Senior Account Executive, Insurance

About Checkr
Checkr is building the data platform to power safe and fair decisions. Over 140,000 companies and millions of people rely on Checkr for AI verification in the moments that matter most: getting a new job, a new place to live, a car ride, childcare, even a date. Customers include Uber, Pennymac, Airbnb, Doordash, Amazon, and Anthropic.
We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.
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.
Pay Transparency Disclosure
We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website.
On-target Earnings OR Base Salary range (San Francisco, CA)
$258,000—$304,000 USD
What We Offer
A fast-paced and collaborative environment
Learning and development allowance
Competitive cash and equity compensation, and opportunity for advancement
100% medical, dental, and vision coverage
Up to $25K reimbursement for fertility, adoption, and parental planning services
Flexible PTO policy
Monthly wellness stipend
 
At Checkr, we believe an in office work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. Individuals are expected to work from the office 3+ days a week. In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.
Equal Employment Opportunities at Checkr
Checkr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.
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