Chief of Staff

Location: New York City, NY Employment Type: Full-time Compensation: 150,000 - 180,000 USD salary + meaningful equity ProSights is a YC-backed AI finance automation company that is eradicating manual data entry with autonomous agents. In the past year, we have onboarded 15 of the 25 largest PE firms and 4 of the top 15 banks without any sales team. Across junior white-collar roles in investing, 15 - 20% of the job is spent copying data into spreadsheets, CRMs, and templates. We eliminate that work by reading unstructured documents, extracting what matters, and writing it directly into firm-specific systems so teams can focus on analysis, judgment, and relationships. We are looking for a Chief of Staff to work directly with the founding team. This is a high-ownership role for someone early in their career who wants to operate at the center of a fast-growing AI startup. You will be a force multiplier across strategy, operations, GTM, product, and hiring, and you should be willing to do whatever the company needs, from detailed execution to company-level projects. What you will do Founder leverage and strategic projects Partner with the CEO and founding team on high-priority initiatives and special projects Prepare materials for investors, customers, and partners, including memos, board decks, and fundraising content Run strategic analyses such as market mapping, customer segmentation, and KPI tracking Business operations Own critical operational workflows across finance, legal, HR, and office operations Build processes and systems that allow the team to scale while staying lean Track and report company metrics and help keep the team aligned on priorities Go-to-market and customer work Support sales and customer meetings by preparing materials, joining calls, and driving follow-ups Help launch and measure GTM experiments, including outbound campaigns, events, and content Assist with customer onboarding, documentation, and coordination with product and engineering Hiring and culture Work with the founders on recruiting, from sourcing candidates to coordinating interviews and closing Support employer brand initiatives, including job descriptions, content, and on-site experience Help reinforce and scale ProSights culture and operating cadence as the team grows Who you are 3 - 4 years of experience in a rigorous environment such as investment banking, consulting, top-tier operations, or an early-stage startup Very strong work ethic and willingness to handle both high-level and highly tactical work Highly organized and reliable, with the ability to manage multiple projects and deadlines in parallel Excellent written and verbal communication skills Comfortable with analytical work, including building models and dashboards Low ego, high ownership mindset, and strong bias toward action Genuine interest in AI and in building a company from an early stage Why this role and our culture This role gives you a front-row seat to how a high-growth AI company is built. You will work across every function, see how key decisions are made, and own projects that directly affect revenue, product, and team building. For the right person, this can be a springboard to future leadership roles in product, operations, or GTM, or to founding your own company. Navy-SEAL small team ethos with a bias to ship value quickly In-office Monday to Friday in our Chelsea office 2 - 3 hours blocked daily after 6:30 pm for workouts and dinner Subsidized gym membership, office nutrition and supplements provided We look for people who are honest, intensely competitive, and committed to world-class performance. If you want to work very hard on problems that matter and learn faster than almost anywhere else, we would like to meet you. Apply Today! Please email your resume to careers@prosights.co with the position title in the subject line. If your background aligns, our team will be in touch.