20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners. In Today's Episode with Maggie Hott We Discuss: 1. The Cold Email that Led to a World-Class Sales Career: How a cold email to Kevin Hartz @ Eventbrite led to Maggie's career in sales? What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset? What does Maggie know now that she wishes she had known when she entered sales? 2. The Sales Playbook: PLG and Enterprise: How does Maggie define the sales playbook? What is it? What is it not? Is it possible for early-stage companies to do both enterprise and PLG at the same time? When is the right time to add enterprise to a PLG motion? What are the steps to build an outbound sales engine in enterprise? Where do many go wrong? 3. Building the Bench: Hiring Your First Sales Team: Should founders look to hire a Senior Head of Sales first or a more junior sales rep? Should they be hired one at a time? What are the benefits of hiring many at the same time? What is the right process to hire your first sales hire? What are the core traits and habits that make the first 10x sales hire? What are the right questions to ask to unveil those characteristics? 4. Making the Machine Work: The Process: What can sales leaders do to proactively build relationships with other parts of the org? How can more junior sales reps build relationships with other functions? Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound? Why is it dangerous to make your self-serve product too good?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I will rarely ever advise you to hire a head of sales, especially early on. And here's why.

• 0:04Harry Stebbings?

  What a cliffhanger. This is 20 Sales with me, Harry Stebbings, and this is the monthly episode where we sit down with the world's best sales leaders to unpack their tips, tactics, and strategies to scaling the best sales teams. And today, I'm so excited to welcome an incredible force of energy and charisma in the form of Maggie Hot. Maggie is the Director of Sales at Webflow, where she leads their Sales Dev, Account Exec, and Solution Engineering orgs. And prior to Webflow, Maggie spent an incredible six years at Slack in a period of real hypergrowth for the company, having joined as the founding AE, scaling to a senior enterprise leader. Before Slack, Maggie was the founding sales hire at a Vendbite. And if that wasn't enough, Maggie's also an active angel investor,

• 0:45Harry Stebbings?

  an advisor to Cowboy Ventures, Scrubal Ventures, and is a founding operator and LP at Coalition Partners. A huge thanks also to Danny Hersberg at Sequoia and Kai Mack for some fantastic question suggestions today. I really did so appreciate that. But before we dive in for show today, planning sales force capacity and successful quota management can define the trajectory of your business. That's why you need Pigment. Pigment is an integrated planning platform that helps sales leaders bridge the gap between strategy and execution by promoting those golden conversations between your sales planning team and the leadership of the reps out in the field. From capacity planning and quota management to accurate territory plans and increased visibility on pipeline health, Pigment's intuitive interface lets you focus

• 1:30Harry Stebbings?

  on what matters, driving that revenue. Integrate all your sales data, your CRM, HRIS, and financial data into a single platform for trackable, predictable success. Introducing an entirely new segment unsure if your team is even set up for success this quarter. Well, with Pigment, you can make changes in minutes and overcome the disruption that moving heads can have on your plans. That's why companies like Figma, Gong, Deliveroo, Carter, and more trust Pigment. Visit gopigment.com/20VC to request a demo and grab a free copy of the report. What's more, if you use that link in the next 30 days, the team has promised me they'll run a personalized sales planning audit for you. And you will get an exclusive discount on the product.

• 2:12Harry Stebbings?

  And to be even credible products, SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals, and get the insights they need to coach seller performance, forecast with accuracy, and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify, and Stripe all love and use SalesLoft, and so can you. It's the new way to sell. Find out more at salesloft.com. And finally, we have to talk about Chargebee. Chargebee is the subscription revenue and billing management platform that streamlines your revenue operations like never before. Chargebee automates the lead to lead your workflow across your revenue stack,

• 2:55Harry Stebbings?

  so you can dream, deploy, and enjoy the breeze while the MRR just keeps rolling in, baby. But don't worry, Chargebee goes so much further beyond just billing. One example, pricing alterations. They allow you the ability to change pricing models with one click. Grandfathering old pricing has never been so easy. That, and for hundreds of other reasons, is why the likes of Freshworks, Opta, and Envoy all love and use Chargebee. Head over to chargebee.com and find out more. But now I'm so excited to hand over to Maggie Hott, Director of Sales at Webflow.

• 3:32Speaker 02

  You have now arrived at your destination.

• 3:36Harry Stebbings?

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

• 3:42Speaker 00

  Likewise, it is great to be here, Harry.

• 3:44Harry Stebbings?

  Now, I want to 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?

