The Twenty Minute VCMaggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960
EVERY SPOKEN WORD
140 min read · 28,285 words- 0:00 – 4:50
How did Maggie get into Sales?
- HSHarry Stebbings
Maggie, I am so excited for this. Uh, this will be an incredibly fun show. But thank you so much for joining me first.
- MHMaggie Hott
Likewise. It is great to be here, Harry.
- HSHarry Stebbings
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?
- MHMaggie Hott
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.
- HSHarry Stebbings
It's amazing how many venture capitalists do it. Um, but anyway, uh... (laughs)
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
I'm kidding. I'm kidding, obviously.
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
Uh, no, I, I think, you know, a wonderful thing with your career is, uh, you know, you did what so few do, which is the importance of the follow-up actually.
- MHMaggie Hott
Yes.
- HSHarry Stebbings
And, you know, I always say to people, um, you know, "You should share your secrets because it's amazing how few people will actually take you up on them." And I think the great follow-up, the art of the follow-up is one that not many people do, and you clearly...
- 4:50 – 5:47
Biggest Lessons from Slack
- HSHarry Stebbings
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
... have done. I do, uh, have to ask, you mentioned six incredible years at Slack there.
- MHMaggie Hott
(laughs) Yeah.
- HSHarry Stebbings
It was such a period of hypergrowth. What was a big lesson or takeaway for you from that experience that really shaped how you think, Maggie?
- MHMaggie Hott
So first one that is probably the most important and something that I carry n- very near and dear is cross-functional relationships and showing appreciation. And I'll break down what I mean by this, Harry, is essentially sales is very often, you know, on an island, on their own, but the reality is no sales team will ever be successful without the support of their cross-functional partners. So finance, marketing, ops, tooling, executives, product, engineering. I mean, there is, the entire company has to swarm around sales in order to make sales to be really successful. So it is so important to nurture and foster these relationships and really show deep appreciation to them. I think that's something that I learned to do v- qui- uh, yep, sorry. You were
- 5:47 – 10:52
Cross-Functional Relationships
- MHMaggie Hott
going to say something?
- HSHarry Stebbings
I'm, I'm sorry. I'm, I'm l- so I, I love like granular, so nurture and foster these relationships...
- MHMaggie Hott
Yep.
- HSHarry Stebbings
... cross-functionally.
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
If we break that down to sales leader and sales rep, what can one do in each position to nurture and foster relationships cross-functionally from your experience?
- MHMaggie Hott
Yes. Great question. So let's break it down to sales leader. Sales leader, it's important just to spend time with these cross-functional partners and this is actually something that Dani talked about when you interviewed her, I believe it was...
- HSHarry Stebbings
Mm-hmm.
- MHMaggie Hott
... over a year ago is the importance of just being there and being on the floor with these different cross-functional partners and really educating them, you know, what is it that sales does? I think it's so common, sadly, that in PLG companies, sales is typically either an afterthought, again, something we'll talk about later, but it's also not necessarily something that gets a ton of investment and people really realize what, you know, what it is this salesperson can do. Very often, we think about sales, we kind of think about, you know, eh, I don't wanna call it a used car salesman, but sales...
- HSHarry Stebbings
No.
- MHMaggie Hott
... can tend to have a really bad rap and it is so important to be those brand holders of our business, to be able to show the company sales is not something that we need to always be struggling or combative with, but really, we should be working in lockstep because when you have a great sales organization, that is going to fuel the revenue and the product development and the roadmap for a company. There is actually...... there's very few world-class companies that I can think of that are out there that don't have world-class sales teams.
- HSHarry Stebbings
I, I'm totally with you. I'm trying to think now. I don't know if Calendly does, but they would probably be the first that comes to mind. But I, I, I'm totally with you. Okay, so that's for the leader. For the sales rep, say I'm coming in fresh, um, bushy-eyed and ready to go, is there anything that I can do to make new relationships cross-functionally?
- MHMaggie Hott
Yep. And it's actually starting from the very beginning. When you start, you know, a lot of times, companies will have these random... We actually do and so does Slack, these random donut meetups where essentially kind of like virtual coffee chats. And you just need to put yourself out there. You need to be in different Slack channels and if somebody posts a question that maybe you wanna know something more about, message them, introduce yourself to them. Also, really think about, you know, as a sales rep, how you're showing up. You know, your b- like essentially your business is your brand. Are you coming at legal saying, "Hey, legal, I need this right now, right away. Get this over the line." Or are you approaching it in a way saying, "Hey, legal, you know, I know you're so slammed. I know things are busy. We're really hoping to close this customer by X date. I was wondering if you would be able to spend some time and potentially prioritize this this week. Let me know if you have questions. Thanks so much. I really appreciate you." And if you look at those kind of two different ways of how I approached it, one makes you feel like a partnership, the other makes you sound like a total jerk.
