Andrew Ostro in

Andrew Ostro

Examiner · DISC type cs
Co-Founder & CEO at PolicyMe
📍 Toronto, Ontario, Canada

Andrew Ostro is the Co-Founder and CEO of PolicyMe, leveraging his deep expertise as a credentialed actuary to modernize the insurance industry. A graduate of the University of Western Ontario, he previously served as a Principal at Oliver Wyman before founding his company to improve insurance accessibility for Canadians.

Beyond his role as a tech CEO, Andrew is a passionate golfer with a highly analytical appreciation for the sport. He dedicates time to serving as an official golf course rater for Golfweek, evaluating various courses on their design, playability, and aesthetics.

His personal frustration with the complex process of buying life insurance was the direct inspiration for co-founding PolicyMe.

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Experience
15 Years
Current Role
Co-Founder & CEO
Job Level
Leadership
Location
Toronto, Ontario, Canada
Personality Overview

How Andrew shows up

Process Oriented
Status Quo Seeker
Late Adopter

Being observant comes to them naturally. They are thorough and always follow a systematic approach. They do not like taking risks at all and go for proven options in the end.

Priorities

Topics Andrew cares about

InsurTech Disruption
Frequently speaks on the need to modernize the legacy insurance industry and is passionate about building simpler, more accessible digital products for consumers.
Insurance Accessibility
Driven by a mission to make financial protection affordable and understandable for all Canadians, highlighted by his company's research on insurance access and affordability.
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Career

Work history

3-2018
Co-Founder & CEO
PolicyMe
1-2022 - 7-2025
Golf Course Rater
Golfweek
10-2011 - 2-2018
Principal
Oliver Wyman
8-2009 - 10-2011
Actuary
Towers Watson
In the press

Media appearances

Andrew Ostro from PolicyMe. Featured in Apple Podcasts
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Andrew Ostro (PolicyMe) - An Insurance Startup & Why You Don't .... Featured in YouTube
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Education
2005 - 2009
Honours BSc.
Western University
Social presence
in
Behavioral profile

DISC profile (public)

c

Calculativeness (C)

Calculativeness (C) reflects the degree to which a person is likely to be cautious, systematic and analytical. Those scoring high tend to emphasise quality and accuracy.

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