Chief Technology Officer

About the role

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.

Responsibilities

• 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.
• 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.
• 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 ID), 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.

Requirements

• 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 ID. You’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.
• HIPAA-grade compliance instincts: Zero Trust, BAA structuring, PHI handling, audit trails. You know what an Azure HIPAA architecture should look like without being told.
• .NET 8 depth.
• Business sense: you can follow a P&L, understand unit economics, and translate operational pain into agentic automation instead of headcount.

Qualifications

• Curious by default. You ask probing, specific questions before you write code. You’d rather take an extra day to understand the problem than ship the wrong solution fast.
• You translate vague vision into concrete acceptance criteria, technical decisions, and trade-offs. You don’t let ambiguity hide in a deck.
• You are willing to challenge up. You push back on the CEO when you disagree — respectfully, with reasoning and evidence. You know “yes-CTOs” build wrong products.
• You are a translator. You can sit with a domain-deep founder who has the vision but not always the words, draw it out through dialogue, and turn it into a buildable spec.
• You are comfortable being wrong. You change your mind when the data changes, out loud, without ego.

What This Role Is Not

• Not a VP of Engineering running standups and approving headcount requests.
• Not an advisory CTO reviewing architecture decks from a distance.
• Not a strategy-only seat — you'll be in the code, the IaC, and the eval harness daily.