions, cadence, talk time percentage, level of pushback and agreeability."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 70 (36:47)

> "Now you can work for a two-person company, be completely young in your career, and — if you're willing to take advantage of these things — get just as good, if not better, of a training and educational experience."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (37:31)

> "I really do worry that heavy use of AI, if not used intentionally, is starting to degrade cognitive ability. You may have to go to a mental gym to make sure your brain can still critically think."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 70 (39:10)

> "Harvard did a big study on what makes people happy, and the punchline was achievement. And it doesn't have to be big — it can be micro-achievements throughout the course of a day."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (46:18)

> "Adaptability and resilience are, in my opinion, the two most important characteristics for any business person — especially in startup stuff."
>
> — Tom Witte, The LeanScale Podcast Ep. 70 (50:48)


## Practical advice by role

### Founders

- Stop framing the workplace as remote vs. office. Decide how much you value the ability to hire anywhere and give people their time back, then design intentional togetherness around that instead of mandating days.
- Expect connection to be a moving target as you scale: a co-located hub gives way to a distributed org and then to localized clusters, and each stage needs its own cadence — plan the next stage before the current one cracks.
- Treat respect for employees' time as a performance-and-retention strategy. The reciprocal-care loop pays back in discretionary effort, loyalty, and lower attrition — often worth more than the flexibility 'costs' you.

### Revenue Executives

- Adopt AI process-by-process against real pain — target the tasks the team hates and ask if AI can do them better, faster, cheaper — after investing in the plumbing that connects tools to your data, email, and calendar.
- Reinvest AI productivity into capacity, not cuts. If a tool makes someone 10x more productive, find a few more of those people and go faster; the appetite to produce is effectively unbounded.
- Lead through the peaks and valleys. Adaptability and resilience beat a better original playbook when the world is changing this fast — expect crises and treat them as character-building.

### Sales Leaders

- Make the office worth showing up for by orchestrating who's there and why, not by adding amenities. The interactions people couldn't get from home are the draw.
- Diagnose low office energy as a Swiss-cheese occupancy problem before recalling everyone five days a week — densify and group the right teams on the right days first.
- Stand up AI self-coaching for reps: personalized, safe self-critique with the exact context of the job now rivals the formal training programs only big companies used to offer.

### RevOps Leaders

- Own the coordination centrally instead of pushing it onto employees. Low booking-system adoption and people not doing what they indicate are signals the flexibility policy has offloaded burden — increasingly a job for an autonomous orchestration layer.
- Segment workplace and operating cadence by team and function; the engineering and sales teams optimize differently, and one-size-fits-all policy underperforms.
- Do the upfront integration work: AI only creates leverage once it can reach your data sources and work systems — then route time-consuming, non-revenue tasks (like turning a meeting transcript into a project plan) to agents.


## AI takeaways

**Thesis:** AI is a productivity multiplier and an orchestration engine that makes the humans who harness it more powerful — it doesn't shrink teams, it grows what they can do. The winning posture is to arm people, connect the tools to your data, use AI to democratize coaching, and guard the critical thinking AI can quietly erode.

- **Orchestration is an AI-native problem** — Coordinating who's where and with whom in a hybrid world is a Rubik's cube that exceeds human capability; an autonomous layer reads enterprise signals, infers groupings beyond the org chart, and allocates people continuously.
- **Better, faster, cheaper — process by process** — Adopt AI by targeting painful, non-human tasks and asking if it can do each better, faster, or cheaper, rather than handing everyone an open-ended LLM — but only after wiring tools into your data and systems.
- **AI as a democratized self-coach** — Purpose-built coaching agents (Anthony's podcast coach grading questions, cadence, and talk-time) put elite, specific training in reach of anyone — the underused frontier beyond executing workflows.
- **More output means more work, not fewer people** — AI hasn't reduced work; those leveraging it most work more. A 10x productivity gain triggers hiring a few more of those people to go faster, feeding an unbounded appetite to achieve.
- **Guard critical thinking** — Heavy, unintentional AI use erodes cognitive muscles (Anthony forgetting how to write a simple email); expect a need for a 'mental gym' and deliberate 'manual mode' practice to stay sharp.

**Agent & automation ideas**

- An autonomous workplace-orchestration agent that reads enterprise signals (team connections, project work, space requirements) and allocates the right people to the right place on the right day — no desk-booking or self-organization required.
- A per-person self-coaching agent that reviews recorded calls or episodes and returns a report card (question quality, cadence, talk-time, pushback), personalized to the exact job.
- A process-audit agent that catalogs a team's recurring processes and scores each for whether AI can do it better, faster, or cheaper — prioritizing the plumbing to connect data and systems first.
- A meeting-to-plan agent that ingests a call transcript, drafts the project plan against a repo of best-practice knowledge, and pushes tasks straight into the PM system.


## Operations takeaways

### Revenue operations

- **Cadence by cohort.** Engineer operating rhythm around how each team actually works — engineering and sales optimize differently; one-size-fits-all workplace policy underperforms.
- **Connect the pipes first.** AI creates leverage only once integrated into data sources and work systems (email, calendar); the upfront plumbing is the prerequisite for usable outputs.
- **Offshore non-revenue work to AI.** Route time-consuming, non-human tasks to agents so operators spend their time on relationships and judgment, not administrative drag.
- **Orchestration is now automatable.** The day-to-day 'who/where/when' problem that humans can't solve at scale can be handled by an autonomous layer monitoring enterprise data in real time.
- **Design the warning-sign dashboard.** Low booking-system adoption and people not doing what they indicate are leading signals that flexibility has offloaded coordination burden onto employees.


