Senior Account Executive, InsurTech

About the team/role

Checkr Trust is not a typical sales role. It's a chance to help build an entirely new business inside a category-defining company — and we're going deep on insurance.

Checkr Trust accelerates solutions that detect bad actors before they impact businesses. We have early traction in the insurance space, strong product-market pull, and the backing of Checkr — but we are still building the plane while flying it.

We are looking for a Senior Account Executive who knows the insurance industry from the inside: the players, the pain points, the buying dynamics, and the relationships. Someone who can walk into a room with a carrier, MGA, or program administrator and immediately earn credibility — not because of a slide deck, but because of deep domain fluency and a trusted network.

This role is for someone who wants:

• A difficult, high-ownership role
• Ambiguity over predictability
• Accountability over excuses
• Long-term impact over short-term comfort

This is not a "manage a book of inbound" job. This is a territory-building, market-educating, first-call-to-close ownership role within the insurance vertical. You will operate like a founder inside a startup — except you have the resources of an established company behind you.

If you want something safe and structured, this won't be the right fit. If you want to build something enduring in insurance — and are willing to do the hard work required — keep reading.

What You'll Do

• Own the insurance vertical: define ICPs across carriers, MGAs, program administrators, and insurtech platforms — then build repeatable motion where none exists yet
• Leverage your existing insurance relationships to accelerate pipeline and shorten deal cycles
• Own the entire deal lifecycle — from cold outreach to multi-threaded enterprise close
• Educate the market on a category that is still forming, translating Checkr Trust's value into the language of underwriting, loss prevention, and claims risk
• Navigate complex insurance buying processes involving underwriting, compliance, legal, and executive stakeholders
• Experiment with AI to find efficiencies across your work
• Partner cross-functionally with product, legal, operations, and leadership to shape how we win in insurance
• Hit ambitious revenue targets

Your fingerprints will be on how Checkr Trust wins in insurance.

What We're Looking For

You are someone who:

• Has 5–7+ years of full-cycle, quota-carrying sales experience — hunting required
• Has deep roots in the insurance industry
• Has sold six- or seven-figure deals in complex, multi-stakeholder environments
• Understands insurance workflows well enough to connect Checkr Trust's solutions to real underwriting and risk management problems
• Has built pipeline when there was no brand awareness in a market
• Has worked in a startup or operated like you were in one
• Has outperformed targets in situations that weren't perfectly set up for you
• Has tangible examples of projects created using advanced AI tactics
• Carries an A-player mindset: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes

More importantly:

• You have grit. Your energy and work ethic raises the bar of others
• You prefer autonomy and ownership to rigid structure
• You don't wait for perfect messaging — you test, iterate, refine
• You are comfortable hearing "no" repeatedly without losing momentum
• You care about building something meaningful, not just closing this quarter's deal
• You hold yourself to a higher internal standard than anyone else will

People describe you as relentless, disciplined, competitive — but collaborative. You understand that building something valuable in a complex, regulated industry like insurance is both rewarding and uncomfortable.