
Shiloh Boss
@shilohboss
Chief of Staff and Organizational strategist who reads organizations as systems and designs the intervention and programs they actually need to scale.
What I'm looking for
Organizational strategist who reads organizations as systems and designs the intervention they actually need — from full operating-model redesign to targeted structural, process, and cultural change — to move them through inflection points in decision-making, accountability, and growth. Fifteen years leading that work, including an enterprise turnaround that scaled a stagnant company from $3M to $30M in three years, alongside a parallel track record building leadership capability, organizational learning, and award-winning culture. Holacracy-certified, with years of experience applying decentralized-governance principles — integrated decision-making, distributed accountability — within consulting and leadership practice. Now focused on bringing that systems-level judgment to an organization built on that same philosophy at enterprise scale.
Experience
Work history, roles, and key accomplishments
Lead Strategic Consultant and Program Manager
LivingSystemsTech
Jan 2016 - Present (10 years 10 months)
Independent consultancy engaged by networks, coalitions, and growth-stage enterprises to architect operating-model and culture transformation. Served as embedded organizational strategist for enterprises and cross-sector networks navigating structural inflection points.
Head of Operations & People, Program Manager, Lead Strategist
RevOffers
Jan 2019 - Dec 2021 (2 years 11 months)
Rapid-growth startup scaling from founding-stage to established mid-market operations; recruited to build the organizational architecture behind 2x year-over-year growth. Operated as de facto COO-level strategic partner to the CEO, CRO, and CTO.
Education
Degrees, certifications, and relevant coursework
Naropa University
Bachelor of Science, Transpersonal Psychology
1997 - 2002
Bachelor of Science in Transpersonal Psychology.
Tech stack
Software and tools used professionally
Availability
Location
Authorized to work in
Salary expectations
Social media
Job categories
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