General Counsel

The posting, as Gyde wrote it

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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 looking for a General Counsel to build Gyde’s in-house legal function and own the legal foundation of the company as we acquire and scale.

Gyde grows by acquisition. Every deal adds entities, employees, benefit plans, contracts, and regulatory exposure, and today most of that legal work sits with outside counsel. Bringing the core of it in-house (corporate records, employee agreements, employment and ERISA diligence, and company-wide contracts) gives us speed, consistency, and institutional memory. It also makes legal a lever for closing and integrating deals faster as Gyde scales.

You’ll take over the corporate and employment work our outside corporate counsel handles today, direct our outside M&A counsel on every acquisition, and run the employee and benefits diligence our deal partners currently outsource. You’ll oversee vendor & partner agreements across the company, and you’ll manage our Head of Legal & Compliance, who owns brokerage and carrier compliance. You’ll partner closely with the COO, CFO, CTO, Head of Strategy, and our HR and M&A team.

This role
[…]
matter tracking, and AI-assisted contract and diligence workflows.

• Own the outside counsel budget, and bring work in-house where it lowers cost without slowing the business down.
• Build legal operations support early, so high-volume work like diligence checklists and records maintenance doesn't depend on the GC.

What you bring / core competencies

• A JD and an active bar license in good standing, with 8-10+ years of experience, including law-firm training in corporate / emerging companies or employment law and 3+ years in-house as the first or most senior lawyer at a high-growth, PE- or VC-backed company.
• A demonstrated record of bringing work in-house from outside counsel and lowering legal spend without slowing the business down.
• Hands-on employment and benefits fluency: multistate employment law, ERISA and controlled-group rules, FMLA, worker classification, and I-9 / E-Verify.
• Command of the mechanics: formation documents and consents, equity plans and grants, CIIAAs, OWBPA-compliant releases, employee reps and covenants in purchase agreements, and BAAs.
• Buy-side M&A experience, ideally across serial acquisitions, and a track record of managing outside deal counsel to scope and budget.
• Insurance distribution, healthcare, or financial services experience strongly preferred; familiarity with CMS and state Department of Insurance regulation is a plus.
• 3+ years managing lawyers or compliance professionals, and the executive presence to advise the CEO, board, and investors.
• Comfort using AI and automation to do more legal work with a small team.
• An entrepreneurial mindset and a strong sense of ownership. You want to build this function, not inherit one.
• Ability to travel up to ~25%, including time in Austin, NYC, and our portfolio agencies.

What we offer

• $300-350K + $50K variable
• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Retirement Plan (e.g., 401K)
• Parental Leave