Culture Uncovered

Ever wonder what it's like to work for the best companies in the world? Maybe you’re actively looking for a new job. Or maybe you’re thinking about your next strategic career move.

Well, you've come to the right place.

Each week we meet with talent leaders at companies you’ve heard of - and many organizations you haven’t. Giving you a behind-the-scenes look at what it’s like to work there…before you even apply.

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Culture Uncovered

PolicyMe

October 15, 2025 • Recruit the Employer • Season 1 • Episode 26

Yes, you can buy life insurance without all the paperwork.

Meet PolicyMe, Canada’s leading digital insurance platform that’s simplifying life, health, and critical illness coverage for families nationwide. In this episode, Jena chats with Vanesa Cotlar, VP of People and Culture, about what it’s like to work for a company that’s modernizing an entire industry while keeping its people curious, humble, and connected (even remotely).

What you’ll learn:

How PolicyMe is transforming insurance from paper-heavy to fully digital
Why “humble high achievers” are the secret to their success
How curiosity fuels growth through AI, leadership training, and learning budgets
What flexible, remote-first work looks like when connection actually works
How PolicyMe keeps culture strong while scaling fast
What their REACH values mean in real life and how they shape hiring

PolicyMe Highlights:

Founded: 2018
Team Size: 100+ employees
HQ: Toronto, Ontario
Work Model: Remote-first with optional in-office Thursdays
Culture: Curious, humble, high-achieving

Unique Perks & Programs:

Work-from-anywhere flexibility
Twice-yearly company events : think Toronto Island trips and circus troupes!
Local hub meetups with budgets for regional gatherings
AI Guild for experimentation and cross-departmental learning
Learning budgets for courses, books, and leadership training
Popcorn tasting Fridays (yes, really!)

To learn more about PolicyMe: