John Blessing Headshot

John Blessing

Area Managing Partner & CSO
Works with CEOs of middle-market companies in various industries to accelerate sales growth and profitability.

About John Blessing

As the Chief Outsiders Chief Sales Program Manager and CSO, John is an accomplished leader who consistently builds success in growth and turnaround situations in a variety of industries, including professional and financial services, retail, and SaaS. He turns around poor performance and accelerates growth by building and executing strategic sales programs. He also drives sales and operations alignment to deliver breakthrough revenue. With experience in several industries, John offers perspectives not hindered by industry-specific paradigms.

How John has Helped Businesses Grow

  • Drove net income growth of 700%, increasing margins by 300%, turning around a 35-year environmental consulting services company by developing and executing a winning sales process and operational strategies.
  • Achieved an annual revenue growth rate of 20% over 6 years developing a comprehensive sales strategy and revamping the proposal process.
  • Attained 100% of revenue and profit objectives five consecutive years for a financial services company building and leading the execution of sales strategy, turning around a consistently underachieving national field organization with 16 offices.
  • Achieved first-year revenue and net income targets for professional services, technology, and financial services companies, successfully integrating seven company acquisitions.
  • Exceeded revenue targets for two consecutive years developing an inside sales team for a software provider.
  • Drove a 400% increase in product and services revenue rebuilding the largest region of a business process software company, replacing the sales staff, and facilitating the sale of the company to Adobe.
  • Transitioned inside and field sales teams from commodity network services to cloud-based and SaaS for a long time ISP, redesigning the sales process.

Client Resources

Executive Experience

  • Chief Operating Officer, Forensic Analytical Consulting Services
  • Vice President of Sales, GE Capital Fleet Services
  • CEO, Marketall
  • Vice President Sales, CrossCom National
  • Sr Director Strategic Solutions, Earthlink
  • Vice President Sales & Marketing, Jayhawk Acceptance


  • MBA, University of Detroit Mercy
  • B.A., Economics, Kalamazoo College


"Alen Corporation is a renowned brand offering reliable and highly rated air purification products since 2005. We cater to both B2C and B2B market segments. However, due to the COVID-19 pandemic, our B2B sales have significantly declined. To address this challenge, we decided to bring in an expert who could help us revamp our sales strategy and process. That's when we hired John, who has been instrumental in determining and revamping our B2B sales strategy and processes.

John's expertise has been particularly impactful in key sectors such as education, hospitality, commercial properties, healthcare, and senior/assisted living homes. His ability to tailor strategies to diverse industries has been instrumental in our growth. Notably, his strategic thinking and hands-on leadership have led to significant improvements in our B2B sales process and market positioning.

Therefore, I wholeheartedly recommend John to any company looking to enhance its enterprise sales efforts. His strategic acumen and ability to manage the execution of complex plans make him an asset for businesses seeking sustainable growth and success."

Marsha Osborn, COO of Alen Corporation


"I would recommend John to any CEO with good products or services but doesn’t believe they are getting the results they should be. He is excellent at building strategies, but more importantly, even better at managing the execution of that strategy.

LRG Investment Group owns and operates several Good Feet stores in multiple states. We have been very successful and have plans to expand. We needed sales and operations process strategies and organizational structure that would enable us to grow efficiently and effectively. We hired John in a Fractional COO role. We tasked him to develop and implement the revision of our organization structure, the execution of a sales process, and business strategy across all the stores that would allow us to be better positioned to achieve our goals. He developed and led the implementation of an organizational structure that has dramatically increased our efficiency and effectiveness in servicing our clients. He revised our sales process by establishing metrics and accountability and introducing new sales techniques and closing tools that have greatly improved our ability to develop the value of our products to our customers. John’s efforts have been successful and helped us, over the past 12 months, increase our revenue by 30% and our average sale per customer by 18%. We are actively looking to expand the number of stores in our portfolio.

John possesses wide-ranging business and sales experience across multiple industries. His most significant value to me is that he can apply that experience to assess and develop effective strategies and lead their successful implementation."

Ryan Gray, CEO of LRG Investments Group


“Forensic Analytical Consulting Services has always been known as the premier environmental consulting company offering clients protection from different types of environmental challenges. What we lacked was a business strategy that would ensure that the company could scale efficiently. John developed and led the execution of a sales process and business strategy that increased the accountability and results for the business. His leadership resulted in increasing our net income and margins to a point that we were able to invest in the business and ensure the long-term stability. I would recommend John to any company that has a good product or service but does not believe they are getting their expected results. John is excellent at building strategies, but more importantly, even better at managing the execution of that strategy.”

 Fred Vinciquerra, CEO, Forensic Analytical Consulting Services

"I thoroughly enjoyed my time working with John, and came to know him as one of the best leaders that I have ever met. He is honest, dependable and incredibly hard-working. Beyond that, he is an impressive problem solver who is always able to address complex issues with strategy and confidence. John is inspired by challenges and never intimidated by them. His knowledge of sales etiquette and expertise in building strategic relationships (internal and external) resulted in developing a sales strategy that increased our total sales by over 38% in just one quarter. Working with him and developing a key account strategy resulted in increasing our net sales with key accounts by an average of 10% year after year. Apart from business acumen, John is an empathetic leader. He is a true team player, and always manages to foster positive discussions and bring the best out of other employees.”

Pearl Hanks, President, P Enterprises

"I have hired John into several companies. He is a hands-on manager, with a solid work ethic, and extremely strong problem solving and strategic sales skills. The first time we worked together I tasked him with developing and leading a middle market sales team, selling a conversion marketing services solution for an Internet based start-up. I then hired him again to turn around a poor performing sales and services team for an enterprise wide software solution organization. In both situations he quickly identified the challenges, developing an effective strategy and then led the successful implementation with strong results. I would recommend John highly to any company looking to grow sales and requires effective sales leadership."

Glen Doody, Vice President, Global Channels SAP

“I had the opportunity to work with John at CrossCom National as a peer. He was given the task to turn around a very dysfunctional and under performing business segment. He personally lead the creation and execution of a new business and marketing plan. In a very short time John was able to expand our revenue and margin within several existing accounts and break into new Major accounts. He personally signed one of the largest contracts in CrossCom history. John is a tremendous team player and brings a great deal of experience in building successful sales and marketing organizations.”

David Rozanski, Vice President Professional Services, Konica Minolta Business Services

“Having hired and worked with John at three different companies over the years, I can attest to his dedication, integrity and work as a sales leader and coach. His exceptional interpersonal skills and customer focus along with his innate ability to motivate and drive a sales team lead to breakthrough revenue opportunities that deliver over plan results.”

Karen Hayward, Managing Partner & CMO, Chief Outsiders

“I have worked with and supported countless sales teams throughout my marketing and product management career, and John is without a doubt one of the most talented, genuine and inspirational sales leaders with whom I have had the pleasure of working. John’s unique talent for sales enablement allows him to coach teams to want to learn more and strive for greater success, and provides motivation to everyone around him. I have learned tremendously from John’s professionalism, integrity and sales skills in our time together at EarthLink Business.”

Michael Barnes, Marketing Product Manager, Equifax

Download John's Resume Here


Industry Experience
  • Financial Services
  • SaaS
  • Technology
  • Retail
  • Sales Growth
  • Turnaround Execution
  • Sales Process Strategy
  • Acquisition Integration
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