4 Steps Of Pivoting In The Age Of AI

The ability to pivot effectively has become less of an occasional necessity and more of a core leadership competency. Especially as artificial intelligence reshapes entire industries at breakneck speed, start-up leaders are discovering that successful pivots require a unique blend of analytical rigor, emotional intelligence, and strategic courage.

The author’s conversations with four leaders—each navigating their own transformational journey—a clear framework emerges for how to orchestrate meaningful change without losing your organizational soul.

1. Go Back To Your Problem.  When Rujul Zaparde, co-founder of procurement platform Zip, saw the emergence of ChatGPT, he didn’t rush to slap AI onto existing features. Instead, he took his team back to fundamentals. “We really took a first principles approach to the company and the product to sort of say, okay, how do we, like, if we were to solve this problem, like, you know, the problem we solve for, like, what’s the best way to solve it today?”  This methodical approach proved transformative. Rather than viewing AI as a trendy add-on—which generally doesn’t solve any real problem—Zaparde’s team recognized they were uniquely positioned as an “orchestration layer” with access to supplier data, contract information, and financial systems that individual point solutions couldn’t match. Their AI capabilities have since been used over four and a half million times.  The lesson? Before pivoting, strip away assumptions and return to core problems.  1. What are your customers struggling with?  2. How intense is this problem?  3. How often do they experience this problem?  4. What’s left short with your current approach?  5. How might your leverage any accumulated strengths and capabilities to develop a new approach?
2. Write A Memo.  Perhaps nowhere is the complexity of organizational pivots more apparent than at Shef, the marketplace connecting local cooks with neighbors. CEO Joey Grassia discovered that even when data clearly indicated the need for change, execution required something more nuanced than compelling metrics.  “It really did take us 12 to 18 months to change the culture of the company so that people were willing to question what we’ve always done and willing to acknowledge that we may have to burn the boats on our old business to make the leap into the new one,” Grassia reflects.  The breakthrough came when Grassia crystallized the company’s direction in a comprehensive memo outlining three specific milestones around growth, efficiency, and scale. “It wasn’t until I wrote that memo and it was like, these are the three milestones of building a great business. Our existing business has no chance of accomplishing these things, so we have to disrupt ourselves. That was really the turning point.”  The transformation was dramatic. Writing a memo is one of the best ways to fast-track clarity.
3. Make Space for Uncertainty.  While data and strategy provide the rational foundation for pivots, Charlie Greene, founder of memory-preservation platform Remento and recent Shark Tank winner, demonstrates why the most successful transformations also require deep emotional intelligence.  Greene learned this lesson through experience: “Pivots are incredibly easy to talk about in retrospect, they’re incredibly difficult to navigate as they’re unfolding. Because you never wake up one day and realize that today is the day you’re going to pivot.”  For Remento, the pivot from a conversation-structuring tool to a book-creation platform wasn’t just about product features—it required reimagining their entire value proposition.
4. Move Quickly, and Comprehensively.  In the next decade, AI will likely disrupt every company and every industry. If you’re not examining how true that’s likely to be for your business, you’ll get swallowed by a competitor.  Bryan Power, Chief People Officer at Nextdoor, shared just how urgent this transformation is. Having navigated multiple organizational turnarounds, Power sees AI as fundamentally different from previous technological shifts.  “One of the major disruptions that AI is doing is certain activities now the turnaround is so fast that managers have a mental model of how long something takes in their head because they did it when they were a contributor. But this is now something that takes minutes that used to take days.”  This speed transformation creates unprecedented management challenges.