Jason Marsdale returned to Monroe Systems for Business as Director of Strategy after building additional experience in software sales, operations, technology implementation, and organizational leadership. In this edited interview, he explains why he came back, what he learned away from Monroe, and why customer feedback is central to his plans.
A return built on relationships
What inspired you to return to Monroe?
“Our people were a big driver. I feel like we all respect each other, know how to work hard, and know how to have fun. Even when I wasn't working at Monroe, I stayed in touch with many on the team and coordinated a few meetups.”
Jason said the small gestures also mattered. A conversation with Monroe's owner reopened the door, and the company's personal culture stood out after time elsewhere.
“I hadn't felt the same connection elsewhere. Ultimately, I felt like there was unfinished business here, and now I know I'm right where I belong.”
How did the first day back feel?
“It felt like I was right where I was supposed to be. It was great seeing the smiling faces I'd grown to miss, as well as meeting newer members of the team. In some ways, it felt like I hadn't missed a beat.”
His first priority was observation: listening to what teams had built, understanding current challenges, and identifying where strategy could support their work.
What strategy means at Monroe
What are you most excited to work on?
“I'm most excited to create growth strategies for Monroe—doubling down on our strengths while finding new and exciting opportunities to expand what we offer.”
That work includes connecting customer needs, product opportunities, internal processes, and digital tools. Growth is not simply adding more activity; it is choosing priorities that improve the customer experience and help the team execute consistently.
Lessons from roles outside Monroe
What experiences are you bringing back?
Jason described experience across enterprise software sales, property operations, CRM implementation, analytics, e-commerce, and organizational leadership. He said selling ServiceNow software and implementation services strengthened his approach to complex sales and client relationships. He also completed partner sales certifications and training.
In later roles, Jason said he worked on initiatives involving retail integration, digital transformation, operational improvement, e-commerce expansion, and technology implementations such as Entrata CRM and AI-enabled leasing tools. Those experiences reinforced several principles he plans to use at Monroe:
Build repeatable processes
Clear ownership and repeatable workflows help teams scale without losing accountability.
Use data in context
Dashboards are useful when they lead to better questions, decisions, and follow-through.
Connect departments
Strategy improves when sales, operations, marketing, and service share feedback.
Keep people involved
Technology should support employees and customers, not make their experience harder.
“Combined with my original seven and a half years at Monroe, these experiences give me fresh perspectives and proven tools to help take us to new heights.”
What he missed most
For Jason, the answer returns to people. Staying in touch with former colleagues, including officiating a former coworker's wedding, preserved the sense of connection he associated with Monroe.
“What I missed most was our incredible people—the mutual respect, hard work, and fun we share. That sense of belonging and unfinished business is what drew me back.”
A message for Monroe customers
Jason wants the company's next steps to be informed by the people who use Monroe products.
“If there are products you'd like to see Monroe make or sell, please let me know. Your input is invaluable. I look forward to connecting with customers personally to learn what we're doing well and what they need next.”
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Tell the team what products, resources, or improvements would make your work easier.
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