Chief of Staff

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.

Responsibilities

Lead the CEO's highest-priority initiatives, end to end, from planning through execution; Pressure-test strategy with customer, competitive, and market research; 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; 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

Requirements

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

Nice to have

Startup founder experience strongly preferred

Benefits

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; In-office perks such as lunch five times a week, commuter stipend, and abundance of snacks and beverages; Relocation stipend may be available