Scott Sinatra is the Chief Revenue Officer of Wisq, the company building what it calls the world's first AI HR generalist — founded by the team behind Glint (acquired by LinkedIn) — whose product, Harper, deflects 40–80% of routine HR inquiries. A career enterprise-software go-to-market leader, Scott was on the original team that developed MEDDPICC, one of the most widely used B2B sales-qualification methodologies, and previously sold an HR product at Glint before the AI era reshaped how these solutions get bought. His thesis: the more chaotic the AI market gets, the more foundational sales discipline — qualification, multi-threading, and influencing decision criteria — decides who wins, and go-to-market leaders should hire RevOps and enablement before the first AE.
“AI is a bit of the Wild West as it pertains to marketing and adoption. I truly empathize with the buyer of AI solutions today, because the rate of change is happening so fast.”
“We were one of two native AI companies in the audience. The other 98 or so were all SaaS companies that were layering AI on top of old architecture.”
“Proof points and proof in the customer's environment are more important today than ever before.”
“Nobody has this nailed. There is no standard. Every company is figuring it out now on the fly.”
“The outcomes need to be clear and definitive. There can be zero ambiguity. Otherwise you're going to get into a conversation at the end of a billing period that you don't want to be getting into.”
“We've sold HR, HR goes to get the deal done, and IT has blocked the deal at the end of the process because they weren't included in the process itself.”
“We're not replacing them. We're aiding them to be the best version of themselves as an HR practitioner doing the best work of their lives.”
“These POCs being implemented now tend to not convert to full enterprise deals because of risk, compliance, and governance.”