About TerminalTerminal is Plaid for Telematics in commercial trucking. Companies building the next generation of insurance products, financial services and fleet software for trucking use our Universal API to access GPS data, speeding data and vehicle stats. We are a fast‑growing, venture‑backed startup supported by top investors including Y Combinator, Golden Ventures and Wayfinder Ventures. Our exceptionally talented team is based in Toronto, Canada.For more info, check out our website: https://withterminal.ComNote: This role is only available to Toronto/GTA‑based candidates.What You'll DoDrive $1M in annual revenue, with quota attainment confirmed quarterly and measured monthly.Own the entire sales cycle end‑to‑end: prospect, qualify, run discovery, demo the product, build value with champions, manage complex stakeholders, close and expand accounts.Maintain a solid sales pipeline and forecasting hygiene, providing a pragmatic view of your book of business with proactive risk assessment.Sell into enterprise and smaller businesses across various industries, including auto insurance, software, financial services and logistics, with deal sizes ranging from $25k to $250k+.Build deep relationships with executives, technology leaders, engineers and data specialists (e.G., CEOs, VPs, Product Managers, Tech Leads, Data Scientists) and earn trust through industry expertise and mastery of our product offering.Regularly take initiative in refining our sales strategy, systems,



tools and processes.Provide structured feedback to engineering to improve the product and identify opportunities for new use cases that expand our addressable market.What You'll Need6+ years of account executive experience.3+ years of enterprise sales experience.Strong sales fundamentals with a proven track record of running complex multi‑stakeholder deals and owning the end‑to‑end process independently.Strong product curiosity and the ability to build deep technical acumen as a seller; you must be excited to go deep with customers, understand their use cases, data requirements and technical needs, and advise them clearly on how to get the most from our product offering.Growth mindset, very high initiative and an extremely high bar for detail.Strong communication skills, both verbal and written.Located in Toronto and able to commute to the office 4× a week.Nice‑to‑HavesStrong bonus points for founder experience and/or previous early‑stage startup experience.Undergraduate degree in a technical discipline (e.G., computer science, engineering).Previous experience selling to insurance companies or financial institutions.CompensationOn‑Target Earnings (base + variable): $180,000 to $200,000.The Interview ProcessScreener with CEO (30 min)Take‑home challenge (2‑3 hours)Sales competency interview (45 min)Final onsite at our office (120 min)Benefits You'll GetStrong compensation and equity packagesBrand new MacBook and computer equipmentTop‑tier health/dental benefits and a flexible healthcare spending accountPersonal spending account for professional development, fitness and wellnessFour weeks paid time off + statutory holidaysIn‑person culture with an office located in downtown TorontoCompensation Range: CA$180K - CA$200K#J-18808-Ljbffr

📌 Founding Account Executive - C$180,000 - C$200,000 A Year (Winnipeg)
🏢 Terminal
📍 Winnipeg