We’re on the brink of one of the most significant technological shifts in recent memory: the mass migration to SAP S/4HANA. With over 80% of the world’s commercial transactions flowing through SAP systems, this isn’t just an ordinary software upgrade—it’s a complete re-platforming of the very core that drives the global economy.
To shed light on this monumental transition, Ross Orrett—a successful software CEO who sold his business to SAP—sat down with Bob Cummings, the CEO of LeapGreat and a seasoned SAP veteran with over 30 years under his belt. Bob’s journey with SAP began straight out of college, spanning roles from hands-on consulting to steering strategic projects. Now, as the head of LeapGreat, he and his team of fellow SAP veterans are tackling one of ERP’s most persistent challenges: reducing the risk and complexity of migrations.
A Conversation With LeapGreat CEO
Q1: Bob, could you share a bit about your journey with SAP and how you’re involved in this upcoming migration?
Bob: Absolutely! I started implementing SAP back in 1990, fresh out of college, and I’ve been immersed in it ever since. I had the opportunity to witness SAP’s evolution—from R/2 to R/3, then to ECC, and now to S/4HANA. Throughout my time at SAP, I wore many hats, including managing strategic projects for the Executive Board Office. I was also responsible for overseeing migration programs between these different versions. Now, I’m genuinely excited to help businesses transition from ECC to SAP S/4HANA. It’s the most significant shift I’ve seen in my career, and it’s thrilling to be at the forefront of it.
Q2: With all that experience and enthusiasm, why did you decide to leave SAP to start LeapGreat?
Bob: Great question. We absolutely loved our time at SAP, but we saw a unique opportunity to address a major problem in the industry. ERP projects are notorious for being late, over budget, and, frankly, quite painful. The complexity doesn’t stem from the software being bad—far from it. It’s because ERP touches every facet of a company, making projects inherently complex. At LeapGreat, we’re leveraging AI and automation to simplify these processes and directly tackle the challenges head-on, aiming to reduce risks and make migrations smoother for everyone involved.
Q3: Let’s delve deeper into why this mass migration to SAP S/4HANA is happening now. What’s driving this exodus?
Bob: Well, the most obvious reason is that SAP ECC is reaching its end-of-life, which naturally pushes companies to consider upgrading. But that’s just one piece of the puzzle. Many organizations are eager to move to the cloud, capitalize on new functionalities like AI and automation, and consolidate their operations. It’s not just a technical upgrade; it’s an opportunity for companies to modernize their digital cores and stay competitive. However, there’s a significant challenge: there aren’t enough consultants to handle all these projects. That shortage makes it even more crucial to find smarter, faster ways to get these migrations done.
Q4: Why is this migration such a big deal compared to past transitions, like moving from R/3 to ECC?
Bob: Previous migrations were not easy but they were technically a bit more straightforward. ERP systems were more self-contained back then—you could upgrade the software and tweak some interfaces, and you’d be good to go. Now with the advent of the cloud, AI, In-Memory computing and decades of new enhancements, as well as all those customer customizations, it’s a bit like transitioning from a horse-drawn carriage to a self-driving car. The system is more deeply integrated into business operations than ever before.
Q5: Earlier, you mentioned project risk. What’s really at the root of that risk in ERP migrations?
Bob: The biggest risk in ERP projects is late visibility. Too often, projects spend months—or even years—in a conceptual phase, and the real system doesn’t emerge until much later. That’s when surprises pop up—misalignments between teams, missing requirements, unexpected system behaviors. These issues can derail projects, leading to delays, budget overruns, or even complete failures. If you talk to any seasoned ERP project manager, they’ll tell you the same thing: getting a real, working system in front of the customer as early as possible is crucial to avoiding these risks.
Q6: So the root cause of project risk is late visibility. Why does the system often come so late in the project?
Bob: ERP projects involve numerous streams of work—architecture design, process design, data migration, custom code remediation, integrations—you name it. These streams are interdependent, so delays in one area can hold up the entire project. Often, teams operate in silos with different priorities and goals, making alignment a real challenge. By the time the first working system appears, it’s often too late to avoid major surprises. That’s why, at LeapGreat, we focus on getting an early version of the system up and running so teams can test it and iterate right from the beginning.
Q7: Wouldn’t vendor demos or proofs of concept help provide early visibility?
Bob: Demos and proofs of concept can be helpful, but they only give you a glimpse of what the system might look like. They don’t capture the full complexity or level of detail of what is needed to bring all streams of work together to create the working system. What you really need is a working system from the start, complete with your data and processes, so you can spot issues early and make necessary adjustments.
Q8: How can customers solve the issue of late visibility and reduce project risk?
Bob: The key is to FrontLoad™ the project. At LeapGreat, our goal is to provide a working version of the customer’s system during Phase 0—before the heavy lifting even begins. This “Version 0” allows teams to test-drive the system, identify issues early, and align all streams of work around a central, tangible system. This approach helps avoid the backloading of tasks that typically cause escalations later in the project. It’s like test-driving a car before you buy it—you get a real feel for what you’re getting and can make adjustments before fully committing.
Q9: It sounds almost magical—how is it possible to deliver a working system so quickly?
Bob: I admit, it might seem like magic, especially to those who’ve endured long ERP implementations. But at LeapGreat, we’re fortunate to have a team with unparalleled experience that even goes back to the SAP R/1 system and the very first customers, and we’ve embedded that expertise into AI and intelligent automation technologies. We use an automated ERP factory that can generate and iterate on a fully documented system rapidly, allowing the project team to start working with their real system right away. This iterative, agile approach significantly reduces risk and accelerates the entire project timeline.
Q10: Can you give us a practical example of how this approach works in the real world?
Bob: Certainly! We recently worked with a customer who had been stuck in the conceptual phase of their SAP S/4HANA migration for nine months. They were struggling because they couldn’t see a working system. We organized a two-day workshop, and within ten days, we delivered a working system with their data and processes. The Head of Transformation told us, “Seeing the system immediately generated ideas to improve today’s business. LeapGreat’s FrontLoad™ of the project is a real game changer.”
Key Takeaways
Bob Cummings shares three core principles for managing the risks and complexities of your migration to S/4HANA:
1. Get Early Visibility of Your Working System: Don’t just plan—get hands-on with the system as early as possible. It’s like test-driving the future.
2. Iterative Refinement: Skip the long, drawn-out implementation. Start refining and improving the system from day one.
3. Transparent Center of Control: Keep everything centralized—think of it as your very own ERP command center.
