Win Sheridan

Beginning with the End in Mind

Beginning with the end in mind.

This timeless adage has been put into practice by entrepreneurs throughout the ages, yet few have implemented it to quite the tee as Win Sheridan and his partners, Brian Callaghan and Jeff Veatch, have.

The three fraternity brothers, only a year or two out of college at the time, had been working at Aerotek (now Tek Systems), an IT recruiting firm in Reston, VA.  It was an era of rapid growth for Aerotek, and the company was sending out its employees to help open offices in St. Louis and Portland.  The urgency and drive of this effort seeped into the very core of these three young men, and after just a few months, they felt as though their skills and expertise would best serve in launching an IT staffing company of their own.

Thus, beginning with the end in mind, Win and his partners met in their living room one night to set the vision and division of their new enterprise.  Among the most pivotal decisions made in that first meeting was in regards to the intended scope of their endeavor: it would not be a local or regional company, but instead a national presence.  Thus, Apex Systems was incorporated in September of 1995 and opened its doors in the first week of October, committing to filling the IT placement needs, both project-based and permanent, of Fortune 500 and larger midsize companies throughout the United States.

Honoring a noncompete agreement with Aerotek, they were not permitted to do business within 50 miles of Aerotek’s office in Reston within their first 18 months of operation.  Happy to abide by that mandate, Win and his partners opened Apex’s first office on the south side of Richmond.  Indeed, their experience with sales, recruiting, and all other front office services and considerations was strong enough to realize the broad ambition they had set their sights on, and the company began to take off.  Enjoying immediate and rapid growth, however, presented unforeseen challenges to the firm’s back office responsibilities such as payroll, accounts receivable, collections, and cash management.  With success coming faster and faster, their cash was draining rapidly.

In fact, Win recalls with a shudder a period in May of 1996 when Apex’s checking account fell to about fifteen thousand dollars, which could only realistically sustain them for another week.  “When you’re growing that fast and running that hard, the business is like a rocket ship, and you feel that turbulence,” he describes now.  Fortunately, the company’s integrity and strong client relationships yielded an influx of cash that could sustain the operation, and Apex was able to pull itself out of the danger zone.  But this served as a vital lesson, and Apex vowed to restructure its back end effectively so that it could quickly scale to handle the rapid growth the company continued to enjoy.

“Banks are not keen on supplying startups, and what few people realize is that rapid growth can actually kill a company quicker than no growth or slow growth can if it’s not managed properly,” he says today. “We had very ambitious growth plans from the very outset, and this required equal performance in the front- and back-offices.”  In large part, it was Apex’s strength in personal relationships that helped them overcome these early challenges with cash flow. “It’s very important to establish relationships with a client’s back-office people as much as with their front office people,” Win acknowledges now.  “We cleared that hurdle, we learned from it, and we haven’t looked back.”

After this initial learning experience, Apex really hit its stride, and at eighteen months to the day of their noncompete, the firm opened its Fairfax office.  Apex hired its first 50 employees from a pool of first-degree past associates and acquaintances, yielding a close-knit and enduring network that made for a tenacious, driven, and cohesive team.

This strong foundation paid dividends, and through plenty of referrals from proven hires, the company continued to experience strong growth.  New offices opened rapidly in Baltimore, Raleigh, and Atlanta, and today—true to their original vision—Apex has 49 offices spanning the entire United States.  In the first year, its sales broached the million dollar mark.  In the next, that figure rose to $5 million. Sales then rose annually to $15 million, followed by $28 million, followed by $37 million, followed by $60 million. Last year alone, Apex drew $550 million in revenues, and for 2011, their sights are set on $700 million.  This marks halfway to their billion dollar milestone—a target they’ve had their sights on since day one, and which they hope to realize in 2012.  Yet, with characteristic ambition, Win is quick to emphasize that this is only a milestone, not an end goal.

