Chief Technology Officer

About PermaFAIR

PermaFAIR operates a proprietary healthcare claims repricing platform built on .NET 8 and EDI Fabric, running on Azure. We ingest and reprice 837P (professional) and 837I (institutional) claim transactions at scale, delivering measurable savings for self-funded plans and the TPAs, brokers, and consultants who serve them.

We’re at an inflection point. The repricing engine is mature; the next chapter is three things at once: (1) productizing our CRM/CSR engagement layer as a true multi-tenant SaaS on Microsoft Dynamics 365 + Azure, (2) embedding AI deeply into the repricing workflow, and (3) operating the business itself on an agentic, AI-native foundation. We’re looking for the technical leader who will architect and build that future shoulder‑to‑shoulder with the CEO.

This is a hands‑on CTO seat, not a management role. You’ll spend most of your time in the architecture and the code — designing systems, writing the hard parts, reviewing PRs, owning the AI layer end‑to‑end — while directing a small internal team (one senior architect/developer, one mid/junior engineer) and outside vendors. You are the technical authority of the company.

You’ll partner directly with the CEO, who brings a decade-plus of domain depth in healthcare claims, self‑funded plans, ERISA, and the legal and business mechanics of this market. He has a sharp product vision that he doesn’t always articulate in technical terms. Your job is to extract that vision through good questions, translate it into specs and architecture, push back when he’s wrong, and ship.

If you’ve been a Principal Engineer or Staff Architect ready for the seat at the table — but allergic to a role that pulls you away from building — this is for you.

• Multi‑tenant SaaS productization. Take the CRM/CSR engagement layer (Dynamics 365 + Azure) from internal platform to a real, sellable multi‑tenant SaaS product. Tenant isolation, onboarding, entitlement, metering, SLA enforcement, and cross‑tenant federation via Entra B2B, APIM, Event Grid, and Synapse Link.
• The AI middle layer. Design and build a model‑agnostic AI abstraction layer: champion/challenger routing, price‑aware model switching, fallback chains, evaluation pipelines, cost telemetry, prompt versioning. We refuse to be locked into any single AI vendor — you’ll make that real in production.
• AI in repricing. Lead the integration of AI into the existing .NET 8 / EDI Fabric repricing engine — claim classification, exception triage, negotiation assist, document parsing, and citation‑grade retrieval over plan documents (SPDs, SPCs, ERISA, Taft‑Hartley, state and local regs).
• Agentic operations. Build internal agents that run the business: task and project agents, eval agents that grade other agents, compliance attestation agents, onboarding agents. You’ll instinctively look at every recurring operational task as an automation candidate rather than a hiring problem.
• Architecture and platform leadership. Own the full Microsoft stack:
  Azure (Service Bus, Event Grid, APIM, Functions, Logic Apps, Dataverse, Synapse Link, ADLS, Key Vault, Entra ), Dynamics 365 Sales + Customer Service, Power Platform, Azure AI Search, Azure OpenAI. Set the bar for security, HIPAA/GDPR compliance, Zero Trust, observability, and CI/CD.
• Team and vendors. Lead and grow a small, senior internal team. Direct outside vendors and implementation partners. Hold the engineering quality line.

• 10+ years building production systems, with recent years as a Principal Engineer, Software Architect, Founding Engineer, or hands‑on CTO.
• Deep Microsoft stack fluency:
  Azure (Service Bus, Event Grid, APIM, Functions, Logic Apps), Dynamics 365 (Sales + Customer Service), Dataverse, Power Platform, Entra ’ve designed cross‑tenant federation in production.
• Healthcare claims domain: hands‑on experience with EDI X12 (837/834/835), CMS‑1500 and UB‑04, ERISA/Taft‑Hartley plan structures, repricing or negotiation workflows. Non‑negotiable.
• Multi‑tenant SaaS scars: you’ve taken at least one platform from single‑tenant or internal to a real multi‑tenant SaaS — tenant isolation, billing, onboarding, SLAs, the…