M&A Technology Integration: Some Advice Before Your Next Deal.
As both a CEO and former CIO who lived through a major merger, here's what I learned from sitting on both sides of the table—and how you can avoid the costly mistakes that derail 30% of mergers.
By
John Ohlwiler
19 min read
As the CEO of Sentry Technology Solutions and a member of ACG Orlando, I've witnessed countless mergers and acquisitions unfold across Central Florida's thriving middle market. But my perspective is a bit unique because I've sat on both sides of the table.
I've been in the boardroom as a founder and CEO, focused on strategic vision and deal structure. But I've also been in the trenches as a CIO during a major merger, watching brilliant strategies have trouble because nobody properly planned for M&A technology integration.
That dual perspective taught me something critical: while executives focus on financials and market synergies, there's often a massive blind spot that can torpedo even the most promising deals.
The Problem: When Boardroom Strategy Meets Server Room Reality
You've just closed on what everyone agrees is a strategic home run. The numbers look fantastic, the market fit is perfect, and your leadership teams are aligned. But six months later, you're hemorrhaging money trying to get basic operations running smoothly because nobody planned for technology integration.
Here's the hard truth: technology integration issues account for approximately 30% of failed mergers¹. That's nearly one in three deals that fail specifically because of technology challenges that could have been anticipated and addressed.
From my experience on both sides of M&A transactions, here's what actually happens when technology integration goes wrong:
The Cybersecurity Nightmare More than 53% of CIOs report that they see cybersecurity as a top challenge in the M&A lifecycle². As a former CIO, I can tell you this number is probably conservative. When you're connecting two separate IT environments under deal pressure, you're essentially creating new attack vectors while your security team is already stretched thin managing the integration. One weak link in either system can compromise everything—and I've seen it happen.
The Data Disaster Nothing kills operational efficiency faster than employees who can't access the information they need. During my CIO days in a merger, I watched productivity plummet as our teams spent hours manually transferring data between systems that should have been talking to each other seamlessly. Your best people end up doing the work of three people just to accomplish basic tasks.
The Bleeding Budget As a CEO, I know technology is already the third-highest transaction cost driver at 2.5% of the deal value³. But as a former CIO, I know that's just the beginning. Poor integration can turn that calculated 2.5% into an ongoing 10-15% drain on resources as you fix problems that should have been prevented during planning.
The Talent Flight Risk Your best IT people didn't sign up to work 80-hour weeks fixing integration nightmares. I've been that CIO pulling all-nighters trying to get systems stable while fielding calls from frustrated department heads. When technology integration is poorly planned, technical talent jumps ship right when you need them most, taking institutional knowledge with them.
The Current M&A Landscape: More Deals, More Complexity
Through my involvement with ACG Orlando, I'm seeing the M&A market heat up significantly. 84% of private equity firms and 48% of corporates anticipate more deals in 2025 compared to 2024⁴.
Here in Central Florida, our ACG Orlando community is buzzing with activity across the middle market. Over 60% of M&A deals in 2024 are motivated by the need to acquire new technology or digital capabilities⁵. Companies aren't just buying market share anymore—they're buying technology platforms, AI capabilities, and digital transformation shortcuts.
But here's the irony I've observed from both the boardroom and the server room: the very technology that makes these deals attractive is often what makes them fail.
Why Technology Gets Left Behind in M&A Planning
I've observed a consistent pattern in how these conversations unfold. In the boardroom, we focus on strategic vision, market positioning, and financial projections. Technology gets treated as a "figure it out later" problem. I can tell you exactly why this happens:
- Different Languages: As a CEO, I speak ROI and strategic positioning. As a former CIO, I spoke uptime, security protocols, and system compatibility. These languages don't always naturally translate.
- Timeline Pressure: Deal momentum prioritizes closing over operational planning. I've felt that pressure from both sides.
- Optimism Bias: In the boardroom, we assume "our systems are pretty similar." In the server room, you discover they're built on completely different architectures.
- Cost Minimization: Technology integration looks like a cost center rather than a value driver when you're focused on deal financials.
