Lead Copywriter, Brand & Product
Jerry Insurance Agency, LLCRole Overview
Jerry Insurance Agency, LLC is hiring a Lead Copywriter, Brand & Product. This is a full-time role in Toronto. Part of Jerry Insurance Agency, LLC's Brand hiring. Full responsibilities, required qualifications, and the apply link are listed in the description below.
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Job Description
What you'll own:
We need someone who knows how to talk about a brand in ways that make people feel something and take notice.
- Phase 1: Your sole focus will be overhauling our existing customer communications, including our CRM, email, SMS, and in-app copy. You will take our messaging from functional and direct to value-additive and relationship-driven. You will work closely with our Product, Design, Growth, and Customer Insights team to understand how to build trust, engagement, and as a result, drive long-tail conversion.
- Phase 2: As our brand and voice begins to take shape, you will start taking bigger creative swings to help us stand out online (e.g., pitching and running a campaign where we give away a $150K car to the best driver on our DriveShield platform), own the positioning and messaging for new products like GarageGuard, and build a team to manage organic GTM launches and our social media presence (like Reddit) with native channel expertise.
Who you are
- A copywriting virtuoso: You know that every word matters. You can translate complex, dry, and even stressful topics (car insurance, loans, repairs) into copy that is engaging, human, and accessible.
- A T-Shaped marketer: Your deep expertise is in copywriting, audience development and product positioning. Horizontally, you have a great sense of the social media landscape and community dynamics (like Reddit).
- A first principles thinker: You avoid making assumptions. You know how to take qualitative data and user pain points and turn them into resonant, empathetic marketing copy.
- Comfortable with discomfort: You've weathered fast-growing startups before and can confidently push back on highly analytical, data-first teams to champion the unmeasurable value of a great brand experience.
Ideal experience:
- 7+ years of experience in copywriting, audience development, or product marketing with a heavy focus on brand voice, activation, and retention.
- Experience operating within a B2C growth-stage startup.
- A strong portfolio demonstrating both your writing and creative chops.
- Proven track record of native channel success (e.g. Reddit or another dominant social platform).
- Bachelor's Degree.
While we appreciate your interest and application, only applicants under consideration will be contacted.
The successful candidate's starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
Frequently Asked Questions
How do I apply for the Lead Copywriter, Brand & Product position at Jerry Insurance Agency, LLC?
Use the Apply button above to submit your application directly to Jerry Insurance Agency, LLC. Most applications take less than 5 minutes if your resume and contact details are ready, and you'll be routed to the employer's official application system to finish.
Where is the Lead Copywriter, Brand & Product position at Jerry Insurance Agency, LLC located?
This position is based in Toronto. Jerry Insurance Agency, LLC has not indicated remote or hybrid options for this role, so candidates should plan for on-site work.
What does a Lead Copywriter, Brand & Product at Jerry Insurance Agency, LLC earn?
Jerry Insurance Agency, LLC has not disclosed a salary range in this posting. Many employers share specifics later in the interview process; you can also ask during a recruiter screen if compensation transparency is important to you.
When was the Lead Copywriter, Brand & Product role at Jerry Insurance Agency, LLC posted?
This role was posted on April 11, 2026 (70 days ago). It's still listed as actively hiring; we re-confirm openings against the source system multiple times per day and remove closed roles.
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