Posted at: 1 December

Director of Brand (Remote)

Company

PolicyMe

PolicyMe is a Toronto-based B2C insurtech startup specializing in digital life, critical illness, and health & dental insurance solutions for the Canadian market.

Remote Hiring Policy:

PolicyMe is a remote-first company based in Toronto, Canada, supporting flexible work arrangements. We welcome applications from various regions, allowing team members to work remotely while also offering the option to collaborate in our Toronto office.

Job Type

Full-time

Allowed Applicant Locations

Worldwide

Apply Here

Job Description

Overview of the role
We’re on a mission to modernize insurance, making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that has remained largely untouched by the digital revolution, and PolicyMe is here to change that.

About This Role:
As a remote-first, Toronto-based startup with big ambitions, we’re looking for a Director of Brand to help us build the future of insurance in Canada and beyond.

As we scale beyond life and into multi-product insurance, brand becomes a company level priority. We need a leader who can turn a solid foundation into a nationally recognized, high trust brand.

We are hiring a Director of Brand to own our brand strategy, integrated campaigns, creative standards, and the consistency of how PolicyMe shows up across every external facing experience. This role reports to the VP of Growth and works closely with growth, content, design, product, and operations. It is a hands on leadership role with material influence on the company’s trajectory.
What you'll be doing:
  • Build and lead PolicyMe’s brand strategy
  • Own and evolve the brand platform, including positioning, narrative, tone, proof points, and our advice philosophy.
  • Translate the platform into clear guidelines and a knowledge base that anchors how the company communicates.
  • Define a consistent system for message architecture across the website, product surfaces, content, and marketing.
  • Own the brand budget, manage our brand and PR agencies, and build a small internal brand bench over time.
    • Lead integrated campaigns and agency partnerships
  • Develop sharp briefs tied to business problems, not just creative asks.
  • Run the full campaign cycle: brief, concept evaluation, production, launch, and post mortem.
  • Manage agency relationships, including RFPs when needed, and ensure creative meets both brand standards and commercial goals.
  • Partner with the Director of Growth Marketing to align creative with media strategy across always on and major campaigns.
    • Elevate the quality of every customer facing touchpoint
  • Work with design and product on website structure, messaging, and polish.
  • Review and improve product copy, explainers, and service communications to maintain consistency and clarity.
  • Ensure all new experiences reflect our brand and advice philosophy.
  • Identify and activate under leveraged channels such as PR, organic social, partnerships, and earned media.
    • Own brand measurement and accountability
  • Establish a brand measurement framework that includes independent tracking, search signals, and funnel level indicators.
  • Tie brand work to conversion, trust, and customer level outcomes.
  • Set quarterly OKRs that define the impact brand will have across awareness, preference, and experience quality.
    • Drive cross functional alignment
  • Co lead a cross functional brand council with product, design, and operations to align brand promise with customer experience.
  • Help articulate and socialize PolicyMe’s brand story internally so teams understand what we stand for and how that should show up in their work
  • Build rituals and systems that keep teams aligned around standards and decision making.
What we are looking for:
  • 8+ years in brand, brand marketing, or integrated strategy roles, with a clear track record of shaping or owning a brand platform.
  • Direct experience leading integrated campaigns, including agency management and creative evaluation.
  • Ability to operate in a lean environment. Must be hands on and comfortable building with constraints.
  • Strong grasp of brand measurement, brand research, and how brand connects to funnel and financial outcomes.
  • Experience in consumer facing categories. Fintech, insurance, telecom, healthcare, or other low trust or regulated industries are strong assets.
  • Exceptional communication skills. Can simplify complex ideas, write clearly, and influence across teams.
  • High standards for creative and design quality.
  • Comfortable working cross functionally with product, design, growth, and customer experience.
    • Nice to have
  • Product marketing, UX writing, or hands on experience shaping positioning in complex customer journeys.
  • PR and communications experience, including managing PR agencies.
  • Prior work on challenger brands competing with large incumbents on smaller budgets.
  • Agency side strategy or creative background, with interest in owning one brand.
  • Bilingual (English/French) is a plus.
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:
At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.

We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit www.policyme.com.

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.
Apply Here