Chief of Staff - Future Opportunities

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

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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, 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, performance-based compensation, and meaningful equity packages.
Pomelo works directly with candidates throughout the search process to identify opportunities that align with their background, career goals, and interests.