The Role
Lead go-to-market at an AI-native commercial insurance startup: own partnerships, events, outbound, direct sales, and hiring BDRs. Run data-driven experiments, convert customers, and build scalable growth motions alongside founders to drive revenue and expand verticals.
Summary Generated by Built In
About Coverwatch
The Role
What you'll own
You
Compensation
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.
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.
- 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.
- 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.
- $120K to $160K base, $170K to $220K OTE
- 0.5% to 1% equity, real founding-level ownership
- Healthcare coverage
The base pay range for this role is $120,000 – $160,000 per year.
Skills Required
- Experience at a top management consulting firm (McKinsey, BCG, Bain) or equivalent strategic consulting experience.
- Experience at high-growth, operations-heavy companies, Chief of Staff at growth-stage company, or prior founder.
- Proven track record building GTM motions, signing partners, planning conferences, or running vertical-focused growth programs.
- Direct sales experience selling to B2B customers and handing leads to operations/risk teams.
- Outbound channel experience: email, LinkedIn, cold calling, and working within a CAC model.
- Experience hiring, managing, and scaling BDR teams.
- Willingness and ability to travel frequently for events (potentially cross-country every other week).
- Located in and able to work in-person in San Francisco.
- Strong quantitative, structured thinking with bias for action and experimentation.
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The Company
What We Do
Coverwatch is an AI-native commercial insurance brokerage and risk management platform built for modern businesses. It serves as an intermediary between clients and insurance carriers, offering smarter, faster risk management with quotes delivered within 24-48 hours. The company focuses on simplifying insurance for businesses managing real commercial risks, including specialization in hard-to-place and complex risk, powered by a combination of experts and world-class AI.
