Product Management Coach

This is a contract coaching role for experienced Product Managers to mentor students and early-career professionals on breaking into product management roles at major technology companies.

What you’d own

Resume reviews
Behavioral and product case interview preparation
Practical guidance on navigating product careers

Who it’s for

A fit if you…

✓You have experience working with students formally or informally
✓You have Product Management experience at top technology companies
✓You are comfortable hosting virtual coaching sessions independently

Not for you if…

✗You are looking for a standard full-time product management role
✗You prefer a structured, non-contractual employment model
✗You want to build products rather than coach others on the profession

Reading between the lines

The 'set your own hours and rates' phrasing implies this is a gig-based engagement with high autonomy over your schedule.
The mention of an 'AI-native environment' suggests you will likely be expected to incorporate AI tools into your coaching methodology.

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Full job description

Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill for a world being rewritten by AI. We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us, and we've built a product that takes that seriously.

We’re seeking experienced Product Managers from top technology companies to coach students and early-career professionals looking to break into product management at high-growth startups, Big Tech, and Fortune 500 companies. Coaches help mentees prepare for PM recruiting through resume reviews, behavioral and product case interview preparation, and practical guidance on navigating product careers. Ideal candidates have PM experience working with students formally or informally. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality coaching experience.

WHY LELAND?

The chance to join a world-class team helping people achieve their career and educational dreams

Work in a collaborative, high-energy environment where your contributions have a direct impact

Operate in a fast-paced, AI-native environment

We don't hire people who merely want to work for a great company; we hire people who want to make a great company

Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.

About Leland

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Leland is a coaching marketplace that connects ambitious users with vetted experts for high-stakes goals — MBA, law/med school, and college admissions; product management, consulting, banking, PE/VC, and other career transitions; standardized test prep (GMAT, GRE, LSAT); and increasingly, learning to build with AI. The platform has 1,000+ coaches (only 5% pass vetting) with 28K+ reviews averaging ~4.99 stars. Founded in 2021 by former Uber/LinkedIn PM John Koelliker, Leland raised a $12M Series A led by Forerunner Ventures in 2024. Notably, the team works in person on purpose out of Lehi, UT — every full-time employee gets equity, 12 weeks fully paid maternity / 6 weeks paternity leave, and a $100K life insurance policy. Small team, fast-moving, and unusually opinionated about culture for an edtech marketplace.

Education & EdTechConsumer & MarketplaceParental leaveEquity for all