- HSHarry Stebbings
I totally agree with you. I always like to be presumptive and say, "I really appreciate your, you know, coordination with this ahead of time. Thank you." (laughs)
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
And it's just like, yeah, there's no, there's no choice for you, but thank you for coordinating with me on this. (laughs) Um-
- MHMaggie Hott
100%. Another learning too, let's chat about, and, and I know we'll chat at depth in outbound, I actually helped to build out our very first ever outbound motion at Slack, was the very first person to ever do it and ever do our first, which we called proactive outreach, um, 'cause outbound was, you know, of course a dirty word back then.
- HSHarry Stebbings
Obviously.
- MHMaggie Hott
But it is so important to build outbound early and build sales early. Again, we'll talk about this later, but that's another key takeaway and key lesson of something that candidly we did pretty wrong at Slack, is we didn't double and triple down on going after the outbound and PLG motion. We were very heavily inbound for the last two years, and it takes a long time to build outbound. And then my kind of third point on things that really stood out to me from my time there is build things for scale. And what I mean by this is, don't buy the cheapest tool now because it's meant for an SMB. If you know you're scaling and if you know you're hyper growth, build something for, you know... Or buy and build for next year, for the year after, for when you are a sales org of 100 people. Because it is so much easier to get it right in the beginning than to try to buy and build for now and then have to rip and replace down the road. So, coming into Webflow, one of the very first things that I did was sit down and take a look at our tool stack and really try to understand what do we have now and where do we need to be, you know, not necessarily for next year, but for the next five years. These are gonna be things like, you know, a couple little bit of our tech stack is DocuSign CLM, is Salesforce, is, you know, world-class forecasting tools like Clari. And most companies of our size, at that point in time when I came in, wouldn't need these things, but now we need them and we're at the stage and we've already got them and they're working really freaking well.
- HSHarry Stebbings
I, I, I love that in terms of buy for scale, not necessarily for today. There, there's so many things that I wanna unpack there. You mentioned kind of, you know, the PLG element and kind of introducing sales into PLG. You mentioned outbound, which I wanna touch on as well.
- 10:52 – 20:31
Product-Led Growth
- HSHarry Stebbings
If we start on the PLG side, can you do PLG and traditional hands-on sales at the same time? Often it's this binary, you do one or the other. Can you do them both at the same time?
- MHMaggie Hott
You can, but I wouldn't fully recommend it. So, what I would actually, a- and this isn't gonna quite be as blanket as a yes or no, but what you need to do is you need to be able to understand, you know, who are you selling to? What is your market? What is your ICP? What is your persona? And that's gonna help dictate what it is that you are doing. So, what I really think a company should do is take their PLG and amplify it to go through and build up their outbound sales motion. And I'll break down a little bit of what this looked like at Slack, as well as what we're doing at Webflow. And then actually, it's okay, if it's okay, let's kind of talk about pure, true to form cold outbound.
- HSHarry Stebbings
Yeah.
- MHMaggie Hott
Because I think the word outbound, it's really big. It's really broad. You know, what is outbound? The hallmark of PLG is really reaching out to self-serve signups or small credit card teams with the goal to either upsell, expand, you know, go wall to wall within a company. But then pure cold outbound, which is kind of that, you know, traditional sense in non-PLG companies, is a completely different animal with very little similarities. So first let's start with PLG and let's start with kind of this self-serve notion. As I mentioned, when I came into Slack, there had been absolutely no reach outs ever to anything proactive. Everything that we were doing, our single biggest goal, our single biggest charter was talk to the customers, was understand what is it that the customer needs, is to be as helpful as humanly possible. We weren't even on commission early days at Slack. Like we were just straight up salaried. We had no other measurements and no other goals. Stewart's charter for the sales team was to help our customers, which I absolutely loved. But over time, of course, you know, we found that this wasn't the most scalable way to approach it because one minute I would be talking to a 10-person company. Half hour later, I'm talking to the single biggest retailer in the entire world. And it just doesn't make sense to do that because you're context switching so much and these different companies are gonna need such different things. And that's really where it becomes important to build out your motion and build out your sales team and scale. But so within-
- HSHarry Stebbings
You also can't get that domain specificity. Do you know what I mean? You don't get the path matching on like messaging as well, like you don't see what hits 'cause you're constantly context switching-
- MHMaggie Hott
Totally.
- HSHarry Stebbings
... so much.
- MHMaggie Hott
Well, and also entire-
- HSHarry Stebbings
And that's a real loss of...Yeah.
- MHMaggie Hott
Yeah. Like, you can't hire someone that is great with SMBs and is the, talking to the single biggest company in the entire world. It just, it doesn't make sense.
- HSHarry Stebbings
You know what I worry about today though, honestly, is we see a lot of companies who do the PLG model with kind of PLG SMB pricing, but then they layer on traditional sales, and that business model does not work. I hate to say it, you know, Harvard grads, um, but clearly you missed HBS 'cause you would have studied the business study there.
