Andrew Olshevski

About

I'm an education-focused product leader with 10+ years experience building technology and experiences that help people learn better.

I've done a bit of everything, but specialize in assessment technology, learner retention, and active & experiential learning.

I started my career as an English/French instructor, and that teaching foundation still drives how I build – start with the outcomes to achieve by the end, ground it in the reality of learners' lived experience, and apply technology to amplify what works.

I live in Brooklyn with my wife & son. My favorite type of birthday party is karaoke and I never miss an Eagles game (go birds).

Professional Experience

Presently, I work as a product consultant for DriveX Labs, helping emerging edtech startups grow user retention, outcomes, and LTV.

Previously, I worked on learner experience at Emeritus for 3 years (2022 - 2025). I reduced bootcamp dropout rates by 50% and introduced AI-powered assessments that increased learner engagement by as much as 3x while reducing average feedback time from days to seconds.

In 2024, I also held a fractional leadership role as Head of Ops at Brooklyn Psychedelic Society, where I built out the core operational infrastructure (budgeting, reporting, financial model), optimized the event programming strategy for community growth, and secured 501(c)(3) nonprofit status.

Before all of that, from 2014-2022, I cut my teeth at Fluent City. I started as a part-time French teacher, then earned a sequence of promotions to increasingly strategic roles. As Senior Enrollment Advisor, I sold & managed custom B2B training programs. Then, as Manager of Talent & Culture, I scaled our best-in-class experience to 4 U.S. cities + online, managing a staff of 200+ instructors. Finally, as Head of Product, I built our learning platform and helped lead the company to successful acquisition in 2021.

Contact

Email me at andrewo@hey.com and/or connect with me on LinkedIn.