3 Signs Your Software Company Needs Strategic Leadership
by Philip Feldmann, Managing Director
1. Growth Has Plateaued Despite Market Opportunity
Your product is solid, your market is growing, but revenue has flatlined. This is often a sign that the company has outgrown its current leadership capacity. What worked to get from zero to one million in ARR rarely works to get from one to ten million.
The strategies, processes, and organizational structures that drive early-stage growth create bottlenecks at scale. Recognizing this inflection point — and bringing in experienced leadership to navigate it — is often the difference between a company that breaks through and one that stagnates.
Top tip
Track your growth rate quarter over quarter, not just absolute revenue. A declining growth rate in a growing market is an early warning signal that leadership capacity may be the constraint.
2. Decision-Making Has Become a Bottleneck
When every significant decision requires the founder or CEO to weigh in, the organization cannot move faster than one person's capacity to process information. This is sustainable at ten people. At fifty, it becomes paralyzing.
The solution is not simply delegation — it is building a leadership layer that can make decisions with the same quality and judgment as the founder. This requires experienced operators who understand both the business context and the technical landscape.
3. Key People Are Leaving
Talented people leave when they stop growing, when they lose confidence in the direction, or when organizational dysfunction makes their work feel meaningless. High turnover in engineering or product teams is rarely about compensation — it is about leadership and vision.
An experienced interim executive can stabilize a team, restore clarity of purpose, and create the conditions for retention. The cost of a leadership engagement is almost always less than the cost of replacing three senior engineers.
