Director, AI First Enterprise Architecture

About JSSIFounded in 1989 and headquartered in Chicago, Jet Support Services, Inc. (JSSI) is the largest independent provider of hourly cost maintenance programs for business aviation. JSSI delivers comprehensive coverage for engines, airframes, and auxiliary power units (APUs) across more than 300 different aircraft makes and models, helping owners and operators stabilize maintenance budgets, maximize aircraft availability, and protect asset value throughout the lifecycle of ownership. JSSI has built a portfolio of complementary business lines designed to simplify the economic and technical complexity of business aviation; these include Maintenance teams, Traxxall maintenance tracking software, Parts & Engines, Conklin aircraft cost and performance data, and Aviation Capital asset-based financing solutions. Together, these offerings support owners, operators, and maintenance providers with integrated tools spanning ownership and maintenance planning, execution, and financial management. With more than 6,500 aircraft supported through programs and software platforms, JSSI leverages its unique independence, unmatched scale, and data-driven insight to deliver customized solutions and support models aligned to the interests of each client — regardless of aircraft platform. JSSI is backed by leading institutional investors GTCR, Genstar Capital, and Blackstone. Learn more at jetsupport.com. Position Summary:As Director, AI First Enterprise Architecture, you define and own the enterprise architecture vision and standards that shape how JSSI builds software in an AI First, agentic engineering model. Reporting to the SVP of Engineering & AI Transformation, you set the reference architectures, API and integration standards, and architectural guardrails that every engineering vertical follows, converting JSSI’s investment in Claude Code Enterprise and the Microsoft/Azure platform into consistent, secure, and scalable systems.This is a hands-on, high-influence leadership role. You chair JSSI’s Architecture Review Board (ARB), where you advocate and uphold shared architecture standards across the AI Solution Architects embedded in each engineering vertical. You directly lead two AI Solution Architects who serve as your enterprise architecture team, and you partner closely with the Directors of Engineering so that delivery teams build on common patterns rather than divergent one-offs. Position Responsibilities:AI First Enterprise Architecture & StrategyDefine and own JSSI’s AI First enterprise architecture vision, aligning agentic engineering, product platforms, data strategy, and modernization with business priorities across maintenance, parts, leasing, programs, asset management, and customer operations.Architect enterprise-scale AI ecosystems spanning multi-agent systems, retrieval-augmented generation (RAG) and knowledge platforms, MCP-enabled tooling, model lifecycle management, and AI-assisted SDLC capabilities.Establish the Microsoft/Azure-first architecture posture (C#/.NET, ASP.NET Core, React/TypeScript, Azure SQL, Service Bus, Entra ID, Key Vault, App Services, AKS/ACR, Application Insights, and secure CI/CD) as the default for new and modernized systems.Operationalize Claude Code Enterprise as a strategic accelerator across specification, code generation, refactoring, testing, documentation, and review, supporting JSSI’s goal of 100% AI-generated code with human accountability for intent, architecture, and quality.Architecture Review Board, Standards & GovernanceChair the Architecture Review Board (ARB), setting the agenda, cadence, and decision rights that drive consistent architecture across engineering verticals.Advocate and uphold shared standards across the AI Solution Architects embedded in each vertical, ensuring teams build on common patterns, contracts, and guardrails rather than divergent implementations.Define and maintain API design, event-driven, data contract, versioning, and interoperability standards, along with the agent behavior boundaries and evaluation frameworks that keep AI deployment responsible and predictable.Establish governance for AI First development: code ownership, review expectations, IP and secrets protection, auditability, approved model usage, and human-in-the-loop accountability, in partnership with Security, Legal, and Infrastructure.Reference Architectures & Platform AlignmentPublish and mature reference architectures, architecture decision records (ADRs), reusable patterns, and engineering playbooks that improve delivery speed without sacrificing quality.Standardize how teams build and consume MCP servers that expose JSSI enterprise systems (Salesforce, Dynamics 365 F&O, Microsoft Fabric, and proprietary products) as secure, model-ready tools.Ensure AI systems and