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. Commercial vehicles now generate data at a scale the industry has never had to handle, and the companies serving those fleets increasingly compete on how well they use it. Insurers price risk based on driving behaviour, fuel card providers validate transactions against vehicle location and duty status, and fleet management and transportation software build core workflows on telematics feeds they cannot afford to lose.

That data sits behind hundreds of telematics providers, each with its own API, schema, and failure modes, and every integration a company adds becomes something its engineering team maintains indefinitely. We move billions of miles of driving data for some of the largest commercial auto insurers, software companies, and fleet operators in North America, and customers commonly grow their usage two to three times a year once a program is live. Demand has outpaced our go-to-market from the beginning, arriving almost entirely through inbound and referral, and our enterprise relationships have been founder-led throughout.

We are now building a sales team dedicated to enterprise, and this role sits at the center of it. Your accounts are the largest companies in commercial auto and trucking insurance, fleet management software, logistics and transportation management software, and financial services for fleets, including the major fuel card providers. Cycles are long and rarely linear, with an executive track, a technical evaluation, and a procurement and security review advancing in parallel.

We go to market across four segments: Insurance: commercial auto and trucking carriers.

Fleet management: the largest fleet management software platforms.

Transportation management: logistics and transportation management software platforms.

Fuel cards: the major fuel and fleet card providers.

Economic buyer: in insurance, the leader who owns the commercial auto, trucking, or specialty lines P&L.; In software and financial services, product or engineering leadership, and often the CEO or CTO at smaller companies.

Technical evaluators: product and engineering leaders and managers, alongside the data science and actuarial teams, who assess data quality and coverage.

- Own enterprise pipeline and account strategy Own a named target account list: the research, entry strategy, account plan, and sequence for each cycle. Source the majority of your own pipeline. Inbound and referral volume is meaningful and you will receive a share of it, but the largest accounts rarely arrive unprompted. Work across Terminal's four enterprise segments: insurance, fleet management, transportation management, and fuel cards. A small number of well-qualified cycles is worth more than a crowded pipeline that never resolves.



Qualified enterprise pipeline by segment, with clear stage definitions and next steps. Self-sourced pipeline as a meaningful share of the total pipeline.

Forecast quality: fewer late-stage surprises, clearer exits from poor-fit cycles, and enough coverage to plan against quota.

- Run complex technical and executive sales cycles Multi-thread the full buying committee, from the executive who owns the P&L; to the engineers and data scientists who scrutinize Terminal's data before anyone signs. Most decisions are made in internal meetings you will never attend, so the quality of what your champion walks in with matters. CEO, engineering, operations, security, compliance, privacy, data governance, SOC 2 evidence, and procurement. Make the economics of building in-house explicit when a prospect is weighing that path. Progression of target accounts through executive, technical, security, procurement, and commercial tracks. Win rate and cycle quality on named enterprise accounts.
- Own commercial terms, close, and early activation handoff Structure usage-based commercial terms. Our pricing scales with the customer's program, so you will negotiate commitments and minimums and build a ramp that their finance team and ours both find credible. Close net-new enterprise logos, then transition accounts to post-sales while staying close through activation and early expansion. Co-author enablement material with product marketing: business cases, segment narratives, competitive positioning, and ROI models written by the person closest to the buyer. Booked value, activated usage, and priority target-logo progress. Quality of commercial ramps against actual customer activation. 8+ years in sales, including 5+ years selling into large enterprises. ~ A track record of landing net-new enterprise logos: attainment across several years against a comparable quota, and a clear account of what came from new business as opposed to expansion or renewal. ~ Fluency selling technical products to technical buyers: you are comfortable going deep on data, APIs, and integration architecture, and credible in a room full of engineers. ~ Exceptional writing: long cycles turn on material that circulates without you present, so your one-pagers, follow-ups, and business cases have to carry themselves. ~ Located in Toronto and able to work from our office four days a week. ~ Willingness to travel to the US regularly, roughly six to eight trips a year for conferences and customer onsites Experience selling to fleet management, logistics, or transportation technology companies. A background in telematics, IoT, or connected vehicle data.

Experience selling APIs, data infrastructure, or other developer-facing platforms. Founder experience and/or previous early-stage startup experience. An undergraduate degree in a technical discipline, such as computer science or engineering.

You need an inbound pipeline to reach your number, as we have no SDR function today. You would rather not run smaller,



faster cycles alongside your enterprise pipeline early on, which is how you build fluency with our buyers and our product while the long cycles mature. You want to work remotely.

Support you will have Our engineering team is a working partner: product engineers here support sales, implementation, and ongoing customer needs, so technical evaluations and architecture conversations are never meant to be carried out alone.

Security and compliance handled alongside you: our engineering and operations teams own SOC 2, privacy, and data governance, and carry most of the procurement and security review workload. A dedicated post-sales team spanning strategic account management, customer success, and customer engineering, so your attention stays on landing accounts rather than running activations. Product marketing is being built alongside this team, which you help shape and then draw on.

A part-time CRO who has worked with us for nearly two years, along with seasoned enterprise sales advisors through our investors. A sales team built around enterprise, so the motion develops with peers rather than in isolation. Build fluency in Terminal's product, data model, integrations, enterprise segments, and existing customer patterns.

Own a named target account list and build account plans for the highest-priority prospects. Begin outbound outreach to priority accounts and build a qualified enterprise pipeline across the core segments. Ship v1 sales artifacts with product marketing: segment narrative, discovery notes, business-case template, and ROI model.

Move multiple enterprise opportunities through executive, technical, security, procurement, and commercial tracks. Close net-new enterprise business and transition accounts cleanly into activation and early expansion. Help shape Terminal's enterprise sales motion without adding process for its own sake.

Travel: regular US travel, roughly six to eight trips a year for conferences and customer onsites.

Sales motion: enterprise net-new, with usage-based commercial terms and support from engineering, operations, product marketing, and post-sales. Meaningful equity, plus the benefits below. You earn on booked value, usage, and activation, since a signed contract only matters once data is flowing.

There are additional bonuses attached to priority target logos. A ramp supports new hires while the pipeline builds. We walk through the full plan and underlying math openly at the offer stage. Robust 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. Intro call with the sales team (30 min) # Account planning + discovery working session (90 min) # On-site culture loop + final (180 min) If you need an accommodation at any stage — applying, interviewing, or completing an assessment — email 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. #

📌 Account Executive (English speaking) (Toronto)
🏢 Withterminal
📍 Toronto