A product team saved $150 million in margin improvement not by building new features, but by decommissioning a long tail of customized, on-prem legacy products. This "unsexy" work eliminated significant operational drain from support and maintenance, directly impacting the bottom line in a way new features rarely can.

When pivoting from a product with existing revenue, avoid the binary choice of killing it or splitting focus. Blue Jay successfully transitioned by putting their V1 product into "maintenance mode"—servicing existing customers but halting all new feature development—and committing the entire team to building the V2 for a defined six-month period.

The Atlantic CEO took the job despite massive financial losses because the core product—the journalism—was exceptional. He believed a broken business model is far easier to fix than a mediocre product, making the high-risk turnaround feasible from the start.

Bloomberg initially built its own computers because PCs didn't exist. Once commercial PCs became available, they immediately abandoned their hardware to focus on their unique value: data and software. This shows a ruthless focus on core competencies and an ability to pivot away from sunk costs.

David Remnick, admitting he didn't know parentheses on a balance sheet meant losses, successfully pivoted The New Yorker to a subscription-first model. He identified the brand's deep reader loyalty as an untapped asset, correctly predicting it could outweigh declining ad revenue in a crucial move for legacy media.

Rather than making an abrupt turn, Sure managed its pivot from a B2C app to a B2B platform gradually. They kept the original mobile app running while they built and validated the new B2B distribution model, only sunsetting the app once the new strategy proved viable and began to ramp up.

The pivot from Arc to Dia was also a cultural and technical reset. The Browser Company gave their team a "blank page," allowing engineers to build a new, faster architecture and designers to rethink the experience. This chance to fix old problems and pursue new ideas was key to getting team buy-in.

In the age of AI, 10-15 year old SaaS companies face an existential crisis. To stay relevant, they must be willing to make radical changes to culture and product, even if it threatens existing revenue. The alternative is becoming a legacy player as nimbler startups capture the market.

Many founders become too attached to what they've built. The ability to unemotionally kill products that aren't working—even core parts of the business—is a superpower. This prevents wasting resources and allows for the rapid pivots necessary to find true product-market fit.