Aimed at senior executives with startup founder experience who thrive in strategic, cross-functional leadership roles requiring AI-driven business transformation.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Checkr via Greenhouse
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, Amazon, 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 USDWhat 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., name@checkr.com or name@ext.checkr.com).
Source: Checkr careers (Greenhouse)