Log in or create a free Rosenverse account to watch this video.
Log in Create free account100s of community videos are available to free members. Conference talks are generally available to Gold members.
Exit Interview #1: Greg Petroff: From Silicon Valley Executive to Sonoma County Possibilitarian
This video is featured in the Josh's test playlist playlist and 1 more.
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
-
•
Greg pivoted from architecture to tech and UX without initially knowing it was called UX.
-
•
Increased competition and ageism impacted Greg’s search for enterprise UX leadership roles recently.
-
•
Greg’s current consulting focuses on outcomes-first AI strategy for SMBs and enterprises using design thinking.
-
•
Letting go of professional identity was key for Greg to successfully pivot away from chief design officer roles.
-
•
Flexibility between startup and enterprise environments comes from understanding core design and leadership principles, not context.
-
•
Greg and Jorge Arango’s Unfinished practice involves service design methods but not building software themselves.
-
•
Successful AI adoption requires understanding an organization’s existing systems, tacit knowledge, and readiness to change.
-
•
Greg uses intention statements and periodic self-evaluation to guide his evolving career direction.
-
•
The biggest challenge in consulting with traditional companies is managing long-term vision versus their readiness for change.
-
•
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."
Or choose a question:
More Videos
"The AI assistant enables ongoing conversation and follow-up questions to refine persona insights dynamically."
Gillian Salerno-Rebic Mark MicheliFrom Insight to Impact: How JourneySpark Used WEVO Pulse + Pro to Drive a 50% Lift in Ad Engagement
June 11, 2025
"If we think about accelerating learning velocity, it's about creating specific altitudes of research questions to answer for the organization."
Jen Cardello Dr. Shadi Janansefat Alex WrightCurating insight: Strategies for integrating knowledge across research functions
March 11, 2025
"Designers need better training to work with off-the-shelf enterprise software like Sitecore, Salesforce, and SharePoint."
Alexandra SchmidtEnterprise UX Playbook
December 1, 2022
"Storytelling helps us speak in the language and context that motivates each team and stakeholder."
Christian Crumlish Wendy Johansson Rich Mironov Aditi Ruiz Adam ThomasAfternoon Insights Panel
December 6, 2022
"This is a conversation, a conference is just a polished snapshot of a conversation that’s happening."
Uday Gajendar Louis RosenfeldDay 1 Welcome
June 4, 2024
"Design ops is actually all about fragility. We do stability, security, planning, but can we add more experimentation and comfort with ambiguity?"
Silke Bochat5 Antifragile Strategies for a DesignOps 2.0
September 23, 2024
"Emotional intelligence is key to navigating situations with senior leaders multiple grades above you."
Isaac HeyveldExpand DesignOps Leadership as a Chief of Staff
September 8, 2022
"The subtle art of taking care of yourself and giving a f in ways that generally encourage coherent behaviors."
John CutlerThe Alignment Trap
November 29, 2023
"Outdated content will erode trust and make folks question whether other information is worth their time."
Gabrielle VerderberDocumentation Your Team Will Actually Use
October 3, 2023
