Founding Account Executive

Terminal (YC S23); Toronto; On-site; CAD 160,000 - 200,000; Full time

Job summary

A leading company in commercial trucking seeks its first Account Executive to spearhead sales efforts in the Toronto area. This role offers a lucrative compensation package, strong growth opportunities, and the chance to work directly with executive leadership in a vibrant startup environment. With a focus on outbound sales, you’ll own significant revenue goals while establishing deep customer relationships across various sectors.

Benefits

Equity options (0.25% - 0.50%)

Top-tier health and dental benefits

Flexible healthcare spending account

Professional development spending account

Four weeks paid time off plus statutory holidays

Brand new MacBook and computer equipment

Qualifications

• 3+ years of account executive experience required.
• Experience with B2B SaaS products and enterprise sales is essential.
• Strong communication and coaching skills preferred.

Responsibilities

• Own and drive at least $1M in annual revenue, focusing 90% on outbound sales.
• Manage full sales cycle from prospecting to closing.
• Provide feedback to engineering to enhance product offerings.

Skills

Communication

Proactivity

Sales Strategy

Technical Proficiency

Relationship Building

Job description

Become the first AE at Terminal and accelerate your sales career!

Since finishing YC, we’ve grown more than 15x and onboarded publicly traded companies—all without a single sales hire or outbound motion. We have more opportunities than we can follow up with. It’s time to bring on our first AE.

Terminal is Plaid for Telematics in commercial trucking. Companies building the next generation of insurance products, financial services and 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 team is based in Toronto, Canada (180 John Street).

Note : This role is only available to Toronto / GTA-based candidates

Responsibilities

• Own and drive at least $1M in annual revenue, with quotas confirmed quarterly and measured monthly.
• 90% outbound, 10% inbound—this role is for a hunter.
• Own the full sales cycle : prospecting, discovery, value-building, closing, and account expansion.
• Selling into mid-market and enterprise companies across insurance, software, financial services and logistics at deal sizes ranging from $30K to $300K.
• Build deep relationships with engineers, product leaders and executives (e.g. CTOs, VP Product, VP Data Science, etc.)—become a trusted product specialist and subject matter expert to our customers.
• Work directly with our CEO to refine our sales strategy, iterate on messaging, and build upon sales systems, tools and processes.
• Provide structured feedback to engineering to help improve our product and identify opportunities for new use cases that expand our total addressable market.
• Maintain sales pipeline and forecasting hygiene—always providing a realistic view with an understanding of what could accelerate or put key deals at risk

Requirements

• 3+ years of account executive experience
• 1+ year of enterprise sales experience
• Experience selling B2B SaaS products
• Proficiency in technical products and APIs
• A fearless hunter mentality and a track record of quickly building pipeline
• Track record of being extremely proactive and always having next steps in mind
• Strong communication skills–both verbal and written
• Willingness to both coach and be coached
• Previous experience in early-stage startups
• Located in Toronto and able to commute to the office 5X a week

Nice-to-Have

• Previous experience selling to insurance companies or financial institutions

Compensation

• On-Target-Earnings (base + variable) : $160,000 - $200,000 CAD
• Equity : 0.25% - 0.50%
• 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