Chief of Staff

Checkr • San Francisco, CA

1d • Hybrid

About The Position

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.

Requirements

• 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

Nice To Haves

• 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.

Benefits

• 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
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed