Executive Assistant at Pasito

Job description

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. The Role We’re looking for an Executive Assistant to the CEO and COO to join our team and work directly with our leadership and business operations team. The role requires someone whois organized, responsive, resourceful, detail-oriented, comfortable operating across multiple clients and systems, and able to exercise sound judgment in situations involving confidential information, executive calendars, client communications, billing, andtime-sensitive operational requests. This is a high-visibility, high-impact role at the center of how Pasito runs: you’ll touch everything from operational processes and cross-functional projects to planning team events. This role is ideal for someone early in their career who wants to learn how a startup operates from the inside out. What You’ll Do Business Operations & Executive Support Deliver daily administrative and operational assistance to executive leadership and team members. Handle executive calendars, coordinate meeting logistics, and ensure timely follow-ups across time-sensitive internal and client requests. Draft, edit, and format critical client materials, including proposals, agreements, job descriptions, and operational handbooks. Manage end-to-end digital signature workflows, verifying details, routing contracts, and monitoring execution status. Administer internal tools and knowledge bases across systems like Notion, Teams, Clickup, Hubspot and Google Workspace. Monitor details that affect quality, consistency, naming conventions, formatting, version control, deadlines, and client experience. Own client invoicing end-to-end, including sending invoices, managing billing communication, and collaborating closely with accounting and finance. Cross-Functional Projects & Operations Help coordinate initiatives across teams by tracking timelines, deliverables, document creation, calendar alignment, meeting recaps, and client interactions. Monitor action items across multiple client accounts and internal programs, flagging high-priority tasks and bottlenecks for executive review. Exercise sound judgment when operating autonomously, asking clarifying questions, or raising critical items to leadership. Support the documentation and improvement of internal workflows, refining operational templates, file organization, knowledge bases, and team transitions. Build AI powered workflows to maintain system updates and ensure sync between teams. Product Support major product launches and strategic initiatives. Assist with product QA and testing before releases. Support team training calendar and certification tracking People & Events Collaborate with marketing and sales to track and execute on in person events. Plan, book and track budget for team events,