Friday I hosted the monthly founding AE meetup. 20 sellers, from AI startups to healthcare to a company trying to crack enterprise grocery. I asked everyone the same opening question: what GTM challenge are you wrestling with right now?
Nobody said "nothing." Here's what they said instead.
1. "I'm the only AE. Where do I put my time?"
One seller took over from founder-led sales. Only full-time AE. SMB, mid-market and enterprise all on his plate. His biggest challenge: coming up with a game plan for the day and sticking to it.
Another is setting up an outbound stack of connected AI tools. In theory it runs itself. In practice it's taking weeks to configure. Meanwhile she's asking the real question: boil the ocean, or pick a small slice of the territory and go deep?
If that's you, you're not disorganized. You're the first person to ever do this job at your company. There's no playbook because you're writing it.
2. "Every AI company sounds the same."
Breaking through on outbound came up again and again. When a hundred companies claim to do what you do, prospects can't tell you apart. Cold email is close to dead. Cold calls are dying.
What's working on the call:
Voice notes after a LinkedIn connection. One AE got one himself, thought it was brilliant, and started sending them. "Hey, thanks for connecting," then the next step. Same message he'd type, just less robotic. He says the response rate has been high.
Saved voice snippets. Another AE records the value prop once in his LinkedIn tool and only re-records the first five seconds with the person's name. Personal at the front, efficient at the back.
Strategic, not mass. A seller who spent four years at LinkedIn warned the room: blast connection requests and you'll get locked. Use it like a scalpel.
Paying for intent, charitably. One AE uses a service that donates $1,000 to the prospect's charity of choice, but only if they actually take the meeting. Expensive. About one a week. Every one so far has been a real decision maker at the right company.
3. "My book just got cut in half."
This one hurt to hear. A founding AE spent three years building the accounts. The company hired a second rep. He's done ramping. Now the accounts get split and new leads get round-robined.
That's success at the company level. It feels like a pay cut at the individual level.
My advice: this is the founding AE pattern, so plan for it instead of resenting it. Negotiate. Keep one meaningful account for a finite period, say through the end of the quarter. Stay in the transition. Get paid on the deals you built. The founder wants a smooth handover more than you think. Trade it for something.
4. "How do I price this so it's repeatable?"
One seller has great product-market fit and no pricing logic. Deal sizes are all over the map, and ROI is hard to measure.
Two pieces of advice from the room. First, look at competitors and decide: premium or market share. Don't drift between them. Second, from me: his product charged per prompt. That punishes the customer for getting better. Price for owning a category instead. Here's the cost to own TV. Want cell phones? Here's the cost to expand. Now growth is aligned with success, not usage anxiety.
5. "Everyone agrees there's a problem. Nobody's buying."
Two sellers had the same wall: shortening the cycle and creating urgency. One sells into hospitals facing new federal accountability for readmissions. Everyone's impacted. Nobody owns it.
Here's what I told her. A problem without an owner isn't a problem. It's a mild inconvenience. Ask three questions: How is this rule impacting your business? When does it have to be fixed? Who's accountable if it isn't? If your contact can't answer the first one, they won't be your champion.
You're not the only one.
That's the point of writing this. Founding AE is a lonely seat. No team. No manager who's done it before. A founder who's learning sales from you. Every problem above feels personal until you hear four other people describe the same one.
That's what the founding AE meetup is for. Monthly call. Free. No pitches, no recruiters working the room. Sellers comparing notes on what's actually working, and getting pushed on what isn't.
Join the next one on November 13 3pm EST. Reply to this email or reach me through daverubinstein.com and I'll send the invite. Bring the problem you're stuck on. Someone in the room has already been there.