About David

David Swift is a proven executive leader with more than two decades of experience driving revenue growth, scaling sales organizations, and transforming go-to-market strategy. He is currently a Regional Practice Leader at Roundstone, a national leader in self-funded health insurance solutions. In this role, David leads market development initiatives and partners with employers to implement innovative cost-containment strategies that improve healthcare outcomes for their teams.

Prior to joining Roundstone, David served as Chief Revenue Officer at Group Management Services, Inc. (GMS), where he played a pivotal role in expanding the company’s national footprint, launching new markets, and building high-performing sales organizations. Under his leadership, the company scaled rapidly, supported by disciplined processes, clarity of execution, and a culture of accountability.

Before being promoted to CRO, David served in several key leadership roles at GMS, including Vice President of Sales & Marketing and Regional Sales Manager. In these roles, he built repeatable sales systems and processes, developed talent pipelines, authored sales playbooks, and designed compensation and training programs that accelerated team performance.

Beyond his corporate leadership, David is a continual learner and growth-minded operator. He has completed advanced leadership and sales strategy programs including the Master Class Sales & Leadership Course by Pathway Strategies, Salesforce Trailhead sales training, and industry-specific education through NAPEO (National Association of Professional Employer Organizations). He is also licensed in Health, Life & Annuities in the State of Ohio.

David’s leadership philosophy centers on humility, service, and developing future leaders. Former team members frequently credit him with shaping their careers, describing him as a mentor who brings clarity, confidence, and purpose to their work. He has also been featured as a guest on the Sales Game Changer Podcast, sharing insights on building winning sales cultures.

Outside of his professional pursuits, David is active in community service, including volunteer involvement with Mobile Meals NEO, Beulah Beach Camp & Retreat Center, and serving as a Junior High Advisor at Grace CMA Church.