How Fractional Executives Help Small Businesses Scale Smarter
In this episode, Benny and Dennis are joined by Jonathan Barnes and Wayne Easterwood to discuss how fractional executives are becoming a practical and powerful solution for small and growing businesses that need experienced leadership—without the cost or long-term commitment of a full-time executive team.They explore when it makes sense to bring in fractional leaders, which roles are most commonly filled in small businesses, and how owners can avoid the common mistake of hiring too early, too late, or for the wrong problem. The conversation also connects fractional leadership to longer-term goals such as improving operations, supporting growth, and preparing a business for a future transition or exit.If you’re a business owner wondering whether you really need a full-time executive—or simply stronger leadership right now—this episode offers a clear, real-world look at how fractional executives can help you scale smarter and be truly ready for what’s next.
Jonathan brings more than 25 years of experience in leadership, strategy, team development, and the disciplined execution of high-growth initiatives. His background spans all core business functions and multiple stages of company growth. He is the founder of Staffing as a Mission, a 2019 Inc. 500 company focused on Healthcare IT delivery. In 2020, he launched Work Heartily, an executive leadership firm serving growth-stage companies, and later co-founded Sitka Advisory Group to provide seasoned perspective, accountability, and strategic guidance to owners and leadership teams navigating inflection points. Jonathan is a Certified Working Genius Facilitator and a Full Focus Certified Pro, equipping teams and leaders with practical frameworks for clarity, alignment, and sustained execution.
With nearly 30 years of technology leadership, strategy, and successful growth through acquisitions, Wayne’s experience is primarily in healthcare technology, enterprise business systems, and administrative services. Most recently he led administrative services for a Nashville-based healthcare provider system.
Contact information:
Jonathan Barnes and Wayne Easterwood
Benny Carreon- Velocity Technology Group- benny@velocitytechnology.group
Dennis Jackson-WorX Solution- dennisj@worxsolution.com
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