AI Operations & Innovation Lead

Were hiring an AI Operations & Innovation Lead!

Summary

• Flexible Title: Can tailor to reflect your skills & experience from AI Integration Specialist to Head of AI Operations.
• Flexible Time: Can do full-time part-time side-gig (off-hours) or fractional (contract).
• Flexible Commitment: Can do short-term long-term or intermittent.

Why so flexible Were a FUNDED startup racing to launch end of Q1 2026. That gives us just 3 months to stack features while raising additional working capital. Feel free to jump in help us ship then bounce >> or stick around. A successful launch translates into lots of permanent jobs for those that want them. Were also interested in long term side gig relationships if thats what youre into - in our experience a few expert hours often beat full-time learning-curve hours.

About Us

Were a credible funded remote-first startup led by a serial technical founder and backed by a 20-person team. The product is live in private alpha.

Learn more about our founder team and comp structures at .

About The Role

This isnt an automation role automation is table stakes. This is about pushing the envelope on AI integration and building systems that make an AI-native team even smarter.

Were looking for someone who sees this as an opportunity to experiment innovate and write about it. Youll have the freedom to try new approaches fail fast and publish your learnings. No red tape no bureaucratic approval chains just a fast-moving team that wants to see whats possible.

Heres where we are today:

Our software devs have already experimented with using AI bots (Runbear) to digest status updates and meeting transcripts generating daily weekly and monthly rollups. It works. But its just the beginning.

Heres where we want to go:

We want to build a system that extracts and structures all this information meeting transcripts status updates project management data from ClickUp and more into a persistent organized knowledge base (think git repo or shared drive). The goal: make this structured data available for intelligent analysis and reporting via Cursor/Claude and accessible to staff as shared files not just ephemeral bot responses.

Imagine: any team member can query the full context of a project get AI-generated insights on velocity trends surface blockers before theyre escalated or generate investor-ready updates on demand. Thats the vision.

What Success Looks Like in 30 Days

• Youve mapped our AI tooling and data flows designed the knowledge base architecture and shipped a working system that ingests data from multiple sources
• Staff can access structured project context as shared files
• At least one AI-powered analysis workflow is live (e.g. weekly rollups blocker detection)
• Youve identified and queued the next wave of high-leverage integrations

What Success Looks Like in 60 Days

• The system is a core part of how the team operates
• AI-generated insights are surfacing actionable information proactively
• Youve shipped several experiments and itterated based on team feedback
• Youve documented the architecture and published at least one external post on your learnings

What Success Looks Like in 90 Days

• The knowledge system is mature scalable and self-maintaining
• Youre advising on the next frontier of AI integration agents proactive assistants or novel applications
• Your work has become a competitive advantage and recruiting asset for the company
• Youre recognized internally (and ideally externally) as a thought leader in AI operations

What Youll Do

• Design and build systems that extract structure and persist operational data for AI consumption
• Integrate data sources: Slack ClickUp meeting transcripts status updates and more
• Create AI-powered analysis and reporting workflows using tools like Cursor Claude and custom integrations
• Make structured knowledge accessible to the team as files not just bot responses
• Experiment with new AI tools techniques and architectures and share your learnings
• Collaborate with engineering and leadership to identify high-impact AI integration opportunities
• Document your work and (optionally) publish blog posts or case studies on your innovations
• Stay on the bleeding edge of AI tooling agents and knowledge management

What Were Looking For

• Hands-on experience with AI/LLM integrations youve built systems that leverage GPT Claude or similar models in production
• Systems thinker you see data flows not just individual tools
• Technical enough to build Python JavaScript or similar; comfortable with APIs webhooks and data pipelines
• Experience with knowledge management data extraction or information architecture
• Familiarity with tools like Slack ClickUp Notion Obsidian git-based knowledge systems or similar
• Curious and experimental youre excited by ambiguity and the chance to try new things
• Strong communicator you can explain complex systems simply and document your work clearly
• Self-directed and proactive you dont wait for permission to innovate
• Bonus: Youve written publicly about AI automation or knowledge systems

Why This Role is Different

Most companies talk about AI but move at a glacial pace. Were an AI-native team thats already experimenting we just need someone to take it to the next level. Youll have:

• Freedom to experiment without layers of approval
• A team that gets it engineers and leadership who understand AI and want to push boundaries
• The opportunity to publish your work and build your personal brand
• Real problems to solve not theoretical exercises but systems that make a growing team more effective

If youve been waiting for the right environment to truly innovate with AI this is it.