Tip
Casey Winters talks about product-led sales: “You can unify self-service loops in a B2B business, which are typically driven by product and your sales loops into one more complex giant loop that operates more efficiently and breaks down the silos. Get sales, product, and marketing working as one larger cross-functional team.”
Turns out AI product strategy works the same way.
Your AI product has two separate worlds: self-service users signing up and using the tool directly, and enterprise sales team selling large contracts with implementation support. Product team owns the self-serve funnel. Sales owns the enterprise deals. Marketing splits budget between both. Three separate dashboards, three separate roadmaps, constant arguments about priorities.
You’ve seen this movie before. At your last two companies, the product/sales divide burned millions. Product built features sales couldn’t sell. Sales promised features product wouldn’t build. Self-serve users who needed help churned because sales wouldn’t touch small deals. Enterprise prospects who could self-serve got annoyed by aggressive sales outreach.
Younger leaders accept these silos as inevitable. “Product and sales just don’t get along.” You know better. You’ve watched enough org structures over decades to know: silos are expensive. Every handoff loses conversion. Every separate dashboard hides the real customer journey. The pattern repeats—companies that unify product and sales motions (Slack, Dropbox, Atlassian) scale efficiently. Companies that keep them separate fight constantly and burn cash.
This judgment—knowing which org structures work versus which ones cost money—comes from watching enough reorgs succeed and fail. You can see the dysfunction in the dashboards: “product qualified leads” that sales ignores, “sales qualified leads” that aren’t ready for human touch. That pattern recognition lets you redesign the structure before it blows up the P&L.
Context
Casey Winters led growth at Pinterest, Grubhub, and Eventbrite. At Eventbrite, he unified separate direct response and lead generation flows to let product and sales work as one cross-functional team.
For experienced executives managing AI product strategy, this isn’t theoretical—you’ve lived through enough product/sales conflicts to recognize when organizational silos are burning money. That pattern recognition comes from seeing both unified and siloed structures play out over decades.