Katelyn Montgomery

Growing and Evolving

Katelyn Montgomery never planned on being a business owner. Hardworking but practical, she foresaw herself climbing the ladder in more traditional ways, playing it a bit safer. But in 2002, only two years into her marriage, she agreed to start a company with her husband, still uncertain that they’d ever do much with it. Together, they filed the papers to create Worldgate that year. Initially, they saw the business as a vehicle to potentially acquire investment properties and flip houses.

But by 2009, a lot had changed. Katelyn and Scott now had three small children—their eldest boy, Evan, and baby twins, Teddy and Phoebe. Katelyn’s two biggest priorities were to support them, and to be there for them. She had spent years burning the midnight oil at other companies, coming home late at night, stretched thin and too exhausted to be present the way she wanted to be for her young family.

“My husband’s really the true entrepreneur,” observes Katelyn, “he’s the one who said, ‘we should do this!’ I was kind of like, we need jobs that pay us. But one night I was working until 1:30 AM. The next morning he brought it up again and I said, ‘Okay.’ And we jumped into this thing together.” Katelyn began by leaving her position at a small technology firm, but offered to continue working for the business as a consultant. She was more client-focused at Worldgate, supporting work needed by the clients, as Scott looked for new opportunities.

At first, Katelyn split her time between consulting for clients and giving time to the young business’s other contracts and Worldgate’s infrastructure. “Finally there was just too much to do at Worldgate,” she recalls, “so I evolved into no longer working on clients, just working on what came into the business. But it was a slow transition, because I was still a little nervous about us jumping in feet-first without any safety net.”

Though the transition hasn’t always been easy, it has been, after all, very successful. In 2009, a former co-worker of Scott’s reached out to ask for his help on a small IT contract with a city school district. Worldgate won that contract, and the young business found its calling. Worldgate continued to win contracts with the school district providing IT consulting services, and soon, it began winning similar contracts at major school districts in other cities.

Today, Worldgate is a thriving company with 32 employees, including a new VP of Sales who plans to expand the business geographically. They’ve continued to focus on supporting school districts, expanding their skill set with each new client. “We support the business side of IT, we’re not doing the true coding and development,” explains Katelyn. “We are supporting enterprise deployments for a full systems implementation life cycle, or we are supporting with people to augment the school districts’ slim staff with project managers, business analysts, change managers, trainers, help desk staff, etc. We both provide staffing, and partner with software vendors to support product implementation. We specialize in K-12, and our understanding of the ins and outs of those school districts is a huge selling point for us.”

Although Worldgate has some state and local contracts that are not schools, they’ve become known for their work in the education sector, particularly at large city school districts around the country. “Our understanding of their culture is a big advantage,” notes Katelyn, “they want you to understand how these school districts work, and that’s the culture we’ve grown up in.”

“One of the things we say about our working relationship,” Katelyn goes on, “is that basically, he’s the kite, and I’m the string. The kite wants to float and explore the universe, but the string can guide and maybe pull back a little sometimes..!”

Katelyn and Scott manage the business efficiently and effectively by dividing the labor according to their talents. Scott handles the sales, customer support, and service delivery side of the business, while Katelyn is in charge of operations, overseeing the HR department and the CFO. If you have read the book “Rocket Fuel”, Scott and Katelyn really align with the leadership roles outlined in that book. Scott is the visionary- he takes the long view, and sees where he wants the business to go. Katelyn is more of an integrator. “He’ll come up with something, and I’m the one who says, well, how will this work,” explains Katelyn. “Who are we going to hire? What are the next steps? So I think I take his twenty-thousand-foot vision and bring it down to Earth.”

“One of the things we say about our working relationship,” Katelyn goes on, “is that basically, he’s the kite, and I’m the string. The kite wants to float and explore the universe, but the string can guide and maybe pull back a little sometimes..!”

Since 2009, Worldgate’s revenue has grown steadily, without any significant peaks and valleys, in large part thanks to Katelyn and Scott’s blend of ambition and practicality. “I feel like it took about eight years to get to the point where we really fine-tuned our approach and created a strong foundation,” says Katelyn, “to get to this point where we’ve positioned ourselves for that bigger growth. We invested in a new VP of Sales, who formerly worked for a number of software and service companies in the K-12 space, as well as a full-time recruiter. We’ve set up our entire infrastructure to now, ideally, be able to grow in a very smart and efficient way.”

