Some searches go beyond finding the right leader. They help a company move forward without losing sight of where it came from.
A few years ago, a second-generation leader of a Michigan-based family-owned business approached Purple Squirrel Advisors with a challenge. They were preparing to take on greater leadership responsibility but were struggling to do so with confidence.
The company had been successful for decades under first-generation leadership. Yet over time, its operational systems and financial processes had not evolved. Month-end closes were delayed, revenue recognition was inconsistent, and financial reports lacked the clarity needed for informed decision-making. The next generation wanted to modernize, but without accurate financial visibility, change felt impossible, and tension between generations began to grow.
The solution seemed clear to the second-generation leader: bringing in a strong CFO who could modernize and stabilize the finance function. But that idea met resistance. The existing CFO was a long-time advisor and friend of the founder, someone who had been there since the early days. Loyalty ran deep, and the first generation valued that loyalty above credentials or modernization
Our role quickly became more than filling a position. It was about navigating the human dynamics of legacy, pride, and progress.
We started by listening to both generations: first separately, then together. We wanted to build understanding, align expectations, and define what success truly looked like for everyone involved. Together, we shaped a profile for a CFO who could modernize financial systems while honoring the company’s history and culture.
Our search focused on leaders who had successfully led finance transformations within family-owned businesses. The ideal candidate needed more than technical excellence. They needed empathy, patience, and credibility, the kind of presence that builds trust through steady progress.
Ultimately, both generations aligned behind a candidate who embodied exactly that. This leader brought calm structure to the finance function, implemented timely closes, improved revenue recognition, and professionalized reporting. Just as importantly, they earned the trust of both generations and the respect of long-standing employees.
With that foundation in place, the second-generation leader gained the confidence to take on a larger role, supported by accurate data, reliable systems, and a trusted financial partner.
What began as a CFO search became a catalyst for a smooth generational transition: one built on transparency, trust, and shared vision.
At Purple Squirrel Advisors, we believe the most impactful searches are those that strengthen both leadership and legacy.
