Special Projects Associate, Office of the Chief of Staff

Harper•San Francisco, CA

7d•$135,000 - $165,000•Onsite

About The Position

Harper is an AI-native commercial insurance company rebuilding its business as software. The Special Projects Associate works in the Office of the Chief of Staff as an operational partner, helping the company run across teams and commitments as it scales. Working closely with the Chief of Staff, the Associate initially supports company-wide operations and progressively takes ownership of more of the operating cadence and cross-functional work. The role is hands-on and operational rather than advisory. It involves translating leadership decisions into owners and deadlines, identifying and fixing process breakdowns, stepping in to clear bottlenecks, and coordinating people across teams to deliver urgent initiatives. The Associate is accountable for execution and follow-through, and may work on priorities such as new-market launches, organizational changes, hiring pushes, and war rooms. The position is based in person in San Francisco, five days a week, Monday through Friday, with a very early start and a schedule described as roughly 5 AM–8 PM. Compensation is $135,000–$165,000, plus performance bonuses and equity. Benefits include Uber commuter benefits, meals and daily snacks, drinks and coffee, a free gym membership, and health, dental, and vision insurance.

Requirements

2–5 years in a high-intensity analytical or operational role, such as investment banking, private equity, management consulting, BizOps or Strategy & Ops at a high-growth company, or founding a company.
Exceptional written and verbal communication skills.
Strong data and spreadsheet skills.
A track record of organizing people and driving cross-functional work to completion.
Based in San Francisco or willing to relocate immediately.
Able to work in person in San Francisco Monday through Friday, with a very early start and a schedule described as roughly 5 AM–8 PM.
Comfortable with frequent follow-ups, shifting scope, and leading people without formal authority.
Willing to take hands-on responsibility for operational work and prioritize outcomes over deliverables.

Nice To Haves

Experience in insurance, fintech, or a regulated industry.
Prior direct work with a founder, CEO, or Chief of Staff.
Experience leading or coordinating a team.
Hands-on experience with AI or automation tools.

Responsibilities

Take ownership of a share of day-to-day operating priorities, follow-ups, and escalations.
Identify stalled work, unclear ownership, and broken processes; diagnose issues using data and address them.
Structure ambiguous problems by defining owners, outcomes, timelines, and check-in rhythms, then organize people to move the work forward.
Perform hands-on work to remove bottlenecks, including making calls, working backlogs, building models, and writing documents.
Lead cross-functional initiatives involving teams such as sales, service, underwriting, carriers, and engineering; set plans, assign owners, run the cadence, and drive work to completion.
Track leadership commitments, identify delays early, and ensure decisions are followed through and shipped.
Build operating cadences, dashboards, trackers, playbooks, and AI tools to replace manual processes and prevent repeat failures.
Take on urgent special projects, including new-market launches, organizational changes, hiring pushes, and war rooms.
Work alongside the Chief of Staff across company functions, initially owning follow-through on leadership commitments and then taking on a cross-functional initiative and recurring operating rhythms.
Run part of the company's operating cadence independently and identify and advance a previously unrecognized operational gap.