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. 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. 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. What You’ll Own 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 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. Required Experience 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. 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 unglamorous parts. 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. Nice to Have Prior Founding CTO, CTO, or VP Engineering role at an early-stage company. Power Platform / Dataverse low-code depth. Experience with TPAs, payers, brokers, or self-funded plan administration. Azure DevOps and IaC (Bicep / Terraform) at production scale. Production agentic systems (LangGraph, AutoGen, Semantic Kernel, or custom orchestration). You are orchestrating agents and creating agentic workflows using tools like Copilot Studio, OpenHands, or OpenClaw. You are building scalable evaluation pipelines to validate model behavior and performance for LLM optimization. Who You Are These traits matter as much as the technical chops: 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. 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. 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. 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. How We Work Small team, high trust, no theater. The CEO is a serial entrepreneur and attorney with deep domain authority — he sets product direction; you set technical direction. The partnership runs on candor: you ask, he answers, you challenge, he challenges back, you commit and ship. We move fast, document what matters, and build for compliance from Day 1. Compensation: Salary for this position ranges from $275,000.00 - $325,000.00. The base pay offered will be determined on factors such as experience, skills, training, location, certifications, and education. Decisions will be determined on a case-by-case basis. In addition to the base salary, this position may be eligible for performance-based incentives. Qualifying positions will also be eligible for comprehensive benefits, such as participation in family medical and dental insurance programs, 401K plan, and PTO. Must be authorized to work in the United States on a full-time basis without Company sponsorship. PERMA FAIR is proud to be an equal opportunity employer. All qualified applicants will receive consideration without regard to race, color, religion, gender, affectional or sexual orientation, gender identity or expression, national origin, ancestry, nationality, age, disability (physical or mental), marital or domestic partnership or Civil Union status, pregnancy, family medical history or genetic information, atypical cellular or blood trait, military service or any other status protected by law.