Founding Product Marketing Lead in Toronto

Terminal builds telematics data infrastructure for the commercial fleet industry. Commercial auto insurers and fleet software companies, including industry leaders like Intact Insurance, depend on our platform to access GPS, speeding, and vehicle data from 330+ telematics providers. We recently raised our Series A led by Battery Ventures and are backed by Y Combinator, Golden Ventures, Penske Transportation Solutions, and Intact Private Capital. Our team works together in person in Toronto, combining early-stage speed with late-stage maturity while processing many terabytes of vehicle data every day.

We're hiring a Founding Product Marketing Lead to build and own Terminal's marketing function from the ground up. This is for a senior, highly accomplished marketer who has already done the work at scale across multiple companies and marketing functions and now wants something different: to leave behind big teams, layers, and stakeholder management, and build marketing the right way, from first principles, with direct ownership and outsized impact on the company's trajectory.

The leverage model is new. Rather than hiring and managing a large team of specialists, you'll orchestrate a roster of AI agents that play those specialized roles: content, demand generation, design, research, social, directing them with the strategy, taste, and editorial judgment that only a seasoned operator brings. You are the strategist and the conductor; AI does the legwork of an entire team, at a pace and breadth a traditional team can't match. Human hires come later and selectively, as force multipliers, not as headcount to manage.

You'll market a deeply technical product, a data and API platform, to a sophisticated technical audience, moving fluidly between high-level category strategy and hands-on execution: you can set the narrative and also write the post, build the deck, and ship the page yourself. Terminal already has product-market fit and an established position; your job is to evolve and amplify it, not invent it.

As Terminal's first dedicated marketing hire, you'll work directly with the founders, own the function end-to-end, and have a clear path to grow into the leader who scales it. You report to the Chief Operating Officer (COO).

What you'll do:

• Own and evolve Terminal's positioning and narrative in the market.
• Build sales enablement that helps reps win.
• Build an AI-first marketing engine.

What we're looking for:

• 10+ years in marketing, including VP or leadership roles, with deep experience B2B marketing technical products ideally data, API, or developer-first products to technical and business audiences.
• A proven track record of category-defining positioning and persuasive thought-leadership that converts.
• Equally strong as a strategist and an operator.
• Fluent with AI and genuinely energized by it as a force multiplier.
• Wants a founding, 0→1 mandate with direct ownership and company-level impact.

Nice to have:

• Prior experience in Telematics, fleet/logistics, or selling into the insurance domain.

What success looks like:

• Pipeline impact: growth in marketing-sourced and marketing-influenced pipeline.
• Inbound quality: month-over-month growth in qualified inbound from target ICP accounts.
• Narrative traction: measurable lift in branded search, share of voice, and engagement on thought-leadership.
• Adoption: founders, sales, and customers consistently articulate Terminal's positioning.
• Enablement coverage: a complete, current sales kit live within 90 days.
• Sales impact: improved win rate and stage conversion attributable to enablement assets.
• Operating cadence: a predictable, high-quality content and publishing cadence established within 60 days.

In the first 90 days:

• Evolve the new website launch, publish the first customer success story.
• Deliver a complete sales kit.
• Establish a content publishing cadence.

In 6–12 months:

• Demonstrate growth in qualified inbound and improved sales conversion.
• Run a repeatable AI-first content and events engine.
• Add the first selective human hire only where it extends the engine.

Practical details:

• Location: Toronto-based.
• Travel: occasional, for industry conferences and Terminal-hosted events.
• Reports to: COO.

Compensation:

• Base salary: $180,000-$220,000.
• Meaningful equity, plus benefits.

Benefits:

• Strong compensation and equity packages.
• Brand new MacBook and computer equipment.
• Top-tier health/dental benefits and a flexible healthcare spending account.
• Four weeks paid time off + statutory holidays.
• In-person culture with an office located in downtown Toronto.

Accessibility and accommodation:

Terminal is committed to an accessible hiring process. If you need an accommodation at any stage — applying, interviewing, or completing an assessment — email careers@withterminal.com and we will work with you to meet your needs.