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
Um, but like it doesn't work to have the f- $100 a month product with the CS team, with the sales team. Do you see this too and does that worry you?
- MHMaggie Hott
Yes. And I would actually say, um, it's, it's something that I advise all founders, d- and I realize we're kinda getting off track here a bit, but it's something that we, that I advise all founders to really think about that product differentiation early days, because it's really hard to get that right as the company gets bigger over time. So, what I mean by that is, if you are building a PLG or a self-serv model, think really hard about what you can do to make that model scale over time. So if I, you know, someday want to be selling into the Fortune 500, Fortune 1,000, what is a different product that my sales team will be able to sell them? Because the single biggest thing that I see PLG companies do wrong is they have their, essentially their self-serve or their lower end product cannibalize what could be their future enterprise product. We ran into that at Slack, we run into it at Webflow all the time, where there has to be a huge product differentiation outside of just security. And actually something that Zenya talked about whenever you interviewed him, I think earlier on this year, is, was, was this idea of SSO and security at Dropbox where they weren't selling a ton of differentiation. And that's very, very common for early stage PLG companies, but that's really where it's so important for the founder to get this right early on, because otherwise if you make your self-serve product too good, then it cannibalizes your sales team's revenue, and it's really hard to go reverse.
- HSHarry Stebbings
Yes.
- MHMaggie Hott
It's really hard to take a product and then take away features and functions, 'cause that's gonna piss off your earliest users.
- HSHarry Stebbings
I'm a, I'm a bit naive here, 'cause I always just use the security and access, so it was like the product differentiation needed scale.
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
What, what else do they need? Like when you sell to CIOs of large, large companies, Fortune 500s, like how does the product differentiation change beyond just security from the more PLG motion?
- MHMaggie Hott
Yeah. Oh my, in so many different ways. So, uh, a l- a big way ... Well first off, have you ever heard of sso.tax? It's a website.
- HSHarry Stebbings
N- no.
- MHMaggie Hott
Oh, e- so it's essentially (laughs) , sorry, can't believe I'm saying this, it's essentially the naughty list of, I'll call it offenders, of people that upsell with SSO to say it's their enterprise product. Take a look at it later on. It's, it's pretty funny, a bit cringe-worthy, but it's so often that companies, the first thing they do is slap on SSO because that truly is an enterprise feature. But some other things. Obviously legal, so the ability to negotiate your legal, your MSA, your DPA. Something else that's very common for kind of those enterprisy features is customer success, customer support. You know, 24/7 phone support. For example, at Webflow we have 250,000 customers every single day hosting their websites on us. It's absolutely massive. Obviously with all of those customers we cannot be giving them 24/7 dedicated phone support. It, it's just not gonna work out. So for our specific enterprise customers, they've got the chat, they've got the 24/7 phone support, they've got the dedicated customer success manager. They've got really that true human partner that's advising them on best practices. Uh, we've also got, you know, and this is actually very common with Slack as well as with Webflow, different roles and permissions. So, as you scale within a company, you want to make sure that not everybody has the same roles and permissions as ... You know, maybe CIO, you want them to have the ability to go and terminate a user really quickly, but you probably don't want, you know, your IT intern to be able to do that.
- HSHarry Stebbings
(laughs)
- MHMaggie Hott
So really differentiating with roles and permissions. You also start to get into a lot of kind of like, you know, enterprise security-ish legal features, DLP, e-discovery, MDM, all kinds of different things that typically go on enterprise packages.
- HSHarry Stebbings
It s- sounds like you're going to a music festival in the UK with all this.
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
MDMs, you know, just missing a couple of letters here, Maggie. Um (laughs) -
- MHMaggie Hott
mobile device management, a lot less fun.
- HSHarry Stebbings
Uh, oh, oh right. Mo- m- ma-, that's what I was thinking.
- MHMaggie Hott
Yes, yes. Mobile device management (laughs) .
- 20:31 – 33:50
Outbound Sales
- HSHarry Stebbings
- MHMaggie Hott
Mm-hmm.
- HSHarry Stebbings
Can I ask, when you think about building an outbound stay, you know, when's the right time and how does one do it properly first?
- MHMaggie Hott
So, again, kind of going back to our original question of self-serve versus outbound, the right time is now. Never, ever wait on outbound and I think that was a big learning that we had. Again, at Slack is we didn't even start building an SDR team until 2017, so we had been around for almost three years at that point before we really ever started dialing up this outbound motion. At Webflow, we've done it completely different. It has been, outbound has been in the forefront of our minds from within the first few months of the sales team. It was actually my single biggest charter to come in, very first day on the job, my boss said, "Go launch outbound in three weeks. Go." And like, you know, just so important to start, there, there's no reason to wait on outbound. So there's the, y-
- HSHarry Stebbings
Can I ask?
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
What is good, what (laughs) I'm like an eight-year-old here, like in class.
