Opportunity

Enterprise AE at Checkr | $350K OTE Fintech Sales in Columbus

Location Columbus
Company Checkr
Source weworkremotely
Posted 2026-10-23 07:31:21

Career & Market Insight

This is a high-ceiling enterprise sales role at a well-funded, YC-backed fintech (Forbes Cloud 100 2025) operating within a $5B+ disruption opportunity in employment and income verification for mortgage lending. The "startup within a startup" framing is genuine — Truework operates with autonomy inside Checkr, meaning you get startup-speed execution with the credibility and resources of an established brand.

Compensation benchmarking: The remote OTE of $229K–$351K is above market for strategic enterprise AE roles in SaaS/fintech, where typical OTE ranges $200K–$280K at this level. The SF range topping at $351K is particularly competitive. Equity is also offered, adding further upside.

Skills you'll develop:

  • Enterprise deal strategy in a regulated, high-stakes vertical (mortgage/lending)
  • MEDDPICC and Force Management methodologies — highly transferable and market-valued
  • Executive-level selling (CXO/EVP relationships), a career accelerant for future VP Sales or CRO paths
  • Cross-functional leadership across marketing, product, and CS in a scaling org

Green flags: Transparent salary disclosure, strong benefits (100% health coverage, $25K fertility/adoption support), flexible PTO, and a mission-driven product in a non-commoditized space. Forbes Cloud 100 recognition signals real market traction.

Potential considerations: The 3+ days/week in-office expectation for hub employees could limit flexibility. Also, commission structure details aren't disclosed — clarify split between base and variable in your recruiter discussion. The role requires a self-starter who can build pipeline independently, so weak SDR support could be a headwind.

Headquarters: Remote, United States; San Francisco, California, United States

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 Role

Truework, recently acquired by Checkr, provides access to crucial employment, income, and asset information needed for mortgage loans, apartment rentals, background checks, and more. We are disrupting a $5B+ industry, dominated by legacy incumbents and outdated processes, with a better product and intense customer focus. Within Checkr, Truework operates independently, allowing rapid iteration while also being able to leverage the strengths and assets from our core business. Think of it like joining a startup within a startup!

As a Strategic Account Executive on the Truework team, you'll help scale our impact across large national and regional lenders, with a primary focus on acquiring new clients to Truework Verification services. As automated verification services become a more common practice for lenders, you'll lead the charge in building and executing a repeatable playbook to drive new customers who will grow with us for years to come. By deeply understanding their unique company challenges and goals, you will pair them with solutions that will help them reach their business objectives and innovate within their organizations.

This role is ideal for a proven sales professional who:

  • Has experience selling transformational solutions to customers, where you can quickly identify and pattern-map where and how the Truework solution can drive impact in a customer's operation
  • Has experience identifying and building relationships with decision makers, business and technology influencers and users, closing 6- and 7-figure pursuits
  • Thrives in a fast-paced, highly collaborative environment — ready to help close the gap between legacy solutions and the competitive, streamlined processes lending teams want to deliver for consumers

You will be an important part of an elite, professional, and rapidly growing cross-functional team that succeeds through collaboration, grit, and learning.

What You'll Do

Deliver Sales Excellence:

  • Consistently achieve pipeline and revenue targets by applying modern sales techniques and processes to efficiently manage top-of-funnel engagement tactics, deal strategy, and close processes
  • Think outside the box to cultivate awareness of the Truework vision; plan and execute targeted campaigns for your territory working with the marketing and partner teams to scale your coverage and build pipeline
  • Partner with and guide the efforts of our internal team to support your accounts in pre-sales activities and deployment to execute on agreed-upon account goals, strategies, and tactics for growth
  • Leverage analytics, case studies, past performance, and market intelligence to create a territory plan and craft your own target account strategies

Manage Account Relationships:

  • Understand the lender's operation and identify the varying use cases where verification services can drive impact
  • Exhibit deep and up-to-date knowledge of our product portfolio in order to communicate the benefits of new features and enhancements
  • Show proficiency in navigating buy-team personas, with intentional activities for executive bridging and champion building

Exhibit Industry- & Customer-Specific Business Acumen:

  • Actively understand each customer's strategic growth plans, technology footprint, internal challenges, and competitive landscape
  • Review public information (e.g., new executive appointments, earnings statements, press releases) to stay updated on key industry trends and issues impacting the prospect
  • Identify and discover centers of value for lenders, and conduct analysis to quantify ROI and impact of our solution on their operation

Be a Good Teammate:

  • Represent both market trends and client needs to the Executive and Product teams to ensure we are serving current needs well and evolving our products and portfolio for future client needs
  • Show unparalleled grit — constantly experiment, be willing to pivot, and have resiliency regardless of the obstacles faced

What You Bring

  • 5+ years of full-cycle sales experience, selling transformative technology solutions
  • Experience closing new business accounts and building pipeline using modern marketing tactics
  • Experience selling to EVPs, CXOs, and end-users (in the same sales cycle) in both individual and team sales environments
  • Ability to navigate large organizations' political landscape to maintain and expand relationships at all levels
  • General knowledge of common sales practices like MEDDPICC, Command of the Message (Force Management), Challenger, Power Selling, or others
  • Excellent written and verbal communication skills — able to simplify complex topics in a friendly and approachable manner, and present executive-level business cases
  • Ability to juggle and complete multiple priorities and projects (internally and externally) in a fast-paced environment
  • Smart, self-motivated, organized, disciplined, inquisitive, detail-oriented, and process-oriented; ownership mentality within all aspects of your work
  • A growth mindset that is always learning, growing, and actively seeking feedback
  • A team-first mentality — you show up for your team and expect the same in return; you enjoy planning, adjusting, executing, winning, and celebrating as a team
  • An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes

Pay Transparency Disclosure

Checkr uses geographic cost of labor as an input to develop ranges for roles, and 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

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]).

To apply: https://weworkremotely.com/remote-jobs/checkr-strategic-account-executive

Frequently Asked Questions

Is this role fully remote or does it require being in an office?
The role can be fully remote within the United States. However, if you work near one of Checkr's hub locations (Denver, San Francisco, Nashville, or Santiago), you'd be expected in-office 3+ days per week. A separate remote pay range is published for those working fully remotely.
What is the on-target earnings (OTE) for this Strategic Account Executive role?
The OTE range for fully remote candidates is $229,724–$351,343 USD annually. For San Francisco-based candidates, the range is $298,642–$351,343 USD. Geographic cost of labor is used to set the exact range for your location.
What sales methodology experience is preferred for this role?
Checkr values familiarity with modern enterprise sales frameworks such as MEDDPICC, Command of the Message (Force Management), Challenger, or Power Selling, though they are open to candidates experienced with similar methodologies.
What industry or vertical experience is most relevant for this position?
Experience selling to mortgage lenders, financial institutions, or in fintech/proptech is highly relevant, as the role focuses on acquiring national and regional lenders as clients for Truework's employment and income verification services.
What benefits does Checkr offer for this role?
Checkr offers 100% medical, dental, and vision coverage, flexible PTO, a monthly wellness stipend, a learning and development allowance, equity compensation, and up to $25,000 in reimbursement for fertility, adoption, and parental planning services.
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