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PolicyMe

•
150 employees
Remote-First

PolicyMe is a Canadian digital insurance company that sells life, critical illness, and health and dental insurance online. In its own words, it is "on a mission to put families first with simple and affordable insurance."

PolicyMe's Remote Policy

From their careers page: "We have no in-office mandate, and do not plan on implementing one. We trust our humans to work from wherever they work best, be it from home or from our beautiful office in downtown Toronto. While we value being in-person, we don't think we need to be together every day to operate at our best."

Benefits & Perks

Health & Wellness

2

Health Insurance

PolicyMe's comprehensive benefits plan starts on day one, and the company pays the premiums in full.

Wellness Programs

PolicyMe runs shared programming on mental and physical performance, such as talks from Olympic athlete guest speakers.

Financial

1

Stock Options

PolicyMe offers employees access to stock options, with eligibility based on performance.

Time Off

1

PTO / Vacation

PolicyMe employees receive four weeks of paid time off, which the company's job postings state as 20 vacation days.

Remote & Equipment

2

AI Tools Stipend

Employees get an AI tooling budget, separate from the learning and development budget.

Company Offsites / Retreats

The company covers the cost of bringing all employees together in person twice a year for experiential socials.

Professional Growth

1

Learning & Development Budget

Employees get a learning and development budget, backed by performance reviews twice a year and ongoing feedback.

Culture & Perks

1

Team Events & Social Budget

PolicyMe hosts in-person events such as a summer island party and holiday celebrations, along with virtual events for its remote team.

Tech Stack

JavaScript & Libraries

React
Redux

Frameworks

Node.js
Python

Databases

PostgreSQL
Bigquery

Infrastructure

OpenAI
Sentry
GitHub

Web Servers

NGINX

CMS & Content

Webflow

Hosting

AWS
AWS Lambda

Payments

Stripe

Integrations

Slack
Atlassian Cloud
LangChain
n8n
LangGraph
Marker.io
20 technologies detected

Why PolicyMe

PolicyMe was founded in Toronto in 2018 by Andrew Ostro (CEO), Jeff McKay (CTO) and Laura McKay (COO). Its values call for challenging "the way it has always been done" in insurance, and in 2025 it was named to both the Globe and Mail's Top Growing Companies list and Deloitte's Technology Fast 500.

Inside, PolicyMe describes itself as "an extremely high performing, low-ego, remote-first team," and one of its stated values holds that "as a start-up, we are always either winning or learning." Its careers page says the company cares about "continuous feedback and open dialogue."

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