Chief of Staff candidates partner with founders and executives on strategic and operational initiatives. Responsibilities include analyzing business questions, building financial models, conducting market and financial analysis, managing cross-functional projects, preparing executive communications, establishing operating processes, and solving ambiguous problems. Candidates must have 2–4 years of experience at a top-tier consulting firm or investment bank, strong analytical and communication skills, and willingness to work in major startup hubs.
ABOUT US
Pomelo is a boutique NYC-based staffing company. We began as an offshore recruiting firm and have recently evolved into an executive search firm that places top-tier US-based business generalists (former consultants and investment bankers) in operating roles at leading startups and high-growth companies across the US. We work with some of the fastest-growing tech companies and iconic consumer brands, from New York to San Francisco.
ABOUT THE ROLE
We are building a pool of exceptional Chief of Staff candidates for opportunities at leading startups and high-growth companies across the US. Chiefs of Staff work closely with founders, CEOs, and executive teams to drive high-priority initiatives, solve complex business problems, and help the company operate more effectively. This is a highly cross-functional role that can span strategy, operations, special projects, business development, finance, and organizational planning. We are specifically looking for candidates with a strong business generalist background, particularly former management consultants or investment bankers who have demonstrated exceptional analytical, communication, and problem-solving skills. As opportunities arise, selected candidates will be considered for Chief of Staff roles that match their experience, interests, and career goals.
KEY RESPONSIBILITIES
QUALIFICATIONS
Pomelo is a boutique NYC-based staffing company. We began as an offshore recruiting firm and have recently evolved into an executive search firm that places top-tier US-based business generalists (former consultants and investment bankers) in operating roles at leading startups and high-growth companies across the US. We work with some of the fastest-growing tech companies and iconic consumer brands, from New York to San Francisco.
ABOUT THE ROLE
We are building a pool of exceptional Chief of Staff candidates for opportunities at leading startups and high-growth companies across the US. Chiefs of Staff work closely with founders, CEOs, and executive teams to drive high-priority initiatives, solve complex business problems, and help the company operate more effectively. This is a highly cross-functional role that can span strategy, operations, special projects, business development, finance, and organizational planning. We are specifically looking for candidates with a strong business generalist background, particularly former management consultants or investment bankers who have demonstrated exceptional analytical, communication, and problem-solving skills. As opportunities arise, selected candidates will be considered for Chief of Staff roles that match their experience, interests, and career goals.
KEY RESPONSIBILITIES
- Partner with founders, CEOs, and senior executives on high-priority strategic and operational initiatives
- Analyze complex business questions, build financial models and business cases, and translate data into actionable recommendations
- Own cross-functional projects from strategy through execution, coordinating stakeholders and driving initiatives forward
- Conduct market, competitive, customer, and financial analysis to support key business decisions
- Prepare executive-level presentations, analyses, memos, and communications
- Establish processes, reporting, and operating cadences that help companies scale effectively
- Identify and solve ambiguous business problems with limited direction or established playbooks
- Support special projects across functions including strategy, operations, finance, product, sales, and business development
- Serve as a trusted thought partner to senior leadership and help ensure key priorities continue moving forward
QUALIFICATIONS
- 2-4 years of experience at a top-tier management consulting firm or investment bank required
- Exceptional candidates may have additional experience at a high-growth startup, technology company, or other operating environment
- Demonstrated ability to solve complex, ambiguous problems with limited direction
- Excellent analytical, financial modeling, and quantitative skills
- Exceptional written and verbal communication skills
- Strong executive presence and ability to communicate effectively with senior leaders.
- Highly organized, proactive, and comfortable managing multiple high-priority initiatives simultaneously
- Ability to operate effectively in fast-paced, ambiguous environments
- Bachelor's degree from a strong academic institution
- Willingness to work in NYC, San Francisco, Los Angeles, or other major startup hubs depending on the specific opportunity
COMPENSATION & BENEFITS
Compensation will vary by company, seniority, and location. Typical Chief of Staff opportunities in our network offer competitive base salary and bonuses.
Pomelo works directly with candidates throughout the search process to identify opportunities that align with their background, career goals, and interests.
Pomelo San Francisco, California, USA Office
San Francisco, CA, United States
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What you need to know about the San Francisco Tech Scene
San Francisco and the surrounding Bay Area attracts more startup funding than any other region in the world. Home to Stanford University and UC Berkeley, leading VC firms and several of the world’s most valuable companies, the Bay Area is the place to go for anyone looking to make it big in the tech industry. That said, San Francisco has a lot to offer beyond technology thanks to a thriving art and music scene, excellent food and a short drive to several of the country’s most beautiful recreational areas.
Key Facts About San Francisco Tech
- Number of Tech Workers: 365,500; 13.9% of overall workforce (2024 CompTIA survey)
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- Notable Investors: Sequoia Capital, Andreessen Horowitz, Bessemer Venture Partners, Greylock Partners, Khosla Ventures, Kleiner Perkins
- Research Centers and Universities: Stanford University; University of California, Berkeley; University of San Francisco; Santa Clara University; Ames Research Center; Center for AI Safety; California Institute for Regenerative Medicine