• 3:59Speaker 00

  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 when they're eight, 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. The Peace Corps. So I spent a lot of time traveling and living in different places all over the world, from Africa, Scotland, Spain, all over the place. So with this, I really had to learn how to make new friends and put myself out there and get to know people. Fast forward 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 in Spanish in university,

• 4:44Speaker 00

  and it's not until my very last quarter, when I'm in university, that I'm taking some business classes. This CEO comes down, his name is Kevin Harts, and he gives this whole talk about entrepreneurship and building this great company called Eventbrite, and they sell events. 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 I send him an email the next day, and I say essentially, hey, Kevin, I want to come work for you. 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

• 5:28Speaker 00

  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 them 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, AJ Tennant, the then head of account management, and essentially

• 6:12Speaker 00

  said, hey, I want to learn about Slack, let's chat. Next week, very similar story here at Eventbrite. I go in, and AJ's like, 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 advice about just- Random stuff. And I get a call from him in March 2015 that is essentially like, hey, Maggie, we want to offer you the job here at Slack. I didn't know what the job was, no idea the title, no idea the comp, because I didn't interview for this. But I was like, you know what? 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.

• 6:53Speaker 00

  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 March 2021, when for the first time ever, Webflow prospected me versus me prospecting a company. 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, I'm actually a pretty 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. Because it is not appropriate in this day and age to go to preschool without clothes on. But hey, here we are.

• 7:38Harry Stebbings?

  I think the wonderful thing with your career is you did what so few do, which is the importance of the follow up, actually. I always say to people, 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 have done. I do have to ask, you mentioned six incredible years at Slack there. 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?

• 8:06Speaker 00

  So first one, that is probably the most important, and something that I carry very near and dear, is cross functional relationships and showing appreciation. And I'll break down what I mean by this, Harry. Essentially, sales is very often 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. 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.

• 8:47Harry Stebbings?

  I love like granny, so nurture and foster these relationships cross functionally. If you 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?

• 9:01Speaker 00

  Let's break it down to 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 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, what is it that sales does? I think it's so common sadly, that in PLG companies, sales is typically either an afterthought, but it's also not necessarily something that gets a ton of investment. And people really realize what it is this salesperson can do. Very often we think about sales, you think about, I don't want to call it a used car salesman, but sales 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,

• 9:47Speaker 00

  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 our company. There's very few world-class companies that I can think of that are out there that don't have world-class sales teams.

• 10:08Harry Stebbings?

  Okay, so that's for the leader. For the sales rep, say I'm coming in fresh, bushy eyed and ready to go. Is there anything that I can do to make new relationships cross functionally?

• 10:17Speaker 00

  Yep, and it's actually starting from the very beginning. When you start, a lot of times companies will have these random donut meetups, where essentially 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 want to know something more about, message them, introduce yourself to them. Also, really think about as a sales rep, how you're showing up. 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? 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

• 10:59Speaker 00

  prioritize 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. Another learning too, let's chat about, 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, because outbound was of course a dirty word back then. 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

• 11:43Speaker 00

  very heavily inbound. 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, 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 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, not necessarily for

• 12:26Speaker 00

  next year, but for the next five years. These are going to be things like a couple little bit of our tech stack is DocuSign, CLM, is Salesforce, is world-class forecasting tools like Clary. 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.

• 12:47Harry Stebbings?

  I love that in terms of buy for scale, not necessarily for stay. There's so many things I want to unpack there. You mentioned kind of the PLG element and kind of introducing sales into PLG. You mentioned outbound, which I want to touch on as well. 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?

• 13:11Speaker 00

  You can, but I wouldn't fully recommend it. But what you need to do is you need to be able to understand who are you selling to? What is your market? What is your ICP? What is your persona? That's going to 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 out their outbound sales motion. Let's talk about pure, true to form, cold outbound. 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, go wall-to-wall within a company. But then pure cold outbound, which is kind of that traditional sense in non-PLG companies,

• 13:54Speaker 00

  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 Slack, like we were just straight up salaried. We had no other measurements and no other goals. Stuart's charter for the sales team was to help our customers. But over time, of course, 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.

• 14:37Speaker 00

  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 your context switching so much and these different companies are going to 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. You can't hire someone that is great with SMBs and is talking to the single biggest. Company in the entire world. It doesn't make sense.

• 15:00Harry Stebbings?

  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. That business model does not work. I hate to say it, but it doesn't work to have the $100 a month product with the CS team, with the sales team. Do you see this too? And does that worry you?

