Varun Rajan

Turn Your Organization Into a High-Trust, High-Output Machine

I work across product, people, and leadership to empower teams to trust their judgment, align across functions, and execute with conviction.

What I've Built

Explore the roles and environments where I helped teams grow, ship, and level up.

2025 - Present

Product Management Consultant and Coach

Magellan AIMagellan AI
Vitality LabsVitality Labs

Currently: exploring how to best coach product teams to work at their best. Uplevel your PMs with Conviction Coaching.

Recently: Led product roadmaping, prioritization, prototyping, and feature development for AdTech analytics startup in the podcast space

Bit earlier: Ran pilot program encouraging K12 students to build resilience through guided AI prompts and reflections

2022 - 2024

Chegg

Chegg
Led growth and monetization initiatives across acquisition, subscriptions, and upgrades—driving ~$8M+ in incremental annualized revenue through funnel modernization, experimentation, and data-informed trust signals.
2021 - 2022

RubiconMD

RubiconMDRubiconMD
Oak Street HealthOak Street Health
Drove adoption of the flagship eConsult product to help secure a $60M contingent cash earnout following acquisition by Oak Street Health.
2020 - 2021

Chegg (Chegg Skills)

Chegg
Served as Chief of Staff to the COO, leading product strategy & rollout, market research, and analytics initiatives that improved UX programs, tooling adoption, and job placement forecasting.
2019 - 2021

Keming / Free Agency / Stealth Talent Startup

KemingKeming
Free AgencyFree Agency
Co-founded and consulted across multiple tech talent initiatives—launching a podcast, newsletter, and community, coaching candidates, and building early-stage recruiting operations and best practices.
2018 - 2019

Teachable

Teachable
As first dedicated Product hire, I had the unique opportunity to shape the Product team and tech operations. Owned internal tools and support systems, reducing inbound ticket volume by 15%, modernizing bug triage workflows, and introducing structured discovery practices across product and engineering.
2015 - 2018

Thinkful

Thinkful
Led product initiatives in education and operations—reducing student remediation by 60%, enabling nontechnical program management, and supporting Thinkful’s rise to the #1 coding bootcamp on Course Report.