Founding GTM Lead

Founding GTM Lead

Toronto · Full-time · Competitive base + uncapped commission + equity

About Ultrassure

Ultrassure is building the AI system of work for commercial insurance.

Insurance is a multitrillion-dollar global industry, but much of it still runs on PDFs, spreadsheets, email and legacy software. We build AI-native software that helps insurers, reinsurers, MGAs and brokers turn complex, unstructured insurance data into structured information, automated workflows and better decisions.

Our platform is used by insurance organizations across Canada, the United States, the United Kingdom, Bermuda and the Cayman Islands. More than $10 billion of premium already flows through the platform.

Our ARR has grown 23× since April, driven by word of mouth, personal connections and a handful of targeted LinkedIn conversations.

We are now hiring our Founding GTM Lead to help turn that early traction into a repeatable approach to finding and winning customers.

We are a small, focused team in downtown Toronto. We ship every day, work closely with our customers and care about building useful software.

The Role

You will work directly with our founder and CEO to build Ultrassure’s go-to-market motion.

You will help determine who we target, how we position the product, how we start conversations and how we turn those conversations into paying customers.

This is a hands-on, quota-carrying role. You will personally prospect, run discovery, demonstrate the product, manage pilots and close business while building the processes, tools and playbook that future hires will use.

Our sales cycles are typically two to three months. You will work with experienced insurance professionals and senior decision-makers who expect thoughtful questions, a strong understanding of their workflows and clear business value.

The product is live and customers are paying. You will join at the stage where individual execution and commercial judgment can meaningfully shape the company.

What You Will Do

• Build pipeline through targeted outbound, LinkedIn, referrals, partnerships, industry events and inbound opportunities.
• Identify promising customer segments, buying signals and use cases.
• Develop and test positioning, messaging and outreach.
• Own the full sales cycle from first contact through signed agreement and paid conversion.
• Run discovery that uncovers customer priorities, workflows, decision-makers and purchasing processes.
• Deliver tailored demonstrations across underwriting, contracts, claims, accounting and operations.
• Manage pilots with clear success criteria, engaged stakeholders and an agreed path to a commercial decision.
• Build relationships with users, internal champions, executives, IT, security and procurement.
• Work with our founder on pricing, proposals, negotiations and strategic accounts.
• Build practical sales materials, customer stories and business cases.
• Establish CRM discipline, pipeline reporting and forecasting.
• Use AI tools extensively for account research, preparation, outreach and follow-up.
• Bring customer feedback to the product team and help identify patterns across opportunities.
• Document what works and build the foundation for future GTM hires.

What We Are Looking For

We care about your ability to create opportunities, earn trust and close business.

You should have:

• Experience selling B2B software and owning opportunities through to close.
• Evidence that you can source and win your own customers.
• Strong discovery, demonstration, communication and negotiation skills.
• The ability to understand complex workflows and explain software clearly.
• Experience navigating deals involving multiple stakeholders.
• Strong commercial judgment and an instinct for focused, practical experiments.
• Comfort writing outreach, building a presentation, configuring a CRM and running a customer meeting yourself.
• Curiosity about AI and a willingness to learn the product deeply.
• High ownership, consistent follow-through and comfort operating with limited direction.
• The ability to work from our office at Bay & King in downtown Toronto.
• Legal eligibility to work in Canada.

You do not need to have held a GTM Lead title before. You might be an exceptional AE who has helped build an early sales motion or an early commercial hire who has taken a product from initial traction to repeatable sales.

We care most about what you have personally built, tested and sold.

Bonus Points

We would be particularly interested if you have experience with:

• Insurance, reinsurance, fintech or other regulated industries.
• AI software or products that change established business workflows.
• Joining a startup before its sales playbook was fully developed.
• Building outbound pipeline without a large marketing team.
• Managing customer pilots and evaluations.
• Developing referral or partnership channels.
• Selling internationally.

Insurance experience is helpful, but curiosity, commercial judgment and the ability to learn quickly matter more.

Why Ultrassure

Real customers and strong momentum

Our ARR has grown 23× since April through relationships, referrals and limited outbound. You will build a deliberate GTM effort on top of that traction.

A significant market opportunity

Commercial insurance is a global industry with complex workflows and substantial demand for better tools.

Work directly with the founder

You will work alongside a founder with insurance and reinsurance experience who remains closely involved in customer relationships and major deals.

Help shape the product

Customer conversations directly influence what we build. You will work with engineers who act quickly on feedback and regularly turn customer requests into production features within days.

Build the GTM function

You will have meaningful influence over our targeting, positioning, sales process and commercial strategy, with opportunities to take on greater responsibility as the company grows.

Meaningful ownership

Competitive base salary, uncapped commission with accelerators for exceeding targets and meaningful equity in a seed-stage company.

Downtown Toronto

We work together from our office at Bay & King. Gym and squash memberships are included.

How to Stand Out

Show us how you create and win opportunities.

Tell us about a customer you won from a cold start. How did you identify them, get their attention, uncover the need and close the deal?

Or choose an insurance organization you think should use Ultrassure. Tell us who you would approach, what problem you would lead with and what your first message would say.

Keep examples anonymized and leave out confidential information. We care about your thinking, judgment and execution.