Today’s leaders are called to do more than manage. They must help their organizations navigate accelerating industry change. The rise of AI, rapid business model shifts, and high-velocity acquisitions demand that they lead with clarity and prepare their organizations for the future.
In Part 2 of the #shifthappens podcast episode with Jeff Epstein – former Oracle CFO and current Operating Partner at Bessemer Venture Partners – the conversation focuses on finance strategy to leadership in the face of massive AI disruption. From culture and board dynamics to the very nature of work itself, Jeff lays out a refreshingly pragmatic view of what it takes to lead well in the age of AI.
Catch up on the first part of our conversation with Jeff on our website.
Culture is Strategic
When businesses acquire other companies, the headlines focus on cost synergies and market expansion. Inside the walls, however, culture is often what makes or breaks integration.
Jeff shares lessons from Oracle’s aggressive mergers and acquisitions history, including the acquisition of Sun Microsystems. Oracle’s approach was direct: acquired companies were expected to adopt Oracle’s systems, structures, and, crucially, culture. If alignment wasn’t possible, attrition was accepted.
Contrast that with the Berkshire Hathaway model, where acquired companies retain autonomy. Both models can work, but only if leaders define the approach they’re taking and who’s accountable for making it stick. Without that ownership, post-merger drift is inevitable.
Leaders managing growth through acquisition should consider culture as an aspect beyond just being an HR initiative. Nowadays, it can be a top-line growth enabler or a silent killer of momentum.
Boards That Lead, Not Just Govern
Jeff brings a boardroom lens to modern strategy. Whether you're scaling a SaaS business or pivoting through disruption, boards that function well ask three deceptively simple questions:
Do we have the right strategy?
Do we have the right team?
Are we executing effectively?
He cites Microsoft’s early struggles to pivot to the cloud as an example. Despite having world-class teams and dominant products, the company lagged in execution and strategy alignment. Under Satya Nadella, Microsoft CEO, those dynamics shifted — and so did Microsoft’s trajectory.
The best boards and leadership teams don’t wait for a crisis to ask hard questions. They build a cadence of strategic reflection into their governance. In a world of exponential change, continuous self-assessment is crucial. "Does our company have the right strategy? Do we have the right team—and particularly the CEO, but even beyond the CEO, the team to execute the strategy? And then, are we executing well?" Jeff posits. "If we have the right strategy, a great team, and we're executing well, it's very easy to serve on a board when everything is going great."
The Incumbents vs. Startups Race
That kind of board-level reflection is critical as the industry experiences shifts. Nowhere is that more visible right now than in how companies respond to the rise of AI.
Jeff draws a sharp parallel to past platform shifts. Just as Microsoft had to reevaluate everything to move from desktop to cloud, today’s companies must rethink how they build, sell, and support software in an AI-powered world. Some will make that leap, and others won’t. “Will the incumbent get innovation before the innovator gets distribution?” he inquires.
It’s the defining question of this moment. Startups are racing forward with AI-first products, while incumbents are figuring out how to retrofit innovation into legacy systems. Whoever moves faster without losing customer trust wins.
AI Teammates Are Coming
For most companies, the AI conversation has been about tools. But Jeff frames it differently: AI agents are the workforce’s digital colleagues.
Imagine a finance team of 50 people managing tasks with the support of 500 AI agents. That’s not sci-fi — it’s on the near horizon. Jeff points to early players like Rillet, which allows users to “ask” AI agents about churn, forecasts, and financial trends in plain language. The agents respond as if they’re part of the team.
This shift raises new questions for leadership:
How do we govern AI agents like employees?
What data can they access?
Who’s accountable for their output?
How does this affect workforce planning, compliance, and culture?
Jeff underscores a crucial distinction: in some roles, AI-driven productivity may reduce headcount. But in others – like sales, engineering, and innovation – it may actually expand the workforce. “Wherever there's a problem in the world,” he says, “there will be a company created.” The implication for leaders? AI won’t eliminate work; it will shift where and how value is created. The company culture has to be ready for both.
The Power of Rational Experimentation
If there’s one consistent leadership theme Jeff returns to, it’s this: the best companies are always experimenting.
At Oracle, his team deployed full-time process owners dedicated to A/B testing operational workflows. Success came not from guessing right, but from designing systems to test and learn quickly.
He highlights Elon Musk’s approach as a powerful example. Musk removes steps in a process until it fails, then adds back only what’s needed. It’s aggressive, but instructive. Failure isn’t the goal, but a signal that the organization has found the boundary.
Jeff urges leaders to embrace this mentality. Most decisions aren’t at the level of a heart surgery — they’re reversible. Controlled risk-taking is how businesses learn to move faster, adjust better, and build resilience into their operating models.
What Leaders Should Really Take Away
These points reflect the core themes Jeff explored throughout the conversation. They touch on the choices and tensions leaders navigate as they adapt to rapid change and emerging technologies.
Lead Smarter Through Cultural Shifts and AI Disruption
Disruption doesn’t pause for planning cycles. Leaders must develop the muscle to act decisively amid constant change, especially when AI and major acquisitions collide.
Make Culture a Priority in Any Acquisition
Integrating systems is hard. Integrating people is harder. The faster your team aligns on values, priorities, and accountability, the faster the organization reclaims its momentum.
Test Your Boardroom with the Right Questions
A healthy board challenges the business with discipline, not doubt. Make it routine to revisit strategy, team strength, and execution fit in real time.
Start Preparing for a Workforce of AI Agents
Your next hire might not be human. Building an AI-augmented organization starts with thoughtful design around access, output quality, and cultural integration.
Experiment Your Way Through Disruption
Resilience is the result of multiple iterations. Permit your teams to test assumptions, track results, and learn in short loops.
Final Thought: Disruption Isn’t the Threat — Complacency Is
Jeff’s insights are a powerful call to action. The most dangerous place a company can be today is comfortable. Whether through acquisition, AI, or changing customer behavior, disruption is the new normal. It rewards those who build the capacity to adapt, not just react.
Leadership in this era means having the courage to change course, the discipline to ask hard questions, and the humility to test what you think you know. The companies that will thrive in the next decade won’t be the ones with the best technology. They’ll be the ones with the best reflexes.
Episode Resources
#shifthappens Research: AI & Information Management Report
#shifthappens Podcasts:
Jeff Epstein on LinkedIn
Dux Raymond Sy on LinkedIn
Mario Carvajal on LinkedIn
