Make the C-Suite Think Like a Startup (Without Getting Fired) | West Stringfellow, VP Product (ex-Target, Blackhawk)
West Stringfellow shares how he turned startup instincts into enterprise transformation, from hand-delivering his product strategy to Target execs to driving AI adoption at Blackhawk Network.
TL;DR
Today we’re joined by West Stringfellow, VP of Product at Blackhawk and former VP of Innovation at Target. West is a master of managing up, having spent his career driving transformation at major enterprises while also founding multiple startups. One of them was acquired by Target, where he went on to become VP of Innovation and launch the company’s still successful startup incubator.
In this episode, West shares:
How he helped a Fortune 100 retailer think and act more like a startup using his years of founder experience and data-driven strategy
Why aligning with executive incentives and real business goals is the fastest way to unlock innovation and get the C-suite to trust your product strategy
The playbook he now uses at Blackhawk Networks to drive AI adoption in a regulated enterprise by empowering AI “culture carriers”
1. Big companies and startups struggle with the same problems (8:40)
Before West ran innovation at a $77B company, he was a startup founder. He discovered something interesting:
Startups and enterprises have the same concerns. They both ask:
Who is the customer?
Where is the competition going?
Where is the market moving?
How do we grow — fast?
Why this matters:
If every company struggles to find growth, product leaders with founder experience can become some of the most valuable innovators inside the enterprise.
2. Managing up without getting fired (09:39)
West has built his career on helping giant organizations move faster, without getting shut down by bureaucracy. One of his most famous moves was printing 300+ copies of his product strategy and hand-delivering them to every executive at Target.
His advice: don’t make it about you, make it about the business.
“I approached sharing this information with Target purely from a place of, Hey, I’m sincerely trying to help you grow your business. Nothing in the data that I shared with them was my opinion.”
What product leaders can do:
Frame every idea around revenue, efficiency, or customer value
Lead with data, not opinion
Make executives the first customers of your idea
3. Speak the language of incentives (13:28)
To influence executives, you first have to understand them:
“Figure out who they are, figure out what they care about, and help them do their jobs. That’s what they really care about.”
West shares that Target’s CEO, Brian Cornell, loved that his data-driven strategy was refreshingly clear:
“Brian said, By the time things get to my desk, all the data has been sandblasted out of them… It’s so refreshing to see the data.”
What product leaders can do:
Map your strategy directly to business-critical KPIs
Execs are busy; give them just enough detail to understand the strategy
4. Transforming a regulated enterprise with AI, one “culture carrier” at a time (26:13)
At Blackhawk, West is leading AI adoption in a heavily regulated financial environment. Instead of top-down mandates, he empowers the naturally curious first:
“Those are the people who are the best to empower. They will carry the culture further in the organization than anyone could ever push.”
The metric he cares about most?
“When I see the light in the team’s eyes… when they do it for the first time, and they go, Oh my gosh. Everything is about to change.”
What product leaders can do:
Start with your AI early adopters
Teach the process of working with AI, not just the tool
Build a peer-to-peer community that lifts the entire org
Links
Chapters
00:00: Introduction
01:17: West’s career journey
02:08: Project Goldfish and West’s startup background
05:43: Making product and strategy decisions at Target
06:25: West building a Techstars Startup Accelerator
08:39: How West’s work at Target inspired his startup, HowDo
09:44: How did West “manage up” at Target?
17:05: An introduction to Blackhawk
21:02: Digital transformation with gift cards
23:44: How Blackhawk is using AI
30:29: Big AI wins
33:09: Conclusion
What does LogRocket do?
LogRocket’s Galileo AI watches user sessions for you and surfaces the technical and usability issues holding back your web and mobile apps. Understand where your users are struggling by trying it for free at LogRocket.com.