Jeanne Grosser

AI agents can automate complex sales workflows by encoding human research and outreach patterns into code.

"My go-to-market engineer is helping me build an agent where we're coming up with, okay, well what's the human workflow that you would've done? And then how do you encode that using Vercel workflows as..."

LLMs can identify the true reasons for deal losses by analyzing cross-channel communication data more objectively than humans.

"We take all of our Gong transcripts and we dump them into an agent called the deal-bott... the biggest loss that quarter according to the account executive was lost on price. When you ran the agent ov..."

For AI agents, building internally is often better than buying because internal context and specific workflows are the primary value drivers.

"I think the calculus on build versus buy is changing... because this whole space is so nascent, often your own esoteric context, your content, your workflow is really key to unlocking the power of the..."

Product-led growth is effective for early scale but eventually requires a sales layer to capture large enterprise deals.

"PLG makes sense for a lot of companies at the outset... The thing that folks get wrong is it does typically have a ceiling. So people are generally not going to give you $1 million via self-serve flow..."

Aligning pricing tiers with actual buyer behavior (e.g., moving enterprise features to self-serve for startups) can unlock significant growth.

"At Vercel... we did a pretty substantial pricing change in August where we have an enterprise at a pro-skew... about half of the folks on the enterprise skew were startups... So we kicked a lot of tha..."

Sales should function as an R&D arm, providing high-fidelity customer signals to the product team.

"I also believe that the best go-to-market orgs on the planet are equal parts revenue driving and R&D... if we can do an excellent job of translating all of that feedback into signal and then feeding t..."

Enterprise buyers are primarily motivated by risk mitigation and pain avoidance rather than visionary upside.

"80% of customers buy to avoid pain or reduce risk as opposed to increased upside, which is a good thing for startup founders to understand. We all love to talk about the art of the possible, everythin..."

When technical differentiation is narrow, the sales experience itself becomes the primary differentiator.

"The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the margin. And so then you really want to..."

AI has increased market saturation, making competitive differentiation a critical strategic priority.

"With AI, it's just intensified because you have 10 players pursuing the same market opportunity and so your ability to actually bring the product to market to differentiate yourself from the competiti..."

Founders should lead sales until they reach roughly $1M ARR and have a documented, repeatable ICP.

"Wait until you're around a million in ARR. When you have a repeatable process... as a founder you want to stay deeply connected to customers and get it to a scale and get it to a point where you use t..."

Effective sales discovery is about deep listening and probing rather than immediate problem-solving.

"Excellent salespeople typically will talk well under half the time in a conversation because they're out asking questions, probing often helping a customer arrive at conclusions on their own. And so l..."

High-performing sales teams in technical companies must possess deep product knowledge and a PM-like mindset.

"The litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you a..."

The sales organization is divided between pipeline generation (SDRs) and deal closing (AEs).

"SDR is typically in charge of generating pipeline... account executives are closers. It's their job to take somebody from, 'Okay, hey, I'm interested in learning about your solution, I have a legitima..."

A diverse sales team mixing traditional AEs with former consultants/bankers creates a more analytical and consultative culture.

"I strongly believe that sales is a skill and so you want salespeople with actual sales experience in your organization, but I think there's value in pairing them with more nontraditional backgrounds,..."

Modern enterprise sales requires deeply embedded technical consultation to help customers implement complex technology.

"Forward-deployed engineering, which on some level is kind of a rebrand of professional services but kind of not. And a big part of that is, hey, how do I actually get into your environment, ride along..."

Interactive whiteboarding sessions provide more value to the customer than standard discovery calls.

"What we started to do at Stripe was that first session was a whiteboarding session, and we would actually get together and have you draw your architecture for payments and all the other things that we..."