General Counsel

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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

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 is ideal for a corporate or employment attorney with top law-firm training who has since been the first or most senior lawyer at a PE- or VC-backed company, ideally in insurance, healthcare, or financial services. You’re as comfortable advising the board on an equity grant as you are redlining a vendor BAA or working through an I-9 audit.

• Own corporate records, governance, and entity management for the holding company and every acquired entity, including formation documents, board and stockholder consents, and minute books.
• Bring the equity program in-house: plan documents, grant agreements, 409A coordination, and plan administration with Finance.
• Work with the CEO, CFO, and outside counsel on financings, and on board and investor legal matters.

• Own the employee agreement library (offer letters, CIIAAs, commission agreements, separation agreements and releases) and keep it current in every state where we employ people.
• Serve as employment counsel to HR and leadership on classification, wage and hour, leave, investigations, and separations, with outside specialists where depth is needed.

• Serve as Gyde's internal legal lead on every acquisition through signing and close, and direct outside M&A counsel on scope, staffing, budget, and turnaround.
• Set Gyde's standard deal positions and playbook so outside counsel works from our terms: indemnities and seller liability, agency E&O tail coverage, earnouts, producer retention and restrictive covenants, and run-off commission and clawback exposure.
• Own employee and benefits diligence, either directly or through a trained team member: worker classification, handbook migration to the Gyde standard, controlled-group and benefit plan review, and I-9 / E-Verify compliance.
• Lead post-close legal integration of acquired entities.

• Own the governance framework for Gyde's voice and chat agents: TCPA consent, call recording, AI disclosure requirements, and HIPAA and state privacy obligations.
• Bring in specialist counsel for detailed opinions, and make sure product and engineering teams can ship within clear guardrails.
• Review data, lead, and technology agreements, including BAAs and vendor and SaaS contracts, and own the templates and playbooks behind them.

• Set the legal and compliance risk framework for the company and report on it to leadership and the board.
• Review carrier, FMO, and override agreements for legal risk, including commission, clawback, and termination terms, and maintain the review checklist and escalation path. Business teams own carrier relationships and commercial negotiations.
• Direct outside regulatory counsel on CMS marketing rules, state Department of Insurance matters, and licensing, working with the Head of Legal & Compliance, who runs day-to-day compliance.

• Own company-wide contract review and the NDA, vendor, and partner templates behind it.
• Manage Gyde's insurance program (D&O, E&O, cyber, and EPLI) with Finance and our brokers, including coverage for newly acquired entities.
• Manage litigation and disputes through outside counsel.

• Lead and develop the Head of Legal & Compliance, and build the legal team as Gyde scales: hiring, intake, 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.

• 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.