Market Director

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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

Our founding team boasts pedigrees from Oscar, Stripe, Vista Equity Partners, Bain & Company 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 looking for a Market Director to own agency origination across a set of metro markets, taking the best independent health insurance agencies from a first conversation to a signed letter of intent.

Gyde grows by partnering with independent agencies, and our model is buy in, not buyout: founders keep a stake and stay in the seat. Most of the owners we want aren't selling, so every partnership starts with trust. The Market Director knows every agency in their markets, opens the door, and earns that trust before a roll-up or banker does. As Gyde scales, a full pipeline of high-fit owners in each priority market is one of the biggest levers on how fast we grow.

You'll map and rank every agency in your markets, run outreach to owners by phone, email and in person, qualify fit early, and stay in the deal with M&A leadership through financials and LOI. You'll work closely with Strategy, M&A and Marketing, and help shape the origination playbook as we add more markets.

This role is ideal for someone from insurance distribution, FMO or agency recruiting, carrier sales, or agency M&A origination who knows how agency owners think. You're as comfortable at a state association chapter meeting as you are working a call list and keeping your CRM clean.

Key Responsibilities

• Own origination across an assigned set of metros (MSAs): build and maintain a complete map of every independent health agency, ranked by fit.

• Run consistent, multi-channel outreach to agency owners by phone, email, text, LinkedIn and in person, including the many owners with no direct contact on file.

• Qualify prospects on line of business (Medicare Advantage first, then employee benefits), size, growth, retention and owner intent, and separate cornerstone partners from bolt-ons and passes early.

• Earn owner trust over months, not one call: explain Gyde's partnership model and platform, handle objections, and keep relationships warm until the timing is right.

• Bring qualified owners to M&A leadership and stay in the deal through financials, valuation conversations and a signed LOI.

• Build Gyde's presence in your markets through state association chapters, regional Medicare and benefits conferences, FMO and carrier relationships, and referrals from Gyde partners.

• Track competitive activity, including national roll-ups and PE-backed buyers recruiting in your markets, and adjust your plan.

• Keep the CRM accurate so pipeline, stage and next steps are visible every week without anyone asking.

• Use AI tools for research, enrichment, sequencing and call prep to cover more agencies without losing the personal touch.

• Help build the origination playbook (target lists, scoring, scripts and sequences) as Gyde adds Market Directors.

What you bring and who you are

• 5+ years in insurance distribution, agency or FMO recruiting, carrier sales, or business development selling to small-business owners; health insurance (Medicare or employee benefits) strongly preferred.

• A demonstrated record of building pipeline from scratch and hitting activity and outcome targets in an outbound role.

• Fluency in how independent health agencies make money: commissions, renewals, book retention, and carrier and FMO relationships. Agency M&A or valuation exposure is a plus.

• Command of the mechanics: territory mapping, multi-touch sequences, cold calling, qualification frameworks, CRM hygiene and weekly pipeline reporting.

• Judgment to read an owner's real motivation and decide where your time goes across many relationships and a few live deals.

• Credibility with agency owners. Existing relationships in Medicare or employee benefits are a plus.

• Comfort using AI tools (enrichment, research, drafting, call notes) to extend your coverage.

• Entrepreneurial mindset with a strong sense of ownership; you want to build a market, not inherit a list.

• Organized and persistent, and comfortable with long sales cycles and "not yet."

• Ability to travel ~25-50% to your markets, owner meetings and industry events

What we offer

Gyde offers a competitive benefits package to all employees.

• OTE $175-$275k

• Flexible (Unlimited) Paid Time Off

• Hybrid Work in Austin or NYC

• Medical, Dental, and Vision benefits for you and your family

• Retirement Plan (e.g., 401K)

• Parental Leave