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Howard Highsmith, CMC EMERITUS

Managing Principal

Endgame Strategist, LLC


Howard Highsmith, CMC Emeritus

Managing Consultant at Endgame Strategist, LLC

Laurel Park, North Carolina


Thinking Strategic

Interview conducted by:

Lynn Fosse, Senior Editor, CEOCFO Magazine

Published – February 14, 2022

CEOCFO: Mr. Highsmith, according to your site, Endgame Strategist, LLC is a best practice strategy for creating exceptional growth. What does that mean, day to day?

Mr. Highsmith: Best practices by an organization means those firms that take the time to organize, establish rules, disciplines, and integrity into their operations at all levels. I try to focus my clients to adopt best practices as a way to ensure their revgen strategies deliver revenue against expectations.

A Best-in-Class status can be the reward for those who fully achieve it. I submit if you don’t follow best practices, your revgen strategy will become Industry’s Average or a Laggard, at best.

CEOCFO: Are people today, in general, less detail oriented? Do they think it will not matter, or they cannot be bothered?

Mr. Highsmith: Under the excuse of being ‘crazy busy,’ much of our society attempts to ‘scan’ for information, in lieu of reading for knowledge, retention and learning. And so, less detailed oriented people are probably the least likely leaders in defining the success or failure of a business. I sat in an online zoom meeting last week with Michael Levine, author of his latest best seller, Broken Windows, Broken Business and leader of one of the largest PR firms in the United States. A participant asked the question, “What separates an industry leader firm from an average or underperforming firm?” Michael’s answer was: “Leaders pay obsessive attention to details.” I concur. In my experience, if a CEO cannot be bothered, they won’t learn. If they won’t learn, they will not be industry leaders. It is that simple and it is that complex. I offer the expression, ‘you don’t know what you don’t know.’

CEOCFO: How do you work with your clients? What is a somewhat typical engagement and maybe something a little more outside the box?

Mr. Highsmith: I serve technology industry sales organizations that are operating in complex sales environments. More often than not, out of the box thinking happens in corporate situations where brainstorming often identifies unique strategies. I offer three levels of sales performance assessments: Level One is a sales performance review for a company that wants to ‘get acquainted’ and to determine what their issues are and how they can improve revenue. Level two is considerably more in depth and includes brainstorming that can often be out of the box thinking. Level Three is custom and based on the specific detailed needs of the client. Mostly these would be medium to larger firms. I am at the service thereafter of companies that have conducted assessments in their organizations.

CEOCFO: When you are engaging with a company, what do you look at about the company, that less knowledgeable people do not pay recognize as meaningful?

Mr. Highsmith: That is a good question. Primarily, I am looking at the core values of the leader and how much detail he or she is interested in. And, if they allow subjectivity to be the driver of internal intelligence and competitive information. For example, if I were a sales rep working for you, and you asked me how the sales call went, and my answer to you was; “It went great, they love me, we should get the business.” What does that REALLY tell you?  Nothing. It’s sounds good, but it’s all subjective, CYA opinion. I try to look for companies that are looking for substance and not subjectivity. In this day and time, the sales process has become considerably more complex, and you are called to work with committees within companies. When large sales purchases are about to happen, committees are formed to talk to vendors vying for the business. Winning or losing this business (and revenue) is totally dependent on a strong set of skills knowing how to handle this type of situation.

Further, I am looking for companies that want to put substance behind the question, ‘what is our next step?’ I have created a sample sales process map based on a set of logical acquisition stages, usually 5. Individual steps in each stage that a company would move through in making a decision to buy from a vendor. This sales process map is given as a draft copy to be edited to fit the particular needs of the client company.  Sales training companies will often have their own set of sales stages and so should be adapted to the map. Also, sales managers are under pressure these days to produce revenue, so as a result they will often allow subjectivity to happen, and it becomes a habit. If subjectivity is the norm in forecasting near term revenue the validity of the data is under question and not recommended.

CEOCFO: Do you typically work with a company on a one-shot deal, maybe over a period     of time, or do you continually engage with some of your clients to keep them on the right track?

Mr. Highsmith: Let me answer that two ways: First, I do not establish relationships that are designed to secretly cause the client to be connected to me at the hip by a service designed only to generate monthly recurring revenue. This hidden agenda type of approach is simply not professional. If a CEO would say, all I really want is for you to give me a thumbnail of what you see in my revenue generation strategy. My Level One Assessment would be used to identify any holes in the way they are doing business.

In the interest of full disclosure, I do offer a subscription service called Governess that reports quarterly on how well an organization is doing compared to goals. The caveat is, Governess is only offered after having already completed a level One, Two or Three assessment, and then working on a monthly basis as long as it is of measurable value to the client. We have quarterly review meetings to determine that the company is still on track with the strategy to meet its revenue goals with suggestions. During each reporting period I will check on certain benchmarks and report as needed. Also, during the period, if a business turndown, what happened, why, and possible responses.

