Rachel Wilde

Rachel Wilde

AI Transformation & CX · Tomboj

Operator-first AI strategist who builds systems that actually stick — from first pilot to enterprise scale.

About Rachel

Rachel Wilde is an AI transformation strategist and the founder of Tomboj, a consultancy that helps mid-market and PE/VC-backed companies build AI systems grounded in operations reality. With 20+ years leading global teams and building functions from scratch — across workforce management, hospitality tech, and frontline worker platforms — Rachel brings an operator's eye to AI adoption: less hype, more infrastructure. Her work spans AI product launches, workflow automation (BPM/RPA/OCR), change management, and the organizational design required to make AI stick across departments. She has led enterprise implementations serving 3 to 80+ person teams and has driven measurable outcomes including a 98% reduction in implementation cycle time and the launch of end-to-end AP automation pipelines impacting 14 departments. Sub-sectors she speaks to include proptech, hospitality tech, restaurant tech, frontline HCM, and fintech-adjacent operations. Rachel is known for a "training wheels" change management philosophy — meeting operators where they are before handing off the wheel.

Speaking topics

AI Strategy & Transformation
AI Talent & the Future of Work
Generative AI & LLMs
AI Governance, Risk & Regulation

Thought leadership

No published thought leadership from this expert yet.

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