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 quick.
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 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 as 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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📌 Founding Account Executive (Ontario)
🏢 Ultrassure
📍 Ontario