AI Deployment Specialist

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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 technical, hands-on operator to be Gyde's next AI Deployment Specialist and own the implementation of the Gyde platform (GydeOS) inside every newly acquired agency. GydeOS is a powerful tool, but requires real configuration with every roll out: mapping a new agency's book of business, wiring up their CRM, standing up commission and contracting logic, and tuning our AI agent, Gia, to that agency's specific book, carriers, and workflows. You're the person who makes that happen, fast.

This is a deploy-and-drive role: you're embedded with the agency, running point on the technical stand-up, and you're resourceful enough to solve most of what comes up yourself, including querying data directly, scripting a one-off transformation, standing up a quick dashboard, or even developing email automations to support downline broker adherence.

You'll help build a tight, repeatable playbook, but need to be able to operate in an unstructured environment today. Your goal is speed-to-value and standardization across agencies, which ultimately matter more than bespok
[…]
ou are

• 4+ years in a technical, field-facing role—solutions engineering, forward deployed specialist, technical implementation, or technical customer success—ideally at a place where you owned client-side configuration end to end
• Comfortable with SQL and Python for data validation, cleanup, and light scripting—you're not afraid of a messy CSV or a broken upload
• Experience using AI coding tools (Codex, Claude Code, or similar) as part of your daily workflow to move faster and stay self-sufficient
• Experience building BI/analytics views (SQL + a BI tool, or equivalent) to give stakeholders visibility into a process or system
• A bias toward executing a playbook well over improvising a custom solution—you optimize for repeatable speed, not bespoke elegance
• Sharp troubleshooting instincts and the independence to resolve issues without defaulting to “let me check with engineering”
• Strong client-facing presence—you'll be a new agency's first real impression of Gyde
• Willingness to travel to portfolio agencies during active integrations (~25%)

What makes you successful in this role

• You default to solving it yourself before escalating—and you know the difference between “I need engineering” and “I haven't tried hard enough yet”
• You run the playbook tightly and flag when a pattern suggests the playbook itself should change—rather than quietly customizing around it
• You communicate integration progress clearly to technical and non-technical stakeholders alike
• You move at pace without cutting corners on data integrity
• You build trust quickly with new agency partners and make complex tools feel approachable
• You are energized by getting dropped into a new, messy environment and making it clean

What we offer

Gyde offers a competitive benefits package to all employees.

• $125,000-145,000 OTE
• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Retirement Plan (e.g., 401K)
• Parental Leave