Technology has transformed from a necessary evil to a strategic business driver, and nowhere is this more evident than in the managed IT services industry. In this candid conversation with Kathleen Shoop, Chief Revenue Officer at Digital Boardwalk, we explore the dramatic evolution of IT sales over the past decade.
Remember when selling managed IT services meant convincing skeptical business owners that paying a monthly fee for technology support made sense? Kathleen takes us back to those early days when the value proposition centered primarily around help desk support and predictable billing. The contrast with today's landscape couldn't be more striking.
Cybersecurity emerges as the turning point in our discussion. Between 2017 and 2020, major incidents like WannaCry ransomware fundamentally changed how businesses approached technology protection. We debunk the dangerous myth that small businesses are "too insignificant" to be targeted, revealing how modern attackers use automation to scan for vulnerabilities indiscriminately. This new reality transformed cybersecurity from an optional add-on to a non-negotiable core service.
The most fascinating shift has been in client expectations. Today's businesses approach IT providers looking to scale through technology—seeking efficiency, automation, and strategic guidance. Through real-world examples, Kathleen illustrates how the right technology partnership can completely transform operations, turning week-long processes into same-day completions. As we look to the future, automation and zero-trust security frameworks represent the next frontier in this continuing evolution.
What technology partnerships have transformed your business? Subscribe to Nerds on Tap for more insights at the intersection of technology and business strategy, and join our community of curious, forward-thinking professionals.

Sponsor of this episode: Digital Boardwalk
Digital Boardwalk is one of the top 10 Managed IT Service Providers in the United States. If you are seeking to outsource your IT Management, or if your IT Team could use some help with projects or asset management, give Digital Boardwalk a call today! They offer a FREE IT Maturity Assessment on their website. If you want to see how your business's IT scores against industry standards, go to GoModernOffice.com now.

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