About Coverwatch
At Coverwatch we are building the next-generation AI-native commercial insurance broker. Commercial insurance is a $1T market where the core work still runs on email, PDFs, spreadsheets, and manual labor. It's the next industry that will be completely rewritten by AI. We’re a team of 2nd time founders (ex-YC) who previously built a tech-enabled services company, and worked at companies like Google and Goldman Sachs. We're backed by top investors and a group of insurance founders and operators.
The Role
This is the founding go-to-market hire. You'll work directly with the CEO and founders and own the entire growth surface area: partnerships, events, outbound, and direct selling. There's no playbook to inherit. You'll write it, prove it with numbers, hire against it, and turn it into the engine that scales.
You'll run this like a scientist. Every week you ship new campaigns, read the numbers, pour fuel on what converts, and kill what doesn't.
What you'll own
- Partnerships. Operators who sit next to our buyers across our verticals
- Events. Vertical industry shows and the niche rooms where we actually convert. You'll have the budget to be on a plane every other week when the numbers justify it.
- Outbound. Email, LinkedIn, cold calling, with the best tooling in the category to build and scale any signal-based campaign you can design.
- Direct selling. Partner with the risk advisory team to sell.
- Team. Hire and lead the first BDRs as we scale.
- Anything that works. We're rewriting how insurance gets sold. If you find an edge, take it.
You
- Raw intellectual horsepower and a bias for action.
- A structured, quantitative thinker who still moves at speed.
- You come from management consulting (McKinsey, BCG, Bain), an ops-heavy high-growth company, a chief-of-staff seat at a growth-stage startup, or a company of your own you're hungry to build again.
- You've built a pipeline, a partnership, or a growth motion from nothing, and you carry the scars and the secrets that only real experimentation teaches.
- You can hold a room with a CEO or a CFO, and you're just as comfortable inside a CAC model or grinding a customized email at midnight.
- You want scope and ownership, and you'd rather build the thing than run someone else's version of it.
Compensation
- $120K to $160K base, $170K to $220K OTE
- 0.5% to 1% equity, real founding-level ownership
- Healthcare coverage
Compensation
The base pay range for this role is $120,000 – $160,000 per year.
