Operations Lead - Founding Team

About Us We are reimagining how people buy and navigate healthcare. More than 80% of Americans receive health insurance through an employer or purchase coverage through individual and Medicare exchanges. Yet the experience remains overpriced, opaque, and inefficient. We replace the traditional brokerage with an AI-native platform built to streamline this process while helping you choose plans, find care, schedule appointments, call insurance, and fight bills. Our goal is not to build a better brokerage. It is to redefine how healthcare is bought and managed across America. Why Join Scaling quickly - We are growing quickly and looking for zero-to-one operators who want an outsized opportunity to learn and shape the company's future. High impact - Healthcare costs are rising at record rates, while the user journey has never been worse. Join us as we rebuild an industry. Best-in-class talent - Work alongside teammates from leading tech companies including Uber, Faire, Airbnb, Rippling, Google, Forward, and Collective Health, as well as brokerage industry leaders including Newfront, WTW, Marsh, and Sequoia. Our team works together in person in San Francisco. Well funded Seed stage startup incubated alongside the healthcare and AI roll-up teams at General Catalyst. About the Role We are looking for an experienced Operations Leader to build and manage the teams, systems, workflows, and operating rhythms that power our brokerage operations. This is an early-stage leadership role with ownership of both the brokerage team and its day-to-day performance. Working closely with the founders, this person will build the core operating model for the brokerage - defining how work moves through the team, how performance is measured, how issues are surfaced and resolved, and how knowledge is captured and shared. They will also hire, develop, and manage the team and ensure these systems work in practice. As we turn a traditionally services-based business into a technology product, this leader will partner closely with product and engineering to determine how work shifts over time from people to software and AI agents. They will help design an operating model that integrates both, with clear systems for managing quality, performance, and accountability regardless of how the work is completed. The right candidate is a systems thinker and experienced people manager who brings structure to complex environments. They are process-oriented, highly organized, and able to move between designing an operating model, leading a team, and managing execution. What You'll Do Own the day-to-day performance and execution of our brokerage operations Recruit, develop, and manage the brokerage team, with clear roles, expectations, and accountability Build the operating model for the function, including how workflows are managed across people, software, and AI agents Establish the metrics, reporting, and capacity plans needed to manage quality, productivity, and staffing Identify operational bottlenecks and recurring issues, then lead improvements through implementation and adoption Partner with product and engineering to determine which work should be standardized or automated and turn operational needs into tools and AI capabilities that enable the business to scale Who You Are You have at least 8 years of experience, with a mix of time in consulting, investing, and/or high growth startup operations You have meaningful experience building and managing teams, including hiring, coaching, performance management, and organizational design You are a strong systems thinker who can understand how people, processes, tools, and incentives work together You are excited by the opportunity to redesign a traditionally services-based operation around software, automation, and AI You are energized by zero-to-one environments and want to build the workflows, systems, and operating foundations that enable a new organization to scale You can move comfortably between high-level operating design and detailed day-to-day execution You use data to diagnose problems, establish priorities, measure performance, and improve operations You are comfortable working with dashboards, workflow tools, automation, and operational reporting You communicate clearly and can establish alignment across teams with different priorities You thrive in fast-moving environments and take ownership of outcomes from beginning to end #J-18808-Ljbffr Stealth - AI Agents for Healthcare