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Head of AI/Architect

Greater Chicago area
AI, cloud, Claude, Co-Pilot, LLM, API, software
Job Category:
Software
About the Role

AI is changing how work gets done — and we want someone who can't wait to build that future here. We're looking for a Head of AI/Architect to design, build, and champion the AI workflows, automations, and tools that will transform how our entire organization operates. This is a rare, high-impact builder role: you'll take real operational challenges and turn them into working systems that people actually use and love — then teach the whole company how to get the most out of them. If you want to see your work create ripple effects across every team, this is that role.


What You'll Do


Build things that matter
  • Design and implement AI-led workflows that transform how we source opportunities, manage information, make decisions, and operate day to day

  • Use AI coding agents to build end-to-end systems with LLMs, agents, APIs, and automation tools — moving fast from idea to working prototype

  • Create internal AI tools people rely on: research assistants, workflow automations, dashboards, and operational support tools

  • Own your infrastructure end to end — design, build, testing, maintenance, iteration, and documentation

Teach and empower
  • Train technical and non-technical teammates alike on how to use AI to work smarter, faster, and with more      confidence

  • Turn cutting-edge AI capability into practical, everyday skill for people across the company — demystifying the tech and making adoption feel easy

  • Build learning resources, workshops, and hands-on sessions that turn curiosity into capability

  • Be the go-to person people come to when they want to level up how they work

Set the standard
  • Define and uphold standards for architecture, governance, documentation, security, and maintainability across our AI ecosystem

  • Continuously scout new AI tools, models, and platforms — running fast experiments to find what's worth scaling

  • Partner across finance, accounting, operations, and portfolio teams to turn friction into opportunity

What We're Looking For
  • Experience building with AI coding agents, LLMs, automation platforms, APIs, and no-code/low-code      tools

  • A portfolio of software or agents you've built that real people actually use

  • A genuine passion for teaching — you love making complex things click for others, regardless of their technical background

  • Proven ability to design full end-to-end workflows, not just isolated prompts or scripts

  • A builder's instinct: bias toward experimentation, iteration, and getting things into people's hands

  • Comfort operating independently in a small, fast-moving, low-structure environment

  • Clear, energetic communication — you can explain technical work in a way that gets people excited

  • Bonus: experience with venture capital, legaltech, operations, or legal industry workflows

Why You'll Love This Role

This is a builder's dream: high autonomy, high trust, and a wide-open canvas. You'll see your work adopted company-wide, shape how an entire organization thinks about AI, and become the person who taught everyone — from analysts to executives — how to work smarter with these tools. Every win you create compounds: the tools you build and the skills you teach make the whole company faster, sharper, and more capable.


Growth Opportunities

This role only grows from here. Over time, you'll have the chance to:

  • Shape foundational AI infrastructure and standards from the ground up, becoming the trusted authority on how AI gets built and used across the company

  • Launch and own a company-wide AI platform that others build on top of

  • Grow your training and enablement work into a full internal AI academy or center of excellence

  • Define how AI agents are scoped, hosted, and maintained company-wide

  • Take on high-visibility, cross-functional projects that shape company strategy

  • Build a track record of shipped, adopted tools and upskilled teams that leave a lasting mark

Ways of Working
  • Builder Mentality — tinkers constantly, moves fast from idea to prototype to working system

  • High Follow-Through — owns tools and training from first build through adoption and mastery

  • Proactive Problem-Solving — brings working solutions, not just observations

  • Clear, Energizing Communication — makes technical concepts land for any audience

  • Autonomy — operates independently with strong judgment and minimal oversight

  • Practical Technical Judgment — balances speed and experimentation with durability and security

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