Lindsay Usherwood – Usherwood Office Technology

Alarms alert of a home break in, but if someone breaks into your computer, when—and if—you discover the breach, hackers may have already sold highly sensitive data. For companies, such breaches can result in millions of damages, not to mention a loss of public trust.

As a third-generation employee at her family’s office information technology hardware and software company, Usherwood Office Technology, Lindsay Usherwood understands the importance of protecting a company against cyber threats. That’s why, as general counsel, she’s helping ensure the company’s clients are protected against such electronic break-ins—and that an alarm sounds if they happen.

Lindsay Usherwood | General Counsel | Usherwood Office Technology

She also helps Usherwood Office Technology develop ways to counsel clients on how to better protect themselves, such as training their employees on cyber-attack and cyber security risks. According to her, even when a company’s digital protection is strong, its employees or executives can make the company vulnerable to external and internal attacks when they click on a non-secure website or connect to public Wi-Fi.

“Cybersecurity is now of national news and key importance,” says Lindsay. “It’s an essential part of the tech stack of services we deliver to our IT clients.”

Securing the present and future 

Usherwood Office provides preventative malware and virus protection, but what sets the company apart are its digital monitoring agents, according to Lindsay. These bots are programmed to identify threats and notify a human network security specialist of intrusions, malware or phishing e-mails.

“Tools and services are important, of course, but staying well-informed is the best preventative measure,” says Lindsay, who participates in the company’s bi-weekly cybersecurity meetings.

In addition to its for-sale products, Usherwood Office offers user training to all its clients. These trainings often include sending client employees sample malicious phishing e-mails or links. If employees unknowingly release either company or personal information, they receive further training provided by Usherwood Office Technology on how to recognize suspicious links, sites and e-mails.

According to Lindsay, the business doesn’t allow any of its 150 employees—family or not—to escape scrutiny, either. In fact, she says that every year, ethical hackers conduct penetration tests, informing her and others if there is a need to upgrade and adapt to increasingly sophisticated hacking methods.

Usherwood Office Technology uses these ethical hackers to audit clients, too. The results alert the companies to potential risks and let Usherwood Office Technology know what new solutions it needs to develop. For instance, Threat Hunting, according to Lindsay, is a new addition to the company’s tech solutions and constantly evaluates a company’s vulnerabilities.

Panels, protection and processes

While Lindsay and Usherwood Office Technology always encourage clients to get better protection, sometimes clients will delay because the process can be daunting or they are unsure of which vendors to trust. That’s when Lindsay realized that Usherwood Office Technology needed more openly address the threats it sees.

Accordingly, she then helped create a webinar, which included conferences and courses as well as the Usherwood Virtual Cybersecurity Panel consisting of experts in the field. In August 2021, and in response to COVID-19, the panel went virtual, drawing over 100 clients across six Northeastern states. With Lindsay as the moderator, the three-person panel included a law firm partner and data breach attorney, a cyber-insurance agent and an ethical hacker.

“We thought, ‘why not lead by example? Here are the people who test our networks and with whom we have cyber-insurance; have a chat with them, too,’” she says.

The interest in the panel may have run particularly high, she thinks, due to the several major ransomware attacks that had already occurred in 2021. Those included the ransomware attacks on the Buffalo, New York, Public School system—putting sensitive information of 34,000 students at risk—and on Colonial Pipeline Company, which led to a multi-day disruption in fuel supply to much of the U.S. East Coast and the company paying a $4.4 million ransom.

Cyber insurance would have helped cover some, if not all, of these damages. But, as Lindsay explains, many companies don’t have it. While the conference helps introduce companies to cyber insurance brokers, Lindsay helps clients complete the often-complicated forms.

“I’ve heard some horror stories about insurers balking or ducking out of satisfying a claim because applications were incorrectly filled out,” she says.

The familial competitive streak

Lindsay’s grandfather started the company in 1976 to sell office supplies after he and his wife had sold cash registers and calculators from their home in Oswego, New York, for over half a decade. He never envisioned the business spanning 6 states with 17 offices, with the newest location opening in Boston about three years ago.

Like their father and uncle, Lindsay and her sisters have a competitive streak that they say is part of the reason for the growth. They and their father—current CEO Lou Usherwood—have an unofficial company motto: Bold and cold. While they’re open to mergers and acquisitions, they prefer learning what clients need and making it a point to offer better services.

The three sisters also like scoring points on the tennis courts. In fact, they’re so competitive that the family lovingly jokes about their tennis rankings.

Whether she’s helping the company expand or working on her backhand, Lindsay says the best choices she’s made were rejecting her father’s offer to sell office technology at Usherwood Office Technology to instead go to law school, then join the company as a lawyer after graduating from Syracuse University College of Law instead of joining a law firm.

“Going to law school helped me think differently, which is so very beneficial because I can look at the legal and business needs not only of our company but our clients’ as well,” she says.

View this feature in the Vanguard Fall IV 2021 Edition here.