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Diligent Tim Moneypenny

Diligent: Moneypenny Moves from Small Change to Big Impact

Photos and Story by Jillian Harman –

While the name Moneypenny may call to mind images of a desk-bound secretary from the James Bond franchise, Timothy P. Moneypenny, founder and CEO of Diligent Electronic Security Systems, has carved a vastly different path. With a story that begins modestly and a career steeped in projects that could inspire a blockbuster of their own, Moneypenny’s journey from a 16-year-old janitor to a security industry leader is one of hard work, resilience, and, above all, diligence.

An Unlikely Beginning

The eighth child of 11 siblings, Moneypenny’s early life was marked by struggle and competition. “Our father passed away in 1962, leaving my mom with nine kids to raise. She did a great job. But I had to fight for everything, from clothes and food to attention and a place to sleep,” Moneypenny recalls. 

However, the competitive environment ignited a spirit of determination that would prove instrumental in his future successes. “I went to work as a janitor at 16 years old and haven’t stopped,” says Moneypenny.

Finding solace in sports, Moneypenny fostered an enduring love for long-distance running. But his true path would take many years to unfold. 

Lighting the Spark

In 1985, Moneypenny’s life took a turn when his wife, Wendy, accepted a position with the National Security Agency, leading them to relocate to Maryland. Following a stint with a construction company and Foot Locker, Moneypenny found his calling in the electrical trade, where he began as an apprentice electrician at Walker Electric. “I’m not mechanically inclined or have an aptitude for electricity. I simply worked hard and used this to my advantage,” says Moneypenny.

Moneypenny got his first taste of the security industry at Walker Electric, a small family-owned company. Despite having no prior experience in electrical work, Moneypenny’s tenacity and determination allowed him to excel.

“I spent many months holding the ladder and running to get parts for the journeyman electricians. My colleagues gave me the nickname ‘Small Change’ because I was 30 years old and making $4.50 an hour,” Moneypenny recalls with a chuckle. 

Rising Through the Ranks

Despite the steep learning curve, he quickly gained expertise. Moneypenny’s hard work and dedication did not go unnoticed. He soon found himself installing security systems at the Pentagon, CIA, and many other government agencies, often completing them in half the estimated time. “This turned out to be very interesting to me, and I excelled,” says Moneypenny. “I spent a year working remotely at a classified location in Charlottesville, Virginia.”

Within a year and a half, he was in charge of his own jobs and managing the very people who taught him the trade.

After years of proving his capabilities in the field, the owner of Walker Electric, Michael Walker, invited Moneypenny to his office and offered him a position as Project Manager/Estimator for Walker Electric’s security division. This opportunity was career-changing for Moneypenny. To this day, Walker remains a mentor to Moneypenny.

In 1990, Moneypenny was hired by Wells Fargo as Project Manager to run all its top-secret work for the Federal Government. This role saw him traveling extensively, managing large-scale projects such as the DEA New York Headquarters security overhaul. “I grew up that year!” Moneypenny exclaims.

Still, Moneypenny yearned for a role that put him in front of decision-makers. In 1992, he accepted an Account Manager position with Glen Industrial Communications (GIC) in Rockville, Maryland. There, Moneypenny was able to leverage his on-ground experience and customer-oriented approach, leading to stellar sales performances. “This role brought together everything I learned as an installer, and my career took off. I was now where I truly wanted to be, in front of customers, says Moneypenny. “I was designing and selling access controls, video surveillance, and security systems. I doubled my quota every year.”

In 1996, GIC was sold to Sensormatic, a national security integrator. Moneypenny’s success continued, and he was awarded National Account Manager of the Year and later promoted to Senior Account Executive. His accounts included several Fortune 500 companies such as The World Bank, Booz Allen, Freddie Mac, Fannie Mae, Sallie Mae, and AARP. 

The Diligent Difference

Despite his success, Moneypenny felt an inner tug to create something of his own. In 2005, he accepted a sales manager position that allowed him to relocate his family back to Ohio. Still, he found himself frequently traveling back to D.C. His journey through different jobs, companies, and states led him to a vital crossroads.

At the age of 62, Moneypenny contemplated the idea of starting his own business. “The hardest part for me was to produce a name that reflected my beliefs,” he said. It was during a family gathering that the perfect name dawned on him. When his older brother called him stubborn, Moneypenny replied, “When I was 10, I was stubborn; now that I’m 62, I’m determined! I never give up!” Hence, “Diligent” was born, epitomizing Moneypenny’s relentless drive and commitment to his work.

ID badges

On His Own Path

In 2017, Moneypenny embarked on a new adventure as the founder and CEO of Diligent Electronic Security Systems. The company, an IT-based electronic security integrator, provides security solutions for a range of institutions.

Diligent has been in business for five years, but only in the past year did the company acquire office space in Copley. “I started the business out of my home. As it’s grown, I hired more people and needed more space. We’ve doubled our business every year except last year,” says Moneypenny.

With clients across the U.S., Diligent provides educational institutions, commercial industries, and assisted living facilities with multi-layered security systems. For educational institutions, this begins with perimeter and interior-integrated electronic security devices with the sole focus of deterring acts of violence and protecting students, staff, and visitors. 

