Parenting is one of the most crucial verbs in the English language. There’s a line of thinking that suggests the window for effectively raising a child closes sometime around the age of eight. By that point, they should know right from wrong, be respectful and disciplined, have a curiosity to learn, and be capable of showing empathy. It is the early years when children are most impressionable and can best absorb parental guidance.
Don’t underestimate the value of repetition. In the Stramaglio household, the word of the day was always “initiative.” Patriarch Mike Stramaglio would greet his children at the breakfast table and ask them, “What’s the word of the day?” Despite the frequency, his children would always respond with “initiative.” With just one word, their father had supplied a key that would unlock countless doors in the future.
Jenna Stramaglio admits her younger self regarded it as a routine. The channel development manager for ConnectWise and the daughter of one of the office tech industry’s most influential personalities, Stramaglio’s appreciation for the paternal patter grew over time. There was method to her father’s word-of-the-day madness.
“Over the years, I’ve realized how deeply that word shaped me,” said Stramaglio, a 2025 ENX Magazine Difference Maker. “When life feels hard or work becomes overwhelming, I can always go back to that lesson: sometimes all it takes is a little initiative to get things moving again. It really comes down to one question: If not me, then who?”
It’s the initiative that she uses to create opportunities and foster relationships with clients and partners, with an eye toward constructing a channel community that can span generations. Genuine relationships, she adds, are fundamental.
“I’ve always believed that business comes and goes, but relationships last,” Stramaglio noted. “Like many of my peers here, I focus on earning trust and building genuine connections which I believe is the true foundation of this industry.
“I want to help the office technology channel find new ways to grow and generate revenue so we can keep this industry thriving for another 100 years.”
Lighting a Spark
The assumption has long been that her father ushered her into the office technology universe. Although he has been an undeniable influence in her professional progression, it was actually her older brother who set an example she found compelling. A newly-minted college graduate, her brother was “crushing it in sales at Ricoh in L.A.” Not wanting him to enjoy all of the fun, she jumped in feet first by selling copiers in Chicago for COTG, a Xerox Business Solutions direct branch. The sibling rivalry was on, and her career was off and flying.
Carving out a name for one’s self can be a daunting task, regardless of your lineage. Stramaglio remembers how longtime Sharp executive Mike Marusic asked her to make presentations at several road show events. This was circa 2010, when she was perhaps not as polished as today, and was frustrated by her nerves and uncertainty as she stumbled through the talks. Marusic, one of the industry’s most easy-going and genuine presenters in his own right, saw her potential.
“Mike offered a piece of advice that has stayed with me ever since: ‘Think less about the titles in the room and more about who these people really are: business owners, parents, friends, humans. Talk to them, not at them,’” Stramaglio related. “That moment transformed how I approach every interaction. I learned to always respect the title but never lose sight of the person behind it.”
Stramaglio is coming off a year in which ConnectWise broadened its office technology partnerships, thanks in part to the unifying qualities offered by IT Nation Secure and Connect. She loves the possibilities offered by ConnectWise’s ASIO platform, AI and hyperautomation, helping partners transform how they work, automating what slows them down, and positions their businesses for the future.
Human Touch
But even in a world increasingly driven by technology, Stramaglio clings to the power of human connection. Automation may augment how we work, she noted, “it can never replace the value of cross-generational conversation, mentorship, and shared experience. Those interactions preserve the inherent knowledge of our channel, our clients, and what truly drives this business forward.”
Away from the office, she has embraced a servant mindset, so to speak. Stramaglio and her husband have three boys, which has solidified several roles for her: chef, chauffer, maid service and “professional target for my oldest’s jokes.” The fulfillment her brood supplies is entirely gratifying, so scrapbooking, photography, skydiving and other pastimes can wait their turn as she absorbs this all-too-brief juncture in life.
“Right now, we’re in that season of life where our kids are our hobbies,” Stramaglio added. “And we wouldn’t change a thing.”
