This Week In GTM - Episode 2 (ft. Brendan Short of The Signal)

Kudos to Lenny for bringing on Jeanne DeWitt Grosser, who's had one of the best sales careers in tech - Google, then founding sales leader at Stripe, and now CBO at Vercel. It’s clear she is a cerebral seller.

I really loved this episode. A few things stood out.

First, she mentioned a single GTM engineer at Vercel reduced a 10-person SDR team to 1 in six weeks using AI. Pretty wild.

However, context matters when people are discussing AI-driven human replacement.

Brendan points out that what he’s seen, this works when you're selling $5-20K ACV, not $500K enterprise deals.

You're not sending AI-generated emails to your 30 target accounts in the enterprise. You're still taking them to steak dinners and golf courses, or hopping on Zoom calls with them, because they want to talk to a human to make large buying decisions.

Second, she echoed the "wait until $1M to hire your first salesperson" advice. We mostly agree, but see our take on when to make that first hire below.

Third, her take on hiring non-salesy salespeople is gold. Stripe wanted sellers to be indistinguishable from PMs in the first 10 minutes. Similar to what Cailen said Dropbox did when they built out GTM.

The proxy I’ve used before: have they sold to developers or product managers? If yes, they've probably trained the "salesy" out of themselves.

I had a more detailed LinkedIn post on this here.

This came up during our chat about Jeanne's take on waiting until $1M before hiring your first rep.

Cailen's updated number: $1.5M - and he keeps revising it upward every six months because founders keep impressing him with their efficiency at VibeScaling.

We're seeing companies hit $3-5M ARR, even $6M, 100% founder-led before hiring a single rep.

One note: it's less about the revenue number and more about repeatability.

Can you demonstrate that you've acquired 100-200 customers using the same playbook? Is it codified and templatized? If you're closing deals in your sleep and spending only 20% of your time on sales, that's when you know it's time to bring in a full-timer.

The key insight from Jeanne (with which we strongly agree): never outsource your sales until it feels repetitive.

I really like this piece from First Round Capital that does a deep dive into when, who, and how to make your first GTM hire. Which, coincidentally, mentions the tactics from Stripe and Dropbox (along with Figma).

Chris Pisarski (CEO @ Crustdata, YC W24) dropped his go-to-market playbook for early-stage founders:

Our thoughts:

LinkedIn-first is the move. Connect with your ICPs, max them out weekly, and then DM 50 people a day to ask for feedback. It's a brute-force approach that works.

Brendan shared an anecdote: when he was running Groundswell, he stopped doing outbound entirely and doubled down on LinkedIn content.

Result?

The VP of RevOps at Notion, VP of Sales at Slack - all inbound from content. He was competing against companies with $50M raised. The only reason he was in those conversations was content and building trust at scale.

One other low-hanging fruit - network-led growth.

Your investors, advisors, angels - milk those intros. The best companies are ruthlessly asking for those to get their foot in the door to build a pipeline in the early days.

In the AI slop era, attention is scarce. Own your audience; create distribution, then create whatever you want.

Gene Lee, co-founder of Ramp, announced that Ramp is shutting down its OAT (Outbound Automation Team).

For context, Austin (Unify co-founder) was one of the original architects of OAT at Ramp. He helped build the POC internally, realized every company could benefit from it, and spun out to commercialize it.

Unify is now absolutely ripping.

So what's Ramp actually doing? Brendan asked Gene directly in the thread. The answer: they're generalizing the benefits of OAT beyond just SDRs to all of sales — AEs, CSMs, RevOps. Instead of a blanket team supporting everyone, they're embedding GTM engineering across every function.

This tracks with what we're seeing: prospecting is the natural starting point for GTM engineering, but eventually you want AI proliferating into expansion, churn prevention, call grading, deck generation, and more.

The other insight worth calling out: buyers are getting cold outbound fatigue.

The common signals are commoditized. Everyone's running the same plays. The bar for what cuts through keeps rising.

Another confirmation of our #3 post above, that LinkedIn > cold email right now.