Director of AI – Strategy, Engineering & Products

Grey Parrot Systems (GPARROT) is placing a Director of AI for a key client engagement — owning and leading AI strategy, engineering practice, product development, and delivery for a fast-growing, AI-first enterprise organization.About Grey Parrot SystemsGrey Parrot Systems (GPARROT) is a women-owned, BEP-certified IT services firm headquartered in Naperville, IL. We connect top technology leaders with high-impact opportunities across our mid-market enterprise client portfolio — spanning retail, logistics, manufacturing, and healthcare.About Our ClientOur client is a fast-moving, AI-first enterprise organization committed to embedding AI across their technology stack, products, and operations. They are looking for a Director of AI to define and own their AI vision — and personally lead its execution across engineering, products, and client-facing delivery. This is a direct placement — the selected candidate will join the client's team full-time.About the RoleThis is a senior leadership role for an AI practitioner who combines deep technical AI expertise with strategic vision, executive presence, and the ability to build and lead high-performing teams. You will define the client's AI strategy — how they build, deliver, and operationalize AI-powered solutions — and you will own its execution across engineering, products, and enterprise platforms.You are not a theorist. You have built and shipped production-grade AI systems — LLM-powered applications, agentic workflows, RAG pipelines, and AI-DLC engineering practices — and you know how to translate that technical depth into business value that executives understand and act on. You lead engineers, inspire stakeholders, and influence C-suite leadership with equal credibility and confidence.If you are a senior AI leader who is ready to own the AI vision and delivery of a growing enterprise organization — this role was built for you.Must-Have Skills10+ years of technology experience with 5+ years in AI, machine learning, or applied AI engineering — including 3+ years in a leadership or director-level roleDeep hands-on AI engineering expertise — LLMs, RAG pipelines, agentic workflows, LangChain, LangGraph, Claude, OpenAI, or similarStrong AI strategy experience — defining AI roadmaps, evaluating emerging AI technologies, and translating AI capabilities into business valueExperience leading and scaling AI engineering teams — hiring, mentoring, and building high-performance AI-first engineering culturesDeep familiarity with AI-DLC practices — Claude Code, Cursor, GitHub Copilot, MCP workflows, and AI-assisted engineering pipelinesExperience delivering production-grade AI products and solutions — from architecture through deployment, governance, and optimizationStrong executive communication skills — presenting AI strategy, product roadmaps, and delivery outcomes to C-suite executivesStrong understanding of AI governance, responsible AI, data privacy, and compliance frameworksExcellent written and oral communication skills — making complex AI concepts accessible to non-technical audiencesWhat You'll DoAI Strategy & VisionDefine and own the client's AI strategy — technology direction, capability roadmap, and competitive differentiationEvaluate and recommend emerging AI technologies, platforms, and frameworksTranslate AI capabilities into compelling business solutions and service offeringsPartner with C-suite leadership to align AI strategy with business goals and market opportunitiesEstablish AI governance frameworks — responsible AI practices, data privacy standards, and compliance controlsAI Engineering & DeliveryLead and govern AI engineering delivery — LLM-powered applications, RAG pipelines, agentic workflows, and AI-DLC engineering practicesDefine and enforce AI engineering standards, architecture patterns, and best practicesDrive adoption of AI-DLC practices — Claude Code, Cursor, GitHub Copilot, and MCP workflowsOwn technical architecture decisions for complex, multi-platform AI engagementsBuild reusable AI engineering accelerators — prompt libraries, agentic workflow templates, and RAG architecturesAI Products & PlatformDefine and drive the AI product roadmap — building AI-powered tools, accelerators, and platformsOversee design and development of AI-native products — LLM interfaces, intelligent dashboards, and agentic automation toolsPartner with product owners, UX designers, and engineering leads to ship production-ready AI productsEvaluate AI platform partnerships — LLM providers, vector database vendors, and AI workflow orchestration platformsTeam Leadership & CultureBuild, lead, and scale the AI engineering team — recruiting top AI talent, defining career paths, and creating an AI-first cultureMentor and coach senior AI engineers, ML engineers, and technical leadsRepresent the organization as an AI thought leader — building reputation and credibility in the marketCollaborate with business development teams to position and win AI engagementsTech StackClaude · Claude Code · LangChain · LangGraph · RAG Pipelines · Vector Databases · OpenAI / Anthropic APIs · Dify · MCP (Model Context Protocol) · Python · Azure OpenAI · AWS · Azure · GCP · Cursor · GitHub Copilot · Docker · Kubernetes · CI/CD · Jira · Microsoft 365Nice to HaveExperience building or scaling an AI practice within an enterprise or consulting environmentPublished thought leadership — blog posts, conference talks, or open source contributions in AIExperience with AI governance frameworks — NIST AI RMF, EU AI Act, or equivalentFamiliarity with MLOps platforms and production ML model deploymentExperience with AI-powered data platforms — Snowflake AI, Databricks AI, or similarAdvanced degree in Computer Science, AI, Machine Learning, or a related fieldWhat Sets You ApartYou have shipped production AI systems that real users depend on — not just prototypes and demosYou can explain transformer architecture to an engineer and AI ROI to a CFO — in the same afternoonYou build AI teams that stay — because you invest in people as much as technologyYou are already using Claude Code, MCP, and AI-DLC practices daily — not planning to startYou see AI governance and responsible AI as competitive advantages — not compliance burdensDetailsLocation: Remote — US-based candidateExperience: 10+ years (3+ years in AI leadership / director-level role)Type: Full-Time — Direct Placement with ClientPlaced by: Grey Parrot Systems (GPARROT)Start: ImmediateGrey Parrot Systems is an Equal Opportunity Employer. As a women-owned, BEP and WBENC-certified firm, diversity and inclusion are core to who we are. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, marital status, or any other legally protected characteristic. We strongly encourage applications from candidates of all backgrounds, identities, and experiences — including those from underrepresented groups in technology. Reasonable accommodations are available upon request.Stay ConnectedFor more job openings, company updates, and AI industry insights, follow Grey Parrot Systems on LinkedIn.👉 https://www.linkedin.com/company/gparrot/We are always looking for talented, driven professionals to join our growing team. Whether this role is the right fit today or not, connect with us and be the first to hear about new opportunities as we expand across Chicago, Detroit, and the Midwest.