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Summary
After years leading design at Google, ServiceNow, and Cisco, Greg Petroff made a bold move—leaving Silicon Valley for Sonoma County and traditional corporate leadership for fractional executive work. Now building two consulting practices while serving as fractional CDO for a fintech startup, Greg embodies what he calls being a “possibilitarian”—seeing opportunity in moments of change. We’ll explore his transition to the emerging world of fractional leadership and how he’s helping organizations navigate our AI-infused moment
Key Insights
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Greg pivoted from architecture to tech and UX without initially knowing it was called UX.
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Increased competition and ageism impacted Greg’s search for enterprise UX leadership roles recently.
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Greg’s current consulting focuses on outcomes-first AI strategy for SMBs and enterprises using design thinking.
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Letting go of professional identity was key for Greg to successfully pivot away from chief design officer roles.
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Flexibility between startup and enterprise environments comes from understanding core design and leadership principles, not context.
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Greg and Jorge Arango’s Unfinished practice involves service design methods but not building software themselves.
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Successful AI adoption requires understanding an organization’s existing systems, tacit knowledge, and readiness to change.
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Greg uses intention statements and periodic self-evaluation to guide his evolving career direction.
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The biggest challenge in consulting with traditional companies is managing long-term vision versus their readiness for change.
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Having trusted partners and accountability structures supports sustainable entrepreneurial pivots.
Notable Quotes
"I know exactly this job, all its problems and dysfunctions, and I don’t want to do that anymore."
"How can I guide my community to design the form and behavior of light on the edge of becoming this?"
"The tools are more important than ever even if the title UX becomes less central."
"The AI conversation is slapping technology on everything versus actually looking at how humans work."
"If I don’t make a dollar doing this, I’ll be okay, but I actually am making a dollar doing it."
"You need to respect tacit knowledge and culture when redesigning workflows."
"I get bored super easily; that’s why I’m super into the AI stuff right now."
"We’re not marketing ourselves as providing UX services, but the toolkit we use is a very strong service design toolkit."
"One super small step of value is better than proposing the big picture if the client isn’t ready."
"End your day by writing the to-do list for tomorrow; it’s easy to get distracted when you’re not in a full-time gig."
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