D. Scott Montgomery

You Can't Do It Alone

Scott Montgomery prides himself on putting his relationships first. Valuing the people around him is both a path to professional success and a closely held personal value.

Growing up, Scott saw firsthand the way bad relationships can have ripple effects on others. Five years after being born in Daytona Beach, Florida, his family moved to Valley Forge, Pennsylvania. His parents divorced when he was nine, and their separation was far from amicable. As a result, Scott witnessed years-long estrangement between loved ones. Scott manifested this familial chaos by causing disruptions in school. Most of his teachers considered him something of a problem child, although there were exceptions. One teacher in particular treated Scott with empathy and kindness. He always appreciated her and recently reconnected with her over FaceTime through a classmate who ran into her in Scott’s hometown.

The first place he was able to build functional relationships and find mentors wasn’t at school, it was through work.

In 9th grade he got his first job at Burger King, then quickly moved on to a local grocery store. On his first day, he was told to wear a white shirt and tie. Ever the troublemaker, Scott showed up in a grey shirt. That’s when he got his first real taste of discipline. “They sent me home, and I had to change and come back in a white shirt,” smiles Scott. “It was the first time I realized that I don’t get to break the rules at work like I had in school. It clicked with me that I wouldn’t have a job unless I listened. My manager was forgiving and I went to work every day thereafter with a white shirt and tie. The grocery store staff really clicked with me. I met my first mentors, and I realized that relationships could be very fulfilling and satiating. Results were mine to deliver, and I appreciated that. It gave me money and a little bit of structure. It was the grounding I needed to launch my understanding of business.”

“It was the first time I realized that I don’t get to break the rules at work like I had in school. It clicked with me that I wouldn’t have a job unless I listened.”

For four years, Scott moved up the ranks at the grocery store, going from bagger, to cashier, to the bakery department. Ultimately, he ended up as a deputy to the boss of the bakery department before realizing upon graduating high school that he did not want to be a baker professionally. Thus, he pivoted from a service-oriented career to a business-oriented one selling insurance.

Scott was hired by National Liberty Insurance, where he quickly topped the salesman leaderboard. However, again he felt the work wasn’t for him in the long run. He felt uncomfortable with some of the sales he was asked to make, especially those to elderly folks who needed insurance. Determined to make a good living and live a good life, Scott moved on and found a more permanent home with Bell Atlantic.

Scott was brought on to Bell Atlantic, later Verizon. His first role was in selling office supplies, and in this, he met quota every month and in general overachieved. Once again, it was a positive relationship with a mentor that propelled him forward in his career. After some time, Scott’s manager insisted that Scott should be part of the team that would help open up a new ISDN office in Virginia Beach. Over the objections of a couple of other managers, Scott’s mentor got her way, and Scott was on his way to Virginia Beach.

With just three other salesmen and two managers, Scott successfully got the Virginia Beach operation up and running over the course of six months. While there, he impressed the higher-ups enough that he was offered a job in the corporate Verizon office. “They told me I was gregarious and knew the systems well,” he recalls. “They said they needed a guy like me on that part of the team. So I accepted the offer and moved to Arlington, Virginia where I doubled my salary. I couldn’t believe my good fortune. I didn’t have my four-year degree and yet was working with people who had their Master’s and doctorates. They also assigned a few junior managers to me to manage while training me how to be an effective leader. Then they promoted me again to senior management. I was handed a department and a call center, and I had to pinch myself to make sure I wasn’t dreaming.” I was fast-tracked to upper management quickly.

Scott may have shocked himself with his success, but it was hardly shocking to those around him. He acquired a reputation as a personable go-getter who was both deeply competent and loyal. He bought a house that he quickly flipped, bought two more houses, and also paid down some debt that he’d accumulated after high school. While at Bell Atlantic, he also made another important connection. He met his future wife, Katelyn.

After 12 years with Verizon, Scott decided it was time for a new adventure. One of his former bosses had started a small consulting firm and invited Scott to join the business as the third employee. Scott jumped at the opportunity and also decided to go back to school full-time. Scott registered to begin taking college classes at Northern Virginia Community College. He graduated from a 2-year program in one year with honors and earned his Associate’s degree. Scott had now achieved a good deal of professional success and completed his first level of higher education.

Underneath all of it, he most cherished his time with his family. He and Katelyn had their first son, followed by twins two years later. He knew that only by setting out on his own (launching Worldgate) would he achieve the kind of flexibility he sought to have in order to be hands-on with raising his children. “Being a father and being a husband are my two most important roles,” Scott affirms. “So for me, the desire to be self-employed is personal.”

We are a relationship-based firm, we care about getting the work done, and we care about being on point for our clients.

He co-founded Worldgate in 2002 with Katelyn, but it was quite some time before the vision and mission of the business would coalesce. At first, it was just a name on a piece of paper. Scott briefly experimented with turning it into a real estate business and obtained his real estate license while still working. In the meantime, Katelyn ran some consulting contracts through the company. “For seven years, Worldgate sort of morphed and rolled around,” describes Scott. “It was 2009 before I finally told myself that I was going to make it happen and turn Worldgate into a career. Initially, it felt risky. Katelyn held the family finances in order through her billable consulting jobs, and I reached into my Rolodex to find people that needed a nimble firm that was able to understand them and meet their needs. A few contacts working in public school systems expressed interest. We decided to develop Worldgate around the notion that we could support school districts.”

“When it was time to go to market with this model, I reached out to folks at school districts where I had worked earlier in my career,” Scott recalls. “Again, the relationships tied it together. They confirmed that they could use our help. After in-depth conversations with them, we learned what they needed and determined what we could offer and how we could satisfy their needs.”