automation integrate reliably with JSSI’s enterprise platforms, coordinating with the data and platform teams that own them.Define observability, lifecycle-management, performance, and resiliency standards that keep production AI systems dependable as they scale.Project Intake, Discovery & Emerging Capability AdoptionServe as the architectural intake gate for new initiatives, assessing incoming project and product requests for architectural fit, AI suitability, feasibility, build-versus-buy options, risk, and alignment to enterprise standards before they enter delivery.Provide clear intake recommendations and sizing inputs to the SVP, Product, and engineering leaders so the organization commits to the right work with full visibility into architectural impact.Maintain a forward view of the AI and agentic landscape (models, tools, frameworks, and vendor capabilities) so JSSI knows what is coming and can plan deliberately rather than react.Leadership, Mentorship & Stakeholder PartnershipDirectly lead and develop two AI Solution Architects, owning their direction, coaching, and growth as the enterprise architecture team.Guide and influence the AI Solution Architects and engineering leaders across verticals through the ARB and technical leadership rather than direct management.Stay close enough to the work to prototype, review designs, challenge assumptions, and demonstrate credible hands-on engineering judgment, setting the standard the organization is expected to meet. Required Qualifications:Core Experience12+ years in software engineering and architecture, including 5+ years in a solution architect, principal engineer, or enterprise/product architecture leadership role with ownership of system design for production SaaS platforms.Demonstrated experience defining architecture strategy for cloud, distributed systems, APIs, integrations, and data platforms at enterprise scale.Production-level fluency in the Microsoft stack (C#/.NET, ASP.NET Core, REST APIs, React/TypeScript, SQL Server / Azure SQL) and distributed-systems patterns such as queues, caching, and scalable APIs.Hands-on experience designing and implementing AI First, spec-driven (SDD) workflows and agentic systems across the software delivery lifecycle.AI & Claude Ecosystem Proficiency (Claude Strongly Preferred)Hands-on experience with AI coding agents and agentic workflows (Claude Code strongly preferred; GitHub Copilot, Codex, or equivalent), including CLI integration and multi-agent pipelines.Hands-on experience with multi-agent design patterns (planning, orchestration, observability) and MCP server implementation against enterprise data sources.Production expertise with LLM APIs (Claude API preferred): tool use, structured outputs, document processing, streaming, and rate-limit management.Strong prompt engineering skills, including structured outputs and retrieval-augmented prompting.Working knowledge of AI evaluation frameworks (quality, cost, latency) and responsible-AI design aligned with Anthropic’s principles.Highly Desired QualificationsExperience in aviation, transportation, asset management, maintenance, aftermarket services, or other complex operational B2B domains.Experience with Azure AI Foundry, Azure OpenAI, Microsoft Fabric/OneLake, Semantic Kernel, Power Platform, or comparable AI engineering ecosystems.Familiarity with DORA metrics, SPACE concepts, and developer productivity telemetry.Integrations with Dynamics 365 F&O, Salesforce or equivalent CRM, and Microsoft Fabric. At JSSI, we are committed to rewarding our team members with competitive and comprehensive compensation packages that reflect their contributions and talent. For this role, the annual base pay generally ranges from $170,000 to $220,000, with the final offer determined by variable factors including but not limited to market location, job-specific knowledge, skills, education, and experience. In addition, your total rewards package may include an annual discretionary bonus plan, incentive or sales bonus plan, or other form of additional compensation, based on your role. Additionally, for full-time employees based in the USA, Canada, or the Philippines, we are proud to offer a robust suite of benefits. This ranges from insurance offerings such as medical, dental, vision, retirement savings programs, among others, starting day one of employment. For a full overview of our offerings, visit the JSSI Benefits Page on our company website. JSSI is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, protected veteran status, or other characteristic protected by law. JSSI does not accept unsolicited resumes from individual recruiters or third-party recruiting agencies in response to job postings. No fee will be paid to third parties who submit unsolicited candidates directly to our hiring managers or Recruiting Team.