Chief of Staff

Checkr; San Francisco (CA); On-site; USD 238,000 - 280,000; Full time

Benefits offered by this job

Learning and development allowance

Competitive cash and equity

Full medical, dental, vision coverage

Fertility/adoption/parential planning

Flexible PTO

Monthly wellness stipend

Job summary

Checkr is seeking a Chief of Staff to partner with the CEO and executive team to accelerate strategic initiatives, shape new product lines, and scale AI transformations across the company. You will drive high-impact programs end-to-end, aligning teams and measuring outcomes.

You will act as a trusted extension of the CEO in key discussions, help the leadership group improve processes, and support investor and executive communications with clear, concise storytelling.

Qualifications

• 10+ years of executive-level experience or equivalent track record.
• Proven ability to lead cross-functional teams and bootstrap initiatives from zero to one.
• Strong written and verbal communication; trusted with customers, executives, board, and investors.

Responsibilities

• Lead the CEO's highest-priority initiatives, end to end, from planning through execution.
• Serve as a proxy for the CEO in internal and external meetings.
• Collaborate with other Checkr leaders to drive alignment and one-team execution.
• Build presentations and financial models to frame critical decisions for investors and the company.

Skills

Leadership

Cross-functional teamwork

Strategic thinking

Data analysis

Executive communication

Startup founder experience

AI impact delivery

Tools

Excel

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.

The Chief of Staff Role

Reporting to and as a strategic extension of the CEO, you will collaborate with Checkr’s executive team to drive strategic alignment, set priorities, and help increase the speed and ambition of the business. You will lead a range of initiatives, from accelerating company-level AI transformations, to shaping new product lines, supporting M&A, and supporting enterprise sales.

What you bring

Leadership and execution

• A bias towards action, equally effective at setting direction and independently executing initiatives from start to finish
• Proven experience leading cross-functional teams and bootstrapping initiatives from zero to one
• Track record of planning and executing complex initiatives with world class project management
• Track record of using AI to deliver impact
• Earns trust quickly with customers, executives, board members, and investors
• 10+ years of experience working at an executive level or equivalent track record
• Startup founder experience strongly preferred

Strategic thinking

• Strong business experience and acumen. You love business as a science
• Strong data analysis and problem-solving skills
• Exceptional, concise written and verbal communication

Responsibilities

Lead strategic initiatives

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

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)

$238,000 — $280,000 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.

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