How to Sustain a Family Business Across Generations
It can be tempting to assume the next generation is ready to take over your company and allow you to enjoy your twilight years, but you must ensure they have time to develop skills and realize their identity.
Preparing the next generation for leadership is one of the hardest parts of running a family business. Whether the company has been run for several generations or just one until now, knowing when to hand over the reins to the next leader is a challenge. Identifying the proper person for the task, and strengthening them for it, is something many family business owners grapple with during their careers.
Of course, not every family-owned business has a successor to take on the leadership responsibilities of the organization. Some company founders may not have children or other relatives they can rely on to run the business, and in other cases, relatives have no interest in taking the helm of the company. Senior leaders with their leadership transition mapped out are at an advantage, but they often worry about their relative’s ability to handle the upcoming challenges they know will arise.
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Steward: Executive Leadership for Family Offices in all 50 States
Steward, the dedicated family-office practice of Cowen Partners Executive Search, helps families secure executive leaders who preserve legacy, enhance stewardship, and position the enterprise for long-term success.
Whether the need centers on a disciplined Chief Investment Officer, a forward-looking Chief Financial Officer, or a steady, operationally minded Chief Operating Officer, our senior-partner-driven approach ensures a search defined by discretion, alignment, and strategic clarity.
For multigenerational families, first-generation wealth creators, and newly formalized family offices, we tailor every engagement to your governance structure, investment posture, and family objectives. The result is leadership that strengthens operational resilience while honoring the values that anchor the family’s identity.
We specialize in identifying executives who bring both technical competence and principled judgment—leaders capable of navigating complexity, supporting continuity, and executing decisions that stand the test of time.
About Shawn Cole, President & Cofounder
Shawn Cole is a serial entrepreneur and executive leader with over 15 years’ experience founding and running successful companies. Shawn’s business career has been centered on value creation for both turnarounds and startups.
Shawn is President and Co-Founder of Cowen Partners, a national CFO executive search firm focused on the key elements of a successful business: sales, marketing, and finance. Business clients across the country trust Cowen Partners to take their companies to the next level by finding them executive talent, such as a CEO, CFO, COO, Chief Revenue Officer, and Chief Marketing Officer. Clients are both small and large, publicly traded, pre-IPO, private, and non-profit organizations, typically $50 million to multi-billion dollar revenue Fortune 1000 companies or have assets between $1 billion and $15 billion.
An active participant in the business community and startup space, Shawn Co-Chairs The Cowen Partners Venture Fund which provides seed funding and early stage investments, focusing on market disruptors in niche markets, community businesses, and minority entrepreneurs.
Shawn attended Oregon State University’s College of Business Austin Entrepreneurship Program and participated in a first-of-its-kind experiential entrepreneurship experiment at Weatherford Hall. He was also a Founding Member and President of Oregon State University’s Students in Free Enterprise, an international non-profit organization working with university students who want to positively change their communities and learn practical knowledge to become socially responsible business leaders.
At the age of 16 Shawn became a volunteer firefighter and EMT, eventually founding and managing a half marathon to raise funds for the community. To date, the marathon is still a success and has raised over one million dollars benefiting the community.
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