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.
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 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.
Qualify out early when a cycle will not close. A small number of well-qualified cycles is worth more than a crowded pipeline that never resolves.
Proposed ways to measure success and progress:
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.
2) 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.
Build the business case and equip your champion to carry it. Most decisions are made in internal meetings you will never attend, so the quality of what your champion walks in with matters.
Bring the wider Terminal team in at the right moments: 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.
Proposed ways to measure success and progress:
Progression of target accounts through executive, technical, security, procurement, and commercial tracks.
Champion strength: written business cases, internal alignment, and ability to move work forward without Terminal in the room.
Win rate and cycle quality on named enterprise accounts.
3) 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.
Proposed ways to measure success and progress:
Booked value, activated usage, and priority target-logo progress.
Quality of commercial ramps against actual customer activation.
What we're looking for
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.
Several enterprise lands you can reconstruct in detail: how you got in, who you built relationships with and in what order, what the business case argued, where each deal nearly died, and what you did about it.
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.
Experience with usage-based or consumption pricing: negotiating commitments and minimums, and forecasting a ramp against them.
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.
The judgment to identify a cycle that will not close, and the discipline to say so early.
High initiative and an exacting bar for detail.
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
Nice to have
Experience selling to insurance companies.
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.
This role is not a fit if
You need an inbound pipeline to reach your number, as we have no SDR function today.
You are looking for a finished playbook, since much of the enterprise motion here is still being built.
You rely on brand recognition to open doors, since many of your prospects don't know us yet.
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 CEO, your manager, has led every enterprise relationship we have today and will be in your deals with you.
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.
What success looks like
In the first 90 days
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.
Run early discovery and business-case work with the CEO and the wider team in active cycles.
Ship v1 sales artifacts with product marketing: segment narrative, discovery notes, business-case template, and ROI model.
In 6-12 months
Carry a credible path against a $1.3M to $1.5M annual quota, with a forecast that the company can plan against.
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.
Turn repeated learning from live cycles into enablement that the next enterprise sellers can use.
Help shape Terminal's enterprise sales motion without adding process for its own sake.
Practical details
Location: Toronto-based.
Travel: regular US travel, roughly six to eight trips a year for conferences and customer onsites.
Reports to: CEO.
Quota: $1.3M to $1.5M annual quota.
Sales motion: enterprise net-new, with usage-based commercial terms and support from engineering, operations, product marketing, and post-sales.
Compensation
On-target earnings: $260,000-$300,000, split 50/50 between base salary and variable.
Meaningful equity, plus the benefits below.
Commission is uncapped with accelerators above quota. 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.
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
Intro call (30 min)
Deal retrospective interview (60 min)
Account planning + discovery working session (90 min)
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.