Chief of Staff

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