• 15:21Speaker 00

  Yes. And I would actually say it's something that I advise all founders. Didn't realize we're getting off track here a bit, but it's something 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. What I mean by that is if you are building a PLG or a self-serve model, think really hard about what you can do to make that model scale over time. So if I someday want to be selling into the Fortune 500, Fortune 1000, 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

• 16:01Speaker 00

  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. Actually, something that Zenia talked about whenever you interviewed him, it was this idea of SSO and security at Dropbox where they weren't selling a ton of differentiation. And that's 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.

• 16:45Speaker 00

  It's really hard to take a product and then take away features and functions, because that's going to piss off your earliest users.

• 16:51Harry Stebbings?

  I'm a bit naive here, because I always just use the security and SSO as like the product differentiation need and scale. What else do they need? Like, when you sell to CIOs of large companies, Fortune 500s, how does the product differentiation change beyond just security from the more PLG? PLG motions.

• 17:08Speaker 00

  Yeah. Oh my goodness. So many different ways. Well, first off, 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, 24/7 phone support. For example, at Webflow, obviously with all of those customers, we cannot be giving them 24/7 dedicated phone support. It's just not going to 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. We've also got, and this is actually very common with Slack as well as Webflow, different roles and permissions.

• 17:49Speaker 00

  So as you scale within a company, you want to make sure that not everybody has the same roles and permissions as maybe CIO. You want them to have the ability to go and terminate a user really quickly, but you probably don't want your IT intern to be able to do that. Really differentiating with the roles and permissions, you also start to get into a lot of kind of like enterprise security-ish legal features, DLP, e-discovery, MDM, all kinds of different things that typically go on enterprise packages.

• 18:16Harry Stebbings?

  Sounds like you're going to a music festival in the UK with all those MDMs. You're missing a couple of letters here, Maggie.

• 18:24Speaker 00

  Device management, a lot less.

• 18:26Harry Stebbings?

  Oh, right. That's what I was thinking.

• 18:28Speaker 00

  Yes, mobile devices.

• 18:29Harry Stebbings?

  Totally. Riotous World of Enterprise Sales with Maggie. That would be a great new podcast segment. The thing I have to answer is like, when we think about this, and that's the question of, there's a huge amount of people who have PLG motions running and they're working well. When is the right time to go, hey, let's layer on the enterprise product. Let's start the product differentiation. How do you advise your founders on when's the right time to layer on the enterprise model?

• 18:52Speaker 00

  Yep. Great question. A couple of different things. First off, you need to have some ARR. This needs to be essentially, not actually a fully proven product market fit, but pretty close to it. You need to be able to understand the pain that your problem is solving. Super, super important. If you can be successful as a founder selling your product, how can you ever expect someone else to be successful?

• 19:12Harry Stebbings?

  Do you need to be able to quantify the pain, i.e. that number of dollars saved, number of hours saved? You name it.

• 19:18Speaker 00

  Unless you are someone who has really done sales and marketing before as a founder, I probably wouldn't expect that. Let's take an example. I don't know if you're familiar with Jaleh. She's the CEO of Mutiny, one of the best marketing world-class leaders out there. I would expect a founder like that to be able to really go build this V1 playbook of the narrative, the marketing and the story and the ROI and quantifying the pain. But for someone who's maybe a very engineering tech-heavy founder that's never truly sold before, I probably wouldn't expect that. The other thing that these founders need to have is they need to be able to show that they can sell outside of what I call the friendlies. Friendlies being close friends, portfolios, sibling companies.

• 20:01Speaker 00

  Can you truly go out there and get people to be interested and to buy your product outside of your already existing close network? That is really important. And once you have conquered those things, again, to recap there, the pain, the product-market fit, some revenue, maybe $1 to $2 million in ARR, as well as sell outside of the friendlies. That's the time that it is to start building an enterprise product to a sales team.

• 20:23Harry Stebbings?

  Speaking of selling outside the friendlies there, I do want to ask about the outbound element. You mentioned it being a big learning from Slack. When you think about building outbound today, when's the right time? And how does one do it properly first?

• 20:35Speaker 00

  Yep. 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. I think that was a big learning that we had. Again, at Slack, is we didn't even start building an STR team until 2017. So we had been around for almost three years at that point, before we've really ever started dialing up this outbound motion. At Webflow, we've done it completely different. It 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. There's no reason to wait on outbound.

• 21:09Harry Stebbings?

  I'm like an eight-year-old here, like in class.

• 21:13Speaker 00

  For everyone listening, Harry's like raised his hand and I'm like, yes, Harry. I will call on you.

