IT Engineer

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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

You are the human face of IT for every agency we bring into Gyde. When we acquire an agency, the people there need their accounts, laptops, and access working on day one — and you own that experience end to end: before, during, and after cutover. You sit on the Infrastructure team, report to our Head of Infrastructure, and act as the bridge between the Infra Engineer's integration runbooks and the users actually living through the change.

This is hands-on work: maintaining device fleets across multiple entities, running MFA and SSO resets, provisioning and deprovisioning accounts across Entra/Okta and Google Workspace/M365, and triaging whatever lands in the queue. It's also high-trust — we operate in a HIPAA-aware environment, so you handle identity verification, device loss, and access changes with care, every time.

The ideal hire has run end-user IT in a fast-moving, multi-tenant or MSP-style environment, stays calm under a cutover deadline, and treats recurring problems as bugs to fix at the root — not tickets to close and forget.

Key Responsibilities

• Own the end-user IT experience for acquired agencies — onboarding, cutover, hypercare, and day-to-day support before, during, and after integration; serve as the primary IT point of contact for agency users.
• Run endpoint and device operations — image, enroll, ship, and lifecycle-manage laptops (provisioning through RMA and offboarding retrieval); operate the MDM (Hexnode) day to day, push policies, and clear compliance failures.
• Handle Tier 1–2 identity and access — provision, modify, and deprovision accounts in Entra/Okta, Google Workspace/M365, and core SaaS; run JML workflows accurately, with same-day deprovisioning as a non-negotiable.
• Execute the user-facing portions of integration rollouts owned by the Infra Engineer — schedule cutover windows with agency leadership, run pilot waves, capture friction, recommend runbook changes, and own status comms during rollouts and incidents.
• Enforce security hygiene at the user level — endpoint baselines, disk encryption, MFA enrollment, and screen-lock policies; support phishing reporting and basic user security education; flag anomalies (impossible travel, unmanaged devices, shadow IT) up to Security/Infra; keep HIPAA-aware support habits.

What you bring / core competencies

• End-user support & troubleshooting — diagnoses and resolves laptop, SaaS, connectivity, and access issues quickly and communicates clearly with non-technical users.
• Identity & access (Tier 1–2) — confident across an IdP (Entra/Okta), Google Workspace/M365, MFA, SSO, conditional access, and clean JML hygiene.
• Endpoint & MDM operations — device imaging, enrollment, lifecycle, inventory, and policy/compliance troubleshooting in an MDM (Hexnode or comparable).
• Communication & stakeholder management — calm, clear, and credible with non-technical agency users and leadership, especially under cutover pressure.
• Operational rigor & security mindset — follows and improves runbooks, documents recurring quirks, and handles HIPAA-aware verification and device-loss scenarios without being prompted.

Technical / Functional Requirements

• 4-6 years in end-user/desktop support, IT operations, or an MSP/help-desk environment.
• Hands-on administration of an IdP (Entra ID, Okta) plus Google Workspace and/or Microsoft 365.
• MDM experience (Hexnode a plus; Intune, Jamf, or Kandji acceptable).
• Comfortable imaging/provisioning laptops and managing the device lifecycle end to end.
• Solid working grasp of MFA, SSO/conditional access, VPN, and AVD or a comparable remote-desktop setup.

Nice to have

• Experience supporting a HIPAA or otherwise regulated environment.
• Multi-tenant, MSP, or M&A / agency-integration IT experience.
• Hexnode and Azure Virtual Desktop (AVD) specifically.
• Light scripting for automation (PowerShell or similar).

What we offer

Gyde offers a competitive benefits package to all employees.  

• Top of the market compensation
• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Retirement Plan (e.g., 401K) 
• Parental Leave