Ultrassure is building the AI operating system for insurance and reinsurance, from submission to settlement. 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. We're a small, focused team that ships daily and moves fast.
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 work, from submission to settlement.
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 contractRun discovery calls and product demos with insurance and reinsurance executivesBuild and manage pipeline in collaboration with the founding teamDevelop outbound strategies targeting carriers, MGAs, brokers, and reinsurersNavigate complex enterprise buying processes with multiple stakeholdersTranslate customer feedback into product insights for the engineering teamHelp define pricing, packaging, and go-to-market strategyRepresent Ultrassure at industry events and conferencesWhat we're looking for
3+ years of B2B sales experience, ideally selling to insurance, financial services, or enterprise buyersTrack record of closing $50K+ ACV deals with complex sales cyclesAbility to learn a technical product and explain it clearly to non-technical buyersComfort with ambiguity. You'll build the playbook, not inherit one.
Robust discovery skills;
you listen more than you pitchExperience with CRM tools and structured pipeline managementInsurance or reinsurance industry knowledge is a major plusBased in Toronto and able to work from our Bay & King office 3 days per weekWhat

we offer

Competitive base salary plus uncapped commissionMeaningful equity in an early-stage company as the first sales hireGym and squash memberships includedHybrid work with a central downtown office at Bay & KingDirect access to founders and influence over company directionA product that sells. Customers are already using it and seeing results.
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📌 Founding Account Executive (Winnipeg)
🏢 Ultrassure
📍 Winnipeg