## Metrics mentioned

| Value | Metric | Context |
| --- | --- | --- |
| 15+ years | Employee-experience tenure | Tom Witte's career across benefits, well-being, employee-experience platforms, and now workplace/workspace optimization. |
| Half or more of waking hours | Time spent at work | Witte's rationale for why improving the experience of work is a mission worth the effort. |
| 50–1,000 employees | Target customer size | The scaling B2B tech companies (some in AI/SaaS) Upflex most often helps orchestrate hybrid work. |
| 75–80% → ~95% | AI first-draft quality | How much of a task AI gets right on the first pass — a jump over just a few months as models improved, shrinking the human cleanup step. |
| ~50% in a couple of months | 2008 business loss | Witte lost roughly half of his wealth-management business almost overnight in the 2008 crash, then rebuilt to some of his best-ever years. |


## Entities mentioned

- **Upflex** (company) — Tom Witte's employer, where he is CRO; a workplace platform focused on orchestrating people in a hybrid world — using AI to solve the day-to-day 'who/where/when' occupancy problem so the right people are together for the right reasons. · https://leanscale-knowledge-hub.netlify.app/company/upflex/
- **LeanScale** (company) — Anthony's firm; the source of the episode's operator stories — starting remote with a co-founder in Brazil, the have/have-nots problem that pushed it fully remote, the sewage-smelling 'dumpster fire' first office, quarterly offsites giving way to local meetups, and a fleet-wide agent deployment on Claude Code. · https://leanscale-knowledge-hub.netlify.app/company/leanscale/
- **Silicon Valley Bank (SVB)** (company) — Where Anthony banked when he started LeanScale in 2021; its 2023-era collapse locked up the company's payroll and capital — his personal example of enduring a crisis through grit and adaptability. · https://leanscale-knowledge-hub.netlify.app/company/silicon-valley-bank/
- **Tom Witte** (person, guest) — CRO of Upflex; 15+ years in employee experience (benefits, well-being, workplace optimization) and an AI-first revenue leader. · https://leanscale-knowledge-hub.netlify.app/guest/tom-witte/
- **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://leanscale-knowledge-hub.netlify.app/guest/anthony-enrico/
- **Claude Code** (tool, AI Dev Tool) — LeanScale's whole team runs as power users of Claude Code (said as 'cloud code'), with purpose-built agents per service; Anthony's example: feed a meeting transcript in and it produces a project plan pushed straight to the PM system.


## FAQ

**Q: Is remote work or return-to-office better for company culture?**

A: According to Upflex CRO Tom Witte, that's the wrong question — it's a false binary. People isolated at home five days a week is as flawed as forcing everyone into an office where they end up on video calls with people elsewhere anyway. Culture comes from how intentionally you bring the right people together, which can be engineered without full-time co-location; the design question is when and with whom, not simply how many days in a building.

**Q: What actually makes an office worth showing up for?**

A: The people, not the building. Witte argues companies over-invest in amenity-rich spaces as a magnet when the bigger draw is the interactions with the right people that you couldn't have gotten from home — shoulder-to-shoulder work on things that matter. Amenities help at the margin, but who is in the room and why is the real value; how you orchestrate people is a more powerful magnet than how nice the space is.

**Q: What is the 'Swiss cheese effect' in hybrid workplaces?**

A: It's a failure mode where a building holds scattered pockets of two or three people with gaps in between, so it's technically occupied but feels dead and low-energy. Leaders often misread it as proof hybrid is broken and mandate a full return. The real cause is usually too much space plus poor orchestration; densifying and grouping the right teams on the right days restores vibrancy far more effectively than recalling everyone five days a week.

**Q: How is AI used to orchestrate hybrid work?**

A: Coordinating people day-to-day — honoring each person's flexibility, team adjacencies, and the actual work being done — is a 'Rubik's cube' that exceeds human capability. An autonomous AI layer can read signals from across the enterprise, infer groupings that transcend the org chart, and allocate the right people to the right place at the right time continuously, so employees never have to book a desk, indicate when they're coming in, or self-organize.

**Q: What is the reciprocal care loop?**

A: It's Witte's idea that when a company demonstrates tangible care for employees — above all, respect for their time, which he calls the most valuable asset in the world — employees reciprocate with dividends: discretionary effort, loyalty, going the extra mile, and staying, statistically even for lower compensation. It reframes flexibility as a performance-and-retention strategy rather than a perk.

**Q: How should a company start adopting AI in its go-to-market?**

A: Don't hand everyone an open-ended LLM. Witte's approach starts with a painful process the business hates and asks whether AI can do it — or do it better, faster, cheaper. Apply that habit to everything, but first invest in the plumbing: connect the tools into your data sources and work systems (email, calendar) so the agents have what they need. He's watched first-draft quality jump from 75–80% to about 95% in months.

**Q: Does AI reduce headcount or workload?**

A: No — Witte and Anthony argue the opposite. AI hasn't reduced work; the people leveraging it most are working more, because new capability just means more becomes possible. A Harvard study ties happiness to achievement, including micro-achievements, so driven people feed on the extra output. Give a leader a tool that makes someone 10x more productive and the instinct is to find a few more of those people and go faster, not to cut.

**Q: Can AI help you get better at your job, not just do it faster?**

A: Yes, and Witte calls this the underused frontier: using AI for self-analysis and self-critique in a safe, personalized environment. Anthony's example is an agent built as his podcast coach that grades every episode on question quality, cadence, talk-time, and pushback. That kind of specific coaching — once available only at big companies with formal training programs — is now within reach of someone young at a two- or three-person company.


