Randall Jackson serves as Chief Security Officer at Income Research and Management, a financial services firm based in Boston, MA. With a career that began in graphic design and evolved through the ranks of IT support, systems engineering, and MSP leadership, Randall brings a unique blend of creativity, problem-solving, and cybersecurity expertise. At Income Research, he leads security initiatives across a regulated environment, ensuring the safety of sensitive financial data through proactive strategies, awareness training, and scalable security processes.
Here’s a glimpse of what you’ll learn:
- How AI is reshaping phishing attacks and cybersecurity defenses
- The importance of help desk experience in IT and cybersecurity careers
- Why regulated industries approach cybersecurity differently
- The evolution from reactive IT support to proactive security operations
- How to build scalable, repeatable cybersecurity processes
- The role of leadership in creating a culture of security awareness
- Advice for IT professionals entering the field today
In this episode…
Randall Jackson shares his unconventional journey from desktop publishing in the late '80s to leading cybersecurity in a modern financial services firm. Starting out on early Macintosh systems and troubleshooting AppleTalk networks, Randall quickly became the go-to IT expert in his organization. After his role was outsourced, he transitioned into the MSP space, gaining experience in systems engineering and eventually leading entire IT operations.
Randall highlights the need for scalable and repeatable security processes within managed services, emphasizing the shift from ad-hoc solutions to industry-standard tools like ticketing systems and RMM platforms. His leadership journey includes developing custom ticketing systems, building career paths for IT staff, and transitioning from reactive support to proactive security services.
He also addresses the rise of AI-generated phishing emails and the battle of AI vs AI in email gateways. Randall shares how his team combats these threats through live and video-based security training, helping employees recognize and report suspicious activity. The episode closes with practical advice for those entering IT: start on a help desk, learn how systems work, and build strong troubleshooting skills.
Resources mentioned in this episode:
Matthew Connor on LinkedInCyberLynx
Randall Jacskon on LinkedIn
Income + Research Management Website
ConnectWise Website
Kaseya Website
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