Join us at PolicyMe! We're modernizing insurance and we'd like your help. The Canadian insurance landscape has remained largely unchanged for decades and we are in the process of changing that. We're a remote-first, Toronto-based startup with big ambitions.

We are seeking a Head of Content who can own our content strategy end-to-end and transform it into a powerful growth engine. You’ll build an editorial center of excellence, maintain a high bar for quality, and roll up your sleeves when needed. As search engine algorithms evolve—especially in an age of AI—our strategy is to lead with quality content rather than produce content merely to rank.

You’ll refresh and optimize our existing library of 500+ blog posts, expand into new content formats, and identify alternate distribution channels beyond organic search. Mentoring a small but growing team, you’ll set a high standard for editorial integrity and ensure that every piece of content tells the PolicyMe story with accuracy, clarity, and impact.

What you'll be doing:

Develop and Own the Content Strategy

Define a long-term editorial vision that positions PolicyMe as a trusted authority in the life and health insurance space
Build and maintain a content roadmap for multiple product lines (Term Life, Health & Critical Illness) and brand partnerships

Scale & Lead the Editorial Function

Establish an editorial “engine” capable of producing high-velocity, high-quality content
Recruit, mentor, and manage writers, editors, and potential content agency partners
Set editorial guidelines (voice, tone, style) ensuring brand consistency

Oversee Multi-Format Content Production

Drive a content-first approach that goes beyond just text, including video scripts, infographics, audio/podcast briefs, etc.
Integrate SEO best practices while adapting to the rapidly changing search landscape (AI-powered SERPs, evolving algorithms, etc.)

Refresh & Optimize Existing Content

Conduct a comprehensive audit of our existing portfolio of blog posts, prioritizing updates based on performance and strategic value
Work with SEO specialists (internal or agency) to boost discoverability while maintaining editorial integrity and brand compliance

Distribution & Channel Expansion

Identify additional distribution channels (e.g., social media, email newsletters, partner co-marketing) to amplify reach
Continuously evaluate new and emerging platforms to keep the brand at the forefront of content innovation

Editorial Integrity & Compliance

Partner with product, legal, and subject-matter experts to ensure content accuracy—especially in regulated topics like insurance
Coordinate with PR agencies when needed, ensuring that all earned media aligns with PolicyMe’s narrative

Reporting & Analytics

Track key performance metrics (e.g., organic traffic, engagement, conversions) and present insights to leadership
Use data to refine content strategy, prioritize projects, and forecast resource needs

What we're looking for:

Proven Experience Scaling Content:

5+ years of leading editorial or content teams—ideally in a high-growth environment where content was a core driver of user acquisition

Editorial Excellence & Brand Savvy:

Strong writing and editing skills with a keen eye for tone, grammar, and brand consistency
Experience implementing rigorous content processes and style guidelines

SEO Knowledge with a Content-First Approach:

Familiarity with SEO best practices and tools, but ability to prioritize content quality amid shifting AI and SERP trends

Multi-Format & Distribution Experience:

Adept at scaling multiple content types (long-form blogs, video scripts, infographics, etc.) and distributing them across various channels

Leadership & Team Building:

Comfortable mentoring junior team members and shaping an editorial culture of ownership, collaboration, and high quality
Track record of building or managing cross-functional teams (full-time, freelancers, agency relationships)

Analytical Mindset:

Uses data to inform editorial decisions, measure success, and iterate on content strategies

Roll-Up-Your-Sleeves Attitude

Thrives in a fast-paced, sometimes chaotic startup environment
Willing to dive into the details when necessary, from keyword research to final edits

Reports To: VP of Growth

Why join us:

Generous PTO - 20 vacation days
Access to stock options and a comprehensive benefits plan
A remote-first team with company paid, in-person socials and the option to work from our Toronto-based office
Resources to help your professional development, including an L&D budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
Work with an empathetic, high-performing team in a flexible, results-oriented environment

About PolicyMe:

PolicyMe is a Venture-Backed InsurTech startup on a mission to put families first, protecting them with the honest and uncomplicated life insurance they deserve. Through technology, PolicyMe is streamlining the traditional insurance process, removing barriers and inefficiencies to deliver a fully-underwritten life insurance policy that families deserve but with fewer steps and lower costs. PolicyMe makes it easy to get a quote and apply for term life insurance online in 20 minutes or less. Since our launch in 2018, we have grown exponentially, selling over $1 billion in life insurance coverage to Canadians.

PolicyMe was also most recently voted as one of Canada's 50 Most Impactful Companies of 2021, and has been mentioned in BetaKit, National Post, the Global & Mail, Global News and more. If you're interested in being considered for this opportunity, please submit a resume.

Commitment to Equal Opportunity:

PolicyMe is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability status. We thank all applicants for their interest, however, only those selected for an interview will be contacted.

Accessibility Statement:

PolicyMe is dedicated to ensuring an accessible experience for all candidates. If you require accommodations during the application process, please let us know in the "Additional Information" section of the job application. We are committed to working with you to provide support and make reasonable adjustments throughout the process.