Chief of Staff

We're hiring a Chief of Staff to work directly with our founders, acting as a force multiplier across strategy, operations, and execution. You'll sit at the center of the business: driving key initiatives end-to-end, keeping the founding team focused on what matters most, and making sure critical projects don't stall. AI is core to how we work: you'll use AI daily, so knowing how it works is a must.

What You'll Do

Founder Leverage

• Act as an extension of the founders, taking work off their plate so they can focus on the highest-leverage decisions
• Prepare the founders for client meetings, investor calls, and other key decisions
• Serve as a trusted thought partner and sounding board, including as a candid internal challenger when needed

Cross-Functional Execution

• Drive projects that span across legal, sales, operations, and support where no single team owns the outcome
• Chase down blockers and ensure initiatives are met
• Flex into whatever function needs support in a given week; comfortable filling gaps as an early-stage generalist

Operating Cadence & Visibility

• Own the founders' operating rhythm: goal-setting, prioritization, and follow-up across the business
• Run weekly/monthly planning, OKRs, all-hands, and leadership syncs
• Build and maintain dashboards and reporting that give the founding team and investors a clear, real-time read on the business
• Track action items and follow up with commitments made in meetings

Strategy & Special Projects

• Lead one-off, high-stakes initiatives: fundraising support, new market entry, hiring pushes, recruitment, organization redesigns, or process overhauls
• Do the analysis (market research, competitive landscape, financial modeling) that feeds founder decisions
• Translate high-level goals into concrete plans and own execution end-to-end

Organizational Glue

• Manage sensitive and confidential matters with discretion and sound judgment
• Represent the founders in select internal and external conversations
• Help shape company culture and internal communication as the team scales
• Support recruiting, vendor management, and operational logistics as needed in the early days

What We're Looking For

• 1+ years of experience in a Chief of Staff, strategy, consulting, investment banking, or startup operating role
• Demonstrated ability to manage ambiguous, cross-functional projects from strategy through execution
• Excellent written and verbal communication skills; comfortable operating at both the strategic and detail level
• Sharp analytical and problem-solving skills, with strong business judgment
• Highly organized, self-directed, and able to prioritize ruthlessly in a fast-paced environment
• Trustworthy and discreet; you'll regularly be exposed to sensitive, confidential information
• Experience in legal services, professional services, or a regulated industry is a plus
• Prior experience at an early-stage startup is a plus
• Must be based in or willing to relocate to San Francisco

Why Join Us

• Work side-by-side with the founders of a fast-growing YC company
• Unmatched visibility into every part of the business, from strategy to execution
• High-trust, high-ownership environment where your judgment shapes real decisions
• Front-row seat to building a category-defining AI-native legal services company

In you application, please answer the following questions:

1. How is your experience relevant to this role?

2. If you're based outside SF, how long would it take you to relocate?