Avi Flombaum

Chief Technology & Product Officer / Entrepreneur-in-Residence

Building AI products inside a small team of founders, operators, and investors.

• Built and launched VCMatch, connecting pitch-deck analysis, investor matching, fit explanations, and founder outreach in one workflow.
• Built PostMoney, turning unstructured company updates into organized portfolio reporting. The product is currently in private beta.
• Created PromptEngine, an open-source Rails engine for managing, versioning, and testing AI prompts without hardcoding them into the application.
• Build with Ruby on Rails and AI-assisted workflows, staying hands-on with prototypes, interface decisions, implementation, and testing.
• Advise four portfolio companies and lead Innovent’s CTO Huddle, alongside hands-on product design and development.

VCMatch’s first six months: 600+ startups matched and $10K in revenue. Milestone reported June 2026.

Chief Technology & Product Officer

Software and learning systems for technical training and staffing.

• Developed RevUP and eXa with the team, connecting candidate preparation, technical training, and progress tracking.
• Introduced Ruby on Rails to reduce sprint time by 50%, and reworked AWS infrastructure to reduce cloud costs by 30%.
• Built a training-event tracking system that connected data across tools so marketing and training teams could act on it. Led a remote product and engineering team of 50.

Founder / Chief Technology & Product Officer

From personally teaching the early cohorts to building the school’s learning platform and product organization.

• Authored Ruby, Rails, JavaScript, and test-driven curriculum. Connected concepts to practical labs, real developer tools, and increasingly independent project work.
• Shaped the learning formats, teacher development, and classroom culture: peer support, public work, constructive feedback, and learning through building.
• Built Learn.co with the product and engineering team, bringing GitHub-backed curriculum, a coding CLI, automated tests, and student progress into one learning experience.
• Led a 60-person product and engineering organization across six squads, with daily deployments supporting the school’s in-person and online programs.
• Helped scale Flatiron to 13 campuses, 10,000 alumni, and $60M in annual revenue.

In 2018, 2U entered a $14.5M agreement for a perpetual Learn.co source-code license and integration services.