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CheckrCheckrSan Francisco, CA

Chief of Staff

Strategic right-hand to the CEO leading high-priority initiatives like AI transformations, new product lines, and M&A. Drives operational excellence, extends CEO presence, and collaborates with executives using strong data analysis, AI, and leadership skills. Requires 10+ years executive experience.

238k – 280k
Hybrid10+ YOEExecutive Leadership

About the role

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

  • 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

Skills

Data AnalysisAIFinancial ModelingStrategic PlanningCross-Functional LeadershipPresentationsMarket ResearchOperational ExcellenceWritten CommunicationProblem-Solving

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