About the Role
This is a rare, high-trust opportunity to serve as the right hand to the CEO at a fast-growing, early-stage insurtech marketplace that is reimagining how consumers compare and purchase insurance. The company connects users with real, bindable quotes from dozens of top carriers — combining technology with personalized advisory to eliminate friction and spam from the insurance-buying experience.
As Chief of Staff, you will operate at the center of the business — owning cross-functional initiatives, supporting fundraising execution, helping scale the go-to-market motion, and ensuring the CEO's highest priorities move forward with urgency and precision. This role is ideal for a high-agency operator who thrives in ambiguity, ships before things are perfect, and is energized by building from zero to one.
This is a fully on-site role in San Francisco, CA, requiring in-person availability 6 days per week including Saturday. No visa sponsorship is available — candidates must be legally authorized to work in the United States.
What You'll Do
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Act as the CEO's operational partner — systematize work, track priorities, and ensure end-to-end project ownership across the business
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Support fundraising activities, including investor communications, deck preparation, data room management, and relationship tracking
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Help recruit, onboard, and scale sales and go-to-market teams
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Build and maintain financial models, business analyses, and dashboards to inform strategic decisions
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Draft and refine investor emails, internal memos, partner communications, and executive-level documents
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Collaborate across GTM, operations, product, and marketing to drive alignment and remove blockers
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Identify operational inefficiencies and design lightweight systems and processes to address them
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Manage special projects from scoping through completion with minimal direction
What We're Looking for
Required
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1–3 years of professional experience in consulting, investment banking, startup operations, strategy, or a similarly high-intensity environment — strong new graduates with exceptional signals will be considered
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Strong analytical skills: advanced spreadsheet proficiency, financial modeling, and the ability to synthesize data into clear recommendations
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Excellent written and verbal communication skills; comfortable producing polished external and internal documents
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Proven ability to own projects end-to-end with minimal supervision in a fast-paced, ambiguous environment
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Entrepreneurial mindset — high agency, bias toward action, comfort operating without a playbook
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Experience with or strong interest in fundraising and investor relations
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Experience supporting the hiring or scaling of sales or GTM teams
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Proficiency with Google Workspace, Excel, and CRM or analytics tools
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High integrity and discretion — this is a trust-foundational role with direct exposure to sensitive business information
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Located in San Francisco or genuinely committed to relocating before the start date
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Must be legally authorized to work in the United States without visa sponsorship
Nice to Have
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Familiarity with investor communications, pitch decks, and fundraising processes
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Background from a top-tier firm or elite institution (e.g., McKinsey, JPMorgan, or equivalent)
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Prior experience at a high-growth startup, insurtech, or fintech company
Compensation & Benefits
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Salary: $130,000 – $180,000 per year, depending on experience
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Early-stage equity participation
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Direct exposure to company leadership and fundraising at the ground floor
Location
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On-site in San Francisco, CA — 6 days per week including Saturday
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Visa sponsorship is not available; candidates must be authorized to work in the United States
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