15-Minute First 90 Days Check-In
A check-in on how the first 90 are actually going.
The plan you came in with usually doesn’t survive month one. The founder is figuring it out alongside you. You’re translating instinct into process and you’re not sure what to push back on. I’ve been in the seat. I see this stretch play out every week across 250+ founder conversations.
What we cover
01
What’s actually working in your pipeline. Which deals are real. Which conversations are noise. Where you should be spending time this week — and where you’re leaking energy.
02
Founder dynamics you didn’t sign up for. Most founders haven’t sold. Knowing when to push back, when to absorb, and what’s worth a fight. The stuff you can’t ask the founder about.
03
A read on whether you’re on track. Across 250+ founder conversations, I know what month one, two, and three actually look like when the motion is compounding — and when it’s spinning.
“Dave just gave me his straight read and coached me through it. If you’re a Founding AE and you’re not in this network, you’re navigating blind.”
Brennen AmannFounding Account Executive
“I’ve sold with Dave. If he calls, I pick up — and I send people his way.”
Jay CaneteFounding AE · First hire on Dave’s team at Outreach