Founder Breakfast - The Elephant in the Room: A Candid Conversation about Enterprise GTM
Hosted by The Open Accelerator
Wednesday, October 28, 2026
9:00 AM–10:30 AM ET
About
Most conversations about selling AI to the enterprise stop at the pilot. The harder part comes after, and founders mostly talk about it in private. That’s the elephant and we want to put it on stage.
Landing a pilot is one thing. Getting the CIO, CISO, legal, compliance and procurement to sign off on a paid contract is another. Then the contract’s signed, and a lean team has to deliver for a customer that dwarfs it.
Join Fidelity Private Shares and The Open Accelerator for a founders’ breakfast with early-stage AI founders who are tackling these challenges right now. Hear firsthand what’s working, what’s not, and lessons learned along the way:
- Build vs. buy: Why would an enterprise buy from a startup if it can build in-house?
- Beyond founder-led sales: When does it stop working and what comes next?
- Delivering at enterprise scale: How does a small team support a huge customer after the deal closes?
You’ll also meet Boston’s B2B AI founders and hear how they’re using local accelerators and the wider ecosystem to move faster.
Building B2B AI? This one’s for you.
Space is limited and founders get priority.
Agenda
9-9:30 Arrivals & Networking
9:30-10 Panel
- Richard Shaaya, Founder & CEO, Sigma Automate
- Nyari Nain, Cofounder, Whiteroom AI
- Stefanie Chiras, PhD, SVP, The Open Accelerator
- Kristen Craft, Head of Partnerships, Fidelity Private Shares
10-10:30 Networking & Departures
Host
The Open Accelerator