Enterprise Sales with CloudKettle Founder, Greg Poirier

Hey, thanks for having me.

So I’m Canadian. I grew up in a very small rural community on the east coast of Canada. Basically, if you leave Maine and then drive really far north and east, you’d reach Cape Breton Island—one of the easternmost points before the ocean begins. That’s where I grew up. It’s not the most remote place in Canada, but it’s probably up there.

Yeah, I was really lucky. I grew up very close to the Cabot Trail, which is one of Canada’s top tourist destinations. People come from all over the world to see the mountains and the ocean. For me, that was just normal. We did stuff in those mountains and in that ocean every day, and you don’t realize how special it is until you move away.

Probably two or three times a year. It’s about a six-hour drive, so it’s doable. But I have two small kids, and that can turn a six-hour drive into eight. You’re definitely committing.

They are seven and nine.

Yes, we are very much in the thick of it.

My immediate family is pretty small—I have one sister. It’s a typical nuclear setup, I guess, but we have a much larger extended family. I grew up across the street from my grandparents, and if you go a bit further—within a couple of hours—there are 14 aunts and uncles, plus more cousins than I can count. So yeah, it’s a really big family.

I think you’re onto something. It’s not Canadians who have big families; it’s probably Catholics. My non-Catholic side of the family has one aunt and one uncle. But on my Catholic side, there are 14 aunts and uncles, and I have no idea how many cousins.

What’s changed is really interesting. I grew up in a very small, rural fishing community. My parents were teachers, so we were one of the only families that didn’t either fish or work at the fish plant or something related to fishing. We grew up on a big plot of land that was probably close to free when my parents bought it. But now it’s really changed—now it’s a tourism hotspot. There’s a mountain that overlooks our house, and as a kid, we’d hike it maybe once a month. If you met anyone on that trail, it was a surprise. But when I took my own kids up there last summer, we must have passed 20 people going up and down—it’s become super popular on Instagram, so there’s a steady stream of people now. Also, when I was a kid, there was this really old, like hundred-year-old fancy golf course none of us ever played. Now they’ve built a bunch of very high-end golf courses. So you see people flying in on private jets, parking huge yachts, and going to play golf—definitely not what was happening back when I was growing up.

Yeah. Our land runs from the water all the way up to the back of the mountain, which is pretty incredible. I know my dad bought it in 1976 for maybe a couple thousand dollars—maybe a thousand. He agreed to build the woman he bought it from some cupboards for her kitchen because he was a shop teacher. I’d guess the return on investment has been pretty high.

I’m in Halifax, Nova Scotia now—the capital city of Halifax and the largest city in Canada east of Montreal. It’s not New York by any means, but it’s big by Canadian standards. I’ve spent most of my career in Seattle and San Francisco. I live on the east coast of Canada, and I love it, but I do travel a lot. Before COVID, I’d spend maybe one week a month in Seattle or San Francisco. I was really lucky: around a decade ago, when I started this SaaS career, I was going to New York and San Francisco quite often, especially after Salesforce acquired Radian6. At that point I was dating my wife (we weren’t married yet), and since we could have moved anywhere, I started thinking, “I can own a house, a yard, and walk to work here, or live in San Francisco and not have any of that.” So I decided I’d rather just fly once a week, drive 45 minutes to work, and come back 45 minutes. That’s the routine every day.

I went to Dalhousie in Halifax. Canada doesn’t really have an Ivy League system like the U.S., but Dalhousie is almost 200 years old and sits in that tier of what would be the Canadian “Ivy Leagues,” if we had such a thing. I did my undergrad there. I had five majors over a couple of years, but eventually graduated with a degree in psychology and political science—which, at that time, wasn’t super employable. So after a while, I went back and did my MBA at St. Mary’s, which is one of the top business schools in Canada.

Well, certainly. My first year was a combination of, I’d say, a really poor high school program that didn’t prepare me for all the options out there, plus way too much partying. In high school, because I was doing well academically, I was pushed in a very specific direction. It was assumed I’d go do that certain thing. When you’re in high school, you don’t know any better. I think kids today are more worldly, but in ’92 or ’93, you just went along with what teachers said you were good at. Then I got to university and realized, “This sucks. I don’t like science labs, biology labs, physics labs…any of it.” And then I’d meet the grad students who were teaching us, and they’d tell me about their jobs, and I’d think, “I don’t want to graduate and do that,” so I didn’t even like the thing I was working toward. That was part of it. The other part was probably partying—coming from a small town to a big city, having too much fun that first year. After that, it was just about figuring out what I wanted to do. It took a couple of years, but I got there.

Yeah, I might have seen my counselor more often than that, because my entire graduating class was about 52 people. It was a big deal, since it was the largest grad class that school had ever had. There’s a group of those 52—if you grew up in a small rural town—who are automatically expected to go to university. Some probably shouldn’t have; they would’ve been happier or better suited to a trade or something else. But if you did well academically, teachers would say, “We don’t get many high achievers, so we’ve got to push them toward university.” And I think the big failing at my school was that the business track was a “non-academic prep” line. So you could do the university-prep “A” stream, or the trade school/other path, and business was lumped into that second category. If I’d taken any of those business classes, I might have realized how much I loved that stuff. But that wasn’t an option with how our high school was set up.

Well, I started working in restaurants and on resorts when I was 14 or 15. I wasn’t even old enough to drive, so I’d get dropped off at work. I kept doing that through high school and university. Then, partway through my MBA, I landed a contract with our big telecom incumbent—kind of like AT&T in the U.S. Doing my MBA, that was the “gold standard” job, the reliable path: “If you’re going into business, this is where it happens,” right? That was the blue-chip route. After that, I did a short stint in nonprofit marketing and realized I really liked marketing. Then I spent seven years doing marketing at a national cinema chain, and that’s when I realized, “Okay, this is what I enjoy. It’s more of a non-branded type of marketing, and I really like that whole marketing and sales aspect.”

I was working at a small, regional, second-tier cinema chain. None of my colleagues would argue with me on that description—it was funded well enough, but still smaller than the big players. I happened to arrive right when the industry started consolidating. Mom-and-pop theaters were getting absorbed by national chains, and we went from being a tri-state operation to the second-largest cinema chain in the country—one of the biggest in North America.

My initial job was about 50% marketing and 50% sales, and I had this gut feeling there was a better way to do both. At that time, I sold the ads that run before the movie—probably not the most popular guy because nobody really likes those ads—but for someone who’d never done sales, these were big deals. We also relied heavily on analog marketing, and I’d finished my MBA with a focus on what we’d now call SaaS companies (although that term didn’t exist back then). I remember discovering this business called Salesforce and thinking we should replace our current systems with their cloud-based solution. But then I had to explain “the cloud” to everyone, because this was over a decade ago and it was still pretty new.

From there, I was fortunate to get recruited by a company called Radian6 to build out what we’d call marketing operations today, though it didn’t have a fancy name at the time. I joined about a year and a half or two years before Radian6 was acquired by Salesforce. That gave me a front-row seat for the lead-up to a high-growth SaaS acquisition by a giant like Salesforce—and after we were acquired, I got to work within the Salesforce machine, which is probably the best education on how to do sales and marketing operations.

I got recruited away to build out what would be called sales ops and marketing ops at two different startups. At the second one, I eventually became COO. Through all that, I realized I thought I wanted to run a B2B SaaS company as part of the C-suite, but I wasn’t keen on reporting to a board, doing constant fundraising, and handling tasks that just weren’t appealing to me. That was when I decided to start CloudKettle, so I could focus on the marketing and sales ops work I really love, without the parts of the job I wasn’t as interested in—like fundraising or running dev teams.