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

Bloom Talent

$160K — $225K *
Legal & Accounting
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 3-6 years in a startup operating role, preferably as Chief of Staff or similar.
  • High initiative with an ownership mindset, akin to a founder.
  • Strong structured thinking; ability to create order amidst chaos.
  • Excellent judgment and comfort with intellectual challenges.
  • Confidence in managing upward; effective in engaging with strong personalities.
  • Experience with venture-backed startups; advisory or investing backgrounds not suitable.
  • Willing to relocate or based in NYC for a full-time office role.

Responsibilities

  • Act as a strategic partner and mini-COO to the CEO.
  • Partner on goal-setting and milestone tracking to keep priorities aligned.
  • Support hiring and headcount planning as the team grows.
  • Translate CEO's ideas into executable processes for scalability.
  • Proactively identify and address risks and operational obstacles.
  • Collaborate with the founding team to expand the NYC office and business lines.

Benefits

  • Equity in a fast-scaling company.
  • 401K retirement plan.
  • Full health benefits.
  • Dynamic work environment within a fast-growing startup.
Full Job Description
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.


*Please Note: Your application will be considered for all open positions. You do not need to apply for multiple roles.

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