• 21:18Harry Stebbings?

  What does good outbound mean? Is it like dialing for dollars? Is it like sending great email? Just so I actually know what good outbound is today.

• 21:27Speaker 00

  Yeah, absolutely. Oh, man, I could talk to you about outbound for hours and hours. Let's talk about actually cold outbound because cold outbound is kind of the thing that people 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 going to be ready to buy my product. No, that is very unlikely the case that I'm going to 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.

• 22:12Speaker 00

  This is what we do. This is the pain it can solve. So maybe someday when you are six months or you're a year down the road and you're thinking, hey, my website is a 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 going to go take a look at this. And I'll tell you actually a really funny story that happened pretty recently. We recently bought a PLG tool to sit on top of our database and surface up insights. And there's a ton of these different PLG tools there coming up. These world-class companies, Endgame, Pocus, Calixsa, 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, I'm really sorry, we actually just purchased one, signed the contract. We're all set here.

• 22:57Speaker 00

  And this founder said to me, 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 have known this company existed, they would have absolutely been in our evaluation stack, but we didn't even know they existed. And if that company would have done outbound email to me probably four months ago, maybe they would have won our business. And that's why it's so important to do outbound early and often for that brand and market awareness.

• 23:25Harry Stebbings?

  Can I ask, again, this is where you learn with me. That there's no point in reading the schedule.

• 23:30Speaker 00

  I'm learning that pretty quickly.

• 23:32Harry Stebbings?

  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 Instagram videos, Facebook videos, short form, you name it. Isn't it not the blurring of marketing and sales? How do you think about that?

• 23:52Speaker 00

  They need each other. So marketing, think about that is, you know, the bigger, broader awareness, the 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 what I think your pain is going to 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 our rule of philosophy for how we do our outbound prospecting. We call it the 108010. 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.

• 24:36Speaker 00

  I saw you were over in 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 web flow 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 ask 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. It 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. This person wrote it directly for me. And that's what beautiful outbound is.

• 25:19Harry Stebbings?

  Well, tell me, how do you allocate resources to outbound when a lot of it is so unknown? As you said there, it can take a lot of time. You don't know what's going to hit. How do you think about allocating resources when there are so many unknowns to the eventual output and outcome?

• 25:35Speaker 00

  Yeah, it's going to be very dependent on your company size and. How much money you have to put towards outbound candidly. So if you are a company of 10 people, you've only raised a couple million funding, you're probably not going to be able to put a ton of resources to outbound. And this is really where you're going to have to think a lot more about what is your strategy here? Is it going to be hit as many people as you can? Or is it really try to narrow down and focus on maybe our top 50 target list? Which that's actually something I would recommend you do is really laser in, figure out who's your ICP, who are very tangential customers, maybe to the current customers you already have. Who are those customers that you want to go down and get? For me personally, so I've now built over the last year, our sales dev team, it's world class

• 26:16Speaker 00

  from zero to 19 people. So really quickly, spun up two different teams, two different offices. Their single biggest charter right now is to respond to our self-serve signups within seconds of the person signing up on the website. So again, you or Harry, you come and you create an account on webflow.com. And my sales dev team, assuming you hit our criteria, you're over a certain size, maybe you have a certain title, my team is going to hit you within minutes of you signing up, or that's the goal there. Because the idea behind that is webflow is top of mind for you right now. You're clearly doing research. You took the steps to go and create an account. So we want to be right there within your inbox, or maybe we, if you gave us your phone number, we pick up the phone and we call you. And this actually works. We actually just closed

• 27:01Speaker 00

  the single largest deal the company has ever had over a million dollar TCV by doing this exact method.

• 27:08Harry Stebbings?

  Can I ask you though, what is a big enough contract size average? What's a big enough ACV to have a targeted 50 list versus a much more, we're going for SMBs between 10 and 50 people that make under $5 million a year, and a much more broad approach?

• 27:24Speaker 00

  It's going to depend on who you're selling to. Are you a Vanta of the world, where you're selling to maybe smaller SMBs and mid-market? Or are you a FiveTran of the world, where you're selling to much larger, much more sophisticated enterprises? And I actually think it is so important to not try to be everything to everyone. And this is a mistake that I see founders make all the time, is they'll start their company and they'll Say, cool, I want to go get Walmart. No, you should not go get Walmart. You know why? Because their procurement is going to take well over a year, their sales cycles, the amount of different companies that are trying to sell to them right now. Can your product even support and staff a company like Walmart? Probably not. It's really important for these founders to have kind of a reality gut check

• 28:08Speaker 00

  and figure out where am I a great fit for these different companies? Who is the type of company I should be selling into? And how much money can I get from these companies? I actually advise founders, and obviously it's going to be dependent on how much money they've raised, but I advise them to not worry too much about the revenue early days. Focus on getting those logos. Very few people ever want to be the very first mover and shaker. It is so important to be able to say, I've got 20 different customers that look just like you or very similar in this same space in order to be able to boost up your reputation.

