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PolicyMe
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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:
- Careers Page (They're hiring!)
- Linkedin Page
- Vanesa's Profile
27 episodes
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