Diligent further enhances its services by giving local law enforcement and fire protection agencies the native ability to actively manage and view inside the school’s security and video systems remotely and in real-time. The result is an efficient, open line of communication between first responders, decision-makers, and faculty inside the building that ensures every safety measure is taken to save lives.

For assisted living facilities, Diligent provides systems that guard against resident wandering using tags and locator badges. Intercom and access control systems monitor the reception area to isolate visitors before allowing access. Combining systems provides peace of mind to residents and employees.

Diligent also works with several automobile dealerships and installed access control at Cleveland State University. “We really don’t have a target business per se. No job is too small or too big,” says Moneypenny. “We’re here to answer any security questions and make recommendations.”

Diligent’s services also include:

  • Intrusion Detection,
  • Fire Systems,
  • Environmental Monitoring,
  • Back-up Systems, and 
  • Training.
Controlled Access. Tim Moneypenny stands next to a typical access control panel his company routinely installs for clients.

Controlled Access. Tim Moneypenny stands next to a typical access control panel his company routinely installs for clients.

From Small Change to Big Impact

Throughout his career, Moneypenny has always been customer-focused, a principle he embedded into the heart of Diligent. “Customers are not always right; they’re just never wrong,” he states, reflecting his commitment to customer satisfaction. Moneypenny’s customer-centric approach, experience, and expertise have been the cornerstone of Diligent’s success.

Even as a CEO, Moneypenny’s approach remains grounded. He sees his role as a business owner as one of responsibility and accountability, stating, “I make the decisions and determine the company focus. I have no one to blame but myself.” Moneypenny’s relentless drive to excel and the wisdom accrued from his vast experience continue to shape Diligent, propelling it towards a future of continued growth and success.

His employees are equally impressed with Moneypenny. Angelia Green, a former customer and now Diligent’s Director of Operations, has known Moneypenny for eight years. “Tim has been consistent, reliable, compassionate, and personable. He aims to ensure every customer walks away satisfied with his solution to their problem. He doesn’t enjoy his days any other way. The living he makes is an afterthought,” says Green.

Diligent Staff

Team Diligent. (left to right) Angelia Green, Director of Operations, Timothy Moneypenny, CEO, and Wendy Moneypenny, Finance Director

Green is also impressed with Moneypenny’s professionalism and drive to do more for customers. From taking over project coordination for a customer without charge to buying weekly lunches for post office employees, Moneypenny ensures his customers feel supported. “Tim is there for people—for life—as a professional and a friend. It was a no-brainer to come on board as his Director of Operations,” Green says. “Diligent is a family with a safe, nurturing vibe. I’ve never been more motivated by or proud of my career path,” Green says. Moneypenny is equally impressed with Green. “Our relationship hasn’t changed. It’s gotten better. There’s a lot of mutual respect.” “She’s tougher than she looks,” quips Moneypenny. “When she was my customer, she always held me accountable.”

Moneypenny is quick to acknowledge his wife, Wendy, who has been his partner since Diligent’s inception. She oversees all of the company’s finances. “I wouldn’t be here if it wasn’t for her. I trust her more than anybody,” says Moneypenny.

Additional staff members include Jeff Bosko, lead technician and expert in video surveillance systems, who has been with Diligent for four years. Roger Turek handles the programming for the access control systems and has been with the company for six years. 

Moneypenny’s son, Matthew, handles the company’s marketing and website. He works for Etactics in Hudson, Ohio.

Customer Support

Success in any business can be measured not only by a healthy financial statement, but also in the number of satisfied customers. Moneypenny’s success is most evidenced by the deep connections he has made with his clients. 

Steve Grace, conferencing and facilities manager for CliftonLarsonAllen, has known Moneypenny for years. He initially handled the security systems for the company’s Akron and Canton offices. Formerly different vendors were selected for each location. ”We developed a good relationship with Tim, and he has now managed the installs at 44 of our locations nationwide. Tim takes care of everything and has been a great partner for our firm.”

Moneypenny was also responsible for installing the security and access control systems at the Greater Akron Chamber. “Knowing who Tim is makes it easy to recommend him. He’s optimistic, on top of his game, and focused on you getting exactly what you need­—not too much or too little.  Tim cares, responds, and delivers,” says Steve Millard, executive director and CEO.

A Legacy of Diligence

Today, Timothy Moneypenny is a testament to the transformative power of hard work and determination. From humble beginnings to a career spanning some of the most secretive and high-stakes projects, Moneypenny’s story resonates with inspiration. 

With a business philosophy focused on customer service and a relentless work ethic, Moneypenny continues to carve a unique path in the security industry. “I never let money drive my decision-making for my customers. Money is a by-product of your hard work and success,” says Moneypenny. “Everyone has a product they provide or sell; it’s how you service the product and the customer that makes the difference!”

Green summarizes the company’s ethos, “Everything is easier with Diligent. Tim makes it easier.”

Moneypenny’s journey from a 16-year-old janitor to a successful CEO is a powerful reminder that it’s never too late to forge your path. Quoting Abraham Lincoln, Moneypenny says, “Good things come to those who wait, but only the things left by those who hustle.” For Moneypenny, the small change has indeed made a big impact, and his story continues to unfold, driven by the relentless spirit of diligence.

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1245 S. Cleveland-Massillon Rd, Suite #4
Copley, OH  44321
(330) 212-1870