## Timeline

- **00:00** — Meet Tom Witte: 15 years making work better
- **02:09** — Where leaders get remote vs. return-to-office wrong
- **04:27** — LeanScale's remote journey and the have/have-nots problem
- **07:17** — What makes an office worth showing up for
- **09:36** — Orchestration beats amenities (the dumpster-fire office)
- **12:30** — The orchestration Rubik's cube AI can finally solve
- **13:48** — Warning signs and the Swiss cheese effect
- **15:56** — Advice for 50–1,000-person scaling companies
- **18:06** — How distributed work scales in stages
- **20:48** — Time as the most valuable asset; reciprocal care
- **27:58** — Being an AI-first CRO: better, faster, cheaper
- **32:44** — LeanScale's agent deployment; V1 to 95%
- **34:11** — AI as a self-coach: democratized training
- **39:10** — Critical thinking, the mental gym, and education
- **45:37** — AI hasn't reduced work; achievement and the Harvard study
- **47:48** — Grit through crisis: the 2008 story and SVB
- **52:21** — Closing: making work better


## Related episodes

- **Ep. 95: Why AI Means More RevOps Hires, Not Fewer** (Jimmy O'Halloran) — The definitive statement of the same thesis Witte lands on — a productivity gain should grow the team and go faster, not cut headcount. · https://leanscale-knowledge-hub.netlify.app/podcast/jimmy-ohalloran-new-relic-revops-consumption-revenue/
- **Ep. 88: Why AI Won't Close Your Biggest Deals** (Michael Kiernan) — A CRO's 'Human + Agentic GTM' view that embeds AI without removing the humans who carry relationships — the same keep-the-people posture. · https://leanscale-knowledge-hub.netlify.app/podcast/michael-kiernan-nextdoor-ai-wont-close-deals/
- **Ep. 85: Why AI + GTM Engineers Can't Replace RevOps** (Tessa Whittaker) — AI as a multiplier for human judgment rather than a replacement — pairs with the 'tools are great, the human beings are more important' frame. · https://leanscale-knowledge-hub.netlify.app/podcast/tessa-whittaker-ai-gtm-engineers-revops/
- **Ep. 15: Where Should RevOps Report?** (LeanScale) — Org-design companion to the workplace-orchestration and cohort-cadence discussion. · 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/tom-witte-workplace-culture/transcript.md_

### 00:00 — Meet Tom Witte: 15 years making work better

**[0:00]** Today, I'm talking with Tom Whitty, CRO at UpFlex. Tom has spent the last 15 years in employee experience from benefits to well-being to workplace, helping companies think about what actually enables people to do their best work. He's built through crises, including starting a wealth management business just prior to the '08 financial crash. And today, he brings that operator mindset to one of the biggest questions leaders are wrestling with. How do you create flexibility, connection, and performance all at the same time? We'll also talk about what it means to be an AI-first revenue leader and how Tom thinks about building

**[0:42]** teams and systems that work in the real world. Tom, you spent 15 years across benefits, well-being, and now workplace, which is a very hot topic. What is the through-line? What problem do you feel you have actually been trying to solve all along? Yeah, thanks, Anthony, and great question. I think for me, first off, I've always been someone that needs to be really motivated by the mission regardless of what I'm doing. And for me, a mission that's been, I guess, really the through-line through all this work in my post-financial days has really been under the banner of making work better in some way,

**[1:23]** shape, or form. And that has taken different forms, as you mentioned, working in benefits and well-being, employee experience platforms, now more recently in workplace and workspace, optimization. But the idea that we spend half, if not more, of our waking hours at work and devote so much of our lives to it, if there's anything that I think is worthy of the effort to try and improve its work in way, shape, or form. It may also have been sparked by maybe one of my favorite movies from the '90s office space and us wanting to see if we could shift the needle away from that being the standard of corporate America.

### 02:09 — Where leaders get remote vs. return-to-office wrong

**[2:09]** That's a classic. I've definitely felt myself wanting to just destroy a printer every now and then. I've never had one that works. It's like printers and ice machines. No, never, never, never. I'm not sure how we have the most powerful AI in the history of the world, but we can't figure out those two things. Exactly. No, I think it's a very, very worthy pursuit. And you're right. We spend so much time in this boat of life. And I'm wondering, what do you think a lot of leaders are getting wrong with their approach, especially with the conversation around remote work or return to office?

**[2:50]** It's tough. I mean, it really depends on the company. I guess I'm somewhat disappointed in how much of a binary conversation it's become, right? And that our organization is either in office or remote/flexible. And the way of evolving how and where we work has been, I guess, behind what I would have maybe anticipated or expected. Some companies, of course, have certain motivations for trying to force folks back into their own corporate locations. Maybe they've made investments into those locations they want to see a lively environment when they walk around. Maybe it's a control issue. And I

**[3:41]** can't really trust that our people are working if I can't see that they're working directly in front of me. Maybe it's antiquated notions around, this is the only possible way that connection and culture can form, is if everyone is forced together in this one particular space, four or five days a week. It's really a bit of a hodgepodge, I think, of motivations. But I think the wrong part that's maybe a bit of a common denominator is we've really failed to, I think, adopt the way of thinking that different teams, different peoples, different organizations are going to do their best work differently. And I think the one common denominator

### 04:27 — LeanScale's remote journey and the have/have-nots problem

**[4:27]** also, another common denominator, is that we don't necessarily have to be co-located in the same space all the time to get the benefit and sort of wring the juice out of connection, collaboration, and culture. And there needs to be some of that for sure, and we can be intentional about that. It just doesn't have to be all the time. Yeah, and I think I've had my own experience with this at LeanScale. We started in 2021, so right after pandemic times. My co-founder is in Brazil, so we had to start remote, unless I want to move to Brazil or him up here. And I found at the very early stage, I really,

**[5:14]** really enjoyed actually being in office. And I had a core team, I'm based in Phoenix, and we had the core team out here in Phoenix where we could get things started and communication flowed really well. And then when we got to a certain point where we had people in different areas all around the world, it started to become a have and have nots issue, where I was present in the office, so people around me had more access to me than people who are remote. And we made the decision to go fully remote, even though a lot of us live nearby each other, simply to even the playing field and have everybody in the same rhythm.

