Operations Lead - Founding Team

About the Role

We are seeking an experienced Operations Leader to build and manage the teams, systems, workflows, and operating rhythms that drive our brokerage operations. This early-stage leadership role involves owning both the brokerage team and its day-to-day performance, working closely with founders to establish the core operating model. The ideal candidate will define how work flows through the team, measure performance, resolve issues, and ensure knowledge sharing. They will also hire, develop, and manage the team while collaborating with product and engineering to transition work from people to software and AI agents.

Responsibilities

• Own the day-to-day performance and execution of brokerage operations
• Recruit, develop, and manage the brokerage team with clear roles, expectations, and accountability
• Build the operating model, including workflows managed across people, software, and AI agents
• Establish metrics, reporting, and capacity plans for quality, productivity, and staffing
• Identify and resolve operational bottlenecks and recurring issues
• Partner with product and engineering to standardize or automate work and develop tools and AI capabilities for scaling

Qualifications

• At least 8 years of experience in consulting, investing, and/or high-growth startup operations
• Proven experience building and managing teams, including hiring, coaching, performance management, and organizational design
• Strong systems thinking skills to understand the interplay of people, processes, tools, and incentives
• Excitement for redesigning services-based operations with software, automation, and AI
• Comfort in zero-to-one environments, building workflows, systems, and foundations for scaling
• Ability to balance high-level operating design with detailed day-to-day execution
• Data-driven approach to problem-solving, prioritization, performance measurement, and improvement
• Proficiency with dashboards, workflow tools, automation, and operational reporting
• Clear communication skills and ability to align cross-functional teams
• Thrives in fast-paced environments with end-to-end ownership of outcomes

About Us

We are reimagining how people buy and navigate healthcare. With over 80% of Americans receiving health insurance through employers or exchanges, the experience remains overpriced, opaque, and inefficient. Our AI-native platform streamlines this process, helping users choose plans, find care, schedule appointments, manage insurance, and fight bills. Our goal is to redefine healthcare purchasing and management across America.

Why Join

• Scaling quickly: Join as a zero-to-one operator with an outsized opportunity to shape the company’s future.
• High impact: Address rising healthcare costs and a poor user journey by rebuilding the industry.
• Best-in-class talent: Work with teammates from leading tech companies (Uber, Airbnb, Google) and brokerage leaders (Newfront, WTW, Sequoia).
• Well-funded: Seed-stage startup incubated by General Catalyst, alongside healthcare and AI roll-up teams.

Our team works together in person in San Francisco.