Technical education at scale through teaching&product.
I’m a programmer who founded Flatiron School and taught its first cohorts myself. As the school grew to 13 campuses, my job became turning what worked in my classroom into curriculum, instructor development, standards, and software so other instructors could deliver the same experience. Today I build with AI every day, and I keep doing the same work: turning what works into training, tools, and teams that scale.
im@avi.nyc · New York · github.com/aviflombaum · resume.avi.nyc
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.
Revature
Oct 2020–Aug 2023
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.
Flatiron School
Jun 2012–May 2020
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 the first two years and led more than eight cohorts in Ruby, Rails, JavaScript, test-driven development, and Git. Used the classroom to work out what was effective, then codified it into the curriculum and the internal tools that became Learn.co.
Wrote the curriculum every campus taught and kept writing it for eight years: concepts tied to executable, test-driven labs, real developer tools, and increasingly independent project work. Kept guest lecturing after leaving the classroom.
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, a mix of alumni and outside hires, on a gated path from student to TA to instructor to lead. I made the call on who was ready to run a cohort.
Set the quality bar in a written teaching guide and rubric. Onboarding was staged and gated: shadow, co-teach, dry-run, solo cohort. Instructors could change how they taught but not what; improvements that worked became canonical in the next release, and instructors who drifted from the curriculum or the culture were moved out.
Measured instruction continuously through Learn.co’s instructor backend: curriculum deployments per cohort, lab efficacy by time to complete, cohort graduation and time to placement, and instructor NPS, with alerts on at-risk signals, weekly check-ins, and end-of-cohort reviews.
Used that signal to improve lessons and teaching. An outlier time to complete on a lab meant finding which tests students got stuck on and rewriting or re-sequencing. The same data separated a weak lab from a struggling student, so we could reach out before they asked.
Turned expert knowledge into instruction: worked with the data science team and outside consultants to define requirements and curriculum for new disciplines, and folded engineers’ guest lectures into the curriculum as stretch challenges.
Owned instruction quality in programs others ran: Amazon’s employee program moving non-technical staff into technical roles, on-demand corporate courses, and 2U’s partner programs such as UC Berkeley after 2U licensed Learn.co as LearnOS.
Led a 60-person product and engineering organization across six squads with daily deployments. Helped scale Flatiron to 600 employees, 10,000+ alumni, and $60M in annual 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.
Program design, curriculum & train-the-trainer guide
Conceived of and designed the program and curriculum with Karlie Kloss. Wrote the teaching guide that let instructors who were not expert engineers run the program well: short explanations followed by exercises, questions rather than taking over, and small, achievable projects.
The program has run every summer since 2015 with a new cohort of instructors each year. The guide is what makes that repeatable.
NYC on Rails
Founder · Founded 2007
Built a community around Ruby on Rails through technical talks, events, and shared work. Where I first learned to explain code to a room.
Designer Pages
Co-founder · 2008–2012
Built a search and specification platform for architects and designers, indexing more than one million products. Patented the ad-matching approach.
03 / Selected work and teaching
The teaching is the portfolio.
Talks, guides, and a case study, all of them public.
From the KWK teaching guide A rule for helping without taking over.
The problem I have kept returning to is how you transfer technical capability from a small number of experts to a much larger population without lowering the bar. At Flatiron the question stopped being whether I could teach a thing and became whether someone in another classroom, on another campus, with another instructor, would get an equally good experience.
The answer was never a script. It was a small set of beliefs that changed what an instructor did next: give people a reason to care before the mechanics, keep the keyboard in the learner’s hands, keep the challenge but remove the needless friction, and make the philosophy observable so feedback can improve the lesson. I build software and teams the same way.