Senior Account Executive, Insurance

Checkr; Chicago (IL); On-site; USD 299,000 - 351,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Learning and development allowance

Competitive cash and equity

Fertility/ Adoption support

Flexible PTO

Job summary

Checkr is seeking a Senior Account Executive to own the insurance vertical, leveraging established relationships to accelerate pipeline and close multi-stakeholder deals. You will educate the market on Checkr Trust’s insurance offerings and translate value into underwriting and risk-management terms.

You will operate with founder-like ownership within a startup framework, backed by Checkr’s resources, and pursue long-term impact over short-term wins.

Qualifications

• 5–7+ years of full-cycle, quota-carrying sales experience in insurance.
• Deep roots in the insurance industry with carrier/MGA/program administrator exposure.
• Proven track record closing six- or seven-figure deals with multiple stakeholders.

Responsibilities

• Own the insurance vertical and define ICPs across buyers and platforms.
• Leverage relationships to accelerate pipeline and shorten cycles.
• Own the deal lifecycle from outreach to close with multi-threaded stakeholders.
• Educate the market on the category, translating value to underwriting and risk terms.
• Collaborate cross-functionally to shape insurance win strategies.

Skills

Full-cycle sales

Quota carrying

Insurance industry

Six-figure deals

AI tactics

Startup experience

Autonomy

Job description

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 .

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

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

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