Avi Flombaum

Chief Technology & Product Officer / Entrepreneur-in-Residence

Hands-on AI product development inside a small team of founders, operators, and investors.

• Build with Claude Code and the Claude API daily: agents, tool use, structured outputs, prompt versioning, and evals, shipped in production Rails applications.
• Built Blastoff Rails, an application generator with an AI development harness of versioned instructions, skills, conventions, hooks, and scripts. The model writes the code and the harness defines the process.
• Taught non-engineers on the team to ship product and code through that harness, with review and guardrails that kept quality high. A small field-readiness program in practice.
• Built and launched VCMatch, using embeddings over investor portfolios and theses to match founders with relevant investors and explain the fit.
• Built PostMoney, which extracts KPIs from founder updates, emails, and PDFs into portfolio reporting. Currently in private beta.
• Created PromptEngine, an open-source Rails engine that manages prompts as data with versioning, rollback, and a testing playground for OpenAI and Anthropic models.
• Advise four portfolio companies on technical direction and lead Innovent’s CTO Huddle.

Socratic Tutor: an LLM tutor that asks instead of answers, watches for frustration in student responses, and adjusts scaffolding. Ten years of teaching, encoded in prompts.

Chief Technology & Product Officer

Technical training at scale: thousands of trainees a year moving through instructor-led programs into engineering roles.

• Built eXa, a learning platform for instructor-led technical training, and RevUP, a free preparation course, connecting candidate preparation, live instruction, and progress tracking.
• Built a training-event tracking system that connected data across tools so training and marketing teams could see what was working and act on it.
• Led a remote product and engineering team of 50. Introduced Ruby on Rails to cut sprint time by 50% and reworked AWS infrastructure to cut cloud costs by 30%.
• Helped scale the company from $60M to more than $260M in annual revenue.

Founder / Chief Technology & Product Officer

From teaching the first class of 20 students myself to building the instructor bench, the curriculum, and the platform that let 13 campuses teach the same way.

Taught

• Taught the first cohorts in person and full time: Ruby, Rails, JavaScript, test-driven development, and Git, in labs of 20 and lectures of 100+.
• Authored the curriculum and labs that ran across every campus. Concepts connected to executable, test-driven labs, real developer tools, and increasingly independent project work.

Scaled teaching

• Built and developed the instructor bench as Flatiron grew from one classroom to 13 campuses: hiring, teaching dry-runs, classroom observation, feedback, and the call on who was ready to lead a cohort.
• Started Learn.co from a faculty meeting about curriculum consistency across cohorts. The answer was to put the curriculum in GitHub, make every lab test-driven, and give every instructor the same material and the same signal.
• Built Learn.co into a social learning platform: GitHub-backed curriculum, a coding CLI, a browser IDE, live community and TA help, and instructor dashboards. Test results and webhooks gave per-student, per-lesson signal that surfaced struggling students and weak lessons alike.
• Set the teaching culture and formats: peer support, public work, constructive feedback, and learning through building. Ran teacher-efficacy surveys so students could tell us how instruction was landing.
• Led a 60-person product and engineering organization across six squads, with daily deployments supporting in-person and online programs. Helped scale Flatiron to 600 employees, 10,000+ alumni, and $60M in annual revenue through its $30M acquisition by WeWork.

Learn.co held a 70%+ completion rate online, against single digits for typical online courses. In 2018, 2U entered a $14.5M agreement for a perpetual Learn.co source-code license and integration services.