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.

📌 Founding Account Executive (Canada)
🏢 Ultrassure
📍 Canada