Senior Account Executive, Insurance

About Checkr
Checkr is building the data platform to power safe and fair decisions. Over 140000 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.

Were a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes CloudList and is a Y Combinator 2024 Breakthrough Company.

About the team/role

Checkr Trust is not a typical sales role. Its a chance to help build an entirely new business inside a category-defining company and were 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 wont 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 Youll 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 Trusts 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 Were Looking For

You are someone who:

• Has 57 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 Trusts 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 werent 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 dont 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 quarters 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.

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 -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 Franciscos Fair Chance Ordinance.

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