- MHMaggie Hott
Yeah, I know. (laughs)
- HSHarry Stebbings
This...
- MHMaggie Hott
For everyone listening, Harry's like raised his hand and I'm like-
- HSHarry Stebbings
(laughs) .
- MHMaggie Hott
... "Oh, yes, Harry?"
- HSHarry Stebbings
How, what, wh-
- MHMaggie Hott
"I will call on you." (laughs)
- HSHarry Stebbings
What does good outbound mean? Is it like dialing for dollars? Is it like sending great email? Just so I actually kn-know what good outbound is today.
- MHMaggie Hott
Yeah, absolutely. Oh, man, I could talk to you about outbound (laughs) for hours and hours. So, (clears throat) good outbound, let's talk about actually cold outbound, because cold outbound is kind of the thing that people, you know, are scared of, say it doesn't work, does it work? For me, cold outbound, your single biggest objective there is to build a marketing machine and build your brand awareness with cold outbound. The main reason that you are doing cold outbound is to educate your prospective buyer about what your product does, what your solution is, what pain it solves. So often people think just because I'm doing outbound to you now, Harry, you're gonna be ready to buy my product. No, that is very, very unlikely the case that I'm gonna get you at the right moment, right when you're thinking about it. The single biggest goal there, though, Harry, is to educate you of, "Hey, this is my product, this is what we do, this is the pain it can solve." So maybe some day when you are six months or you're a year down the road and you're thinking, "Hey, my website is a, you know, total piece of crap, I need a new website. Huh, I remember that sales rep from Webflow reached out to me six months ago, I'm gonna go take a look at this." And I'll tell you actually a really funny story that happened pretty recently. Uh, we recently bought a PLG tool, you know, to sit on top of our database and surface up insights, and there's a ton of these different PLG tools there coming up, you know, these world-class companies, Endgame, Pocus, Kalixa. There's so many of them that are out there. But one of these PLG tools reached out to me and said, "Hey, do you want to evaluate our product? I see you're a PLG company." And I said, "You know, I'm really sorry, we actually just purchased one, signed the contract, we're all set here." And this founder said to me, "Well, can I ask why you didn't evaluate us?" And my response was, "I didn't know you even existed." Because I can near guarantee if I would've known this company existed, they would've absolutely been in our evaluation stack, but we didn't even know they existed, and if that company would've done outbound email to me probably four months ago, maybe they would've won our business. And that's why it's so important to do outbound early and often for that brand and market awareness.
- HSHarry Stebbings
Can I ask, and a- again, this is where you learn with me that there's no point in th- reading the schedule. Um...
- MHMaggie Hott
(laughs) I'm learning that pretty quickly.
- HSHarry Stebbings
Yeah. Ah. (laughs)
- MHMaggie Hott
(laughs) .
- HSHarry Stebbings
Uh, the question that I have is, like, is this not the complete blurring of sales and marketing? And what I mean by that is in this new world of customer education, I fundamentally think TikTok is the biggest opportunity in B2B marketing, but there's many different ways, whether it's, you know, Instagram videos, uh, Facebook videos, short form, you name it.
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
Like, is this not the blurring of marketing and sales, and how do you think about that?
- MHMaggie Hott
They need each other. I mean, marketing and sales should be working hand-in-hand and that's y- so often you see them rolling up to a chief customer officer or wherever. So marketing, think about that as, you know, the bigger, broader awareness, the... I don't wanna call it billboards or articles or whatnot, but marketing is really out there just trying to get the name recognition. And then you think about sales outbound. That needs to be personalized, targeted, directly tied with the hypothesis to you- to what I think you, your pain is gonna be and what you're going to care about. There is no way that a marketing team could get so hyper-targeted or hyper-personalized that a sales rep can do. And I'll actually share with you kind of our, our rule of philosophy, um, for how we do our outbound prospecting. We call it the 10-80-10. So, 10% personalization within this email needs to be about, "Hey, Harry, I saw you live, you know-... in London. Here's some common things that people like you struggle with. You know, I saw you were over in, uh, Finland last weekend," or whatever it might be. All right, and then I've got the 80% of content, and that's usually the very, you know, Webflow or marketing speak that's written by the company. And then I close off there with this 10% of personalization that ask for the call, that asks for that meeting, that playful closing statement. So now you, as the CEO or whomever I'm selling to, you feel like this note was sent directly to you, was hyper-personalized, hyper-specific for you. But really me as the rep, I was able to scale this because I spent maybe five minutes doing a little bit of research, knowing my ICP there. But you're landing this email and you're like, "Wow, I feel so good. Like, this person wrote it directly for me." And that's what beautiful outbound is.
- HSHarry Stebbings
What you don't know is that we do that exactly when we share the shows. I will say to Lauren Schwartz, "Hi, Lauren. God, I so enjoyed our show last week and hope you had a great weekend." I'll copy and paste the blurb about our episode and then-
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
... I'll finish with, "By the way, say hi to the team at Fivetran from me."
