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? Visa: Will sponsor.