**[5:54]** Yeah, I don't know. Like I said, to me, it's not a binary, right? I think that people being isolated in their homes, you know, five days a week is just as wrong, you know, for lack of a better term than people being forced to spend 40 hours a week in the office, right? Where we know, almost guaranteed, they're gonna be spending a good chunk of that time on Zoom meetings or Teams meetings with other folks distributed somewhere else in the world, right? You know, the distributed way of working has taken such root across most organizations at this point, especially when they hit a certain point in the scale, that it's gonna

**[6:35]** be, that's just gonna be the nature of things. And so, but again, being home, you know, locked away in your room, that's not great either, right? But there's a balance and there's I think a way of ensuring that those human connections, those moments that matter, that magic X factor, which is undeniable, right? Like no one's saying that this doesn't exist, that comes to fruition when folks spend time together with the, you know, in person. That can still happen. That can still be harvested and engineered even to a large degree by just being intentional and how, you know, how you bring folks together. I'm just of the opinion personally, that we

### 07:17 — What makes an office worth showing up for

**[7:17]** don't need to, you know, hope that it happens by chance and luck by forcing everyone into the same space all the time. Yeah, I think there is an intentionality behind how you design this. On the office side, in your opinion, what makes an office worth showing up for? That's a great question. Something we think a lot about and especially in my current line of work here at my company, UpFlex, where, you know, now I've again sort of moved, I'm in the workspace phase of my employee experience journey, if you will. And because again, I'm certainly not anti-office and I think that, you know, that there's a lot that comes from,

**[8:04]** you know, having that great office environment. But for me, it goes back to the old saying, "It's not what you're doing. It's who you're doing it with." Although I might adapt that old phrase a little bit to say it's not sort of the building that you're doing it in. It's who you're doing it with, right? Because so many times companies have really focused on the space itself to be that magnet or to be that draw. We want to have the best office possible with all the amenities and all the right types of workspaces and the niceties that will make being there great. And don't get me wrong,

**[8:46]** that stuff is important. It's helpful. It does enrich the experience for sure. But on the other side is this much bigger piece of the pie, which is it's the interactions with people that I'm going to have there that either makes it a fulfilling worthwhile experience, something I couldn't have gotten from home, right? If I'm not working with Anthony on something and I don't then get to spend time with Anthony, like shoulder to shoulder working on that thing, whatever it might be together, right? In that really kind of X factor of magic way, that's the thing, right? And so I would argue that we've, we've sort of overlooked

### 09:36 — Orchestration beats amenities (the dumpster-fire office)

**[9:36]** that piece of the pie a bit in really what I tend to speak about is, you know, the concept of orchestrating folks in this hybrid world that we live in, you know, how we orchestrate folks day to day within space is actually the much more powerful magnet than, you know, how nice the space is itself. I'll share the first lean scale office was an absolute dumpster fire. Yeah. I'm pretty sure nobody maintained the building. There was a constant smell of sewage throughout the entire building, inches of dust around everything, but it was dirt cheap. And everybody that we cared about working with was there. And I will tell you those moments were magical.

**[10:25]** We had an amazing time. Yes. And yeah, it didn't have anything fancy. We had a horrible Keurig machine in the corner of our room that we rented out of this space. And that was about it. Those are the amenities. So I think I, from my own experience, I agree. It's all about the people. If you're doing work that matters with the people that are in proximity, then that's where being in person can be really valuable. Really agree. And, you know, so where we read a rigid for like, for a long time, I tried to come at that, that problem by working with companies on playbook strategies for intentional

**[11:07]** connections. And we worked with all sorts of workplace and culture and IO psychologist type experts, um, to help really companies help companies really think about how to win. We asked folks to come together. How do we make sure when they show up, it's that kind of intentional experience, right? It's not just haphazard, but they're not going to show up and sit on zooms, right? But there's a reason why they're there. The right people are there for that particular reason. Um, and they can have that kind of experience, which may only need to be every so often or these days a week, or obviously every team

**[11:43]** company is different. Um, what we still found though, is even when we had that playbook, it was really, really hard for companies to implement that into practice. Um, using traditional approaches to occupancy planning or, you know, organizing team, you know, adjacencies and calendars and which, you know, which teams, people, et cetera, came in on which days and where were they sat? It was a really, really hard problem, um, to solve even pre COVID and then became an exponentially harder problem to solve post COVID when hybrid became the mainstay model. And now you had hybrid variability and choice introduced at the person and team

### 12:30 — The orchestration Rubik's cube AI can finally solve

**[12:30]** level in terms of largely where and when they would be. And so that orchestration problem, that Rubik's queue problem of orchestrating people on a day-to-day basis that honored their requirements, team connections and adjacencies and the work that they were actually doing at any given point with one another, that quickly exceeded the capabilities of humans. And that's where I think, you know, we've really latched onto AI as being really sort of like what AI is best at, um, to help solve that problem for companies on a day-to-day basis. And so that's really where we spend the majority of our focus these days is how

**[13:13]** can we leverage these types of modern tools to solve that Rubik's cube on a day-to-day basis to ensure that when folks do show up, it's that perfect experience and they didn't have to do anything like they didn't have to book and book a desk. They didn't have to indicate when they were coming in, right? That self-organization and friction that is associated with it is sort of gone and now we can just guide them to when and where with the right people to have those incredible experiences. So that's been a, I would say one of the certain upsides we've seen, you know, emerge out of AI.

