Founding Account Executive

Ultrassure Inc.; Toronto; Hybrid; CAD 90,000 - 180,000; Full time

Benefits offered by this job

Equity stake

Gym and squash memberships

Hybrid work with Bay & King office

Direct access to founders

Job summary

Ultrassure is building the AI operating system for insurance and reinsurance, and seeks a Founding Account Executive to be the first sales hire. You will own the full sales cycle from prospecting to close, engaging underwriters, ops leaders, and C-suite with complex, consultative selling.

This founder-led role shapes how we sell, who we target, and how we position the product. Hybrid work with downtown Toronto office; equity opportunity included.

Qualifications

• 3+ years of B2B sales experience, ideally in insurance 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.

Responsibilities

• 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.

Skills

B2B Sales

ACV 50K+

CRM tools

Pipeline management

Insurance industry knowledge

Tools

CRM software

Job description

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 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.