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Enterprise Account Executive

Terminal
CompanyTerminal
CategorySales
LocationToronto
RemoteHybrid
EmploymentNot stated
LevelNot stated
SalaryUSD 260k
Posted4 Feb 2026
Last verified9 Aug 2026
SourceEmployer ATS (ashby)
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Description
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, 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 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. The difficulty is access. 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. Terminal is the infrastructure layer that removes the burden. 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. We are looking for sellers who can work across our segments, with some able to focus solely on insurance, our largest segment by both usage and revenue. 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. Deals begin around $300K and reach seven figures against a $1.3M to $1.5M annual quota. Cycles are long and rarely linear, with an executive track, a technical evaluation, and a procurement and security review advancing in parallel. We hold a high bar on talent and protect it even when that means growing more slowly, so the scope any one person carries here is wider than it would be at a larger company. The enterprise motion is still being shaped, and you will have a significant hand in shaping it. WHO WILL YOU SELL TO 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. The buying committee is consistent across all four. - Champion: the person who owns telematics, IoT, connected vehicle, usage-based insurance, or integrations, and through whom the entire cycle runs. - 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. WHAT YOU'LL DO 1) Own enterprise pipeline and account strategy - Own a named target account list: the res