Enterprise Account Executive

About Terminal Terminal 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.com Note: This role is only available to Toronto/GTA-based candidates What You'll Do Drive $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 strong sales pipeline and forecasting hygiene. Always provide a pragmatic view of your book of business with a proactive understanding of what are the key risks to each deal. Sell into enterprise and smaller business across various industries including auto insurance, software, financial services and logistics at deal sizes of $25k to $250k+. Build deep relationships with executives, technology leaders, engineers and data specialists (e.g. CEOs, VPs, Product Managers, Tech Leads, Data Scientists, etc.). Earn trust with stakeholders through your 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 help improve our product offering and identify opportunities for new use cases that expand our total addressable market. What You'll Need 6+ years of account executive experience. 3+ years of enterprise sales experience. Strong sales fundamentals with a track record of running complex multi stakeholder deals and owning the end-to-end sales 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 4X a week. Nice-to-Haves Strong 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. Compensation On-Target-Earnings (base + variable): $180,000 to $200,000. The Interview Process Screener 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 Get 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