Chief of Staff

About Checkr
Checkr is building the data platform to power safe and fair decisions. Checkr’s innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted workplaces and communities. Checkr has over 100,000 customers including Amazon, DoorDash, Netflix, Kimpton, 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.

Reporting to and as a strategic extension of the CEO, the Chief of Staff will be a force multiplier for Checkr’s leadership team. You will lead a range of initiatives, from accelerating company-level AI transformations, to shaping new product lines, and supporting M&A. As the right hand to the CEO, you will collaborate with Checkr’s executive team to drive strategic alignment, set priorities, and boost productivity across the business.

What you bring

Strategic thinking

• Strategic pattern-matching across ambiguous, evolving problems, often in low-information environments. Zooms out to see the system at the meta level, zooms in as needed to execute

• Strong data analysis and problem-solving skills

• Exceptional written communication. Can turn ambiguity into a clear one-pager

Leadership and execution

• Proven experience leading cross-functional teams and bootstrapping initiatives from zero to one

• Track record of planning and executing strategic initiatives with operational excellence

• Track record of using AI to deliver impact

• Earns trust quickly with executives, board members, and external stakeholders

• 10+ years of experience working at an executive level or equivalent track record

Bonus

• Entrepreneurial and product leadership background

• Consulting experience

Responsibilities

Lead strategic initiatives

• Lead the CEO's highest-priority initiatives, end to end, from planning through execution

• Stand up new functions, products, or business lines from zero to one

• Pressure-test strategy with customer, competitive, and market research

Extend the CEO

• Serve as a proxy for the CEO in internal and external meetings

• Collaborate tightly with other executive direct reports with a one team mentality

• Lead functions or initiatives during transitions or while key roles are being hired

• Take the pulse of the company and surface what the CEO needs to hear

• Collaborate with and coach other Checkr leaders

Drive operational excellence

• Optimize current processes and drive efficiency

• Improve communication and coordination across strategic initiatives

• Effectively communicate complex topics to junior and executive audiences alike

• Build presentations and financial models that frame critical decisions, including investor pitch decks and company narratives for external communications.

What you’ll get

• 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

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 (San Francisco, CA)
$238,000—$280,000 USD

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.

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