The ChiefOptimizer

Many parents encourage their children to find part-time work from an early age. Some kids do yard work around the neighborhood, while others might apply for a paper route or work in a local shop. Jonathan Smith, on the other hand, found himself swinging hammers and wielding drills as he helped his grandmother rehabilitate properties for one of his family’s many businesses. From the age of seven, he lent a hand down at his grandfather’s liquor distribution factory. And, young though he was, he understood entrepreneurship at an age other children might have had trouble pronouncing the word. “I would always think it was okay to be at the board table, or to be part of a business conversation,” Jonathan recalls. “I’d say I have a lot more business experience than a traditional person my age, and at this point, it almost feels like entrepreneurship is part of my DNA.”

Since childhood, Jonathan has witnessed the way entrepreneurs successfully—and, at times, unsuccessfully—assemble their teams, handle their financials, provide intelligent leadership, and establish respected core values. Today, he is able to manage and quickly improve the myriad workings of complex operations by drawing on his deep understanding of the way businesses succeed or fail to promote the former and avoid the latter. And now, as a high growth business strategist known as an EOS Implementer, and as the founder and CEO of ChiefOptimizer, LLC, he’s created the perfect avenue to make this experience available to the businesses that need it most.

When a business can’t achieve its desired level of growth, is in need of restructuring, or simply doesn’t have a clear vision for the future, Jonathan and his team are there to provide guidance and leadership skills. Generally, they’re businesses who who want to “Make It Big.” They aren’t start-ups, but instead have existing structures that ChiefOptimizer can observe and mold as necessary. “I work with second-stage entrepreneurs because there are more levers to pull,” Jonathan explains, “They have cash flow, they have the people in place, and they have some strategy. But oftentimes they don’t have a clear vision of where their business is going.”

These emerging-growth businesses range in size from $2 million to $50 million and typically have teams between 10 and 250 employees. All of the companies are growth-oriented—in other words, they are businesses that are well off of the ground, but in need of assistance as they climb to the next level. “I show up when someone’s hit the ceiling,” says Jonathan. “They say, ‘I have a $10 million dollar business, and I want to have a $20 million dollar business. The market’s there, but my people aren’t right, or I’m not profitable enough, or my processes aren’t in place properly.’”

In these situations, Jonathan helps management teams analyze their structure, clarify their goals, and establish a long-term vision using the Entrepreneurial Operating System, a set of management tools that can be implemented over a two-year period. Originally developed by Jonathan’s friend Gino Wickman, the system helps management teams communicate, prioritize, and make impactful changes, with the goal of ultimately “graduating,” and running their business on EOS without the need for Jonathan’s input. “My ultimate goal is to successfully graduate my clients so everyone can celebrate,” he says. “When a company gets to that point, it’s not only great for them. We’ve achieved what we initially set out to do, and I have another great referral source. It’s deeply gratifying to create significant value for my customers and help them be their best.”

The type of progress Jonathan aims for can only be achieved with a comprehensive understanding of the organization and its group dynamics. This aspect of his work distinguishes his skill set from that of an executive coach. Rather than working with individuals, he focuses on understanding the business as a whole and implementing a system that involves the entire leadership team. In many cases, confusion and inefficiency in an organization is the product of breakdowns in communication, so this comprehensive approach proves exceptionally effective. “Oftentimes employees don’t have a clear vision of where they’re going,” he says. “If I sit in a meeting with a leadership team, I often find that the CEO, the COO, the CFO, and the President all have very different ideas of where the business is going. They also often aren’t clear on their objectives for the next 90 days, which we call traction.”

Providing clarity in such scenarios is crucial, and developing strong and consistent values is another important piece of the overall success puzzle. “If true accountability doesn’t exist in the organization, or if a leader lives by a totally different set of rules than the rest of the organization, it doesn’t work,” he affirms.

