The Strategist: Why Datto’s Rob Rae Is Looking Out for All of Us

There’s no talking with Rob Rae without his enthusiasm for what he does becoming evident. But the way he defines “what he does” goes way beyond his official job title as Senior Vice President of Business Development at Datto. It’s clear that he has an eye on the health of the channel as a whole, having watched it grow from his early days with Compaq and then with Level Platforms.

“What I really want is to build trust,” Rob says. “When we all trust each other, we all benefit.” It’s work that the pandemic has made difficult because, according to Rob, “Trust is built by looking someone in the eyes.” But when asked what he’s going to do to continue that work, he doesn’t hesitate.

“Online or in person, I’m going to do what I always do: Expose wounds on stage.”

It’s a dramatic image, but an accurate one. Anybody who’s seen Rob’s personal blend of honesty, vulnerability, and energy come together on stage knows he doesn’t hesitate to point out issues that affect the whole channel or to offer the passion needed to overcome those challenges. “When executive leadership puts itself out there and encourages the channel to come together and solve community problems, we all benefit.”

And that’s good because, as Rob points out, “There are a lot of eyes on the channel right now.” Some of that, he says, is due to headlines. “But it’s also the result of two decades of exponential growth.” The words “channel” and “MSP” are “close to being household words,” Rob shares. Most of all, though, attention equals vulnerability — to both bad actors and bad press.

But what channel vendors are really curious about, at the end of the day, is how things are going to change in the coming year after a highly-turbulent 2020. Rob is in a unique position here because unlike many companies, Datto didn’t slow down as much as it might have. “We looked at the landscape,” he says. “And it was grim! But the more we thought about it and leaned into the things we knew were a given, the clearer the picture got.”

The biggest “given”? “Hybrid is the name of the game from here on out, from now until eternity,” Rob laughs. “If you’re selling at a channel event, you’re going to need a strategy for virtual as well as in-person. It’s just not optional anymore.” Rob’s coming at this from the events side of the house as well as the vendor side. At the end of last year, Datto threw their massively successful MSP Technology Day event on our very own Big Red Virtual platform, while they were still coasting on the high of a very successful IPO. Or, as Rob puts it, “It was a busy few months!”

And it put into stark relief many of the lessons from 2020. Many vendors had a chance to cut their teeth on virtual events last year, which will benefit them in the year to come. But in order to really take advantage of virtual events, a vendor is going to have to be a strong strategist — something Rob already excels at.

The Trade Show Tactician

Rob will tell you that he “only got on stage when [his] boss decided he wasn’t gonna deal with one more heckler, ever,” but there is nothing accidental about the way he works an event or trade show. “I’d always watched what worked for others and what didn’t,” he says. “Why was that vendor everywhere this weekend? How did this strategy succeed or fail? Over time, I developed a trade show playbook.”

Central to that playbook is taking events seriously. The fact that he always gets Datto (and every other company he’s been with) to invest in Robin Robins’ top sponsorship spots is actually a back-end strategy: “Robin runs national events. That investment maximizes exposure and guarantees we don’t go home from any show with anything left in the bag.”

It’s an investment that pays dividends every year, Rob says, but never more than in the past 12 months. “First, TMT is the only company that managed to throw serious in-person events during the pandemic — and they did so in a safe manner. That’s huge.” But the game-changer is TMT’s Big Red Virtual Software, which allows for secure, channel-focused events of all sizes. “There hasn’t really been anything like this platform before,” Rob tells us. “It enabled us to do things with our MSP Technology Day that wouldn’t have been possible otherwise, even though it’s stuff that channel vendors expect from in-person events.”

And that’s something else he wants us all to remember: In-person is coming back, probably sooner than we think. For that, his playbook strategy is to hit it hard with a dedicated events team. “They aren’t salespeople or marketing directors who usually sit in an office behind a computer. Their job is events, and they keep what they hunt. We get rid of the chairs and tables and engage with everyone.” And the sponsorship spots and other back-end planning make sure their brand appears often and in different places. It’s been a winning formula for Rob and Datto, and others are catching on.

Rob Rae, presenting on the main stage at the 2018 IT Sales And Marketing Boot Camp in Nashville

The Keeper of the Channel (and His Chickens)

You might ask how a man with this much passion for his work (and the channel) unwinds, and there you’d be surprised. It may seem like an enigma that the guy who jumps on stage without qualms and whose adventurous career is an open book is, in fact, so private about his home life. But in this way, Rob Rae is a true introvert.

He’s also a chicken keeper — the one hobby he opens up about — and has never lost a bird to predators in five years of doing it, a feat any farmer would love to boast about.

But in many ways, Rob’s home is the channel itself. “I love what I do, and I love this industry. And I’m very optimistic about the future of our space. I feel like we’ve grown up together after experiencing growth that nobody was forecasting.” Rob wants the best for everyone, just as siblings want the best for each other even as they compete. “It really is like a family. When you see people leave, they often come back. If you ask them why, they’ll say that they missed the close ties and the family aspect of our space.”

“I’m very optimistic about the future of that space,” Rob says. “There’s still so much room for this family to grow.”

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