Lead Product Manager

About Us

• Insurance brokers sit at the intersection of care, cost, and access — yet remain one of the most underleveraged assets in the $5T healthcare value chain. They guide millions of Americans through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.
• Gyde is reimagining this. We’re building the first AI-native insurance brokerage platform—a system that learns from every client interaction to automate operations, power intelligent voice and chat experiences, and predict the right coverage and products for every individual or business.
• Our approach combines acquisition and AI: we acquire traditional brokerages and transform them into next-generation, data-driven organizations. Through Gyde’s platform, agencies run more efficiently, serve clients more personally, and scale faster than ever before.
• Join us if you’re excited to:
  • Redefine how millions of people access and understand their healthcare coverage, by building systems that turn unstructured data, human conversations, and fragmented processes into intelligence.
  • Build AI systems that improve how people access healthcare
  • Design production-grade voice, chat, and predictive models for a highly regulated domain
  • Launch technologies that augment human judgment and make complex decisions transparent and scalable
  • Help reinvent an entire industry from the inside out
• We’re creating the future of brokerage — where every interaction, insight, and decision is powered by intelligence.
• Our founding team boasts pedigrees from Oscar, Stripe, Vista Equity Partners, and Alpine. Lightspeed led Gyde’s $60M financing, with participation from Optum Ventures, Crystal Venture Partners, Virtue, MVP Ventures, and multiple endowment funds, among others. Hear why on LSVP Investment Memo.

Role Summary

We're hiring a Lead Product Manager to own key areas of our AI agent portfolio — production voice and SMS agents that handle real client conversations across the insurance lifecycle for the agencies we acquire. You'll report to the Head of Product and operate as a senior, hands-on individual contributor with direct accountability for outcomes.

As an early product hire, you will carry broad ownership rather than a fixed surface area, and your focus will evolve with the roadmap. You will be responsible for taking AI agents from concept through production, adoption, and measurable revenue impact in a CMS-regulated, high-stakes domain.

Key Responsibilities

• Set the product strategy and roadmap for your area of the agent portfolio, and evolve it as the market and our learnings shift.
• Take conversational AI agents from concept through production launch, adoption, and measurable revenue impact.
• Own prioritization for your area — what ships, what waits, and what we don't build.
• Define what "good" means for every agent — call success rubrics, eval coverage, escalation behavior, zero-tolerance compliance — and drive the improvement loop with engineering.
• Translate broker, agency operator, and client insight into the roadmap, spending real time in the field (~25% travel) and validating with fast proof-of-concepts before committing engineering time.
• Define success metrics for every initiative and tie them to revenue per broker.
• Align founders, engineering, design, and partner success around direction, scope, and sequencing — communicating strategy and progress clearly, from working sessions to leadership reviews.

You may be a good fit if you

• Have 8+ years of product management experience, including 2+ years shipping AI/ML-powered products to production — ideally in a regulated or workflow-heavy domain
• Have a demonstrated record of owning product strategy and roadmaps end-to-end — from vision through launch and iteration.
• Are fluent in how LLM products are built and improved — evals, prompt iteration, quality/latency/cost trade-offs — enough to earn engineers' trust.
• Have a track record of defining metrics and designing experiments to drive product decisions, balanced with strong qualitative customer insight.
• Use AI tools daily to prototype, test, and validate concepts.
• Are hands-on by default — you listen to the calls, read the transcripts, and write the first draft yourself.
• Would rather ship a scoped V1 that generates signal than a complete V3 that doesn't.
• Have a point of view on how AI agents will change insurance distribution — and want to test it in production.
• Communicate exceptionally and drive alignment without relying on authority.

Strong candidates may also have: experience with voice AI or telephony products; Medicare/ACA or adjacent insurance domain knowledge; early or founding PM experience.

What we offer

Gyde offers a competitive benefits package to all employees.  

• OTE: $180,000 - 210,000
• Flexible (Unlimited) Paid Time Off
• Hybrid Work in Austin, TX or New York, NY
• Medical, Dental, and Vision benefits for you and your family
• Retirement Plan (e.g., 401K) 
• Parental Leave