RoundTable Strategy Advisors is a leading firm specializing in CFO and NetSuite services, providing innovative and strategic solutions to empower businesses in their financial management and operational efficiency. With a team of seasoned experts, The company’s CFO services go beyond traditional financial management, offering tailored strategies and insights to drive growth, manage risks, and achieve long-term financial success.
Free admission
Limited capacity
1 Speakers
Signature Cambridge
UGLY TALK: HOW TO ACTUALLY BUILD AT THE SPEED OF AI AND OUTSHIP A BIGGER TEAM
Event Ended Free Admission
Right now, AI is a sports car.
In the hands of a small team that knows what it is doing, the right AI stack outships companies 10 times their size. The advantage is no longer who has the bigger team. It is who can drive faster without losing control.
The same stack that lets you outpace a competitor 10 times your size can also send the company off the road. Bad data. Hallucinated decisions. Customer trust shredded by an agent doing what an experienced operator would have caught.
For this Ugly Talk, we are bringing in Greg Cucino. He has been inside enough AI bets at growth-stage companies to know what wins and what wrecks them. He will walk you through what it takes to drive the sports car, and the mistakes that put founders in a wall.
In the room
Inside the room.
The pitch
Why you should be in this room.
- Hear the actual practices founders are using to build fast on tiny teams.
- See where AI is already replacing the back office, and where it spins out in real companies.
- Walk away with a test for what to keep, what to automate, and what to never hire for again.
- Catch the specific mistakes that turn an AI advantage into a wreck before you make them.
- Meet Boston founders scaling without the headcount drag.
Audience
Who's getting in.
We’re bringing together idea-stage founders, pre-seed teams, and early operators who want to build the company right from the start.
This room is for people who care about product and know product alone will not save a company with bad systems behind it.
- Pre-seed to Series B founders building AI-native companies
- Operators running ops, finance, or product on small teams
- Founders deciding whether their next big check is a hire or a tool
- Boston-based builders and visiting founders in town for Tech Week
- Investors watching their portfolio companies bet on AI to scale
Speakers
Featured speakers.
Greg has watched AI rebuild company back offices at close range for 2 years. He has the receipts on what worked and what did not.
He was the CFO at CognitiveScale, backed by Microsoft Ventures and IBM Watson, until Tecnotree bought it. He did the same at Sensera before Abiomed. He then built RoundTable Strategy Advisors to #138 on the 2025 Inc. 5000, with 2,730% three-year growth.
He writes for Inc. Magazine and Entrepreneur on what AI is doing to operations and finance. In 2024, he hosted a fireside with Daron Acemoglu, the Nobel laureate in Economics, on AI and institutions.
Greg has run operational diligence on dozens of growth-stage companies betting on AI to scale. He has seen what actually works. He has also seen what breaks.
MIT Sloan MBA. Harvard Law. Harvard Kennedy.
Topics
What's on the table.
- The functions you should automate before you hire a single person for them.
- How to tell when AI is the real answer and when it is a stalling tactic.
- The mistakes founders make when they hand the back office to AI too fast.
- The hidden tax of headcount that founders only see at 25 people.
- How to design your stack today so it does not become an acquirer's red flag tomorrow.
Partners
Who's backing this.
InfinixIQ
InfinixIQ is an AI-powered ERP that connects finance, operations, supply chain, and CRM in one intelligent platform. Use it to replace your existing stack or layer it on top of the tools you already use. Built for companies that need their systems to move as fast as they do.
RoundTable Strategy Advisors
Startup Boston
Startup Boston is the front door to the Greater Boston and New England startup ecosystem. We make it easier for founders, startup operators, investors, and startup-curious individuals to find opportunities, build meaningful connections, and navigate the resources already available across the community.
GREY Journal
GREY Journal – Media partner spotlighting modern entrepreneurs (featured on Apple News + Google News).
CIC Massachusetts
CIC is the global leader in driving innovation at scale. Founded in 1999, CIC manages more than 1.5M square feet of workspace, laboratories, and event space across North America, Europe, and Asia. Additionally, CIC develops bespoke programming, builds and enables industry clusters, and provides world-class district consulting—all focused on advancing innovation.
Venue