Founding Product Marketing Lead

ABOUT TERMINAL Terminal builds telematics data infrastructure for the commercial fleet industry. Commercial auto insurers and fleet software companies, including industry leaders like Intact Insurance, Penske, and Progressive, 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. For more on working at Terminal, see our careers page at withterminal.com/careers http://withterminal.com/careers. Note that this role is only open to Toronto/GTA-based candidates. ABOUT THE ROLE 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 1) Own and evolve Terminal's positioning and narrative in the market - Take over and evolve Terminal's positioning, messaging, and category narrative: building on a strong foundation, not starting from zero. - Continue to evolve Terminal's new website and the publication of our first customer success story, then build a repeatable pipeline of customer and partner case studies. - Carry and sharpen the narrative across conferences, events, and customer engagements. - Own the surfaces where that narrative lives: website, LinkedIn, industry outlets, and a thought-leadership blog. - Write and publish persuasive, high-conversion thought-leadership that earns attention in a technical market. 2) Build sales enablement that helps reps win - Create the core sales collateral: decks, one-pagers, and standard narratives mapped to each segment. - Build success stories, customer testimonials, and ROI models that move deals forward. - Partner with the sales team (scaling to four reps) so enablement directly unblocks pipeline and conversion. 3) Build an AI-first marketing engine - Design and run an AI-first marketing engine: orchestrate a set of specialized AI agents (content, demand generation, design, research, social) that execute the work of a full marketing team, with you directing the strategy, taste, and editorial bar. - Stand up the operating rhythm, tooling, and systems that make the engine repeatable, high-quality, and measurable. - Own Terminal's event presence: industry conferences and Terminal-hosted events (e.g., dinners). 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. - Has operated across the full marketing stack (positioning, content, demand generation, brand, enablement, events) and understands how the whole function fits together - not a single-lane specialist. - A proven track record of category-defining positioning and persuasive thought-leadership that converts. - Equally strong as a strategist and an operator: you set direction and still do the hands-on work yourself, to a high bar. - Fluent with AI and genuinely energized by it as a force multiplier. You would rather orchestrate a roster of specialized AI agents than manage a large team, and you have the judgment and taste to direct them well. - Wants a founding, 0→1 mandate with direct ownership and company-level impact — and is done with big-org layers and stakeholder management. - You don't need to check every box. If you're missing some but confident you'll close the gap quickly, apply anyway. NICE TO HAVE - Prior experience in Telematics, fleet/logistics, or selling into the insurance domain. WHAT SUCCESS LOOKS LIKE How we'll measure success - Pipeline impact: growth in marketing-sourced and marketing-influenced pipeline. - Inbound quality: month-over-month growth in qualified inbound from target ICP accounts (enterprise/insurance), not just raw volume. - Narrative traction: measurable lift in branded search, share of voice, and engagement on thought-leadership among the technical and industry audience. - Adoption: founders, sales, and customers consistently articulate Terminal's positioning, with a documented framework in active use - Enablement coverage: a complete, current sales kit (Sales deck, one-pagers, ROI model, segment-specific case studies) live within 90 days. - Sales impact: improved win rate and stage conversion attributable to enablement assets. - Leverage: deliver the output of a multi-person marketing team operating as one strategist plus a roster of AI agents. - 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 and build a plan for a customer success story for all other customer segments. - Evolve and document the positioning/messaging framework, adopted across sales and marketing. - Deliver a complete sales kit (deck, one-pagers, ROI model, case study). - Establish a content publishing cadence, including but not limited to LinkedIn, and the next wave of thought-leadership pieces. In 6–12 months - Demonstrate growth in qualified inbound and improved sales conversion attributable to marketing. - Run a repeatable AI-first content and events engine that produces team-scale output, with a measurable thought-leadership presence. - Add the first selective human hire (events/field) only where it extends the engine. PRACTICAL DETAILS - Location: Toronto-based - Travel: occasional, for industry conferences and Terminal-hosted events. - Reports to: COO. A 0→1 mandate to build the product marketing function and hire under it. COMPENSATION - Base salary: $180,000-$220,000 - Meaningful equity, plus the benefits below. - Variable is tied to your impact on Terminal's position in the market. The structure is defined before you start. You won’t be negotiating it in your first week. BENEFITS - Strong compensation and equity packages. - Brand new MacBook and computer equipment. - Top-tier health/dental benefits and a flexible healthcare spending account. - Personal spending account for professional development, fitness and wellness. - Four weeks paid time off + statutory holidays. - In-person culture with an office located in downtown Toronto. THE INTERVIEW PROCESS 1. Intro call with the COO (30 min) 2. Product marketing deep-dive (60 min) 3. Work product + presentation (72 hrs prep period + 60 min) 4. On-site culture loop + final (180 min) 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. Accommodations are available under the Accessibility for Ontarians with Disabilities Act (AODA) and the Ontario Human Rights Code, and requesting one will never affect how your application is considered.