### 13:48 — Warning signs and the Swiss cheese effect

**[13:48]** Absolutely. What, what potential warning signs start to show up in organizations when this org design really starts to demand your attention? It'll probably start to show up when, you know, the, usually the conditions we see are first the company has put the onus on employees to have to figure it out, right? We think we're doing a good job in giving you flexibility and degrees of choice, but then that just creates work and burden for me to now have to navigate that, to make those decisions and to coordinate those decisions en masse with my colleagues in the best possible way. And so there'll be some, I think natural friction

**[14:43]** that shows up in that type of motion, whether it's low adoption of booking systems, people not actually doing what they indicate that they'll do. You'll see it when you walk around those spaces. And we sometimes refer to it as like the Swiss cheese effect, where there's two or three people over here and two or three people over there and a lot of gaps in space in between. So you may have a bunch of people in your building, but it kind of the, the energy feels really low, right? It doesn't feel very vibrant. And you're like, what are we doing wrong? Right? Like the space, and that's oftentimes actually where company like

**[15:24]** you kind of get the company will get to a fork in the road. We're like, there's no one. It feels like there's no one here, right? And the energy feels dead. We need to get everyone back in five days a week now, right? This, this whole hybrid thing's not working for us, right? We're losing our culture, right? Because it walks around, it feels that way. When in reality, it's just, well, if we could just organize people better in that space, right? You probably have too much space statistically. And if we could just organize people and sort of densify it a bit and make sure that we were getting the right groups together each

### 15:56 — Advice for 50–1,000-person scaling companies

**[15:56]** day, that energy and vibrancy would come up pretty dramatically. And it would feel like a completely different experience for we work with a lot of companies that are maybe in a scaling phase. So they probably have anywhere from 50 to a thousand employees and everything in between, mostly B2B tech startups, some in AI, SAS. What recommendations would you give them? What, what have you seen to work well in that context that still helps foster that human connection, keep a through line of culture across the whole organization, but also gives the flexibility that people are looking for?

**[16:42]** I think it first starts with because, as I mentioned now, a couple of times, every company, every team is different. They're all going to work differently. A finance company versus a tech company versus a food and beverage manufacturer, right, are going to have different ways of working that need to be optimized. And then from there, it's very different even at a team level, right? The engineering team and the sales team probably have different needs or are going to be optimized in different ways in with regards to their workforce and workplace policies. And so you need to first be willing to sort of raise your hand in the

**[17:25]** air and say, I recognize that it's different, right, that there is variability in what's best, what structure and what policy and what accommodations are best for each different group, each different cohort. And if you're willing to do that and then willing to listen and work with those teams to understand, well, what's the best way for you all to work, right, and try and engineer around that to a degree, that's, I think, the best first step, right? And that may change and evolve as your company gets bigger and bigger and bigger, right? And like with your own example that you just gave, right, like everyone being together,

### 18:06 — How distributed work scales in stages

**[18:06]** and I think you said that there was the Phoenix, if I'm not mistaken, right, like when you were all there, this makes a lot of sense, right? We've got this hub that we come into, you know, regularly and we're all together and we're figuring stuff out. And then pretty quickly we have employees here, there, and sort of everywhere. And then the next stage after that, typically, is there starts to be these localized clusters of folks in different pockets around the country or world, right? And so there's going to be different strategies for making sure that those localized clusters spend good quality time together for, again,

**[18:44]** very intentional reasons, that we get the whole company together for different sets of reasons. And then on a day-to-day basis that we allow teams to organize and sort of work in the way that's uniquely right for them. So it takes a little bit of work to do that, right? But I think it's work that's certainly worth the effort because if you can get that right, I mean, all of the, you know, pick an outcome. It's going to be there, whether that's, you know, sort of retention and productivity, but just, you know, precursors to that would just be satisfaction and, you know, the level of collaboration that people feel that they have in space.

**[19:30]** It's been a very difficult puzzle for me to solve. And it's something we actually spend a lot of time in meetings talking about, testing different things. And, you know, from the beginning, we had that in-person time and then we went fully remote. Definitely felt like we lost some connection. So then we started doing whole company off-sites. So we would meet for a week once a quarter. That was manageable when it was a small team. Then as we got bigger to bring the entire company, every single quarter was just not reasonable. It's a lot. So then we started doing smaller local meetups with local teams. And I think something that

**[20:08]** you mentioned that I think is really important for people to understand that this requires a lot of effort. You have to be intentional and it's something that you'll continually need to adapt and work on. And I don't know if people really have that realization. I agree. I mean, either they do in there and it's, you know, there's someone that makes a decision that says, you know what? That's too much, right? Like it's too much to handle. And I guess that, you know, it just really depends on if you feel that, you know, the ability to hire anywhere, right? How important is that to you, right? The ability to give

### 20:48 — Time as the most valuable asset; reciprocal care

**[20:48]** people flexibility back in their lives, right? Or the ability to give them time back, which I would argue is the most valuable asset in the world. And, you know, to be with their family, not miss certain moments, etc. How important is that to you as a business, right? You may just say it's not, right? And we don't care. And, you know, we haven't -- there's enough talent in, you know, Springfield that we're going to be able to meet our talent needs and we feel strongly that work is work and, you know, you're paid and so your time is our time and that's it, right? And if that's you, that's fine, right? That's okay. But

**[21:31]** if you do value those other things and if there is a way to do it and that way is getting increasingly easier and easier with the advent of modern tools. >> What are some good technologies you've seen? Because I think I've seen some like virtual office platforms. I've seen other, you know, very, very well built out presentation and meeting platforms that are specifically for like off-sites. Is there anything that you say, hey, I've seen this, it's worked really well and people trying to build a culture remotely should use this? >> I'm not too much an expert in like the virtual collaboration space. I mean, we have,

**[22:16]** you know, messaging and Zoom and, you know, pick your platform kind of thing. I think all that's great. I think most companies have adopted, you know, sort of those basic things. I haven't seen honestly too much novel there. I think, again, where we tend to focus is what tools can we use and deploy to help make orchestrating folks inside space or in coming together that much easier? That, you know, shifts the burden off of the employee, makes the administrative aspects of it, you know, very, very easy, if not fully autonomous, which is, you know, kind of quickly where we're getting to. You know, AI nowadays is

**[23:00]** good enough that it can read various signals from across the enterprise. It can understand team connections, people connections, what space requirements those teams and people may need, who should be with whom, when, right? And then understand also a level of collaboration dynamics that transcends the org chart to really infer like that proper grouping of folks on a day-to-day basis within space, and then actually do that. It can actually then allocate. And so that is sort of, I think, the next frontier of things in saying we can now adopt this autonomous model that's constantly monitoring data from around the enterprise