Eleven years later, Worldgate has had great success with this model. In December 2009 we got started with our first contract with a significant school district and from there went on to win major contracts with several of the top ten districts in the country. Worldgate helps K-12 public school districts meet their IT needs and offers everything from staffing, to project management, to technical expertise, and more.

Our proven track record has meant increased investment in Worldgate’s services over time. “If a school system doesn’t have the resources to develop software, to train staff, and to roll it out to the teachers and administrators, we can add a lot of value and help them,” explains Scott. “Being a small business means we can be more nimble and more flexible in cost, unlike a lot of the larger consulting organizations. We are a relationship-based firm, we care about getting the work done, and we care about being on point for our clients. And by the way, many of our employees once worked for ‘the big 6 consulting firms’ and feel more engaged with our mission and the culture of Worldgate than their bigger firm experiences. The bottom line is that we have talented people and our customers are getting great value. It’s a win for everyone.”

Scott’s career in ensuring children are adequately resourced at school is a poetic full-circle moment for the kid who never engaged much in his own schooling.

Unsurprisingly, Scott’s title today is Chief Customer Officer. He’s responsible for marketing the business, bringing in the clients, maintaining relationships, and making sure everyone gets what they need. One anecdote in particular sheds light on Scott’s commitment and loyalty to his clients and friends. Scott really likes to tell the story of winning their contract with a prominent public school district. During the bidding process, there was a mandatory meeting that Scott’s team couldn’t make due to an emergency. In this scenario, most businesses would be withdrawn from the bidding process. Worldgate took a different approach. “I instructed my lead salesperson to go into the school district, knock on procurements’ door, and simply apologize for our inability to make this meeting,” says Scott. “I wanted our sales person to shake their hand, look them in the eye, and say we are here to help them when the opportunity presents itself again. Shortly thereafter, we got a call back from procurement advising that we were able to continue in the fair bidding process. In the end, we were awarded the contract. I think that was in large part because of the integrity we showed by showing up, looking them in the eye, and letting them know we’re here to help. They were really impressed with us. We create partners and relationships with our clients in order to maximize our value and satisfy their needs.”

“Katelyn is 50%, if not more,” nods Scott. “This wouldn’t be half as rewarding without her. We say that I’m the kite and she’s the string; we compliment each other perfectly.”

Scott has not forgotten his childhood and the role that it played in forging the hardworking, successful man that he is today. Soon after his parents divorced, his father moved back to Florida, where Scott spent summers. In Florida, his fondest memories are of attending minor league baseball games at a local stadium. “The stadium was the Jackie Robinson Ballpark and was where the Astros played,” Scott reminisces. “On Tuesday game nights I would indulge myself in the hometown baseball experience. There were a lot of cracker jacks and promotional items that were given away.” Scott kept one piece of memorabilia in particular, a plastic orange trumpet with a noisemaker. Today, he considers it one of his most prized possessions, because of what it represents.

“I’ve had it for 38 years, and it’ll never get thrown away,” Scott laughs. “When I was learning to drive, I would place the orange trumpet in front of the car with an egg on it. The goal was to get the car as close to the trumpet without knocking off the egg. So the trumpet represents the good times I have had and the work I did to achieve things. Nevertheless, being at the ballpark gave me a sense of freedom. If I was not with a parent, I could breathe and have the freedom to run around and have a good time on a beautiful Florida night. I basically was in a big playground.”

Now a parent himself, Scott is committed to giving his kids the same freedom. Aside from organizing his schedule so that he always has time for them, he’s also committed to being a positive role model. To that end, he’s also heading back to college. He prides himself on being a continual learner. Right now, he’s enrolled in pre-requisite courses in order to apply to the University of Virginia’s bachelors program. “On New Year’s Eve, I was in Charlottesville with some friends, and we went to watch a UVA basketball game,” Scott says. “One of the things I noticed with that team was that the kids were helping each other up when they were getting blocked or knocked down by the opposing team. Their assists far exceeded the other team’s assists. It wasn’t about the score; it’s about how they were playing as a team.” Scott was inspired; he called the school to ask about their programs, and they were eager to help. “Last night I was doing my school work on the couch while my kids were doing theirs,” smiles Scott. “I felt like I was teaching them about the value of education. That’s what it’s all about to me. Role modeling is important, and Worldgate offers me this opportunity.”

Through it all, Katelyn has been an incredible partner in both marriage and business. “Katelyn is 50%, if not more,” nods Scott. “This wouldn’t be half as rewarding without her. We say that I’m the kite and she’s the string; we compliment each other perfectly. I’m the visionary and am always looking forward for the next opportunity. She’s conservative, tactical, and oriented toward making sure it all stays stable. She’s grounded, and I need that. It completely works for us.”

As a leader, Scott emphasizes collaboration. “In team meetings, as issues are discussed or problems that need to be solved are brought up, I ask for team inputs on how to fix the issue we are discussing,” relates Scott. “I own my own spot at the table, but I give everyone else their spot or opportunity to contribute. There is no ‘I’ in team.”

To young people entering the working world today, Scott reaffirms his commitment to his relationships. “You can’t do it alone,” he urges. “You don’t know what you don’t know. If you come out of college with a 4.0 GPA thinking you know it all, you don’t. You still don’t know what you don’t know. I’ve been doing this for 35 years, and even I still have to look to others for their input and feedback. It’ll be easier to move forward if you can come to grips with the reality that others can contribute and can teach you things.”

D. Scott Montgomery

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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