Such an insatiable and ambitious drive is rarely displayed, and even more rarely realized—evident of an inner fire lit by a unique flame which we all might like to ignite in ourselves.  Success is certainly integral to the equation, but Win’s example highlights the fact that setbacks play a role that is perhaps just as vital.  As an English major in college, he certainly experienced his fair share of rejection letters before landing at Aerotek after his classmate, fraternity brother, and now business partner, Jeff Veatch, referred him.  Despite its status as an IT recruiting firm, the job did not require skills in technology, but rather a rare personality with an eye for talent and a mind for the strategic pairing of talent with need.

Though he accepted his position at Aerotek thinking he would later attend law school in the tradition of his father, who had owned his own law firm for 40 years, it quickly became clear that his path lay elsewhere.  His partners were finance and psychology majors, and this robust set of skills and backgrounds is a true testament to the unique and far-reaching nature of the industry in which Apex operates.

“This is very much a business about building great relationships,” Win notes today. “It is a great asset to be extroverted, and to be able to communicate with people effectively.  It’s not the kind of talent that can be captured solely on paper.  You’ve really got to know people.  Our people are our number one competitive advantage, and one of our top goals is to create a winning culture where they can be highly successful and have fun with their career along the way.”  Forming strong bonds both internally and externally in this manner has played a pivotal role in Apex’s success thus far, and promises to remain a major building block in the future expansion of that success.

While the ability to form strong, genuine relationships with others is indeed a tremendous asset in the IT staffing realm, Win also emphasizes the importance of that inner drive that compelled him to set such a lofty bar the night Apex was born.  “You have to want to win, and it’s got to burn you to no end if you don’t,” he explains passionately.  His partners mirror Win’s spirit in this regard, and it is perhaps for this reason that their personalities harmonize so effectively to strike that ideal pitch of compelling and effective leadership that companies so often strive for.  “We all feel that sense of urgency to get out there, grow the business, ensure our people are always improving, and do the right things,” Win explains.  “We are an ever-evolving work-in-progress.”  He and his partners emphasize these ideas to their employees through their expectations and through positive reinforcement, and it is this leadership philosophy that drives Apex today.

The roots of Win’s professional savvy and leadership style have certainly been honed through his experience in the IT staffing realm, but they actually extend far back to the earliest days of his youth.  Growing up in Alexandria, VA, his first job was delivering the Alexandria Gazette in the sixth grade.  As a child, he had observed older kids doing the job of wrapping and banding the papers before putting them in bags if it was raining, and he would even help out.  When he actually assumed a position of his own, however, he learned about the behind-the-scenes aspects of the business, including collections and customer complaints.  The importance of back office management and of developing relationships with clients was underscored even at this early age and foreshadowed the lessons Win would learn from Apex many years down the road.

His entrepreneurial flair was also evidenced early in life when he decided to start his own lawn mowing service after working the summer of his sophomore year of high school for a company that paid him ten dollars an hour to do 25 to 30 lawns per day.  “After one summer of that, a partner and I decided we could do it on our own, so Fannon and Sheridan Lawn Service was born,” Win laughs now.  “Taking that small step and having that experience at an early age was a great lesson in entrepreneurship.”

In advising young entrepreneurs entering the business world today, Win advocates for choosing passion over a paycheck.  “Don’t be a slave to the almighty dollar,” he warns.  “Too many people focus on this, and it’s a mistake.  If money is your only motivation, you will ultimately fail one way or another.  Find something you’re great at and passionate about, and then put together a business plan.  Have fun with it.  Money should not be the end goal, but a byproduct of doing what you love to do.  Today, I certainly have my sights set on goals, but it’s never about what’s going into my pocket.  Money is just the byproduct of what we’re accomplishing as a company.  The better payoff is the satisfaction you get from seeing your people get rewarded as they grow with the company.”  By keeping your sights on goals in this manner, and on the passion that truly inspires the inner will to win, one can truly begin with the end in mind, setting the course for success from the very first step.

Win Sheridan

Gordon J Bernhardt


President and founder of Bernhardt Wealth Management and author of Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area. Gordon provides financial planning and wealth management services to affluent individuals, families and business owners throughout the Washington, DC area. Since establishing his firm in 1994, he and his team have been focused on providing high quality service and independent financial advice to help clients make informed decisions about their money.

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