AI Bootcamp for Entrepreneurs: AI-Powered Go-to-Market
AI Bootcamp for Entrepreneurs: AI-Powered Go-to-Market is a five-week bootcamp that teaches students how to build an AI-assisted go-to-market engine for an early-stage venture. The program works down the funnel, from defining who your buyer is to preparing for the conversations that close a deal.
Across five sessions, participants will use AI to research a market and build an ideal client profile, draft personalized outbound outreach, build an inbound play that attracts the right leads, research and advance individual leads, and prepare for sales conversations. Sessions also cover where AI-generated work tends to fall short and how to keep human judgment in any decision involving a real person.
While this bootcamp includes some lecture components, it is highly interactive and hands-on. Participants may work on their own venture at any stage, including idea stage, or on an example venture provided by the instructor. Although many AI tools support go-to-market workflows, this workshop will focus on getting the most out of Claude Enterprise, as made available by the University of Chicago. No prior sales experience or technical background is required.
Who should attend
This bootcamp is designed for students who want practical, immediately usable go-to-market skills:
- Founders and aspiring founders who need a pipeline but don’t yet have (or can’t yet afford) a sales team
- Students headed into GTM, sales, or growth roles at startups, where AI-assisted funnel work is quickly becoming table stakes
- Corporate innovators and product leads who want to validate demand for new offerings with founder-style speed
No prior sales experience or technical background is required. Participants are encouraged to bring their own venture or idea; those without one will work on a fully developed fictional venture supplied by the instructor.
Bootcamp facilitator
The bootcamp is facilitated by Phil Leslie, MBA ’09, an entrepreneur, investor, and ecosystem builder with a career spanning startups, venture capital, and corporate innovation. Leslie founded and scaled ProOnGo Expense (acquired) and later led RIVS/interviewstream to consecutive Inc. 5000 rankings and a successful growth equity exit.
As managing partner at Workbox Ventures and managing director at TechNexus, he backed and advised dozens of high-growth startups across SaaS, future of work, and emerging technologies. He recently led two AI-focused Entrepreneurship Essentials workshop sessions at the Polsky Center. His teaching blends founder grit with investor discipline, equipping students to build, test, and iterate in the real world.