It takes an acutely-honed entrepreneurial sense to be able to identify the distinct issues plaguing each business and the specific management tools needed to address them, and Jonathan began accruing the experiences that lend expert nuance to his perspective from an early age. He grew up in an entrepreneurial family in Berkeley Heights, New Jersey, and from a young age, he knew he wanted to be an entrepreneur. His father, Dennis G. Smith, juggled the family’s wholesale liquor distribution business—a venture his grandfather had single-handedly built—with more than a few other entrepreneurial efforts. Young Jonathan watched with fascination as his father leased cars, ran a temporary staffing company, acquired apartments, and flipped houses, all at the same time.  He was an old school serial entrepreneur and encouraged thoughtful problem solving in his three sons, inventing brain teasers and demanding creative answers.

The value of hard work became readily apparent to Jonathan, and at the age of seven, he refused a $5 payday from his grandfather after spending the day “working” at his father’s factory. Showing a sense of work ethic and integrity at a young age, Jonathan acknowledged that he had played more than he had worked and had not earned the $5, and this dedication to adding value—and to honesty—carries over to his work today. In fact, Jonathan offers a session guarantee that, if clients don’t feel they get the value they expected, they don’t have to pay.

Jonathan went on to attend college at Wesleyan University in Connecticut, where he completed an interdisciplinary major that emphasized history, economics, philosophy, and government. As he neared graduation, however, joining the family business began to look less and less likely, as profits had begun to decline. In fact, just a few years after Jonathan’s graduation, his father declared bankruptcy—an event that, to a great degree, shaped his more cautious approach to business as an adult. “I like things structured so that there’s very predictable revenue, and so that expenses are very predictable against those revenues,” he says. “I don’t believe in putting on an expense if you don’t have some kind of recurring revenue.” This philosophy has shaped Jonathan’s hyper-analytical, almost scientific approach to the business world, setting him apart as a force for smart, organic growth.

After graduating from Wesleyan, Jonathan took a job with Arthur Andersen in Hartford, Connecticut, where he worked in accounting and attended an accounting graduate program part-time. After receiving his Master’s Degree, he transitioned over to JP Morgan, where he realized his interest in the field was waning. He did, however, closely observe the structure of the giant firms, and absorbed everything he could of their efficiency. “It was amazing how eight people could run a business of 50,000 people as effectively as they could, with the controls they had in place,” he remembers. Learning all he could, but lacking enthusiasm for the corporate world, Jonathan was cognizant that his caution in business might prove the perfect foil for his risk-taking father. Thus, the two men began to toss around the idea of a new venture, which would become Wave Dispersion Technologies in 1995.

Meanwhile, Jonathan left JP Morgan for Deutsche Bank, where his work was similar but his pay was increased by almost 50 percent. Unfortunately, he soon discovered that high dividends came at a high cost. Ever faithful to the values instilled by his father and grandfather, Jonathan was disappointed to find that his new employer placed little importance on these beliefs. “I learned what it was like to have a business that was a series of fiefdoms with few shared values,” he says, “The fiefdom’s only shared value was to make money at all costs.”

During his tenure there in late 1990s, Jonathan was adamant that the mortgage-backed securities market, which Deutsche Bank played heavily in, was a terrible idea. “I didn’t want to work in that environment,” says Jonathan. “I didn’t have enough power to change things, and they were making so much money doing those kinds of transactions. I knew their approach wasn’t sustainable and that the process was totally illiquid.” Time, of course, bore out these dire predictions with the Great Recession of 2008, and his experiences at the bank again reinforced his belief that strategy, planning, execution, and transparency are core tenets needed to create a strong and resilient business.

Jonathan’s disillusionment with Deutsche Bank led him to leave for his first almost-fully entrepreneurial experience, which came in the form of a marketing position at a boutique investment firm. From there, he moved to Michigan to work with his brother’s web development company, where he became interested in search engine optimization (SEO) and quickly excelled. “I basically taught myself SEO by practicing it, going to conferences, and reading about it,” he says. “I was just voracious and wanted to learn how it worked.” Jonathan’s enthusiasm paid off, and in 2003, he was invited to speak at Google, where he was hosted by Sheryl Sandburg, the now-famous COO of Facebook. After his talk, Sheryl praised his work and invited him to join the team of Google, which was still a modestly-sized organization at the time. He turned her down, bound and determined to make his dream of true entrepreneurship a reality.

