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CardlessCardlessSan Francisco, CA

Chief of Staff, Office of the CEO

Act as a force multiplier to the CEO by solving the company's hardest, most complex interdisciplinary problems across business, product, and operations. Requires 5+ years of hard problem-solving experience, intellectual curiosity, drive, and comfort with data, writing, and technical thinking in a high-intensity onsite environment.

150k – 235k
On-site5+ YOEBusiness Operations

About the role

Responsibilities

  • Work extremely closely with the CEO as a force multiplier, tackling the hardest, most complex, and interdisciplinary problems to ensure the company runs well and succeeds.
  • Shadow the CEO to understand company operations, joining exec team meetings, external pitches, interviews, product workshops, traveling to visit partners and customers, and diving deep into key problems.
  • Solve initial problems across the business, such as rebuilding operational or product processes, designing new product features, or creating new business lines, taking items off the CEO’s plate.
  • Progress to handling increasingly complicated and impactful problems, potentially specializing in a company area, launching a new business line, or other high-impact work.

Requirements

  • Intellectual vitality and endless curiosity about building great businesses, finance, and technology.
  • Extremely driven to build an amazing company and career.
  • 5+ years of experience doing hard things (e.g., consulting, banking, engineering, product, operating, founding a company).
  • Analytical with comfort in data, combined with intuitive thinking.
  • Use writing as a tool to think precisely and clarify messy problems.
  • Technical way of thinking.
  • Move quickly, take ownership, and feel compelled to fix issues.
  • Humility.
  • Willingness to work long hours, often on weekends (Sundays but not Saturdays), and lean into discomfort for continuous learning and growth.

Nice-to-Haves

  • Experience that builds problem-solving skills across diverse domains.

Compensation

  • Annual starting salary range of $150,000–$235,000 + equity + benefits.
  • Benefits include: meaningful start-up equity, 100% health/vision/dental for primary coverage, 75% for dependents, catered lunches, $250/month commuter benefit, parental leave, team events, flexible PTO (min 15 days), Apple equipment, 401k plan.
  • Headquartered in San Francisco with relocation assistance available.

Skills

Problem SolvingData AnalysisTechnical ThinkingBusiness StrategyWritingLeadership
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