The Elephant in the Room: A Candid Conversation about Enterprise GTM

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
• Logan Currie, Director of Residency Programs, The Open Accelerator
• Kristen Craft, Head of Partnerships, Fidelity Private Shares
• 10-10:30 Networking & Departures

Fidelity Private Shares

Fidelity Private Shares is committed to supporting the startup & venture capital community. Fidelity helps founders prepare for their next round of funding with our cap table management and data room platform, events that give you access to seed stage capital, equity scenario modeling, and premier support to generate, execute & store legal documents.  No matter where you are in your journey - from inception to IPO - Fidelity has the expertise to support you.

The Open Accelerator

The Open Accelerator, led by Red Hat with IBM Ventures and the Massachusetts AI Hub, is where startup innovation meets enterprise experience. We help early-stage AI startups building for business become enterprise-ready faster through two complementary pillars: Community and Residency. Our Community brings together founders, investors, enterprise leaders, technical experts, and ecosystem partners to share knowledge, build connections, and advance AI innovation across Massachusetts. Our curated 16-week Residency gives selected B2B AI startups hands-on access to the expertise, experience, and networks of Red Hat and IBM, drawing on decades of building, selling, and deploying technology in some of the world’s largest enterprises.