AI Deployment Specialist

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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 bespoke solutioning. You'll spot patterns in the field and feed them back to Engineering so the playbook gets sharper. This is a quintessential “building the plane while flying it” role.

Key Responsibilities

Systems Integration & Configuration

• Own end-to-end GydeOS stand-up for each newly acquired agency, from kickoff to go-live
• Integrate GydeOS with the agency's CRM; you’ll help build a defined connector set for future agencies and execute our conversion playbook to migrate them onto a supported stack
• Drive book-of-business (BoB) and broker RTS (ready-to-sell) upload—validating, cleaning, and troubleshooting data before it lands in the platform
• Configure the commissions and contracting modules: commission and override mapping, carrier/upline hierarchy, agency-specific incentive structures
• Work with Engineering to configure Gia to the specific agency and help build a playbook with line-of-business entitlements, agency branding, and eligibility rules that determine how the agent behaves for future partners
• Build lightweight BI views and reporting (dashboards, reconciliation checks, adoption tracking) so agency owners and Gyde leadership can see integration health in real time
• Identify and resolve integration blockers quickly, escalating to the Partner Growth and Engineering teams when appropriate

Training & Enablement

• Train the full downline of agents at each agency on GydeOS—BoB uploads, commissions, contracting, and day-to-day usage
• Help build and maintain scalable enablement collateral (walkthroughs, SOPs) across the Partner Success team so agencies can self-serve on the basics
• Support rollout of new GydeOS/Gia features to existing agencies as they ship and drive user adoption post-go-live through hands-on reinforcement so the features stick

Ongoing Support

• Own inbound support requests from agency owners and brokers post-go-live—triage, troubleshoot, resolve
• Use AI coding tools to move fast on data debugging, one-off scripts, and config troubleshooting without pulling in Engineering for routine issues
• Escalate genuine product bugs or platform gaps to Engineering—not workflow or configuration questions you can resolve yourself
• Feed recurring issues and patterns back into the playbook and Product roadmap

Cross-Functional Coordination

• Work alongside the Partner Growth Director to ensure tight coordination with the strategic growth plan while independently driving your own technical workstreams at pace
• Partner with agency leadership and staff to meet desired implementation timelines
• Provide tight feedback loops to the Product, Engineering, and Data organizations

KPIs and Outcomes

Success in this role is measured on systems/tech integration and configuration, including:

• Time to complete systems integration (target = within 30 days of close)
• % of eligible brokers activated on GydeOS
• Support ticket resolution time and % resolved without engineering escalation
• Owner and broker satisfaction (NPS) with implementation and ongoing support

What you bring and who you 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