Founding Account Executive

In Office (Toronto or NYC) Full Time Compensation: $130,000-140,000 OTE with uncapped commission; 0.15% equity About Starboard Starboard is building the default agentic OS for global trade. We’re used by freight forwarders around the world to quote faster, procure smarter, and operate with AI-level efficiency. Today, our platform reads unstructured rate sheets, interprets customer emails, automates sourcing, generates quotes, and connects forwarders to a powerful digital procurement network to help them get the best rates in a fraction of the time. Our vision is to build the automated global marketplace for freight. We’ve raised over $5.5M from top investors including Eclipse Capital, Garuda Ventures, OTPP and Everywhere Ventures and are HQ’d in Toronto and NY. We’re scaling rapidly across the North American market, and this role directly drives that growth by owning revenue and customer expansion. The Role We’re looking for an Account Executive to own full-cycle revenue generation for Starboard across North America, with a primary focus on SMB and mid-market freight forwarders. You will be responsible for converting qualified opportunities into long-term customers while helping shape our sales motion, messaging, and product feedback loops. This is a builder AE role designed for someone who wants to help define how modern AI-driven freight software is sold, not just execute an existing playbook. In this role you will:
Run discovery, product demos, technical validation, and commercial negotiations with prospects from initial qualification through to close.
Build ROI-driven business cases that tie automation to revenue growth, margin expansion, and operational efficiency.
Partner with BDRs to refine outbound targeting, messaging, and qualification criteria.
Work closely with founders, product, and engineering to relay customer feedback and influence roadmap priorities.
Help create and iterate sales collateral, demo flows, pricing strategy, and objection handling frameworks. Why you should join us:
You will own real revenue impact and help shape how AI software is sold into one of the world’s largest and most operationally complex industries.
Work directly with founders in a high-accountability, high-velocity culture.
Help modernize a massive, underserved $2T+ global trade market.
Play a foundational role in building Starboard’s early sales team with clear growth paths into leadership or strategic sales roles. Qualifications
3 - 5+ years experience in SaaS sales, Account Executive, or full-cycle closing role.
Track record of consistently hitting or exceeding quota in a closing role.
Strong discovery and consultative selling skills, with ability to translate operational problems into software solutions.
Comfortable selling technical or AI-driven products that require customer education and workflow change.
Highly organized with strong pipeline management, forecasting discipline, and CRM hygiene.
Builder mindset. You want to shape the sales motion, not just execute it.
High ownership and urgency. You thrive in fast-moving startup environments with ambiguity and accountability. Nice to Haves
Experience selling to freight forwarders or supply-chain teams.
Experience selling AI SaaS or agent-assisted products.
Experience running short, high-velocity sales cycles (30-45 days).
Early-stage startup experience is an asset. Benefits
Compensation: $130,000-140,000 OTE with uncapped commission; 0.15% equity
Daily paid lunches in office
Company provided laptop and equipment