Growth Strategy & Consumer Insights
Research that actually gets used, segmentation that drives decisions, and a clear view of where AI helps versus where it doesn't. These days, I also build the tools.
AI can run your competitor benchmarks and market sizing. Any intern with Claude can do that now. The question is: what do you do with it?
The hard part was never the analysis. It's the judgment calls: knowing which segments matter, what the data isn't telling you, and when to ignore the spreadsheet and trust your gut.
And now that AI has made building things the easy part too, the same rule applies twice. Anyone can generate. Knowing what good looks like — which insight survives a CMO's cross-examination, which story a creative team will actually work from — that's the twenty-year part. People are starting to call this profile the "systems thinker" or the "deep generalist." From the inside, it's always been one job: notice the system, find the gap, build the bridge.
And now that AI has made building things the easy part too, the same rule applies twice. Anyone can generate. Knowing what good looks like — which insight survives a CMO's cross-examination, which story a creative team will actually work from — that's the twenty-year part. I build with the machines and judge with my name on the work. Because it is.
Running consumer research for a music royalty startup. 50+ open-ended survey responses. The usual qual analysis grind.
Fed them into ChatGPT on a whim. Asked for a summary, an investor pitch, and (as a joke) a Barack Obama speech selling the product. It nailed the synthesis. The Obama speech ended with: "Let's make some beautiful music together, folks."
That's when I got it. AI will do whatever you ask. The judgment is in knowing what to ask, and what to do with the answer.
I've also been writing code since the mid-'90s — first steering Logo's little turtle around a screen, then BASIC, then C++ back when the AP exam still ran on it, then Java, and eventually the languages researchers actually use, STATA and SPSS. So when people ask when I became a builder: before I became anything else. The AI tools didn't turn me into one. They just removed the excuses.
Started at Monitor Group. M&A, growth strategy, insights research across consumer, fintech, edtech. Then a year inside Chiat\Day and two years of media-and-tech deals at a boutique investment bank. Built QC Strategy in the gap I'd just lived from both sides — Monitor rigor, Chiat\Day creativity, quantitative work in service of creative, before that was a category. These days: Partner & Managing Director at RedSky Strategy, based in LA, building in a new gap. Also in there somewhere: a 2011 Emmy (Golf on CBS, technical team, long story).
Also: dad, surfer, kombucha brewer.
The pattern is always the same: find the question nobody's asking, then answer it with research that actually gets used.
3,000 respondents, three segments, and clear rules on what AI does versus what humans decide.
Fenty needed segments they could use for casting, activations, and media buys. Demographics alone weren't cutting it.
3,000 respondents (2K gen pop, 1K from Fenty's CRM) with a Strategic Fit Score to measure brand alignment.
AI: synthesis, persona visuals, implications brainstorming. Humans: segmentation design, crosstab analysis, final recommendations.
Aspiring Star (self-expression), Beauty Boss (expertise), Cosmetic Connoisseur (craft).
The segmentation drove a Roblox activation (4.2M visits), refocused diversity messaging, and changed talent casting.
The segmentation work gave us a framework we actually use. It's informing casting, activations, how we think about the brand. Ian Roskovitch, VP Analytics, Kendo Brands
3,000+ moviegoers across the US and China, four segments, and a complete tonal pivot.
Transformers was cooked. The previous film had a 15% on Rotten Tomatoes and critics were done with "spectacle over substance." Could a Bumblebee spin-off save the IP?
3,000+ moviegoers, 28 clips tested, and 20 PR messages across the US and China.
Four personas (Movie-Savvy Parents, Opinionated Adult Fans, Gen Z Males, Multicultural Gen Z Females), each needing a different hook.
73% wanted "light and funny" over "dark and intense," and fans kept pointing to the 1980s cartoon. Our recommendation: go Spielberg.
It worked.
Most personas die in a slide. These don't.
