Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960

Maggie, I am so excited for this. Uh, this will be an incredibly fun show. But thank you so much for joining me first.

Likewise. It is great to be here, Harry.

Now, I wanna start with a little bit of story time. So you've worked at the incredible institution that is Slack before. Now you're head of sales at Webflow, or director of sales, sorry, at Webflow. Talk to me, how did you make your way into the world of sales? And how did you come to be director of sales at Webflow today?

Yeah, absolutely. So very similar to most of your guests, I've had a very non-traditional path into sales. I don't think anyone really ever wakes up, you know, when they're 8 or 10 or 15 and says, "I'm gonna go be in sales." I hope that changes later on down the road, but that's not quite the reality for right now. So growing up actually, both my parents were very heavily involved in nonprofits and the Peace Corps. So I spent a lot of time traveling and living in different places all over the world, from Africa, Scotland, Spain, um, all over the place. So with this, I, I really had to learn how to make new friends and put myself out there and get to know people. So fast-forward, you know, following my parents' journey, I think I'm gonna go in the nonprofit world. Don't know quite what, but that's really my goal. I study global studies and Spanish, uh, in university, and it's not until my very last quarter when I'm in university that I'm taking some business classes. And this CEO comes down, his name is Kevin Hartz, and he gives this whole talk about entrepreneurship and building this great company called Eventbrite, and they sell events, and my mind was just blown and I was just like, "Wait a second, I can get paid to talk to people and to sell people on going to events? I love going to events." So fun. So I send him an email the next day and I say essentially like, "Hey Kevin, I wanna come work for you." You know, clearly you're 21, you have no idea what's appropriate or not, but here we are. So he actually invites me to come in to interview. I fly up to San Francisco the next week, I meet the team, and fast-forward, I get a job at Eventbrite. I spend the next five years going from the second SDR all the way up until the top-performing AE globally. And about four and a half years in, I start to hear about this new company called Slack. They're starting to get some investment, they're starting to get some buzz. We start to use 'em at Eventbrite and I'm kind of like, "Huh, what is this interesting company?" I'm looking at them, they have no sales, they have no account management. And then all of a sudden one day, I'll never forget, October 2014, a head of account management pops up on LinkedIn and I was like, "I'm gonna figure out how to talk to this person." I saw that we had a mutual friend in common so I ghost-wrote a note for that friend, Kyle, to send to this gentleman, A.J. Tennant, the then head of account management, and essentially said, "Hey, I wanna learn about Slack. Let's chat." Next week, g- very similar story here at Eventbrite, I go in and A.J.'s like, "Uh, I don't have a spot for you, but you seem great." I spend the next five months religiously just prospecting into him, sending him news articles, sending him tidbits, sending him, you know, advice about just random stuff, and I get a call from him in March, March 2015 that is essentially like, "Hey Maggie, we wanna offer you the job here at Slack." I didn't know what the job was, no idea of the title, no idea of the comp because I didn't interview for this, but I was like, "You know what?" I, at this point in time, I was dating my now husband, no kids, didn't have a mortgage, and it was like, "YOLO. This seems great. Let's go for it." So pure luck there. I start at Slack as the first sales rep out of Slack headquarters. I spend the next six years there helping to take Slack from 12 million in ARR to over a billion, and then it is in March 2021 when, for the first time ever, Webflow prospected me versus me prospecting the company. Um, so went over to Webflow to help build out their entire sales team, which I'm sure we'll talk about a ton today. On the side, uh, I'm actually a pretty, uh, active angel investor and advisor to a handful of different CEOs, and then I'm also a mom to two little girls. This is probably the most chaotic part of my life, is trying to get my two-and-a-half-year-old daughter to wear clothes to preschool 'cause it is not appropriate in this day and age to go to preschool without clothes on. But hey, here we are.