Photo: Len DiCostanzo (third from right) displays his MSP 501 Honorary Lifetime Achievement Award.

One of the managed services industry's most enduring contributors — someone who has shaped the careers of thousands — just received an honor that didn't exist until he helped create the need for it.

Len DiCostanzo received the first-ever MSP 501 Honorary Lifetime Achievement Award at the MSP Summit's MSP 501 Gala. What makes this especially meaningful is that he ushered in an entirely new category for the recognition. This award is one built for individuals who have shaped the channel not as MSP operators, but from the vendor, analyst, supplier, distributor, consultant or marketplace side. That matters, because so much of what MSPs are able to build rests on people like DiCostanzo, working tirelessly just outside the spotlight. In keeping with the body of work he has built over decades, this new category will open the door for many deserving honorees to come — with DiCostanzo aptly leading the way as the first.

DiCostanzo has spent decades in senior leadership roles across sales, business development, product management, and channel development at Accordo, Datto (via Autotask), and Kaseya, as well as founding his own MSP and a technology consulting firm. He is currently CEO of MSP Toolkit. But ask anyone who's worked with him, and the titles are almost beside the point. What he's really done is help thousands of partners build real managed services practices.

DiCostanzo was inducted by Jason Rincker of New Charter Technologies and Sam J. Ruggeri, the legendary MSP who is himself an MSP 501 Lifetime Achievement winner. Introducing him, they said it plainly: "He has been a leader, a mentor, an advisor, a connector, and someone who has consistently given his time and experience back to this community. And for many of us, he's a great friend."

Len DiCostanzo

They also gave the room a window into who DiCostanzo is beyond the résumé because he is one colorful character whose idiosyncrasies are legendary. He came from humble beginnings on Staten Island, the son of a longshoreman. His father instilled the work ethic and character that DiCostanzo credits for much of his success. Through life's ups and downs, Len has stayed upbeat and devoted to family — especially his son Brandon, of whom he is immensely proud, and his mother on Staten Island, whom he still rushes home to support whenever she needs him.

There was even a note on the evolution of his name: to old friends, he was always "Lenny." Somewhere along the way, as he climbed the ranks, Lenny became "Len" — and, in more formal settings, "Mr. DiCostanzo." The room agreed: no matter what name he answers to, they hope he never stops, if only because he keeps providing such good material.

Congratulations, Len. This channel is better, sharper, and a whole lot more fun because you've spent your career building it up, one partner at a time.