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
And they go, "Wow, it's so nice. Fivetran, they're ra-ba-ba." And yeah, totalmente-
- MHMaggie Hott
10, 80, 10 right there.
- 33:50 – 35:12
Net Payment Terms
- HSHarry Stebbings
you've got... America's ba- banking is so backwards. Anyway, uh, like net payment terms. What's normal? How would you advise a seed stage founder that you're invested in on net payment terms?
- MHMaggie Hott
Net payment terms? Normal is net 30 in my mind. Um, we will go up to net 45, maybe even net 60 with approval. Um, the main thing that I actually want to know, though, Harry, if you're asking me, you know, "Hey, I want net payment terms of net 90", I want to know why. Is it a cash flow thing? Do, do you need help? Like, do you not have enough cash in the bank? Are you maybe doing another raise? Are you waiting for other contracts to pay you so that way you can pay me later on down the road? Or are you simply just asking for this as a point of pride because you want to get all you can get because, you know, why not shoot for the stars and ask for it? So, uh-
- HSHarry Stebbings
Oh, that's so anno- that's so annoying. I hate to work with a customer like that. Um-
- MHMaggie Hott
Oh, yep. It's, it's many, many, many of them out there. I mean, and that is... the, the role of procurement at larger companies, we can also talk about this forever, is to get the best deal for the company. Not just in terms of price point, but in terms of all of these other things. You know, net payment terms, split payments. We also have people asking a lot for quarterly payments, biannual payments. Sometimes we have people asking for monthly payments, which I usually just laugh at that. It's like no one pays monthly for any software. Um, but people are gonna ask for everything they can get.
- HSHarry Stebbings
You know, you mentioned kind of building out SDR teams.
- 35:12 – 58:55
Tips for Hiring Salespeople
- HSHarry Stebbings
- MHMaggie Hott
Mm-hmm.
- HSHarry Stebbings
And we've mentioned kind of, uh, different outbound. Uh, do I... I'm the founder, you're advising me. Do I hire a head of sales, a seasoned leader, if I can get them? Um, or do I hire junior sales reps early and start smaller? How do you advise me on that first sales hire? Which profile do I go for?
- MHMaggie Hott
Yup. I will rarely ever advise you to hire a head of sales, especially early on.
- HSHarry Stebbings
Okay.
- MHMaggie Hott
And here's why. Is you don't... You know, yes, again, you have your first couple customers here, but you don't really know just yet who you're selling to, what's your deal size. A head of sales is gonna be someone that's gonna come in. First off, they're probably gonna be really freaking expensive. But if you don't know actually what it is you need, it's gonna be really hard to find that right person that's gonna come in and build for you. Also, if you think about a head of sales, right away they're very likely gonna be asking for ops, for enablement, for marketing, for tooling, for all these different supporting systems. And someone that is a true-to-form head of sales has probably not been down in the weeds building... You know, really, really down on the ground. Cold calling, cold emailing. Of course, a bit here and there, but they're probably pretty far removed from it. So everything I just talked about really points to me that a head of sales is gonna be expensive, need a lot of high overhead, and probably hasn't done the job in quite a while. You also probably don't want someone who's super, super junior and green, because you as the founder are presumably gonna be their manager. And that's gonna be a lot of work for you to do, to go to teach someone, you know, how to write an email or teach someone how to put together a pricing proposal. That's not the best use of your time. So the sweet spot here is to look for maybe two different types. Someone who has been an AE at a hyper growth company and they have proven success, bring on that type of person. You know, and, and when I say this, it's really important that you are... I can't emphasize enough how important it is to bring in someone that's done this before. There are many great companies out there. You know, the Salesforce's of the world. But unless somebody was there early days at Salesforce actually building, you probably don't want to hire your very first AE from there because they haven't built it. They haven't seen it. They haven't done the playbooks. The other-
- HSHarry Stebbings
So, so, so when we say done this before, what's more important? That they've sold to this type of customer or they've sold this size of deal?
- MHMaggie Hott
... that they, actually neither. That they, what's most important is it they have built from the ground up before or they have seen it very closely. They've been a spectator sport in building, in setting up tooling, in setting up pitch decks, in practicing how to tell a story. I actually don't mind, you know, obviously bonus points if you can hire someone that has sold to this type of company or this type of persona, but it is not needed because when I think about it as a founder, you can teach them that. You can teach them, you know, the persona, the ICP, your product, but what you can't teach is hustle and grit and drive and what it looks like to be down on the ground building again.
- HSHarry Stebbings
I totally agree with you, so it's actually stage of experience that they've seen before.
