Chief of Staff Job

Our client, an AI-native commercial insurance startup, is seeking a Chief of Staff to serve as the CEO's operating partner and force multiplier. This is the highest-leverage generalist seat in the company — you'll own the ambiguous, cross-functional, mission-critical work that drives execution and keeps the company moving in one direction, with a clear path to growing into a GM, functional lead, or COO role.

What You'll Be Doing:

Own day-to-day operations, partner follow-ups, and pilot execution to free up the CEO and CTO for strategic work

Drive prioritization of initiatives, KPI tracking, and cross-team communication

Run go-to-market efforts, partnership diligence, and vendor onboarding end-to-end

Build the financial model, board materials, and analytical backbone behind major business decisions

Define — and potentially build out — the "Office of the CEO," including hiring special projects associates if justified by scope

What We're Looking For:

Experience

5–6+ years in strategy, operations, or BizOps, combining consulting with hands-on execution in high-growth tech

Startup or zero-to-one experience where you owned initiatives end-to-end, not just advised — able to speak to specific individual contributions, not just team-level outcomes

Fits one of two archetypes:

Archetype 1: MBB consulting (2–4 years) followed by an operating role in high-growth tech (e.g., BizOps, GM, product, or strategy at companies like Uber, Robinhood, DoorDash, or Airbnb)

Archetype 2: 5+ years in high-growth startup/scale-up operations, strategy, or a founding role, without a consulting background

Prior experience as a co-founder, founding team member, or Chief of Staff at a seed-to-Series B startup is a plus

Skills & Mindset:

Demonstrated high agency — takes vague problems, defines the path forward, and drives to outcomes with minimal direction

Sharp analytical problem-solver who can break down complex issues, prioritize, and execute systematically
Proactively identifies what needs doing and acts without waiting for direction; makes assertions, not just asks questions

AI-native workflow — actively uses AI tools to automate and augment daily work

Genuinely excited about seed-stage risk and ambiguity; values equity upside over cash maximization

Education:

Bachelor's degree from a highly selective university

MBA from a top program (Booth, Stanford, Wharton, HBS, MIT Sloan) is a plus

Pure advisor mindset needed

**Please forward PDF resume to [email protected]