Director of AI Engineering

Jet Support Services, Inc. (JSSI)

. Define and execute delivery roadmaps for applications using Claude Code Enterprise and agentic development .

Posted 9/24/2026full-timeChicago • Illinois • United StatesLead💰 $170,000 - $250,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive experience in delivering production software and leading engineering teams, with a strong focus on AI integration, governance, and measurable business outcomes. Proficient in creating reusable engineering assets and implementing secure development practices across diverse environments.

Highest-signal resume keywords

Claude Code ProficiencyC# ProgrammingAI Delivery SuccessEngineering Team LeadershipGovernance and Secure Development Practices

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

C#.NET / ASP.NET CoreREST APIsReact/TypeScriptSQL Server / Azure SQLAI Coding AgentsDORA MetricsDeveloper Productivity TelemetrySecure CI/CDCloud-Native Patterns

Soft Skills

Stakeholder ManagementProject ManagementJudgment in Balancing Speed and QualityCommunication of Technical Concepts

Tools & Technologies

Azure DevOpsGitHubSonarQubeSalesforceDynamics 365 F&OMicrosoft Fabric

Industry Keywords

Enterprise SoftwareAI GovernanceSaaSB2B EnvironmentsAI Evaluation Frameworks

Tech Stack

Tools & technologies

ASP.NETAzureCloudReactSDLCSQLTypeScript.NET

About the role

Key responsibilities & impact

Define and execute delivery roadmaps for applications using Claude Code Enterprise and agentic development
Embed AI across the delivery cycle, including spec-driven intent, agent execution, automated verification, and production insight
Maintain accountability for the reliability, accuracy, and business impact of shipped software, AI agents, LLM-powered features, and automation
Align engineering standards, roadmaps, reusable patterns, and architecture recommendations with peer leaders
Prototype, review examples, challenge assumptions, and apply hands-on engineering judgment
Manage hiring, onboarding, performance management, and career development for a team of three to eight AI solution architects, engineers, and verification architects
Operate a unified delivery model across onshore and offshore teams
Coach solution architects and build team capability through learning paths, enablement sessions, office hours, and communities of practice
Drive responsible enterprise adoption of Claude Code through onboarding, usage patterns, guardrails, training, and coaching
Create reusable engineering assets, prompt libraries, MCP and context-sharing patterns, testing patterns, API standards, architecture decision records, and secure coding standards
Establish AI First governance covering code ownership, reviews, IP and secrets protection, auditability, model usage, and human accountability
Ensure responsible AI practices covering fairness, explainability, monitoring, security, and regulatory alignment
Integrate AI systems and automation with Salesforce, Dynamics 365 F&O, Microsoft Fabric, and proprietary products
Standardize MCP server development and consumption for enterprise systems
Establish observability and lifecycle-management standards for production automations
Define and report engineering, AI adoption, productivity, quality, reliability, and cost metrics
Build relationships across Engineering, Product, Architecture, Security, Infrastructure, Data, Finance, Sales, and Operations
Evaluate AI engineering capabilities and vendors for JSSI’s Azure/Microsoft environment and enterprise risk posture
Communicate progress, risks, investment needs, adoption, and business impact to executives
Partner with Product and business stakeholders to deliver on time, on target, and on budget

Requirements

What you’ll need

10+ years delivering production software in enterprise or product-led environments
5+ years leading engineering teams and distributed or global teams
Recent hands-on AI delivery success with production systems and measurable outcomes
Claude Code strongly preferred
Fluency with C#, .NET / ASP.NET Core, REST APIs, React/TypeScript, SQL Server / Azure SQL, cloud-native patterns, and secure CI/CD
Experience leading engineering transformation, developer enablement, or SDLC modernization across multiple teams
Experience implementing governance, guardrails, and secure development practices in enterprise environments
Ability to define metrics and connect engineering practices to business outcomes
Excellent stakeholder and project management skills
Ability to explain engineering and AI concepts to executives and technical audiences
Strong judgment balancing speed, quality, security, cost, and AI adoption
Hands-on experience with AI coding agents and agentic workflows
Experience creating reusable AI assets, including skills, agents, prompt libraries, workflow templates, MCP/context patterns, and codebase-specific instructions
Working knowledge of LLM APIs, preferably Claude API, including tool use, structured outputs, document processing, streaming, and rate limits
Understanding of AI evaluation frameworks and responsible-AI design aligned with Anthropic’s principles
Experience with DORA metrics, SPACE concepts, and developer productivity telemetry or dashboards highly desired
Experience with Azure DevOps, GitHub, PR governance, SonarQube or similar quality tooling, and secure software supply chain practices highly desired
Experience integrating Dynamics 365 F&O, Salesforce or equivalent CRM, and Microsoft Fabric highly desired
Experience in SaaS, aviation, asset management, or complex B2B environments highly desired
Bachelor’s degree in Computer Science, Engineering, or related field, or equivalent experience; advanced degree a plus
Ability to work across onshore and offshore teams

Benefits

Comp & perks

Annual discretionary bonus plan
Incentive or sales bonus plan, or other additional compensation based on role
Medical insurance
Dental insurance
Vision insurance
Retirement savings programs
Benefits starting day one of employment for full-time employees based in the USA, Canada, or the Philippines