Why leadership alignment and readiness in the first 100 days often determines the trajectory of value creation
By James Brocket
As software valuations compress and capital becomes more selective, the success of Private Equity investments increasingly hinges on the speed and quality of operational execution. Value creation plans typically focus on go-to-market efficiency, product expansion, and pricing optimization, there is one factor is common to all of these levers — executive talent.
Despite this, leadership assessment and intervention are often reactive, episodic, or limited in scope. In our experience of advising both sponsors and portfolio companies, the firms that outperform consistently treat executive talent not as a human resources concern, but as the most important strategic lever to drive enterprise value.
1. The First 100 Days: A Critical Inflection Point
The period immediately post-close is typically rich with activity — 100-day plans are drafted, value creation initiatives launched, and governance structures established. However, the assumptions underpinning these efforts often rely on the capability of the existing leadership teams to execute against a new mandate.
We routinely encounter cases where the team that succeeded in building a business to a certain stage lack the experience to scale 2x-3x and beyond, or where functional leaders are unprepared for the rigour and accountability expected in a PE-owned business. In one recent transaction, delayed intervention on an underpowered CRO cost the business two quarters of growth and significant commercial momentum.
Investors would benefit from making leadership evaluation a central component of the 100-day process — not just at the CEO level, but across the C-suite and functional heads. Early misalignment is rarely self-correcting.
2. Investor-Management Alignment: A Predictable Source of Execution Risk
Misalignment between the board and management rarely presents as overt conflict — but it frequently manifests in inconsistent prioritization, poor velocity of decision-making, and resistance to change. The issue is not typically a lack of capability, but a lack of clarity and alignment around how value will be created.
We see this particularly in software businesses undergoing strategic pivots where leadership may have emotional or intellectual attachment to a legacy strategy. In these cases, investors need leaders who are not only aligned to the investment thesis, but who have demonstrated capacity to execute transformative change at pace.
Search partners should be briefed not merely on competencies, but on strategic context. The right executive is one whose experience, orientation, and decision-making style reflect the priorities of the investment — not just the job description.
3. The Evolving Profile of Software Leadership
The leadership attributes required to succeed in software companies have evolved markedly in the past three years. Today’s operating environment demands a blend of strategic agility, digital fluency, and capital discipline. However, many leadership teams remain over-indexed on legacy skillsets.
Examples include:
- CROs needing to lead hybrid PLG/enterprise motions, manage usage-based pricing models, and drive efficiency across longer sales cycles.
- CTOs expected to deliver innovation (e.g., AI enablement) while modernizing infrastructure and leading globally distributed teams.
- COOs required to scale systems and teams in low-burn environments, often across multiple geographies.
Boards and sponsors must rigorously test whether the existing team is fit for the business’s next stage — not just whether they have performed historically.
4. Executive Search Should Be Strategic, Not Transactional
Traditional search processes are too often reactive, triggered only by performance failure or resignation. Leading firms take a proactive approach: building talent pipelines early, mapping succession risk, and creating pre-close scenarios that include potential leadership change.
In our work, we’ve seen significant value unlocked by sponsors who introduced senior executives 9–12 months ahead of exit — giving them time to operationalize impact, drive growth, and present well in diligence. Conversely, we have seen otherwise high-performing businesses penalized in valuation due to perceived leadership gaps or succession uncertainty.
The opportunity cost of delaying a key executive hire can be considerable — in growth rate, in internal execution, and ultimately in exit valuations.
Conclusion: Leadership as a Primary Driver of Value Creation
In the current environment, success is less about the originality of the value creation plan, and more about the team’s ability to deliver it. This means elevating executive talent to a first-order consideration in both pre- and post-close phases. It requires moving beyond resumes and references, toward a structured, strategic view of what leadership success looks like in best-in-class software companies — and a readiness to act early when gaps emerge.
This isn’t about good governance. It’s a source of outperformance.