A board member asks whether the platform is ready to absorb three more acquisitions this year. The honest answer is: probably, but not without trade-offs nobody has discussed yet. That tension, between the demand for certainty and the reality of complex, inherited technology, defines modern CIO leadership inside acquisition-led businesses.
“There is a particular weight that settles in when you realise that the questions being asked of you have no reliable answers,” says Daniel J. Jacobs, a technology leader and the founder of Starkhorn. Jacobs serves as an interim and fractional CIO to private equity-backed organisations navigating this disconnect. These businesses are often expanding faster than their technology foundations can realistically support, inheriting fragmented systems and inconsistent controls through acquisition. As scrutiny intensifies ahead of diligence or exit, uncertainty tends to surface in the form of delayed integrations, unclear cyber exposure, and unresolved questions at board level.
The role of the CIO has expanded alongside these pressures. Technology leaders are now expected to hold credible views on business strategy, operating models, regulatory exposure, talent, and long-term economics, frequently across multiple jurisdictions. “The technical complexity is almost the easier part,” says Jacobs. “What has expanded more dramatically is the range of questions I am expected to have views on.” In M&A-heavy organisations, that expansion carries real consequences. Each acquisition introduces inherited systems, uneven data quality, and security postures that cannot be fully assessed on day one. Yet boards and investors still look for certainty, particularly where valuation and exit timing are concerned.
When Confidence Becomes a Liability
One of the most underappreciated risks in technology leadership is the pressure to project confidence at all times. It’s treated as a proxy for control and competence, but it can become a mask for unresolved risk. “We make business cases knowing the numbers are approximations. None of this is dishonesty. It is simply the nature of operating in conditions of genuine uncertainty,” says Jacobs. The issue is incremental: small uncertainties go unchallenged, assumptions harden into fact, and by the time someone asks the difficult question, the gap between what has been presented and what is actually understood has become structural.
In M&A contexts, overstating confidence can lead to missed synergies and cyber issues that surface late because the organisation lacked the space to confront risk early and honestly.
Jacobs’ approach challenges the idea that technology leaders should always have definitive answers. Instead, he focuses on creating clarity about what is known, what is not, and how uncertainty will be managed, all critical for making capital allocation and timing decisions.
Integration Without the Illusion of Control
In his work at Starkhorn, Jacobs sees this play out most clearly during integrations. As a consultant and fractional CIO, he’s typically brought in when deals have closed and leadership needs a clear view of what’s actually working and what’s not. Instead of promising certainty, as is tempting to do, he focuses on getting the basics under control, untangling inherited complexity, and giving boards a realistic picture of risk, progress, and trade-offs. In one private equity-backed healthcare platform, that approach translated into acquisition integration blueprints designed to absorb variability, cutting onboarding timelines while maintaining control across multiple jurisdictions and inherited systems spanning hundreds of sites. “The honest answer to many of the questions I am asked is ‘I do not know, and neither does anyone else,’” Jacobs says. What matters isn’t eliminating uncertainty, but reducing avoidable risk and ensuring leadership is in place early enough to respond when assumptions prove wrong.
What Exits Actually Reward
For acquisition-led businesses, technology either compounds risk or accelerates value. Jacobs has seen both outcomes, often within the same portfolio. The difference is leadership. Where uncertainty is acknowledged and managed, technology becomes a force multiplier for EBITDA and valuation. Where it is masked, it surfaces later, usually when options are narrower and costs are higher. “The moments of greatest uncertainty are the moments when accurate information is most valuable,” Jacobs says. Creating environments where leaders can admit limits without penalty is a prerequisite for making sound decisions in complex M&A environments.
Follow Daniel J. Jacobs on LinkedIn
