Founder Strategy, Operations & Growth Chief of Staff
About The Position
HireNow Staffing is actively recruiting a highly driven Founder Strategy, Operations & Growth Chief of Staff to join one of our valued client partners in New York City. This is a high-leverage, high-trust opportunity working directly alongside the CEO of an early-stage AI-native consumer insurance technology company. The successful candidate will operate as an extension of the founder, taking ownership of whichever priorities matter most to the business—from fundraising and financial analysis to operations, GTM strategy, partnerships, hiring, and special projects. The scope is intentionally broad and changes quickly. One day may involve investor materials and financial modeling; the next could require evaluating vendors, improving lead conversion, supporting carrier relationships, or building a new operational process from scratch. The strongest candidate will demonstrate exceptional agency, analytical horsepower, written communication, judgment, integrity, and execution speed. This role is designed for someone who can take an ambiguous objective, determine what needs to happen, execute it independently, and then systematize or automate the solution as the company scales.
Requirements
- 1–3+ years of highly analytical professional experience, ideally within a top-tier consulting, investment banking, strategy, finance, or comparable high-performance environment.
- Exceptional new graduates with outstanding academic, analytical, and leadership credentials may also be considered.
- Strong quantitative and analytical capabilities.
- Advanced comfort working with spreadsheets, business metrics, and financial or operational models.
- Ability to independently analyze data and identify meaningful business insights.
- Exceptional written communication skills with the ability to prepare polished investor, executive, partner, and internal communications with minimal oversight.
- Demonstrated ability to operate effectively in highly ambiguous environments.
- Strong bias toward action and ability to execute without waiting for detailed instructions.
- Excellent organizational and project-management capabilities.
- Strong business judgment and ability to prioritize rapidly changing responsibilities.
- Exceptional integrity, discretion, and reliability appropriate for a highly trusted founder-facing position.
- Ability to manage multiple unrelated projects simultaneously while maintaining execution quality.
- Must currently reside in New York City or be genuinely committed to relocating.
- Must be available to work in person in New York City.
- Must be authorized to work in the United States without current or future visa sponsorship.
Nice To Haves
- Professional experience with a highly selective organization such as Goldman Sachs, McKinsey, Bain, BCG, or a comparable firm.
- Previous startup experience, particularly within Seed or Series A environments.
- Experience within fintech, insurtech, financial services, or AI-native technology.
- Exposure to fundraising processes, investor relations, or venture-backed companies.
- Experience developing financial models and conducting operational analysis.
- Experience managing complex projects involving multiple internal and external stakeholders.
- Partnership development or external relationship-management experience.
- Experience supporting GTM strategy, growth initiatives, or customer acquisition.
- Familiarity with insurance carrier relationships or insurance distribution.
- Demonstrated ability to automate, systematize, or operationalize previously manual processes.
Responsibilities
- Partner directly with the CEO on the company's highest-priority strategic and operational initiatives.
- Support fundraising activities from end to end, including investor research, pitch deck development, data-room management, financial analysis, and investor follow-up.
- Own special projects from initial problem definition through execution and measurable results.
- Build financial and operational models supporting executive decision-making.
- Analyze lead conversion, unit economics, carrier performance, customer acquisition, and other critical business metrics.
- Identify patterns and actionable insights from business data without requiring detailed direction.
- Support GTM strategy, including lead-generation experiments, partnership development, and market-expansion initiatives.
- Help develop and manage relationships with insurance carriers and external business partners.
- Evaluate vendors, agencies, technology providers, and other external resources.
- Build recruiting pipelines and support hiring initiatives as organizational needs evolve.
- Draft investor updates, internal briefs, strategic documentation, partner communications, and other executive-level materials.
- Develop early-stage processes manually, when necessary, validate what works, and then systematize, automate, or delegate them.
- Coordinate cross-functional initiatives involving Product, Growth, Operations, Partnerships, Finance, and leadership.
- Identify urgent business challenges and take ownership of solving them quickly.
- Represent the CEO's priorities with sound judgment, professionalism, discretion, and integrity.
Benefits
- Meaningful early-stage equity opportunity.
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