- MHMaggie Hott
It's stage of experience, that's right. The other type of person you can hire, just to kind of close up this thought is, is someone who has maybe recently moved into frontline management, or maybe they've done it for one to two years, but they also have a proven track record as an AE, and they're really taking a bet on your company with the hope that they can then grow into that head of sales type role, so they're not too far removed from, you know, rolling up their sleeves and actually doing the building. But the bonus here is they have managed people before, so that way, you know, assuming they do really well off the bat, you can start hiring people under them and you won't have to teach them how to manage.
- HSHarry Stebbings
Before we do the hiring process, I do have to ask, do we do two by two on these hires? Jason Lemkin suggests kind of doing Hunger Games style of competition where one eventually praying mantis style eats the other at the end-
- MHMaggie Hott
Yikes.
- HSHarry Stebbings
... of the quarter. Yeah. (laughs)
- MHMaggie Hott
(laughs) Sounds like a great way to go.
- HSHarry Stebbings
Yeah, that's really, that's really unf- that's really unfair. He doesn't.
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
It's just Sunday evening and I thought I'd get creative with a David Attenborough analogy. Put, sorry Jason, if you're listening.
- MHMaggie Hott
(laughs) .
- HSHarry Stebbings
Um, so like, should you do two by two or should it be one at a time because resources are constrained.
- MHMaggie Hott
Yeah. First off, that sounds like a great way to get an HR violation on you.
- HSHarry Stebbings
(laughs)
- MHMaggie Hott
But, uh, in all seriousness, the only reason... So you should always hire in multiple sets of sellers, not for competition, but because it's actually not, not that much more work to teach people, you know, to teach a group of people than to teach one person. So if you bring in one seller, you're still gonna have to spend, I don't know, whatever it is, 100 hours getting them up to speed, enabling them, coaching them. If you bring in four sellers, you're probably gonna have to spend 120 hours, because all of those same sessions are gonna be the exact same for those four people. The other reason you should hire, you know, clusters of people is because they're gonna be there to support and build with each other. It's always more fun when you're working together in a group. You're shooting off ideas, you're staying up late, you're hacking through things, you know, like early days at Slack, I mean, it was nights and weekends, we couldn't even handle the load of inquiries that were coming in, and it was always best to be able to do it in groups versus to be kind of solo and alone. So if you can quite literally afford to hire multiple people, you should always do that.
- HSHarry Stebbings
I mean, the amount of companies, you know, with 50 million in the bank and no product market fit, I'm sure they'll be able to afford it. That's the least of the problem.
- MHMaggie Hott
(laughs) Exactly.
- HSHarry Stebbings
Um, uh, but now we know the profile.
- MHMaggie Hott
Mm-hmm.
- HSHarry Stebbings
Uh, and we know that we need to hire two. I want to actually just dig in on the hiring process. So-
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
... we're the two co-founders, you know, you have your wonderful, amazing experience and you're gonna help me. What non-obvious characteristics or traits would these reps have that we want to see in the interview process first? Obviously besides ambition, hard work, and all the other normals.
- MHMaggie Hott
Yep. So, there's two that are single most important that I look for in early stage hires. First one is ambiguity. Or the ab- the ability to deal with ambiguity. And this is actually something I tell every single person that I interview for Webflow, is if you are not okay with ambiguity, meaning things are gonna change every day, every week, every quarter, if you need stability, this is not the place for you. And so often you'll see people are like, "Yeah, yeah. I'm, you know, I want to build, I want hyper growth." Then they get there and they just can't handle the thrash of the constant change.
- 58:55 – 1:02:29
How to Choose Which Startup to Work For
- MHMaggie Hott
- HSHarry Stebbings
(laughs)
- MHMaggie Hott
(laughs) Love it.
- HSHarry Stebbings
Okay, fi- final one before we move into a quick fire, and it's like, that's all from the employer side. If we take on the hat, literally, of the, uh, candidate, uh, what advice would you give them on choosing the companies that they do commit many years and many, many hours of their lives to building?
- MHMaggie Hott
Yup. There's two big things here, and my single biggest North Star, which I think has served me pretty well in my career, is choose the company, not the role. I so... I'll start with the problem statement here. I so often see people chasing, you know, VPs of sales titles at a 10-person company that, you know, ends up oftentimes going nowhere. It is so important to choose that rocket ship and, you know, was it, hitch your wagon to it, hitch your saddle, and join on with that rocket ship. I started at Eventbrite as essentially, you know, SMB mid-market AE, and by the time I left, I was leading enterprise sales for the West, which was really amazing. And so much of that success is because I chose the right company versus going and chasing that title. Same exact thing at Webflow, same exact thing, which I didn't know it back in the time, early days at Eventbrite. Choose that rocket ship and you will ride it far, and presumably, if you do great work, all those new roles and responsibilities and pay will come over time. The other thing that I advise the candidates to do, which is probably the single biggest mistake, is that you see candidates chasing OTE and equity without knowing really what's behind either of them. I'll give you some tangible examples here.
- HSHarry Stebbings
Hmm.