• 28:43Harry Stebbings?

  The number one mistake fund managers make fundraising is they go out for the big tickets first because they think they need to solidify the base for them and then add the little tickets afterwards. You need people in your restaurant first to bring more people in. Get your friendlies in.

• 28:57Speaker 00

  That's exactly right. In this case, get the friendlies in because you want to show that you have people that are using your products successfully. And you get now those people singing from the rooftops. This company is so wonderful. They're doing all these great things. And then that's going to allow you to move into that next phase and really build out this big old sales team and have kind of the fuel and the revenue. And now maybe you can go raise another round that's going to just help continue to accelerate your business.

• 29:24Harry Stebbings?

  Do we give discounts for testimonials? How do we think about testimonials?

• 29:28Speaker 00

  Man, I love thinking about all the nuances behind discounts. But discounts for testimonials, yes, but first off, if you don't have to discount, don't discount. I actually think discounts should be used very selectively. And the single biggest reason to discount should be used is to control the close date of the deal. To tie a discount and say essentially, hey, Harry, I've heard you're asking for this price point. This is a really big stretch for us. I don't know if I'm going to be able to get there, but here's what I'm going to do. I'm going to go to my VP of Finance and I'm going to ask him that if this company, if they can commit to closing by December 15th, will we honor for them this $50,000 price point outside of bringing it all the way down from $80,000?

• 30:08Speaker 00

  Harry, will you commit to me that you can sign by December 15th if I go make this case internally for you? Yes. Thank you. Great. So then here, what I would do is I'd follow up with that in writing. But now, of course, Harry, we get back on the call. I present to you, hey, so excited we got this approved for $50,000. Well, of course, you're going to want more. Now you're going to want net payment terms. You're going to want split payments. You're going to want all this other stuff. And heck, you might even want some more discounting. That's then where I start to bring in things like testimonials, like customer reference stories, like different videos I might film of you. That being said, the other time, though, that I might do this differently is if you are a tier one logo that I want, that's when I would lead with putting that directly within our negotiation in the very beginning and setting this up front and saying,

• 30:53Speaker 00

  "Hey, Harry, it's actually standard for us that we have all of our customers, that we have logo rights, and we have the ability to do customer testimonials. Of course, we want to make sure you're a happy customer. Assuming you're going to be a happy customer, are you willing to commit to that?" And then leading with that upfront. It's just going to depend on who you are and really what company you're coming from and how gladly do I want your logo.

• 31:12Harry Stebbings?

  I'm so happy you're talking about this and also being very granny there because there's so many founders are like, "Net payment terms?"

• 31:17Speaker 00

  What?

• 31:18Harry Stebbings?

  I remember when I started doing partnerships, I do it was like seven days and then people were like, "No, no, we need more than like seven days."

• 31:23Speaker 00

  Yeah, what?

• 31:25Harry Stebbings?

  I'm like, "Well, I didn't fucking know. I was 18." No, how do I suppose to know? I'm just chatting shit on a podcast from London.

• 31:31Speaker 00

  Like, I can't even get you a check in the mail in seven days.

• 31:34Harry Stebbings?

  America's bad banking is so backwards. Anyway, like net payment terms, what's normal? How would you advise a seed stage founder that you are invested in on net payment?

• 31:43Speaker 00

  Net payment terms, normal is net 30. In my mind, we will go up to net 45, maybe even net 60 with approval. The main thing that I actually want to know, though, Harry, if you're asking me, "Hey, I want net payment terms of net 90", I want to know why. Is it a cash flow thing? Do you not have enough cash in the bank? Or you may be 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 practice? Because you want to get all you can get because why not shoot for the stars and ask for it? The role of procurement at larger companies, and I'll 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, net payment terms, split payments. We also have people asking a lot for quarterly payments, biannual payments.

• 32:27Speaker 00

  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, but people are going to ask for everything they can get.

• 32:35Harry Stebbings?

  You mentioned kind of building out SDR teams and we've mentioned kind of different outbound. I'm the founder, you're advising me, do I hire a head of sales, a seasoned leader if I can get them? 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?

