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Founding Account Executive
LOCATION
Toronto, ON
EMPLOYMENT TYPE
Full-Time
DEPARTMENT
Sales
About Ultrassure
Ultrassure is building AI-powered contract intelligence for the insurance and reinsurance industry. Our platform is trusted by insurers, MGAs, brokers, and reinsurers processing $10B of platform premium across Canada, the United States, the Caribbean, and the United Kingdom. We've raised a pre-seed round and are on track to close our seed this summer. We're a small, focused team that ships daily and moves fast.
The Role
We're looking for a Founding Account Executive to be our first sales hire. Founder-led sales has gotten us here—design partnerships with major reinsurers, a growing pipeline, and more inbound than we can handle. Now we need someone to own the sales motion and scale it.
You'll run the full sales cycle: prospecting, discovery, demos, negotiation, and close. You'll sell to underwriters, ops leaders, and C-suite at insurance carriers, MGAs, brokers, and reinsurers. This is a complex, consultative sale—you're not pushing software, you're helping buyers understand how AI changes their contract workflows.
This is a founding role. You'll shape how we sell, who we sell to, and how we position the product. If you want to build a sales playbook from scratch at a company where the product actually works, this is it.
What You'll Do
- — Own the full sales cycle from first touch to signed contract
- — Run discovery calls and product demos with insurance and reinsurance executives
- — Build and manage pipeline in collaboration with the founding team
- — Develop outbound strategies targeting carriers, MGAs, brokers, and reinsurers
- — Navigate complex enterprise buying processes with multiple stakeholders
- — Translate customer feedback into product insights for the engineering team
- — Help define pricing, packaging, and go-to-market strategy
- — Represent Ultrassure at industry events and conferences
What We're Looking For
- — 3+ years of B2B sales experience, ideally selling to insurance, financial services, or enterprise buyers
- — Track record of closing $50K+ ACV deals with complex sales cycles
- — Ability to learn a technical product and explain it clearly to non-technical buyers
- — Comfort with ambiguity—you'll build the playbook, not inherit one
- — Strong discovery skills; you listen more than you pitch
- — Experience with CRM tools and structured pipeline management
- — Insurance or reinsurance industry knowledge is a major plus
- — Based in Toronto and able to work from our Bay & King office 3 days per week
What We Offer
- — Competitive base salary plus uncapped commission
- — Meaningful equity in an early-stage company—you're the first sales hire
- — Gym and squash memberships included
- — Hybrid work with a central downtown office at Bay & King
- — Direct access to founders and influence over company direction
- — A product that sells—customers are already using it and seeing results
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