- MHMaggie Hott
We have had so many AEs come to us and saying, you know, "I have this counteroffer from this other company for $50,000 more. Can you match that?" And my first questions are gonna be here, "Well, how many people from that other company are actually attaining?" "Well, I don't know." "Uh, well, what's the quota that you're gonna be, you know, given for this 300K OTE?" Because usually there's always a quota to OTE ratio behind the scenes. "Oh, I don't know what the quota's gonna be." Well, you could have a 300K OTE ratio, or sorry, you could have a 300K OTE, but if you have a $5 million quota and nobody is bringing in more than $2 million, you're not gonna get anywhere close to hitting your number, and goodbye to any chance of getting accelerators. Um-
- HSHarry Stebbings
And then that also shows you actually how they think. Like, it's a bit of a self-identifier for like-
- MHMaggie Hott
Y- yeah.
- HSHarry Stebbings
... "Really? You didn't think that?" Like...
- MHMaggie Hott
"You- you didn't think to look into it?" Right. Uh, the other thing is equity, is very often, and equity is obviously a very complicated thing, but very often folks don't realize equity. You need to ask a lot of questions about the equity. $200,000 of equity at Figma is gonna be very different than $200,000 at maybe a small company that doesn't have a good chance of success and is probably either gonna get acquired for a nominal amount or just fizzle out. Because you know what? That $200,000 of equity at Figma is pretty much a guarantee at this point, whereas $200,000 of no name is absolutely nothing. And so it's so important to understand the components of equity, the fair market value, the strike price. People get so fixated on the amount of options that they're getting, but options don't actually mean anything if you don't know how many options are outstanding or what the actual value is of those options.
- HSHarry Stebbings
I love that. God, you are this font of wisdom. I love this. This has been so much fun.
- MHMaggie Hott
Well, thank you (laughs) .
- HSHarry Stebbings
I'm like, it's very rare where I'm like, you, I, genuinely where it's like, the schedule just, um, we don't have enough time (laughs) . Um, so I'm gonna do a quick fire round now, and then we're gonna
- 1:02:29 – 1:04:30
Which Sales Tactics are Dead?
- HSHarry Stebbings
do a part two.
- MHMaggie Hott
Okay. Mm-hmm.
- HSHarry Stebbings
So next, next one for me, 60 seconds per one. What's the sales tactic that has not changed over the last five years?
- MHMaggie Hott
Curiosity, empathy, personalization. Every step of the process should be personalized from the first outreach, to the actual demo that you do. You know, incorporate in their name, their logo, their branding, everything. So important.
- HSHarry Stebbings
So often I have, uh, founders like DM me on LinkedIn or Twitter only and they're like, "Oh, you know, this is perfect for..." and then the name of my old fund or old funds. And I'm like-
- MHMaggie Hott
Exactly.
- HSHarry Stebbings
... "Literally you just haven't Googled me."
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
Like Google me, number one page you'll see-
- MHMaggie Hott
Yep.
- HSHarry Stebbings
... like, shit. Um...
- MHMaggie Hott
Yep. Well I mean, that's when you just unsubscribe or you just say, "No thanks, and we're done here."
- HSHarry Stebbings
Yeah, totally. What sales tactic has died a death?
- MHMaggie Hott
Onsite travel. You no longer need to be on site every single time you need to meet with a customer. I used to be on the road at least once a week. I was always on the road. And yes, it's so important for relationship building, but it just, it doesn't need to be that way anymore. Maybe one or two on sites over the course of a big deal, but you just don't need to be on the road like that anymore. People value time above all else, and if you can be efficient with their time, you can save time for them, you can resolve their pains, they're gonna care more about the actual product that you're selling than the lunch that you're buying them.
- HSHarry Stebbings
Do you miss the in-person interactions? I had Frank on from... Frank Filmon, who's the head of sales at Tableau, and he was like, "Oh, I miss in person so much." Uh, do, do you miss it?
- MHMaggie Hott
I- I do and I don't. I, I still get a great high going out there in person. I'm not saying I don't go in person, but I don't go in person every week anymore. I'm at home, I'm a mother, I'm, you know, with my children, I'm exercising, I'm focused on other things and I just have so much time back in my life that I'm not, you know, boarding United couple different times a week anymore.
- HSHarry Stebbings
I'm totally with you. The one thing I find hard as a manager is I just have no idea if like, you're happy. I didn't see you at the end of the day and so I'm like, "Maggie, is she, is she happy?" I hope so, but I have no
- 1:04:30 – 1:06:44
Parental Leave
- HSHarry Stebbings
idea.
- MHMaggie Hott
Yeah.
- HSHarry Stebbings
I find that tough as, as a manager.
- MHMaggie Hott
It's definitely tough.
- HSHarry Stebbings
Yeah. Uh, tell me, you mentioned being a mother there. Parental leave in 2022. What can be done to keep moms in work?