• 32:52Speaker 00

  Yep, I will rarely ever advise you to hire a head of sales, especially early on. And here's why. Yes, again, you have your first couple of 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 going to be someone that's going to come in. First off, they're probably going to be really freaking expensive. But if you don't know actually what it is you need, it's going to be really hard to find that right person that's going to come in and build for you. Also, if you think about a head of sales, right away, they're very likely going to 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 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.

• 33:37Speaker 00

  So everything I just talked about really points to me that a head of sales is going to 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 going to be their manager. And that's going to be a lot of work for you to do, to go to teach someone 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. 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.

• 34:20Speaker 00

  The Salesforce is 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.

• 34:33Harry Stebbings?

  When we say done this before, what's more important than they've sold to this type of customer or they've sold this size of deal?

• 34:40Speaker 00

  Neither. What's most important is that they have built from the ground up before or they have seen it very closely. They have 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, 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 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.

• 35:16Harry Stebbings?

  I totally agree with you. So it's actually stage of experience that they've seen.

• 35:20Speaker 00

  Stage of experience, that's right. The other type of person you can hire 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 rolling up their sleeves and actually doing the building. But the bonus here is they have managed people before. So that way, 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.

• 35:53Harry Stebbings?

  Before we do the hiring process, I do have to ask, do we do two by two on these hires? Jason Lemkin suggests doing Hunger Games style of competition where one eventually praying mantis style eats the other at the end of the quarter.

• 36:05Speaker 00

  Yeah.

• 36:07Harry Stebbings?

  That's really unfair. He doesn't, it's just Sunday evening and I thought I'd get creative with the David Attenborough analogy. Sorry, Jason, if you're listening. So should you do two by two or should it be one at a time because resources are constrained?

• 36:19Speaker 00

  Yeah, you should always hire in multiple sets of sellers, not for competition, but because it's actually not that much more work. To teach a group of people than to teach one person. So if you bring in one seller, you're still going to 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 going to have to spend 120 hours because all of those same sessions are going to be the exact same for those four people. The other reason you should hire clusters of people is because they're going to 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. Early days at Slack, it was nights and weekends. We couldn't even handle the load of inquiries that were coming in.

• 37:04Speaker 00

  And it was always best to be able to do it in groups versus to be solo and alone. So if you can quite literally afford to hire multiple people, you should always do that.

• 37:15Harry Stebbings?

  I mean, the amount of companies 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. But now we know the profile and we know that we need to hire two. I wanted to actually just dig in on the hiring process. So we're the two co-founders, you have your wonderful, amazing experience and you're going to 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.

• 37:42Speaker 00

  Yep. So there's two that are single most important that I look for in early-stage hires. First one is 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 going to 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 want hypergrowth. And then they get there and they just can't handle the thrash of the constant change. But in building a company, it's really important that people can handle ambiguity. If you want something that is steady, that has playbooks, that is well baked out, go somewhere that is already 10,000 plus.

• 38:21Harry Stebbings?

  Joes aside, everyone says, oh yeah, yeah, that's me and love a bit of ambiguity. How do you test if they actually are happy with changing tides and ambiguity in the workplace?

• 38:30Speaker 00

  Yeah, you actually asked for examples. Tell me about a time that a process changed right away. How did you handle it? How did you learn about it? What did you do? How did you react? How did you help implement this process that you identified needed to be changed? What did you do? How did you spot it? What was the impact that you knew making this process change would be? And that also is helping me really look and understand, is this someone that's a bit of a go getter? And I'm going to take the bull by its horns? Or are they going to wait for all of the process to change on their own and just go with the flow? People who can embrace the chaos. I absolutely love that term of just embracing the chaos. There are very few things in a startup or a hyper growth company that are ever going to be stable. So it's very similarly tied to notion of ambiguity, but it's going to be crazy.

• 39:14Speaker 00

  Are you okay with that? And do you thrive on that? Or is that just again, too much? And do you just need something a little bit more stable? In my case in Slack, I think I probably had seven different jobs within my six years there. It's been very similar at Webflow. One day, hey, can you take on your SEO work? Can you go build out sales dev? Go build out partner dev. Cool. We're going to build out enterprise majors. Start thinking about that. Cool. Let's build out our growth team. Start thinking about how you're going to do that. And you have to find someone who can work on different levels of multi-altitude and be able to be very high up top here, thinking through strategy, but also really roll up their sleeves and be in the weeds.

• 39:50Harry Stebbings?

  So we know now that we need embracing chaos and ambiguity.

• 39:54Speaker 00

  Yes.

