Hire Learning: How PolicyMe ensures career development

The remote-first digital insurance company is steadily hiring to match its growth.

In this series, we talk to talent execs at high-growth startups about what they look for in new hires.

The mission of PolicyMe is clear, says Vanesa Cotlar, the company’s vice president of people and culture. “Our purpose is to make it simpler for people to get insurance coverage.” Recent research from market research association LIMRA found that more than a third of Canadian adults say they either need life insurance or more coverage. And according to PolicyMe’s 2026 Insurance Gap Report, nearly one in four Canadians said that they were unsure that their families would be financially secure if they died unexpectedly.

The Toronto-based insurance company’s online platform is designed to help more Canadians access the protection they need. Predictive models and AI-powered underwriting tools help the company approve applicants in under 20 minutes, reduce the need for medical exams and offer premiums up to 20 percent lower than the industry average.

That streamlined approach has resonated with the market. Since joining in 2021, Cotlar has helped the PolicyMe team grow from just over 30 people to more than 135 employees and counting.

Last year, the MaRS Momentum venture secured $30 million in new funding, and has partnered with education-savings company Embark, the Association of Science and Engineering Technology Professionals of Alberta and Wealthsimple to give their members and clients term life and critical illness insurance at preferred rates. To date, PolicyMe has insured more than 50,000 Canadians, surpassing $20 billion in coverage in 2026.

As PolicyMe ramps up hiring to develop its home and auto insurance coverage, Cotlar shares what she looks for in prospective team members and how a digital-first company keeps employees connected — whether it’s on a video call or on a pickleball court.

How do you guide customers through the process of purchasing insurance online?
Buying insurance is a unique thing because people don’t do it every day. While our coverage is mostly self-serve and online, we have licensed insurance advisors who are able to guide customers through the process, which helps build trust. For our advisors, compensation isn’t tied to the size of the sale, which means they aren’t incentivized to sell a policy just to earn a paycheque. Their focus is on helping customers get the coverage that’s right for them.

What qualities make a job candidate stand out?
We look for life-long learners, the types of people that are looking for opportunities to grow and develop — the kind that go to company and industry events on their own time. We have some of the smartest people I’ve ever worked with. They’re insanely humble and we’re a place where the day-to-day feels so fun to be a part of. Because the calibre of colleagues is so high, there’s a ton of trust.

How does PolicyMe help foster career development?
We are always looking for ways to give people career advancement. Any time that there’s a new opportunity, we look internally to see if there’s a way for someone to step into a new role or do something they’re interested in. And when a manager leaves or a new team is spun up, we always put that opening up to our internal advisors.

How does hiring factor into the growth of the company?
We’re super intentional in how we add headcount. We ensure there’s meaningful work not just immediately, but also down the road. This has helped us grow year-over-year in a sustainable way.

How do you keep a remote-first company connected?
We have a team across Canada, which means that people don’t often get to meet in-person, but we do many things to make people feel appreciated and connected. Every new hire is paired with an onboarding buddy who shows them the ropes. We also host monthly townhalls, spotlight employees who are doing incredible things and host online socials. In September, we sent bubble tea kits to all of our employees’ homes and had a virtual mixing party. We also partner with Lululemon for swag and send gift cards to celebrate milestones.

What are the in-person events like?
Each office holds unique activities, such as trivia nights or pickleball. Twice a year, we also bring the entire company together in-person at our Toronto headquarters. This summer’s big company celebration included a cruise on Lake Ontario. We had some great food and some pretty incredible karaoke. This November, we’re doing a winter wonderland at Casa Loma to celebrate the end of the year.

What’s next for PolicyMe?
Engineering will continue to be our biggest area of growth as PolicyMe expands its home and auto insurance offerings. The team is working to improve the existing life insurance purchasing process and design an AI-enabled buying experience, while continuing to offer advisors for people who want to speak to a real human.

MaRS Momentum, which helps companies scale to $100 million and beyond, is currently recruiting leaders at high-growth ventures for its Fall 2026 Executive Peer Pods. Apply today.

Photo credit: Kelvin Li