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.
About the job
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 Analysis, AI, Financial Modeling, Strategic Planning, Cross-Functional Leadership, Presentations, Market Research, Operational Excellence, Written Communication, Problem-Solving
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