Chief of Staff to CEO at Fast-Growing AI-Native Legal Startup

AI-native, outcome-based law firm reinventing how consumer legal cases get evaluated and represented is looking for a Chief of Staff to support their CEO. Just months removed from an exciting fundraising round and already scaling revenue fast, this is a ground-floor opportunity to bring real structure to a high-growth, fast-moving startup. In this role, you'll partner closely with the CEO on goal-setting and milestone tracking, support hiring and headcount planning as the team scales, and function as a mini-COO who can look around corners and turn big, fast-moving ideas into scalable execution. This is not a scheduling or inbox-management role. Someone who is highly structured, intellectually curious, and comfortable managing upward with a fast-moving, big-personality founder, with the initiative to push back and hold their own in the room. Startup operating experience is strongly preferred. This is an in-office role, 5 days/week, based in NYC. 160-225K DOE + equity, benefits, and 401K.

Responsibilities:

• Act as a strategic partner and mini-COO to the CEO, bringing structure to a fast-moving, big-picture working style.
• Partner on goal-setting and milestone tracking to keep company priorities on track.
• Support hiring and headcount planning as the team scales.
• Help translate the CEO's ideas and plans into scalable, executable processes.
• Look around corners to flag risks, gaps, and operational obstacles before they become problems.
• Collaborate closely with the broader founding team as the company builds out its NYC office and expands into new business lines.

Qualifications:

• 3-6 years of experience in a startup operating role, ideally with prior Chief of Staff, founder's associate, or general operating experience.
• High initiative and an ownership mindset, someone who operates almost like a founder looking for the right seat.
• Strong structured thinking, with a track record of bringing order to unstructured or fast-changing environments.
• Excellent judgment and intellectual honesty, comfortable being challenged and pressure-tested on their thinking.
• Confident managing upward and able to hold their own with a strong, fast-moving personality without being overpowered.
• Prior experience at a venture-backed startup preferred; pure investing or advisory backgrounds without operating experience are not a fit.
• Based in or willing to relocate to NYC for a full-time, in-office role.
• Proficient with standard workplace tools such as Google Workspace, Slack, and Notion.