With contracts in several states, most of Worldgate’s staff doesn’t work at their headquarters in Reston, Virginia. The executive staff is still lean, a structure Katelyn preferred to keep overhead low, but their new recruiter is charged with bringing in a variety of talent now that the business can afford to invest in growth.

Katelyn admits that being less conservative with expenditure has been a process for her. “I’m the person who just wants all my money under my mattress,” she laughs, “but I’m learning to let go of that fear to make smart investments to help the business grow.”

Katelyn has been conservative with money since childhood, when she watched the financial toll divorce took on her newly-single mom.

Until Katelyn was eight years old, she had something of an adventuresome childhood, travelling from country to country as her father, an Africa specialist in the CIA, was assigned to new posts. The family bounced between its home base in Northern Virginia, and years spent abroad in far flung locales like Haiti, South Africa, and Mauritius. Katelyn and her younger sister were accustomed to a life spent in comfortable government housing with domestic staff. Though she was young, Katelyn still remembers some of the more exciting tales of her childhood travel. There was the time when, in South Africa, her father killed a poisonous snake outside her bedroom door with a golf club and brought it to a party to show it off. There was the time she encountered something called “Bottle Brush” in Mauritius and was covered in a terrible rash. Her cousins remind her that, for a time, she and her sister came home speaking with South African English accents.

But when Katelyn’s mother and father divorced, life changed dramatically. She and her mother and sister moved in with their maternal grandparents in Salem, Massachusetts, while Katelyn’s mother began working to support them. Gone were the country club dinners and foreign excursions; instead, Katelyn remembers her mother counting out change to simply buy a cup of coffee. “My grandparents became like my second parents, basically,” recalls Katelyn gratefully. “My mother was working so they would take us to dance classes, to basketball, to soccer, to softball. They helped keep our lives normal during the transition.”

Her grandparents also helped them financially, although they did so subtly. “My grandmother would go shopping with a friend every Monday, and every week she would drop off some groceries,” remembers Katelyn. “It never felt like they were giving us food, it was more like she just happened to pick up a few things when she was shopping.”

Though she worried about money, most of her memories from Salem are happy and picturesque. She remembers playing kickball under streetlamps, catching fireflies in the summer, and wading in the little beach at her grandparents’ house. Her father’s brother and his family lived nearby, and she grew up very close to her cousins. Salem was a largely blue-collar town, and she never felt out of place among the other kids with working parents.

Her other major mentor was, of course, her mother, whom Katelyn calls “the world’s biggest cheerleader”. “My mom, no matter what, was the biggest supporter of everything we did,” smiles Katelyn.

Fortunately, Katelyn had always had an easy time making friends, and her move to Massachusetts was no exception. She got along with everyone, never settling into one clique, but preferring to make friends with everyone. “I never remember having any concerns about moving,” Katelyn muses. “I don’t know that I was a natural leader, but I was a natural relationship builder. My best friend today is a girl who came up to me on the playground that first day we moved back to Salem.”

Academically, Katelyn thrived. She always maintained good grades, though she split her time between school, extra-curricular activities, and work. As a younger kid, she loved participating in after-school sports, but when she hit 14, she committed herself to earning her own money. From a young age, she’d begun babysitting, but now she could make a real income, and she wasted no time in doing so. She started a paper route, then began working in a flower shop called “The Plant Lady.” And although neither of her parents had gone to a four-year college, she considered it a given for herself.

As she focused on her studies, she remembers one high school English teacher in particular, Mr. Kenney. The man was tough, but fair, and she decided to ask him to write her a recommendation letter. “I was so scared of him,” Katelyn laughs. “I remember wondering if he was the right person to ask, thinking he might really screw up my chances. But he gave me a copy of his recommendation letter, and he had written all of these really amazing things about me. That was a huge confidence boost for me.”

Her other major mentor was, of course, her mother, whom Katelyn calls “the world’s biggest cheerleader”. “My mom, no matter what, was the biggest supporter of everything we did,” smiles Katelyn, “She’d say, I’m so proud of you, I can’t believe you achieved this, you worked so hard for this. Everything we did was the greatest thing she’d ever seen! And to this day, she’s the same way, still telling us she’s so impressed with us. I hope I emulate that with my team.”

She graduated 13th in her class, and was accepted to UVA and Boston College, among others. Ultimately, however, she chose to attend the University of New Hampshire, as the school had given her significant grants and scholarship money.

