Senior Account Executive, InsurTech

• 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, 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)

$298,642 — $351,343 USD

Pay Transparency Disclosure

One of Checkr’s core values is Transparency. To live by that value, we’ve made the decision to disclose salary ranges in all of our job postings. 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 (Remote)

$229,724 — $351,343 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 .

• Applicant Privacy Policy
• If you are a California resident or are located in Alberta or British Columbia, our Applicant Privacy Policy applies to our collection and processing of your personal information when you apply for a role with us or otherwise participate in our recruitment process.

For applicants in Massachusetts: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

*Legitimate Checkr emails will always include our official domain name after the @ symbol (e.g., [email protected] or [email protected] ).