Bigger, Faster … Better? Under Magee, ConnectWise Looks to Maintain Dominance in a Channel It Helped Build

Jason Magee is lounging lazily in his chair, a vodka – neat, three olives – in hand. We’re out of the office after a full day of interviews, sitting in the back room of Del Frisco’s during happy hour, about to conduct a video interview over drinks.

It’s been a few months since Magee took over as the ConnectWise CEO after it finally accepted private equity investment — one of the last big channel lifestyle businesses to do so. Like every other company that accepts a buyout, ConnectWise’s message during the transition was business as usual. Executives insisted that nothing would change during the rounds of media interviews that surrounded the announcement.

ConnectWise’s Jason Magee

But Magee is clearly a different beast than his predecessor, the near-legendary Arnie Bellini. Where Bellini was uber-polished and exuberant when speaking with the public, Magee is quieter, steadier. Bellini built a tiny company into a lifestyle behemoth, and over the last nearly-four decades, he acquired a deep, intimate knowledge of the IT channel — or, more accurately, through ConnectWise he helped write its history and decide its future. Magee is no stranger to the C-suite, and he can rattle off his PR talking points with the best of them. But in contrast to Bellini, who, at least with this reporter, stubbornly stuck to his script no matter the questions thrown at him, Magee knows how to weave those talking points into a comprehensive narrative that’s both educational and engaging.

It’s a skill he’s learned through hundreds of conversations with partners during a long career that spans both sides of the channel. After all, the CEO of one of the IT channel’s most dominant players wasn’t always on the supply side.

In the Beginning …

In 1999, Magee was entering the VAR world in the fast-paced Manhattan market. It was a good time for tech: the quick proliferation of PCs, broadband and productivity software meant high margins and a steady stream of clients. But as history teaches us again and again, all booms lead to busts, and the dot com boom of the late 90s to early aughts was a doozy for the IT world. The company for which Magee served as the director of marketing, Interactive Futures, soldiered on until September 11, 2001 — the day everything changed.

And then it was a bad time to be in tech. Hundreds of companies across the nation issued the dreaded “we’re going in a different direction” euphemism, including Interactive Futures.

Unlike many of tech businesses at this time, ConnectWise was one of the lucky ones: right place, right time, right solution. Arnie and David Bellini were just starting to really focus on the professional services automation (PSA) solutions that would eventually make ConnectWise a chief enabler of the modern channel. The aughts saw a change in ConnectWise that mirrored the changes that were happening in the channel itself. While those changes hurt many businesses, they were a boon to the RMM/PSA industry. The channel began to see the decline of break/fix models, and vendors like ConnectWise ushered in the era of managed services.

“I remember using the early Agreement capabilities of ConnectWise PSA when there were four fields. Wow, has that come a long way,” recalls Curtis Hicks, president and CEO of MSP Center for Computer Resources. “I do remember years ago when we …