
Harry Siggins
Helps teams build AI-first operations
harrysiggins
Seattle, Washington
Joined January 2025
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Summary
Systems-focused operator who turns strategy into repeatable operating rhythms. Across five years as an early hire and Chief of Staff at Quantive (Gtmhub), Harry built customer-success and U.S. GTM operations, led leadership initiatives and offsites, and built OKR programs that prioritized co-creation, focus, and iterative learning rather than top-down bureaucracy. readoperator+1
Practical AI adoption lead: Harry now helps growth teams scope and ship AI-enabled operational systems. He emphasizes starting with workshops to map pain, running atomic pilots tied to clear metrics, creating internal ambassadors, and treating AI work like a product with measurement and iteration. onetwogrowth+2
Portfolio / fractional operator and mentor: after scaling himself out of day-to-day work at a hypergrowth startup, Harry moved into fractional Chief of Staff work, workshop facilitation, and mentoring—helping other Chiefs and leaders design operating systems, adopt OKRs meaningfully, and use AI without creating chaos. youtube+2
Work
Education
Projects
Writing
Issue 65: How Chiefs of Staff Can Drive AI Adoption—Without Chaos (author contribution)
April 1, 2025Practical, structured playbook for AI adoption targeted at Chiefs of Staff: how to scope pilots, create an AI function/pods, use ambassadors, and tie AI to OKRs and Rhythm of Business.
Owners: The Good, The Bad, and The Ugly
April 1, 2023Substack piece on ownership, leadership and long-term thinking in professional football (soccer) — part of his newsletter 'The Beautiful Game Plan'.
Hobbies
Writes and analyzes soccer tactics and strategy via his Substack 'The Beautiful Game Plan'. substack
Notes
SMsibi msaid they've seen
HSHarry Siggins
excel at juggling multiple priorities and driving key initiatives in a fractional Chief of Staff role.Jul 28, 2025