• 39:54Harry Stebbings?

  Now we need to actually engage in the hiring process.

• 39:57Speaker 00

  Yeah.

• 39:57Harry Stebbings?

  How do we structure the process? Just walk me through, is it one meeting and then job offer?

• 40:02Speaker 00

  Yep, absolutely. So let's talk about structuring the process. And if it's okay, I can actually talk to you too about what are some of my favorite interview questions? First, let's start about talking about the process, maybe some do's and don'ts there. I am a big believer in hire thoughtfully, but fire fast. And I'm sure we'll talk about the fire fast later on. But it's really important to call out here that a hiring mistake can cost a company to the tune of $1 million. And that's because of all of the time it takes to interview candidates, to write the job rec, to get the recruiters prepped, to get this person their offer letter, to get them started, to all the time it takes to train and enable them. I mean, enterprise sellers can be upwards of six months.

• 40:43Speaker 00

  To then only have them be crap and not bring in any revenue and then all All of a sudden, now you're nine months down the road. They've brought in nothing and now you're firing them and you have to start that whole cycle all over again. All that time lost, time savings, also just bad morale when people are getting fired. And so really important to be extremely thoughtful about your hiring process. There is nothing that you can do that is more important than hire the right people to help you build your ship. So let's talk about what that hiring process should look like. For us, it's pretty lengthy. It's a recruiter phone screen, hiring manager phone screen, whole panel of what we call a chronological interview, which is essentially a very deep dive into your resume. It's then a bit of kind of a cultural-ish assessment where you're just meeting different members of the team.

• 41:28Speaker 00

  Then you have a final round. One of the most common things I think people do quite wrong in their final round is they ask people to demo their product. I think this is one of the absolute worst things that you can do. I'll tell you why. One, no one is going to know your product as well as you're going to know your product. So Harry, you're an AE, you're coming and you're pitching to me and you're pitching Webflow. In the back of my mind, I'm going to be like, I would have said this differently there. Oh, you missed this thing. You missed this key spot. I will almost never be able to fully remove out any previous bias in what I know from my own product. The other thing too, is candidly, quite frankly, I just think it's a bit disrespectful to ask someone to really learn and lean in and know every single nuance of your own product.

• 42:13Speaker 00

  This person, if they're a top performer, they are probably working at another company, another job, maybe they have families, maybe they have girlfriends, boyfriends, they have another life and the ROI is just not going to be there for asking them to demo your product for the amount of time it's going to take for them to actually learn how to do it. So I'll tell you what I like to do instead. It sounds pretty funny, but I love to start off all of our final round interviews with a pitch something you love. One, it's a warm-up exercise, but two, I want to see how do you pitch when you are so excited and passionate about something? Maybe you love baking so much and you just want to talk about baking. I want to see, Harry, how are you lighting up when you are pitching something that you're passionate about?

• 42:58Speaker 00

  Because the assumption is you're probably not passionate about Webflow just yet. Hopefully you'll be there someday, but you are darn passionate about baking. How do you light up? Because that's going to show me how you light up when you're presenting to customers. The second thing that I am looking for here. How do you explain concepts? So if you're coming in and you're pitching to me about baking, I'm going to ask you all different types of questions about heat, about temperature, about how long it needs to be in the oven, but all these different areas. And I want to see how you are teaching me as your prospective buyer, all these different things that I might not know about. Because in selling a technical software product, there's very often going to be a lot of teaching. And I want to see how you can teach your prospective buyer.

• 43:41Harry Stebbings?

  Say I pitched something I love and you love it. And you think that's great and you want to move forward. Comp is always a big part of any discussion with any sales team or anyone really joining any company, unless it's about nonprofit, which was a word you said at the beginning, which I didn't really fully understand being a venture capitalist, but I hear it's something. So tell me, in terms of lessons around comp, how do you advise founders on structuring a package that's enticing for sales reps and really doing comp well?

• 44:05Speaker 00

  To wrap up kind of the hiring thought, we also after pitch something you love, we actually do a mock discovery call. And that is equally as important, if not actually more important than pitch something you love.

• 44:15Harry Stebbings?

  That's a mock discovery call. You held that back?

• 44:18Speaker 00

  Yeah, okay. So I'm actually going to tell you what our prompt is. So for anyone listening that someday is going to interview a Webflow, here you go. You have some insight into our prompt. Okay, so here's our prompt for the mock discovery call. Essentially, myself or our panelist of internal, usually it's always hiring managers. We are going to pretend to be a company. In our case right now, we actually pick Miro. So every single person that ever interviews with us, they are doing a mock discovery call against the company Miro. And the AE, so the person that's interviewing to actually be one of our AEs, they are pretending to be a Webflow AE. And we make it very clear to them that you don't need to know the nuts and bolts of the product, kind of going back to my standpoint on demos. But what you need to be able to do is you need to run a very thorough discovery.

