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 a Rails 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. An eval confirms the harness follows the workflows and conventions.
• 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.

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 cohorts myself to building the instructor bench, the curriculum, and the platform that let 13 campuses and an online program teach the same way.

Taught

• Taught full time for two years and led more than eight cohorts in Ruby, Rails, JavaScript, TDD, and Git, then codified what worked into the curriculum and the tools that became Learn.co. Wrote the curriculum every campus taught for eight years.
• Taught and led the first year of the online program, with remote lectures and mentoring for 1,000+ students, then wrote the online teaching guide and trained the mentor bench that took it over.

Built the instruction function

• Hired, onboarded, and developed more than 30 instructors across 13 campuses on a gated path from student to TA to instructor to lead: shadow, co-teach, dry-run, solo cohort. I made the readiness call.
• Set the quality bar in a written teaching guide and rubric. Instructors could change how they taught but not what; improvements that worked became canonical, and instructors who drifted from the curriculum or culture were moved out.
• Measured instruction through Learn.co’s instructor backend: curriculum deployments, lab time to complete, graduation and time to placement, and instructor NPS, with at-risk alerts, weekly check-ins, and end-of-cohort reviews. Outlier labs got rewritten; struggling students got outreach before they asked.
• Turned expert knowledge into instruction with the data science team and outside consultants, and owned instruction quality in programs others ran: Amazon’s employee reskilling program, corporate courses, and 2U’s partner programs after 2U licensed Learn.co.
• Led a 60-person product and engineering organization; helped scale Flatiron to 600 employees, 10,000+ alumni, and $60M revenue through its $30M acquisition by WeWork.

In person: 90% graduation and 95% job placement. Online on Learn.co: 70%+ completion and 90% job placement, against single-digit completion for typical online courses. In 2018, 2U entered a $14.5M agreement for a perpetual Learn.co source-code license and integration services.