I am currently writing one of my Strategic Thinking Briefs right now, and the focus is on the impact of COVID. I don’t know whether you heard this number, but the Harvard Gazette is saying that the estimated cost of COVID will be 16 trillion dollars! That is a massive number, and my concern is, it will have a major, long-time, effect on our business models and strategies going forward.  

CEOCFO: How do you help your clients stay on track and not fall back to old habits?

Mr. Highsmith:  Honestly, I can be a pain in the butt! I have never run from confrontation. Having said that, I have been fortunate to be well-served in this regard, as most CEOs want real information and real data. Relationships matter a great deal to me, I deal in facts and reality, so I don’t hold back sharing my opinion.  

CEOCFO: Are there trends you see today? Have things changed over time that might be stumbling blocks, certain during COVID, but in general?

Mr. Highsmith: There are two big trends I believe will change the face of generating revenue in complex sales environments.

First, COVID has caused the traditional face-to-face meetings between a buyer or a seller to become virtual. And, from a buyer and seller point of view, this approach is fast becoming the preferred method. I would hasten to point out three things about this change: I.) This approach works great with large enterprise companies as the buyer is often on-par knowledge-wise or close as the seller. II.) Smaller companies, on the other hand, are likely to want to retain a face-to-face relationship going forward.

So, it will be important that sellers offer an either-or option in serving a wide range of client companies, virtual or face-to-face. A word to a wise buyer. Sales organizations will more often than not take the least point of resistance and choose virtual over face-to-face. So, if you are a small company needing a face-to-face relationship, be warned, this may become a critical issue in determining who you will work with going forward. III.) Which brings up marketing. Marketing over the years has been a step child to direct sales. Not anymore, marketing is and will become the differentiator in a competitive sales environment. I am currently vetting marketing companies with industry expertise now so that I can be an effective resource for them.

The next trend in the world of business intelligence and quality data, called, is analytics which is absolutely crucial to all businesses, regardless of size. Predicting revenue can be a total W.A.G. (Wild Ass Guess). The next big thing in my opinion is ‘What if Modeling’ using business intelligence and for planning and executing revenue growth strategies. FYI, Tableau Software has just announced this new capability in its software, and I predict it will be the next big thing for all best-in-class B2B sales organizations.

CEOCFO: Would you tell us about Roadmap to AI. How does that fit into what you offer and how you work with your clients?

Mr. Highsmith: Roadmap to AI is a book and my way of crying out to companies to avoid the mistakes of the past such as SFA (Sales Force Automation).  In writing the book I honestly didn’t recognize the connection between AI and automation. Twenty plus years ago large companies invested millions of dollars in the promise of SFA (sales force automation) only to find it did not work well, if at all. Artificial Intelligence is the 2022 SFA, and it is not an inexpensive investment. Those who profit from AI will be the ones that prepare their companies in advance for AI. That is what Roadmap to AI is about. AI is a very powerful tool that is also an unforgiving application requiring quality data. Words like ‘I think’, ‘maybe’, and many more will never work in an AI environment or we will see a resurgence of the phrase ‘garbage in, garbage out.’

CEOCFO: What does the next year look like for you?

Mr. Highsmith: As the Managing Principal of Endgame Strategist my game plan is to work with clients where there is a good fit between us. I am at a place where my acceptance as an industry expert re: revenue growth and goal attainment, will dictate how big of a company I will want to build. I am not a sales training company but am glad to recommend one. My plan is to recommend companies that I have vetted such as Mr. Lynn Taylor, founder of Taylor Protocols. I think Lynn is the Abraham Maslow of today. Lynn invented the CVI (Core Value Index), an assessment tool for selecting top performers. His company is the go-to firm for organizations committed to growth. After all, the cost of business is so high these days, that it is an expensive proposition to make a wrong decision. Therefore, CVI allows companies to have a better way to hire the right person for the job.   

CEOCFO: Why consider Endgame Strategist, LLC? Why pay attention to the company?

Mr. Highsmith: Personally, I became a member of the Institute of Management Consultants (IMC USA) in 2000 because of their strong commitment to ethics and integrity and they have lived since what they preach. In addition, I created a revenue generation strategy some years ago, that was incredibly successful, and before I leave this earth, I would like to pay it forward by sharing what I know about integrity and generating revenue. I have been pretty successful at it, I know what to do and what not to do, and I think I can help companies achieve significant revenue growth. I am running a podcast called “Grow Revenue or Die that runs the third Tuesday of every month. It is hosted on Check it out.

Finally, I am not in it for the big bucks. I want to leave a legacy where a CEO client would say, “He helped our business find its way in a highly competitive environment and we generated exceptional revenue in the process.”

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‘I am not in it for the big bucks. I want to leave a legacy where a CEO client would say, “He helped our business find its way in a highly competitive environment and we generated exceptional revenue in the process.”
Howard Highsmith, CMC EMERITUS