Forward Deployed Specialist at Gyde

About Us The insurance broker is a critical, yet underleveraged asset within the healthcare value chain. Despite being the first point of contact for patients and providing critical guidance on everything from insurance plan selection to care navigation, many still rely on manual workflows and spreadsheets to run their business, and are unable to grow at their desired pace. Gyde is building an AI-native brokerage platform by acquiring traditional agencies and supercharging them with workflow automation, voice and chat AI applications, and predictive product and plan selection guidance. Our vision is to be the premier partner for ambitious agencies, streamlining their operations through the Gyde platform to enable their success in the current regulatory and technological paradigm shift. 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 Forward Deployed Specialist to embed directly with Gyde’s partner agencies and FMOs — building production AI applications that make their operations faster, smarter, and ready to scale. This is fundamentally a technical role: you will build API integrations, ship lightweight AI applications for frontline agency staff, and deploy end-to-end automations across the workflows that matter most to our partners. The work is hands-on and high-stakes. You’ll work within partner environments — understanding their data, their systems, and their quirks — and translate that understanding into working software. In health insurance operations, the details are everything: a client-to-broker attribution rule, a commissions reconciliation nuance, a carrier-specific data format. Getting those right is what separates a useful tool from a trusted one. Immense attention to detail is not optional in this role; it is the job. You’re equally at home in a terminal and across a conference table. You’ll partner with agency operators to identify the processes that would break at 2x scale, break them into modular workstreams, prioritize what to build first, and ship solutions that the existing team can actually use. You leave behind production-grade tools, not decks. Travel across the U.S. is expected and embraced — our partners are the job. The ideal background: 3–5 years in a role where you owned technical outcomes for external stakeholders — solutions engineering, technical program management, implementation consulting, operations analytics at a tech company, or hands-on product/software engineering with a heavy customer-facing component. You've shipped working software that real users depend on, and you're comfortable writing code to do it — even if code wasn't your primary job title. Experience with LLM applications is strongly preferred. Key Responsibilities • Embed with partner agencies and FMOs to map operational workflows end-to-end, surface processes that would break at 2x scale, and scope the right technical intervention • Own the full implementation lifecycle: discovery, technical scoping, build, deployment, adoption, and ongoing iteration • Build production applications and workflow automations that solve real operational problems for partner agencies and FMOs • Manage full end to end client data pipeline — understanding client/broker attribution logic, commissions structures, carrier data formats, and the field-level rules that make an integration correct rather than merely functional • Rapidly prototype, test, and adapt: use fast feedback from real users to iterate on solutions under constraints and timelines • Lead change management and enablement with agency staff so that tools get adopted, not abandoned • Identify and codify repeatable deployment patterns and contribute those learnings back to Gyde’s product and engineering teams • Partner with Value Creation Directors to triage and prioritize the highest-leverage automation opportunities across the portfolio What you bring and who you are We screen for seven core competencies in this role. Here’s what we’re looking for across each: • Past Success — 3–5 years of experience in solutions engineering, operations analyst, or technical program management, or a highly technical implementation/consulting role. You have shipped technical work that external users depended on — ideally including LLM applications. Your career trajectory shows upward focus and a track record of excelling in environments where technical output matters. • Attention to Detail & Precision — When working with data, the details are everything. Client-to-broker attribution rules, commissions reconciliation logic, carrier-specific field formats — all of it matters to achieve a complete and correct solution. You do not approximate; you get it right. You are the person who catches the edge case before it becomes a production incident. • Entrepreneurial Spirit — Goal-oriented and self-motivated; resourceful and innovative under constraints. You don’t wait for a spec. You find the problem, scope the solution, build it, and own the outcome. You are comfortable creating structure where none exists. • Problem Solving — You quickly identify root causes (not symptoms), evaluate solutions systematically, and drive toward a decision. You can decompose a messy, ambiguous operational challenge into clean technical modules and ship them in the right order. • Project Management — You efficiently manage and execute complex, multi-workstream deployments. You sequence work intelligently, track dependencies, and deliver on time — communicating clearly with stakeholders from agency owners to Gyde’s internal leadership. • Relationship Management — You build trust quickly, maintain high emotional intelligence, and bring a service-oriented mindset to every interaction. You understand that the best technical solution means nothing if the people who need to use it don’t trust it or understand it. • Team Fit — Positive attitude, genuinely passionate about their work, collaborates well with others, and will always do the right thing for the business. You make the team better by being in the room. Technical requirements • Comfort writing Python to build working prototypes, debug, and iterate independently • Experience building and shipping end-to-end applications — not just scripts or notebooks, but tools that real users depend on • Ability to work with structured and semi-structured data, and understand enough about data infrastructure to make sound architectural decisions • 3–5 years of relevant engineering, product, or implementation experience Nice to have • Working knowledge of data privacy, security, and compliance in regulated industries (HIPAA, PHI, PII) — and the judgment to apply it correctly in client environments • Production experience with LLMs, advanced prompt engineering, agent development, evaluation frameworks, and deployment at scale • Experience with health insurance, brokerage, or adjacent regulated data environments • Background in post-merger integration or deploying tools into acquired business environments • Prior work with commissions data, carrier integrations, or insurance enrollment systems What to expect in your first 90 days Milestone Expected Outcomes 30 Days Ramp quickly on Gyde’s platform, partner data environments, and deployment toolchain. Shadow at least one client deployment and demonstrate the ability to contribute to discovery, technical scoping, and initial build. 60 Days Lead the technical delivery of portions of client-facing deployments with limited oversight. Own at least one end-to-end automation that is live in a partner environment and used by their team. 90 Days Independently lead full client deployments end-to-end. Build repeatable technical playbooks, identify data integration patterns, and serve as the go-to technical problem solver for both clients and internal stakeholders. What we offer Gyde offers a competitive benefits package to all employees. • Top of market compensation • Flexible (Unlimited) Paid Time Off • Remote, or Hybrid Work in Austin or NYC • Medical, Dental, and Vision benefits for you and your family • Retirement Plan (e.g., 401K) • Parental Leave