A year later, Wave Dispersion Technologies and its primary product, Whisprwave®, began experiencing success in earnest. Jonathan’s friends at Morgan Stanley had agreed to serve as angel investors, and closed a deal with the United States Coast Guard. By this time, Jonathan had earned the nickname ChiefOptimizer. After the attacks of September 11, 2001, web development calls had morphed into search engine optimization requests, and he was just the man for the job. The skill came naturally, and he found it carried over into everyday life. “I can optimize search results, but today I optimize networks,” he says. “I can see how people fit together.  I am a connector at heart.”

Jonathan’s skills were critical as the fledgling business began to grow. “My role there is basically to run relationships,” he says. “That entails either business development or government affairs. I run finance, as well as the legal piece, and I set up structure.” In 2008, Wave Dispersion Technologies signed a $100 million dollar contract with the Critical National Infrastructure Authority in Abu Dhabi. “That was one of my proudest moments,” Jonathan affirms.

In 2011, Jonathan founded ChiefOptimizer, a business he created in order to utilize the skill he’d long put to use in his professional and personal life. He calls his style of leadership “servant leadership,” explaining, “I have great respect for the military and its commitment to lead by example.   I’m not above doing whatever needs to be done to get the job done, and I can also motivate people to do amazing things because it’s not about me—it’s about the greater mission.”

Jonathan has utilized this model to great effect, both in his businesses and in other settings. From 2007 to 2008, he served as the President of a faltering chapter of the Entrepreneur’s Organization in Detroit. After accepting the volunteer position, he spoke personally at every forum under his purview, addressing issues and bringing ideas back to the board. Putting his belief in servant leadership to the test, he made sure members felt heard, and today, the chapter is flourishing as a perennial EO Rock Star Chapter.

Jonathan’s contribution to the Entrepreneur’s Organization is no anomaly. He’s volunteered extensively and been involved with a number of charitable causes, none more dear to his heart than his work for an organization called Leader Dogs for the Blind. In support of this effort, he trained two Leader Dogs that went on to serve visually impaired persons, and he continues to provide leadership training with their Harness the Power of Leadership program. Jonathan has also been involved with the American Diabetes Foundation and The Leukemia and Lymphoma Society. In fact, in 2004, the Leukemia Society named him its “National Man of the Year” after he successfully raised over half a million dollars for their cause. And true to his reputation as the Optimizer, Jonathan prefers to contribute not only money, but also his time and expertise where he can. “I tend to donate my time to objective-oriented projects where I can make a difference by utilizing my entrepreneurial skills for social good,” he explains. “I want to have that first-hand experience with the organization and its mission.”

The importance of first-hand experience is a value he encourages in offering advice to young people entering the working world today. “I’m not the kind of guy who likes to sit on a soapbox and tell people what to do,” he affirms. Instead, Jonathan leads by example, volunteering with the Global Student Entrepreneur Awards to work directly with college students to guide and encourage their ambitions. He also takes the initiative to mentor the young people he knows personally. In 2011, he traveled to Jakarta, Indonesia, as an Ambassador for Entrepreneurship for the U.S. Department of State, and he brought his 15-year-old godson, Matt, for the immersive cultural exposure.

The experience was so educational that Matt wrote his college admission essay about the trip, and, like Jonathan at his age, is now certain that entrepreneurship is the career path for him. “This type of experiential learning is the most effective and informative education possible,” Jonathan says. “I believe in showing, not telling.” It’s this ambition, emphasis on connections, and unmatched ability to build a network that allow Jonathan to optimize not only his own life outcomes, but those of countless others, whether they’re close family and friends, the employees and customers of the businesses he works to transform each day, or the young people he’s inspired on the other side of the globe.

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