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David Sobel
CEO CoachSales & Growth Operator
SENIOR PARTNER · LEADERSHIP TEAM BUILDCertified coach

David Sobel.

Three-time sales-org founder and partner who built Home Warranty of America from start-up to a $50M sale.

25+
Years operating
5
Core specialties
2
Industry experience

The operator behind the coach

David Sobel has served as a Senior Coach at CEO Coaching International since July 2014, and in 2026 was named the firm’s Chief Revenue Officer. He partners with CEOs and presidents of $5M–$100M companies to build scalable revenue engines, strengthen leadership teams, and drive profitable growth. With more than 25 years as an operator and entrepreneur, he brings a practitioner’s perspective to every engagement: he has built the systems he coaches others to build.

Over his career, David founded three sales organizations from the ground up, established a global distribution channel for one, and played a key role in two successful company exits. Most notably, he served for 13 years as Partner and Vice President of Sales at Home Warranty of America (HWA), where he designed a repeatable, scalable sales model that drove the company’s growth and culminated in its $50 million sale. During his tenure, HWA was recognized on the Inc. 5000 list from 2006 to 2010, and was the only insurance company to earn that distinction in two of those years.

David’s coaching style is direct, data-driven, and grounded in accountability. He is the creator of the Win the Day Accountability System, a framework that helps leaders and their teams translate long-term goals into focused daily execution. Guided by the principle that what gets measured gets done, he helps clients install the metrics, operating cadence, and disciplined follow-through that turn strategy into results. His areas of focus include sales organization design, compensation and hiring, channel strategy, operational scaling, and exit preparation.

David is a graduate of the Stagen Integral Leadership Program and holds a second-degree black belt in Tae Kwon Do, where he also serves as an instructor. He applies the same commitment to self-awareness, discipline, and personal accountability that he brings to his own life to his work with every client.

Selected accomplishments

  • Built HWA from start-up to a $50M exit over 13 years
  • Created 3 sales organizations from scratch, with 2 successful sales
  • Developed global distribution channel for one of the orgs

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Working with David

Questions CEOs ask about David

Who is David Sobel best suited to coach?

CEOs and presidents of $5M–$100M services, insurance, and growth-stage companies that need to scale a repeatable sales engine, professionalize the leadership team, and install real accountability.

What is David's operating background?

David built three sales organizations from start-up and contributed to two successful company sales. As Partner and VP of Sales at Home Warranty of America for 13 years, he built a replicable, scalable sales model that led to a $50M sale. HWA was an Inc. 5000 honoree from 2006–2010.

What is David's coaching style?

Direct, measurement-driven, and unapologetically focused on accountability. He works from the philosophy that what gets measured gets done, meaning the cadence, the metrics, and the difficult conversations are non-negotiable.

Does David coach on sales organization design specifically?

Yes. Sales-org design, compensation, hiring profiles, channel strategy, and the operating cadence of a high-performing revenue team are core to his work. He has built three from zero and exported one globally.

Where is David based and how does he engage?

David is based in Buffalo Grove, Illinois. He coaches CEOs across North America through 1:1 sessions, board observation, and strategic sales offsites, and is a graduate of the Stagen Integral Leadership Program.

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