**[23:52]** in a way that humans could never have done in real time and continuously to optimize for right people in the right place at the right time on a day-to-day inconsistent basis. Is there anything in the data that has surprised you about what can increase productivity or satisfaction when considering how people are working in space? Surprising. I mean, I guess maybe a lot of times when we look at the starting point that companies have when it was a very, when, you know, there was variability due to some hybrid level choices available, and how inefficient humans are at self-organizing. That was a bit surprising, right? Because,

**[24:55]** you know, in the line of our work and we first, you know, kind of see, well, what's your starting point here? It's just hard, right? You know, it's just very, very hard, especially with large companies, right, and very complex workflows and team interactions. Trying to get that right, like when you tell a group of folks, like, hey, figure it out, right, and here's like some basic things you can use to, you know, signal to each other or indicate what, you know, what you're going to do and whatnot. Like, it doesn't get the needle very far. Going back to this again, I just think it's a much more complex problem than people appreciate,

**[25:39]** and I think the data that you have access to that you're seeing shows that as well, and I think there needs to be more investment in getting this right, because when you do get it right, I've worked in some very vibrant cultures before the pandemic, post pandemic, and you can tell the difference of when people are intentional about facilitating that culture, and like you said, not putting the onus on the employee to do it themselves or to figure it out amongst themselves, but intentionally creating those opportunities to collaborate and connect, it shows up in the results too. Productivity, satisfaction, retention, recruitment,

**[26:24]** it just really greases everything to make everything smoother. So what you just said, you know, it reminds me of when I was in my well-being employee experience days, like, we used to talk a lot about reciprocal care, and this loop, if you will, where if the company really demonstrated care for the employee, and that was felt and it was tangible, the employees will reciprocate that care back into the business, probably with dividends, right, and one of the most profound ways I think that employees can feel cared for is with respect to their time, right, and the type of life that you allow them to

**[27:06]** live, and that's where they'll fight, right, they will put themselves back into that job, they will fight for your business, they will go the extra mile, they will stay, they will work to keep that job even for lower compensation, statistically speaking, right, because that's how much they value these things, overwhelmingly. And so if you kind of get into that mindset of like, yeah, like, it's work, but that care is going to come back to us, and then some, that's where, you know, companies really get excited about, well, how do we figure it out? Yeah, and it's probably one of the most important problems for your company to solve. Agree, 100%. Yeah.

### 27:58 — Being an AI-first CRO: better, faster, cheaper

**[27:58]** We've talked a lot about how AI is being leveraged to make more intentional collaboration connection in space. I would love to hear as a CRO, how you're leveraging AI for your own go to market. Sure. So we're a really small team. We're really lean and scrappy, right? And unfortunately, you know, the team's gotten leaner over recent years. And the opportunity for us was to say, how can we offshore work that was really time consuming, that wasn't things that we could uniquely as humans do with respect to interacting with people in a sales pursuit or our customer relations, whatnot. How can we get more of that time back for ourselves? And that's where

**[28:57]** it started with us on our journey for, you know, adopting tools and really embedding them into our workflows. It's not like everyone here just has access to an LLM that they can use for, you know, whatever they want, although they can. But that wasn't the main thing. It was here's a process that we have as a business that sucks, right, that we hate doing, right? That is really problematic for whatever reason, right? Can we get AI to do this for us, right? Or can we use it to complete that process or task better, faster, cheaper, right? And we started to really adopt that mindset to basically everything that we do, right?

**[29:44]** And I still do it to this day whenever I find myself, catch myself going to do something, I ask myself, can I do this better, faster, cheaper through the use of, you know, our AI tools? Oftentimes the answer is yes, right? And if we prove that out, then we then say, all right, well, this is the way as a company that we're going to operate with respect to doing X, right? And so we had to really take a leap of and the upfront work of connecting these tools into our whole data ecosystem, right? Because it can only do certain things if you give it obviously the access to the requisite data and information it needs to

**[30:27]** perform that task. But once we had sort of the pipes connected and integrated with not only our data sources, but the tools that we, you know, used for different work functions like email, calendaring, et cetera, then we found that we could really increase the output of folks pretty dramatically or the time spent on non-revenue producing activities pretty dramatically by offshoring that work to AI. And even just over the last couple of months as models continuously get better and better and better, those outputs are just getting, you know, that much better. And so even the time that we used to have to spend saying,

**[31:12]** all right, the initial output from the AI model is going to be our V1 that's maybe 75, 80% of the way there. And now we're just going to spend the remaining time, you know, finishing that last 25% or so. Now, you know, the initial V1 outputs are coming out like 95% good, right? And that's just over the last few months. And so it's insane to think about where we'll be in, you know, just another few months or gosh, even a few years where you have to believe that there'll be just, you know, purpose-built agent armies like just ready to deploy and, you know, for different team functions and whatnot. And that seems to be where we're

**[31:54]** headed. And so we're trying to stay ahead of the curve and become the skilled operators of these kinds of agents and tools as we can and figure out how to maximize ourselves, especially knowing that, you know, we're trying to still grow revenue at no less of a rate, but with a good amount less resources. The last quarter, I'd say, is when AI felt interesting to completely profound and completely changing the way I personally approach work, the way LeanScale is a business approaches work. LeanScale, highly operationally intensive company. We're doing revenue operations for

### 32:44 — LeanScale's agent deployment; V1 to 95%

**[32:44]** VC-backed B2B startups. We have to move quickly. It's managing a multitude of systems and a wide breadth of services as well from marketing ops, sales ops, CS ops, and partnership ops. And what we've been able to do, and to be specific, we're leveraging everyone at LeanScale as a power user of cloud code. We've done a major deployment of OpenClaw. So every single person has their agents. We have purpose-built agents for our services as well. And we've been able to dramatically reduce the time it takes to deliver a project, deliver a service, and not just reduce time and make it more efficient, make it better. When you have access

