Chief of Staff to the CEO (Ex-MBB) | Insurance Tech | San Francisco | Up to USD $300K + Equity

About the role

A late‑stage, venture‑backed insurance technology company in San Francisco is creating its first Chief of Staff seat, reporting directly to the founder‑CEO. Backed by top‑tier Silicon Valley investors and well capitalised for years ahead, the firm has a proven core business that is growing fast while it invents the next few business lines. With ~200 employees and a leadership team drawn from strong scale‑ups, the CEO seeks a genuine operating partner—not a diary manager—who will eventually own a P&L for a business unit they helped build.

Responsibilities

• Act as the CEO’s operating partner from day one, owning the hardest cross‑functional problems that currently have no clear owner.
• Identify bottlenecks, devise fixes, and drive them to outcomes; sit with the CEO and business‑unit leaders to spot patterns, remove blockers, and accelerate growth.
• Travel with the CEO 10‑30% of the time to other offices and key meetings.
• Shape the company’s next moves: pressure‑test new opportunities, build data‑driven business cases, and potentially quarterback the launch of a new vertical.
• Design operating rhythms—business reviews, data and insights cadences, board storytelling, and systems that will scale the company from 200 to 600+ people.
• Build with AI: actively create automations and internal tools using Claude, Cursor, or similar, and demonstrate shipped work (e.g., automating a reporting pack over a weekend).

Requirements

• Six to ten years of total professional experience.
• Two or more years at McKinsey, BCG, or Bain early in your career (investment‑banking or private‑equity analyst programmes also count).
• Followed by real operating experience at a venture‑backed startup through its Series B to D scaling phase—you have been inside a company while it doubled and know what breaks.
• Promoted early and given increased scope without changing companies; your resume shows a pattern of growing trust, not lateral moves.
• Founder DNA: a prior startup that didn’t work out counts in your favour.

Skills

• Strong financial modelling ability—you can parse data, build models yourself, and make the call.
• Executive presence to push back on senior leaders and operate with minimal direction; you can thrive in ambiguous situations with no brief, no owner, and no deadline.
• AI‑native mindset: proven ability to build automations, agents, or internal tools that improve efficiency.
• Comfortable working five days a week in a downtown San Francisco office (relocation support and visa transfers available).

Benefits

• Fully paid medical coverage.
• 401(k) match.
• Relocation support and visa transfers (H‑1B, OPT) available for candidates outside the Bay Area.

Pay

Up to USD $300K base salary plus equity with genuine upside at this stage.

Schedule

Five days a week in the downtown office (non‑negotiable); expect to travel with the CEO 10‑30% of the time.