- MHMaggie Hott
Oh man, how much time do we have? Just kidding. Uh, so I actually helped to change our parental leave at both Slack as well as Webflow. This is something that I'm really passionate about. And a pretty horrifying stat is that last year in 2021, there was more women that left the workforce than any other time in the last 35 years. Horrible.
- HSHarry Stebbings
Wow.
- MHMaggie Hott
There was $800 billion in lost wages to women that happened in 2021. So let's let that sink in. Number one thing that companies... Well, actually two things that companies can do, but the number one thing is support your working parents. You know, of course there's the whole big talk about time off, of parental leave, and here in America it's absolute shit (laughs) . I think everyone knows that. Compared to the rest of the countries in the world. Um, but it's actually support them. It's give them benefits. It's give them, you know, all these different resources from mental health to coaching. Give them support groups. Actually at both Slack and Webflow we have a pregnancy support channel that is the freaking best. It's a whole bunch of moms in there being like, "What's happening today? I don't understand this. Can someone help me?" And it's making women and parents feel like they have a community and that they are no longer alone. And that is the single most important thing that you can do to support parents is, is really give them that, that place where they know where to go seek advice and help.
- HSHarry Stebbings
I- I love that in terms of the channel. I didn't know that. But that- that's really special and I totally agree in terms of them not feeling alone. Uh, from something very wholesome and- and- and meaningful to, you know, back to the world of sales...
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
(laughs) Uh, what one piece of a d- sorry, I didn't mean that rudely about it being a human being.
- MHMaggie Hott
No, sure. No, no, no. It's okay. (laughs)
- HSHarry Stebbings
(laughs) Uh, just moving from children to sales seems a little bit callous.
- MHMaggie Hott
Yeah. Mm-hmm.
- HSHarry Stebbings
Um, what piece would-
- MHMaggie Hott
I mean, my entire life is sales though. It literally is like, bribing... I mean, last night I was trying to try on a pair of shoes to, for my daughter to see if they still fit her and she wouldn't let me put on shoes, so I gave her a cookie instead. I literally held the cookie in front of her and said, "Do you want a cookie?" "Yes." "Okay."
- HSHarry Stebbings
(laughs)
- MHMaggie Hott
"Mom used to put these shoes on and see if they still fit." Guess what? Now we know the shoes don't fit anymore.
- HSHarry Stebbings
Uh, b- bribery works well. The trouble is, my mother used to bribe me with Armani jeans, so you got off lightly with a cookie.
- 1:06:44 – 1:07:33
Advice for Sales Leaders
- HSHarry Stebbings
So uh-
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
... at least appreciate the light expenditure.
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
Um, tell me, what one piece of advice would you give to a sales leader today starting a new role?
- MHMaggie Hott
Do not super rep. Uh, I, the single biggest mistake I see new sales leaders making is they go super rep their team's deals and they run their deals for them and they just burn themselves out. You don't actually teach someone anything if you're busy super repping all of their deals. The other thing, and hopefully I can squeeze in a part two here, is to understand the why and what motivates your teams. So I'm a new leader, you're my AE. "Harri, what is it that's driving you? Is it money? Is it pride? Is it you wanting to move up into management someday?" Because if you can understand that person's why and what motivates them, you're gonna know exactly how to coach and how to motivate them.
- HSHarry Stebbings
I love that. I totally agree
- 1:07:33 – 1:08:53
Who has the most impressive sales strategy?
- HSHarry Stebbings
with you in terms of understanding the incentive structure there. Uh, final one for you. What one company sales strategy have you been most impressed by recently?
- MHMaggie Hott
Oh, there's a lot actually out there. There's a lot of bad sales strategies. There's a lot of good ones. Uh, one company, a tool, I had mentioned this earlier, that we recently bought was Clari. It's a forecasting app. Uh, which, you know, doesn't sound necessarily all that sexy or exciting. This is probably the tool that I'm the single most excited about because it gives me about ten hours a week back, you know, f- to do other things. And the way that this was presented in the sales strategy that this team did was really understanding, you know, what is our pain to forecasting? Where do we want to go as a business? And then really just demonstrated all these great different customer stories on how sales leaders saved so much time. So I think for me that was a, a very recent top of mind one that we purchased that I've just been so obsessed with.
- HSHarry Stebbings
Maggie, as I said, we, we did the worst job at getting through this schedule (laughs) . I mean, it's my fault. I'm the interviewer. Um, this is-
- MHMaggie Hott
(laughs)
- HSHarry Stebbings
... all on me. Uh, but like, I'm thrilled because it was a fantastic conversation. We're gonna do a part two next year on actually-
- MHMaggie Hott
Oh my god.
- HSHarry Stebbings
... post-hiring. But thank you-
- MHMaggie Hott
Great.
- HSHarry Stebbings
... so much for doing this with me. I love doing this and you've been-
- MHMaggie Hott
You're welcome.
- HSHarry Stebbings
... a star.
Episode duration: 1:08:53
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