**[33:30]** to a repo of the best knowledge in the world and then you have a meeting with someone, you feed it the transcript and it creates the project plan and pushes those to your PM server. That's not something that you can replicate in any other way. And like you were alluding to, we're just at the beginning. There's so much more that cloud code just released their own version of OpenClaw today as we record on March 24th, 2026. And every single week it feels like a whole new foundational addition and change here. I agree. And it takes effort to keep up with it all. It really does, but it's been a great

### 34:11 — AI as a self-coach: democratized training

**[34:11]** investment for myself and for our team for sure. I think this will only continue to be the case. I think one of the things though that maybe I'm not seeing too widely adopted potentially at this point, like everyone's using it for the basics of things, like particularly in a revenue organization, the next tier up from that or developing agent systems to solve for workflows or help basically autonomously support common workflows for reps or managers, et cetera. But using it for self-improvement and self-learning has been for me one of the things that I'm trying to lean into is sort of the next frontier, at least internally

**[35:03]** here where we don't have a huge sales enablement team. We don't have professional trainers coming in every couple of months or so. But with a little bit of effort, you can use these tools to self-analyze and self-critique in a completely safe, personalized environment and help improve your skillset in basically anything that you're doing or that's germane to the performance of your job. First, people need to be hungry for that input. They have to have a mindset of I want to get better at something. But hopefully you've solved that in the hiring process of figuring out who those folks are. But then to make it now

**[35:51]** this easy for folks to in the moment, even if their manager wasn't on a call with them or they're learning a new product, to get instant feedback or to think about how could I have fleshed out X better or asked this Y question better or something to that effect. How could I have said the explanation of that with 30% of the words? Any of those things is now instantly there for you. So it's beyond just executing on workflows or tasks, but to be thinking of it in terms of a training and improvement capacity I think is still an opportunity on the table for most. Can I share something? I think you'll find it interesting, probably funny. I have a agent

**[36:47]** purpose built to be my podcast coach. So every single episode is reviewed and I get a report card on quality of questions, cadence, talk time percentage, level of pushback and agreeability. And I think it's helped. It gave me suggestions that I would have never even thought about and there aren't a lot of podcast coaches on the market that I could have hired to help me do this. So a lot of that specialized training that also has the context of exactly what you're trying to do. It's not just generally speaking, I wholeheartedly agree. That's now become massively available to anyone. And I think whoever takes advantage of it is going

**[37:31]** to be an absolute weapon in the workforce. A hundred percent. The democratization of that type of training and coaching is massive and is not really being talked about much because in the old days you used to have to work for this big old company that had this really robust training program and you went away to sales school or had this formalized progression of training and whatnot, but that's gone, right? Now you can work for a two person company, a three person company, be completely young in your career and if you're willing to take advantage of these things, get just

**[38:16]** as good if not better of a training and educational experience for now your particular job in your particular application and company, which I think is really cool. Yeah, the specificity of it is completely unmatched compared to what alternatives have been up to date. I'm also thinking about I have three young kids, six, four and one and I obviously have some like existential AI questions as I'm guiding them through their stages. I'm like, I don't know if anything I did is going to be relevant. I do think one of the skills that's going to be absolutely crucial is critical thinking and I do worry

### 39:10 — Critical thinking, the mental gym, and education

**[39:10]** that heavy use of AI if not used intentionally is starting to degrade cognitive ability and I really do think that we're going to be at a place where you may have to go to a mental gym to make sure your brain is able to function and critically think and then use these tools in the right way or do things in manual mode on purpose just to train yourself. I completely agree because I mean, listen, the risk is you just start leaning on the AI to do everything and you take for granted its ability to do so in the right correct manner and I guess you could say the same thing about any traditional education, right?

**[40:04]** You can't just take for granted what you're being taught or what was said or it was even read, right? Sometimes like you need to have a critical thinking layer to everything and be willing to challenge ideas but I agree with you very much. That's a skill set that needs to be maintained for sure but the question is, yeah, is like your kids, I think you're just a bit older, my daughter's three and a half and so 15 years from now, you know, I honestly can't imagine she'll go to college, not in the way we know it today. Like that doesn't seem like it'll be a thing at that point, right? Like there'll be probably education

**[40:54]** but it'll probably be so focused on a very specific set of skills to do a particular job or to, you know, execute a particular function, right? Rather than this generalized kind of concept of a four-year degree, right? That's one of the shifts at least that is in my mind but at a base level, it won't be teaching like everyone like a surface layer of all the things which has been our approach to education for the last 60, 70, 80 years but be much more, we need to give people like you're talking about Anthony, like basic human skill sets around critical thinking, adaptability, resilience, like logic and other, you know,

**[41:49]** foundational skill sets that are not topic or subject specific and then allow people to have that base to use tools and get, you know, very, you know, sort of, you know, a deep siloed kind of education in one particular area based on whatever they want or need to do at that time. On the college topic because I think that's a spicy one, I think there's always going to be some way to differentiate status. I don't know if college will look exactly how it is today but there will be something expensive you can send your kids to. You can be sure of that. That will exist. I don't know exactly what they'll be learning

**[42:41]** you're doing but that 100% will exist because, you know, we have to keep the strata in order here or else maybe chaos can soothe but maybe and I think we'll experience significant mental atrophy if we don't address it and start doing things. I'm finding it myself. I have a tough time writing an email sometimes and like when did I forget how to write emails when I've been leaning on my AI agents to do everything for me and now I can't write a simple two sentence response like that's when I've had some of those moments it's making me think I've grown up doing this every single day and now I'm starting to have a tough time

**[43:26]** doing things in manual mode. How's a kid going to be able to handle that? Agree. I mean the other if we really I mean this is I mean this alone could have been an hour. Right. But if you have to then start to unpack and say all right but like do we really care that a kid can't write like they should have the ability to write and express their ideas through written language. Right. For sure. But like the things that we may lose I think are you know it's worth questioning are they really worth keeping like or should we be prioritizing their ability to do other things like or spend their time in a fundamentally different way. Right. If

