4 Steps Of Pivoting In The Age Of AI

Forbes

02-06-2025

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.
My 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.
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?
That requires writing, which brings us to step number two.
Perhaps nowhere is the complexity of organizational pivots more apparent than at Chef, 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. Since the pivot, Chef moved from standalone orders to standardized subscriptions, reducing customer cognitive load from 25 minutes per order to under 75 seconds for subsequent weeks. Forty percent of existing users opted into the new recurring model without any marketing push, and user spend tripled.
Grassia found that successful pivots require what he calls "the wisdom to know that you need to do it and the courage to actually take the leap." But between wisdom and courage lies the critical work of building organizational conviction through clear, logical communication.
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. The original product had high download rates but low usage. "While we had built a product that aligned perfectly with what users told us they wanted, we quickly learned that our solution didn't remove nearly enough of the friction needed to spur adoption."
Greene's approach to managing this uncertainty offers a lesson in communication. "One of our values is clear as kind," he explains. "Being able to say to your team, look, here's where we are right now. Does anyone disagree with where we are right now? You know, like, okay, we can agree this is where we are right now. Can we all agree where we need to be in three months?"
Greene emphasizes bringing teams into the decision process while maintaining ultimate accountability—a delicate balance between vulnerability and authority.
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, Head of People 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. As Power explains, "What happens to those five days has not really been worked through because as an employee I'm like, you're paying me to do this thing. It doesn't matter. Fifteen minutes, five days. I did what you told me to do."
Power's response at Nextdoor has been characteristically direct: comprehensive AI training programs and a cultural mandate that everyone must engage with these tools. "I can actually tell if someone's been using AI for a month or three months or for six months," he notes. "I can see the learning moves that people make in the early going, and by extension I can see when they haven't made them yet."
The broader implication is sobering: "I saw people not embrace the Internet. And like, think about that point of view today is just mind boggling to me. But in my time, in my career, my early 20s, I saw the people that embraced it and it just completely made the first five to 10 years of their career because they were out front."
Four key insights emerge from these leaders' experiences:
Start with your problem. Before implementing any change, return to fundamental questions about the problems you're solving and whether current approaches can scale to meet future demands.
Build internal logic through clear communication. Successful pivots require more than good ideas—they need comprehensive strategies with measurable milestones that help teams understand not just what's changing, but why change is inevitable.
Balance data with emotional intelligence. While metrics provide direction, the human element of change management—creating psychological safety, maintaining transparency, and holding space for uncertainty—often determines execution success.
Move quickly. Rather than viewing artificial intelligence as an optional enhancement, treat it as a fundamental shift that requires organizational learning and adaptation at every level.
Finally, the leaders profiled here share one crucial characteristic: they didn't wait for perfect information before acting. Instead, they developed frameworks for making decisions under uncertainty while building organizational capabilities to execute those decisions effectively.
In an era where the pace of change continues to accelerate, the question isn't whether your organization will need to pivot—it's whether you're building the cultural and strategic capabilities to do so successfully. The most successful pivots combine analytical rigor with human wisdom, creating organizations that don't just survive change but thrive because of it.