There she joined a sorority, worked in the library, and had no idea what to major in. Ultimately, she decided to become a Psychology major and a French minor, because those were the classes she liked. “I enjoyed my psychology classes immensely, but I knew I wasn’t going to have a career in that,” Katelyn says. “That’s probably part of the reason why I went back to get my MBA.”

After graduation, Katelyn headed back to Virginia to live with her dad for a period. It was their first opportunity to spend real time together in many years, and Katelyn wanted a change of scenery. Her first job out of school was temping with a group called Kelley Services, where she got assigned to work for Mobil Oil in Fairfax. There, she was completing the time consuming, mundane work of compiling information sent in on floppy disks from operations all over the world. A big part of her job was just waiting for the diskettes to run, something another woman, Sarah, in the office fortunately noticed.

“Sarah was responsible for the internal newsletter and saw that sometimes I would just be sitting there while the diskette was running,” laughs Katelyn. “So she asked me, ‘do you like to write?’ And I said, ‘yes, I love to write.’ So she asked me to help her with some things, and that’s when I got my first taste of marketing. I learned how to spin things for the internal newsletter. That was probably how I started thinking about my MBA. Sarah had hers, and I remember thinking she was really cool and smart. It was a nice chance she gave me.”

“One of the things I learned from the women leaders at MCI was how to truly be a leader that develops people,“ Katelyn affirms.

After her time at Mobil, Katelyn went to a small non-profit in DC, where she worked as an Executive Assistant and learned the ins and the outs of that side of the business world. There, she began applying for graduate school.

She decided to attend the MBA program at the University of Maryland, in part because of their terrific graduate assistant program. In exchange for teaching, she was provided with in-state tuition, five credits paid for each semester, and a stipend. During her first summer, she fatefully interned at Bell Atlantic, where she met and fell in love with Scott.

Katelyn concentrated on marketing, and after graduation interviewed with many major corporations. During her interview with Intel on the west coast, Scott sent her flowers but confessed, “I hope you don’t get the job!” She decided to stay on the east coast and accepted a job with MCI in 1997. For nine years, she stayed at the company, weathering the economic downturn, but deciding to leave after the Verizon merger. The culture was becoming too large and bureaucratic for Katelyn’s taste, but the lessons she learned there stayed with her. In particular, she remembers learning from a group of fantastic female mentors at MCI.

She wasted no time striking out on her own; her final day at MCI was a Friday, and she began a marketing consulting contract with AARP on the next Monday. She stayed on the contract for over a year, then moved on to work at a small company firm in 2007. She was hired as the VP of Sales and Marketing; it was in this role that she found herself working until 1:30 AM and looking to restructure her life for the sake of her children. It was then that she dove headfirst into Worldgate.

It hasn’t always been easy, but Katelyn has continued to evolve with her business. “It has been a huge growth trajectory for me, to be in this uncomfortable space of not having a boss to tell me, help me, and guide me,” she explains. “Plus, I also very much like to have external praise, I like to hear that I’m doing a good job. It motivates me. I don’t have that so much anymore. I have to dig deep inside myself to say, you’re doing a good job. That’s been a big shift for me.

Today, she’s fulfilling that role for other people—her staff. “One of the things I learned from the women leaders at MCI was how to truly be a leader that develops people,“ Katelyn affirms. “A lot of that is allowing people to do their job without too much intervention. Provide guidance, pick them up when they fall down, but don’t always give them a direct roadmap. I’d say I’m a leader that empowers people, and also tries to be collaborative. I am always open to conversation and I want people to feel that they have complete flexibility to get their job done as they see fit, in ways that will help them grow and achieve their goals.”

To college students entering the working world today, Katelyn advises authenticity and relationship building. “I think that when people are playing a part, they’re never going to be able to keep up with that,” she says, “You need to be you, to show your strengths and show the things that you’re able to contribute to an organization. Playing a part gets really old, and I think if you can shine by truly being yourself, that’s huge.”

Katelyn’s kids are older now. Her eldest son is 13 and her twin son and daughter are 11. But she’s grateful that all those years ago, she chose to take a risk so that she could have the freedom to attend baseball games, be involved in the PTA, and always be there for her three children. “I have to say, I feel like I am continually moving,” she nods, “but having the ability to be there when I’m needed, that’s why I do what I do.”

Katelyn 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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