**[44:11]** you know there's a lot of suggestion on well people may not need to work at some point. OK. Or at least you know a large swath of people may not need to work and you could work if you want to. But you may not need to. The answer to which of course is the only one answer I can think of is UBI universal basic income. And so in that in that world like let's say that that came to be then it's a question of well what should how should people be spending their time. What should they be doing. Right. That's satisfying. That's worthwhile. That gives them a sense of purpose and fulfillment. But you know if they can't

**[44:52]** send an email you know if they're not great at writing emails in that environment in that world. Do we care. I'm hoping it evolves into higher order activities and doesn't degrade into I just can't even do anything or think about things. But time will tell time will tell. I know it's it's it's a it's a tough topic a lot of people are wrestling with and I just think we're starting to get some interesting signals. But like there's that side and then there's also AI hasn't reduced work. People who are leveraging more are working even more. So once you realize there's tasks that you couldn't do before and now they're possible

### 45:37 — AI hasn't reduced work; achievement and the Harvard study

**[45:37]** now just more work gets put on your plate. So there's just some interesting things that are happening that I don't know if we were expecting as a society. Yeah that's that's an interesting one. I mean like my working hours certainly aren't less right. The amount that I'm able to accomplish and my output is certainly much higher. But I'm not working any less. But then again like I think you're going to have you know there's always going to be some types of folks that are just very driven to accomplish accomplish accomplish right to get stuff done. And you give them these kinds of tools that enable that and

**[46:18]** they keep getting that satisfaction of that beat that output. And you know Harvard did a big study many years ago on what makes people happy. The dominant the punchline of the study was it was achievement right. And it doesn't have to be big achievement can be micro achievements like even throughout the course of a day right. And so you give you play into that by AI being able to allow people to achieve slash produce things. People kind of will feed on that right. They're going to want to run right. They're going to run run with that and that's great right. But you know that that probably means that you know they do work more right or someone

**[47:01]** who is managing that kind of person and be like great like to handle do this too right. Keep going. If I can find a couple more of you to be 10 x productive you know more the merrier. Well I think I think one common thread that is going to be important for people who come out on top in this new era is just having that level of grit adaptability agility when the entire world is changing and the playbook you had before doesn't work anymore. There are people that can adapt to that well and then people who fall behind. And I think you have one of the most interesting experiences that sounds unbelievably challenging of starting

### 47:48 — Grit through crisis: the 2008 story and SVB

**[47:48]** a wealth management company right during the oh eight financial crisis. And I'll share with you my dad did work for Lehman Brothers. My mom was a she created a company doing loan officer recruitment for for banks. So I was coming up through high school right at the center of experiencing everything that was going on. And but you made it and you made it through. And I'm curious what was it that helped you adapt during that time and bring you to the new era. So yeah I mean my timing was impeccable. I had a few years. You know I graduated college and I didn't want to go start taking a I didn't want to go right into

**[48:41]** like a corporate type job. I wanted to see if I could do something for myself. So I started I started with this firm and started building out a team and then a practice and you know just managing money for folks. And we were cruising along building building. And then oh eight oh eight hit. And you know that was a job where you know it was it was my business it was an entrepreneurial. There was no there was no salary or anything like that. You know you either made money or you didn't. And so when that hit and I lost half of my business and the span of a couple of months basically it was pretty it was bad. And that just persisted

**[49:23]** for a bit. But it tell you you know that's the character building kind of pain right that helps you figure out that you know. I'm not going to give up on this. There's people that are depending on me and we're going to keep fighting and we're going to hang on and sort of you know build back again. And we did. And you know the years post oh wait we're some of our best ever. And you know for the folks that hung on we were able to shepherd them through that you know quite well. But that was like probably the first real big test for me in business. And in particularly you know that that experience and others and

**[50:09]** you know having to you know survive for yourself and just figure it out and persevere and in the face of tremendous adversity was something that I was able to carry forward through my startup experiences which are debatable whether they're more or less painful than the OA crisis. But you know the lessons were applicable because there's a lot of times and especially in early stage stuff where it's hard. It's just really really hard. It's a knife fight. You're going to feel like quitting and giving up from time to time and you just have to keep making the choice to keep going and keep fighting for it. And then figuring out ways to win as the

**[50:48]** circumstances change around you and the hand that you have to play even internally you know is constantly changing. And so that's where that adapt you know adaptability and resilience or in my opinion two most important characteristics for any business person. And so especially in startup stuff. Yeah my beginning wasn't as dramatic as the OA crisis but 2021 I started the back half of 21 and you know off the highest high of tech possible and then right into tech winter as I also banked with SVB and our entire payroll and capital got locked up there. So yeah I think expect the challenges take them as character building opportunities

**[51:39]** and just keep your eyes and ears open and be adaptable because I think it's going to happen whatever it is. There's going to be these peaks and valleys and when you're in there I think just hanging in and enduring has been the only thing that is for me. Just grit your teeth and keep going. That's right. That's all you can do. Just keep making the best decisions you possibly can. Work hard and yeah just don't give up. That's it. Never give up. And I think we're in places where like you mentioned we have a lot of people depending on us and giving up really isn't an option. Tom this was really really incredible.

### 52:21 — Closing: making work better

**[52:21]** Thank you so much for taking all of your experience that you've had and especially the mission of making work better, making it enjoyable. We're all spending so much time invested into our careers, our jobs, professional lives and that is worth pointing attention to and making it the best experience possible and from a business perspective when you do that as you mentioned there's plenty of data to show that it's going to show up in the results as well. You'll retain your employees. They'll be more productive and you'll show up better in the market and I love the stories that you shared about the grittiness of making

**[53:01]** it through it. I think if you can make it through that you could probably make it through anything and I'm just really excited to see what you do next. So thank you for being on the show and can't wait to keep up. Thank you so much Anthony. Very much enjoyed the conversation and love what you all are doing here at LeanScale and so all the best. Appreciate it.


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