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Founding Technical Lead, Applied AI

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Witlore
Full Time position
Listed on 2026-10-15
Job specializations:
  • Software Development
    AI Engineer (Applied/Software), Machine Learning/ ML Engineer, Software Engineer, Backend Developer
Salary/Wage Range or Industry Benchmark: 180000 - 240000 USD Yearly USD 180000.00 240000.00 YEAR
Job Description & How to Apply Below

Witlore is building professional services companies that run themselves. We automate the work to expand capacity, speed up delivery, and accelerate economic growth.

The founding technical lead will design the systems, own the architecture and make the service run

Own technical delivery inside the businesses we invest in. Write the code. Make the hard calls. Raise the team’s standard. Ship software people can rely on.

What you own

  • Architect the whole system. Connect data, documents, AI models, APIs and existing software into systems that scale across businesses. Decide what runs autonomously, where people step in, and how results get checked.
  • Ship it. Keep it running. Build critical components. Own deployment, monitoring, access controls and recovery. Get on site. Understand the work. When something fails, take responsibility.
  • Raise the engineering standard. Review designs and code. Make engineers better. Turn proven solutions into reusable components. Make clear technical decisions and carry them into production.

Results that count

Reliable systems in daily use. Faster delivery. Lower cost per job. Reusable technology that carries proven improvements across businesses.

What you bring

  • Proof in production. You have designed, shipped and operated systems customers rely on. Show the architecture. Explain the failure modes. Put numbers behind the business results.
  • Technical judgment. Know when to use AI, conventional code or human review. Reason through data quality, evaluation, security, cost and performance. Defend the tradeoffs.
  • Lead from the work. Write and debug code. Make clear decisions. Give direct feedback. Raise the capability of the engineers beside you.

Compensation

Initial equity: 0.5-2.0%.

Related roles and keywords

We welcome experience across these related roles, tools and workflows. Familiarity with every item is not required.

Automation and implementation roles: AI Automation Engineer; AI Automation Developer; AI Automation Specialist; AI Workflow Engineer;
Workflow Automation Engineer;
Automation Engineer;
Business Process Automation Engineer;
Intelligent Automation Engineer; RPA Developer;
Integration Engineer; AI Integration Engineer; AI Implementation Engineer;
Implementation Engineer;
Solutions Engineer; AI Consultant; AI Automation Consultant;
Low Code Developer;
No Code Developer.

Career paths and builder backgrounds:
Junior AI Engineer;
Entry Level AI Engineer;
Graduate AI Engineer;
Junior Software Engineer;
New Grad Software Engineer;
Early Career Engineer;
Associate Forward Deployed Engineer; self-taught developer; bootcamp graduate; freelance developer; independent builder; startup engineer; founding engineer; technical founder; open-source contributor; hackathon projects; AI-native; entrepreneurial; resourceful; self-directed; ownership; rapid learning; practical problem solving.

AI assisted development: AI coding tools; AI coding agents; AI-assisted software development; agentic coding; AI pair programming; vibe coding; rapid prototyping; debugging AI-generated code; code review;
Cursor;
Claude Code;
OpenAI Codex;
Git Hub Copilot;
Windsurf;
Gemini CLI;
Replit;
Lovable;
Bolt.new; v0.

AI models and application capabilities: artificial intelligence; machine learning; generative AI; large language models; LLMs;
OpenAI API;
Anthropic API;
Claude;
Google Gemini;
Llama;
Ollama;
Hugging Face; model selection; prompt engineering; context engineering; function calling; structured outputs; JSON Schema; multimodal AI; natural language processing; NLP; information extraction; speech to text; text summarization; conversational AI; AI assistants; chatbots; voice agents.

Enterprise AI platforms and services:
ChatGPT;
Azure OpenAI;
Azure Foundry;
Microsoft Copilot;
Palantir Foundry;
Palantir…

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