You don't need more data. You need real understanding — and a company aligned around it. So instead of another PDF, your research becomes a living hub: the persona rendered as the stuff she actually lives in (her camera roll, her group chat, her weekly calendar — or his buying committee map and CRM account plan), with every detail traced back to your quant and your qual. Then you sit down and talk with her: AI personas you can interview, one-on-one or as a roundtable, built from research you actually did — not synthetic anything.
In the field with teams from retail fashion to B2B finance, built at RedSky Strategy. Public demo coming soon — for now, ask me and I'll show you. It's more fun that way anyway.
Paramount · NBCUniversal · TED · IMAX · Playboy
DuckDuckGo · Headspace · Mercari · Toshiba
Fenty Beauty · Pattern Beauty · Starface · HUM Nutrition
Gap · Scotts Miracle-Gro · Cali Bamboo · Lovepop
Patrón · Del Monte · Kahlúa · GoGo squeeZ
Abbott · Amgen · Humana · Boehringer Ingelheim
United Way · Susan G. Komen · Colorectal Cancer Alliance · Swipe Out Hunger · Schools Beyond Screens
Board Chair. Helped scale from scrappy campus initiative to national movement.
Students founded it in 2010, and I joined when they formed their first board in 2014. I was Chair from day one through 2018, then stayed on through 2024. The role went beyond governance: growth strategy, campus partnerships, and impact research.
We grew from a few dozen campuses to 500+ programs across all 50 states. Swipe Out Hunger is now the leading nonprofit addressing college student hunger.
Looking for my next board seat. Ten years of governance experience. Prefer orgs doing real work over orgs that talk about doing work.
Keynotes, panels, and workshops on the stuff I actually do, not abstract thought leadership.
How we built segments that drove decisions. AI did the clustering. Humans made the calls. Co-presented with Kendo Brands.
Where AI helps, where it doesn't, and how to tell the difference. Drawn from client work, not demos.
AI is great at synthesis, persona development, implications. It's bad at knowing what questions to ask. Here's how to split the work.
Essays from Easily Fascinated, my Substack. Noticing small clues in a noisy world.
An economic case for the #Abundance version of Homeland Security.
Read itGen Z isn't bad at money — theirs just doesn't go nearly as far.
Read itOn noticing small clues in a noisy world. The essay that named the newsletter.
Read itQuality over quantity. Most business content is noise.
Strategy & tech. Pivot (Kara Swisher & Scott Galloway), Hard Fork, Tech Brew Ride Home.
The edge. Every.to, A16Z Podcast, Anthropic Red Team.
Economics & markets. Money Stuff (Matt Levine), Kyla Scanlon, Derek Thompson.
Culture. The Surfer’s Journal, This American Life, Tetragrammaton.
News. LA Taco, Today Explained, The Daily.
“News.” The Ezra Klein Show, Pablo Torre Finds Out, What Now? With Trevor Noah.
I skip: TechCrunch churn, LinkedIn influencers, most business books.
Things I build when I'm not working — which is trickier to define now that building is half the job. Mostly vibe-coded with Claude, sometimes fermented or waxed.
Subscription management calendar. Track what's active when, see how much you've saved by pausing services you don't need year-round.
Try it"What do they actually do for work?" Paste a LinkedIn profile, get a plain-language explanation tailored to your generation.
Try itA rainbow-themed adventure game I built for my daughter. She provided creative direction; I provided the prompts.
Play it"Is this message safe?" Drop in a screenshot of a sketchy text or email and get a straight answer on whether someone's trying to scam you.
Try itEvery time you watch, they lose. Get matched with a fan of the opposing team, swap games, and let the jinxes cancel out.
Try itFour 1-gallon small-batch brews. Current rotation: pineapple, black cherry, blueberry, ginger maple, and green juice.
Six boards from 6'9" to 10'2", with the 9'2" fish getting the most water time lately, mostly at point breaks in Malibu and Ventura.
Growth problem? Research question? Something worth building? Need a speaker? I respond to email.
bwoo@redskystrategy.com