The statistics bear this out: only 32% of CIOs say they are "significantly" meeting deal objectives such as technology synergies and closing the deal on time⁶. Having been that CIO, I understand why two-thirds of technology leaders feel like they're failing their integration targets—they're being set up for failure from day one.
How Sentry Bridges the Boardroom-to-Server Room Gap
This is one of the reasons I founded Sentry Technology Solutions. I've lived the pain of poor technology planning and I know there's a better way.
At Sentry, we speak both languages fluently. We understand the strategic imperatives driving your deal, but we also know the technical realities that can make or break your integration. We've positioned ourselves as the guide that bridges this gap because we've personally experienced both sides of the equation.
We Understand Where You Are Whether you're the CEO excited about growth opportunities but nervous about operational complexity, or the CIO who knows you'll be held accountable for making incompatible systems work together, we get it. We've been in both seats.
We Know the Way Forward My team and I have worked with businesses throughout their M&A lifecycle, from due diligence technology assessments to post-merger integration strategies. We've seen what works, what fails, and most importantly, how to avoid the pitfalls that derail otherwise successful mergers.
Our M&A Technology Integration Plan
Based on my experience from both the boardroom and the server room, here's how we approach M&A technology integration:
Phase 1: Technology Due Diligence Before you sign anything, we assess both organizations' technology maturity using our proven framework. Technology integration planning should begin early, ideally during diligence⁷. As someone who's been the CIO discovering "surprises" after the deal closed, I can't overstate how critical this early assessment is.
Phase 2: Integration Strategy Design We create a detailed technology integration roadmap that speaks to both business timeline and technical reality. This isn't a generic checklist—it's a custom strategy that balances your deal objectives with operational constraints. I've been the CIO trying to implement an unrealistic timeline, and I've been the CEO wondering why integration is taking so long. Our approach addresses both perspectives.
Phase 3: Secure Implementation Using advanced cybersecurity frameworks and proven integration methodologies, we execute the technical integration while maintaining business continuity. Acquirers can reduce one-time M&A technology integration costs by one-third to one-half in partial integrations by using innovative software and technology applications⁸.
The Time to Act is Now
As both a CEO and former CIO, I can tell you that the companies getting M&A technology integration right are gaining sustainable competitive advantages.
The Cost of Inaction (From Someone Who's Lived It)
- Delayed synergy realization costing millions in missed opportunities
- Security breaches that destroy deal value overnight
- Operational inefficiencies that persist for years (I've seen 3+ year integration timelines)
- Talent departures that gut your technical capabilities
- Integration costs that spiral beyond original budgets
Your Success Story Starts Here
Partner with Sentry and transform technology integration from your biggest risk into your greatest competitive advantage. While your competitors struggle with basic system connectivity, you'll be leveraging integrated data platforms to drive growth, efficiency, and innovation.
Having sat in both the CEO chair and the CIO chair during mergers, I know what success looks like from both perspectives. More importantly, I know how to get there.
Ready to Transform Your M&A Technology Strategy?
Schedule a discovery call with me and my M&A technology integration specialists. We'll assess your current technology landscape and show you exactly how to approach your next acquisition with confidence—from both a strategic and technical perspective.
Whether you're planning one strategic acquisition or building a platform for multiple deals, Sentry has the expertise to ensure technology amplifies your success rather than jeopardizing it.
Your competitors are making the same technology mistakes that have been derailing mergers for decades. As someone who's been on both sides of these failures, I can help you avoid them entirely.
Contact me directly at Sentry Technology Solutions and discover how proper M&A technology integration turns deals into sustainable competitive advantages.
Ready to dive deeper into how technology can support your merger and acquisition strategy? Learn more about our comprehensive M&A technology services and discover how Sentry guides businesses through successful technology transformations.
Sources:
- Deloitte Research on Technology Due Diligence
- 2024 EY CIO Sentiment Survey
- EY M&A Technology Integration Research
- KPMG Technology M&A Survey 2024
- PwC M&A Technology Trends 2024
- 2024 EY CIO Sentiment Survey
- Plante Moran M&A Technology Integration Study
- EY-Parthenon M&A IT Integration Analysis
