PolicyMe

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

Transcript

Jena Dunay: Hello friends, welcome back to another episode of Culture Uncovered. I have a great organization to present to you: Vanesa Cotlar of PolicyMe, VP of People and Culture. She’s here to talk about what it’s like to work for their organization. Vanesa, thank you so much for joining us today.

Vanesa Cotlar: Yeah, thank you for having me. Excited for the conversation.

Jena Dunay: So why don’t you start and tell us a little bit about what PolicyMe does?

Vanesa Cotlar: For sure. We’re Canada’s leading digital solution for insurance. We focus on making insurance straightforward and simpler for families across the country. Our products include life insurance, critical illness, health, and dental. What’s interesting is we also do B2B2-C. We’re the technology provider for some partners so they can sell insurance digitally too. Insurance used to be a paper-based process. You’d go to a broker and fill out forms for weeks. Now, you can do it all online. It’s much faster and more convenient.

Jena Dunay: Okay, so you’re saying it’s B2B2-C. Explain for people who might not know what that means.

Vanesa Cotlar: Sure. Two ways. You can buy directly from PolicyMe, which is B2C. You go to our website and get insurance quickly, you get a quote right away. Party trick at events! For B2B2-C, our business partners with another business who then go to their own customers. That’s also enabled by our tech.

Jena Dunay: Amazing. When were you founded, and how many employees now?

Vanesa Cotlar: 2018. We’re just over 100 employees.

Jena Dunay: That’s a sweet spot! Where are you headquartered, and where do people work? Is it remote?

Vanesa Cotlar: Headquarters is Toronto, where a large portion of us are based. We have employees coast to coast: Vancouver, Montreal, Winnipeg, Calgary, BC, Alberta. We’re remote-first, no mandate to go into the office. Toronto has an office, optional to go in. People go in on Thursdays. If you have a conflict, no problem. Remote is respected and it’s a great balance.

Jena Dunay: That connection piece is so important for building relationships and getting work done efficiently. I love hearing the differences between Canadian and US-based companies. How did you come across PolicyMe? What’s your background?

Vanesa Cotlar: Throwback to 2021. I was doing my MBA while working. I was happy where I was but considering another opportunity. An executive coach said, “You aren’t really looking, but you might switch. Are you thinking about other options?” I realized I should be open to change, so I re-evaluated what’s out there. One of PolicyMe’s founders, Laura, messaged me on LinkedIn about hiring their first Head of People. Someone on the exec team knew me. I met the whole exec team in a week.

Jena Dunay: It’s like speed dating!

Vanesa Cotlar: Very fast-paced. I met Laura, Andrew, Jeff, the co-founders. Then I wanted to meet all the leadership team because joining a company at the exec level means understanding your future peers. I look for any “problem child” on the team. Didn’t find any, which is rare, so something felt right. The idea behind PolicyMe is really big, not just niche. If it takes off, it can disrupt the market and become a new household name.

Jena Dunay: Absolutely. Points for being open and exploratory. Don’t just run away from something, run toward something. PolicyMe seems like something you ran toward. You really made sure you met future teammates. That’s so important for culture. And, kudos for working full time and doing your MBA!

Vanesa Cotlar: Yeah, chaos. It was a lot.

Jena Dunay: Let’s talk about PolicyMe’s culture. How would you describe it in three words?

Vanesa Cotlar: Normally I use two: humble, high achievers. People here are some of the smartest you’ll meet, but you wouldn’t know just by talking. They aren’t flashy and are just great at what they do. The third word is curious. We focus on learning and continuous growth. Every year, we reinvent or add new elements to the business, so there’s always change. It’s great for curious people.

Jena Dunay: What does learning look like practically in your organization?

Vanesa Cotlar: Lots of things. Each employee has a budget for courses, books, whatever furthers their learning. I run manager and leadership training, sometimes company-wide. It’s never too early to start learning how to lead. We’re also big on AI. Last year, we planned our AI strategy and set a budget for people to try new tools. Our CTO and I co-lead the AI strategy. We have an AI Guild for cross-departmental presentations, meeting regularly to share what’s happening in AI and how it applies to our business. Product managers and designers are currently piloting seven different tools. Each is testing two to find the best fit for us.

Jena Dunay: What about cool perks or practical benefits that make PolicyMe unique beyond culture?

Vanesa Cotlar: Major one is work-from-anywhere, home or office. Trust is huge. Many companies are forcing returns to office, but we maintain flexibility. For connection, we curate social experiences, twice yearly big events, from trips to Toronto Island to bringing in a circus troupe for team activities. Company events are memorable, social, and something people look forward to. This differentiates a remote-first business. We’ve also done events with Olympic athletes and treetop trekking. Now, with city hubs across the country, employees have budgets for local meetups. We keep virtual events fresh. A recent one was Friday Pop, a popcorn tasting with boxes sent to everyone’s home.

Jena Dunay: Who comes up with these ideas?

Vanesa Cotlar: It’s a mix. My team plans a lot, and we ask for employee input. As we grew, planning was easier with a smaller group, but everyone loves events. Holiday parties are back with entertainment and photo booths. We replace some virtual events with city hubs where employees get together locally.

Jena Dunay: The whole employee experience sounds thoughtful and fun, but also structured. Tell me about your organization’s departments.

Vanesa Cotlar: All the standard ones. We have product, growth and marketing, finance, customer success, engineering, business operations, and people.

Jena Dunay: No company’s perfect. What are areas for improvement in PolicyMe’s culture?

Vanesa Cotlar: Scaling culture is an art, not a science. There’s no perfect playbook. The challenge is hiring consistently, finding high-achievers who are also humble. HR enables culture but doesn’t drive it. It’s mostly at leadership and management levels. Managers are the real culture drivers. Individual employee experiences depend more on their manager than anything else. We promote from within, but sometimes hire externally, which brings new ideas. Bridging internal and external ways of doing things is key.

Jena Dunay: Are you hiring? What does hiring look like for the next year?

Vanesa Cotlar: Yes, across almost all departments. Everything from entry-level customer success roles, engineering, data science, growth marketing, design. Lots of opportunities.

Jena Dunay: How does someone stand out with their resume?

Vanesa Cotlar: Good outreach works. Curated, well-written LinkedIn messages. I scan messages and forward the good ones to my team. Personalized outreach referencing podcasts or our values stands out. At the interview stage, living our REACH values is key. The first is reliability. You need to own your work. In startups, that means responding if something breaks or if there’s a customer impact. We look for ownership and reliability throughout.

Jena Dunay: Can you walk me through those values?

Vanesa Cotlar: REACH stands for Reliable, Entrepreneurial, Ambitious, Collaborative, and Humble. Reliable is essential. Entrepreneurial means owning your work and looking for ways to improve. Ambitious covers being self-motivated. Collaborative is about enabling teamwork. Humble is living that humble high achiever standard. These values are in our performance and review processes and are central to our regular conversations and rewards.

Jena Dunay: Where can people learn more about jobs, culture, and PolicyMe?

Vanesa Cotlar: LinkedIn’s a good start, PolicyMe’s page or my own. The website policyme.com/careers has more information about our values, culture, and open roles.

Jena Dunay: Great! Thank you so much, and thank you all for listening. See you next week on another episode of Culture Uncovered.

Vanesa Cotlar: Thanks so much!