• 45:03Speaker 00

  You need to be able to understand pain. You need to be able to articulately pitch what Webflow is and the problem that we solve. We're also looking for things like, are you wrapping in relevant customer case studies? Are you finding that Mural, who is one of Miro's competitors, is actually one of our customers and has a whole case study on our site? So we're looking. Looking for curiosity, we're looking for research. We're also looking for coachability. At the end of the mock discovery, we actually give them live coaching on the spot on what we would have liked to see differently. And we look for how they react to that coaching. Are they making excuses? Are they blaming? Or are they taking this and owning it and being like, oh, my gosh, you're so right. Can we actually just redo it and redo that role play?

• 45:45Speaker 00

  And that's what I love to see. It's okay if someone doesn't do an excellent job. These are high stakes, high pressure. But what I want to see is how are you taking that coaching? And are you applying a growth mindset? Or are you getting defensive and blaming? And you would be so surprised at the amount of people that we see that either write off the feedback or they get super defensive about it. And we will point blank, never hire them.

• 46:08Harry Stebbings?

  Wow, I totally agree. How do you think about just insecurity there? I could just be a really insecure person and I'm getting the feedback and I'm like, oh, I put so much time and effort into it. And actually, I'm unloved and alone in my personal life. And now I'm unloved and alone in this web flow interview. And I could actually be really talented, but I could just be quite insecure.

• 46:26Speaker 00

  I mean, should you be in sales?

• 46:28Harry Stebbings?

  Aren't most people in sales insecure?

• 46:30Speaker 00

  Yeah, but it's all about how you handle that feedback. Again, it's, are you someone that's gotten feedback before? Because like, I can tell you, there's a lot of times that I've been given really tough feedback. And it's all about how you handle and how you implement that feedback and how you use it moving forward for your next steps.

• 46:48Harry Stebbings?

  What's the hardest bit of feedback you've ever been given?

• 46:51Speaker 00

  Oh, boy. So I'm going to take you back on a little bit of a journey to two weeks into my management career, where I had probably the biggest learning lesson that I will ever have that just to this day, it just makes me squeamish. But let me tell you what it was, because here we are now, many years removed, and I can talk about it quite a bit easier. So I was early on management career. I thought, coming in, Maggie, I'm a new manager. I have all the authority in the world to approve big old pricing discounts. You know, I can do whatever I want. So I gave the authority to approve a $200,000 credit to a customer at Slack that my team was selling into. Oh, yeah, your face right now. Yikes. Got the deal done. Got it closed. I'm celebrating.

• 47:32Speaker 00

  You know, we're about to close this massive deal and I get a call from my VP of customer success. I will never forget this call. I wanted to pass out and vomit. And she was basically like, Maggie, what the bleep did you just do? And what did you offer to this customer? Tell me this did not happen. And really, the lesson that I learned here is it is so important to go slow, to go fast. And what I mean by this is even in a hyper growth, hyper scaling company, it's so important to take that step back, to look at the problem, the objective from all different angles and really try to understand what is it that I need to do? What are all the steps I need to follow? Where are my blind spots?

• 48:15Speaker 00

  Because what I'm going to, whether it be offer to a customer or change within an entire org or whatever structure I'm going to implement is going to have huge, long stream impacts and effects down the road. So again, just because your hyperscale does not mean that you should be reckless. And I'm actually so thankful this happened to me early days in my career. Because since then, every single project or problem or big process that I'm thinking of, these things, if I make a big comp change or a big team structure change, that can actually have huge impacts on my org's careers and the money that they make. And that's why it's so important to always slow down, cross your Ts, dot your Is.

• 49:00Harry Stebbings?

  My word, I'm feeling your pain on that one.

• 49:02Speaker 00

  Oh, it was horrible, but so glad it happened then.

• 49:04Harry Stebbings?

  What are your favorite questions to ask? What are most revealing of great quality candidates?

• 49:09Speaker 00

  Yep. So I'll walk you through some of my more tactical ones. And really, the thing I'm looking for here is a lot about accountability. First question that I'm going to ask you as a hiring leader, to pretend you're an AE coming in the door. The first thing I want to know from you, tell me about a deal that you've lost. And I'm looking here, within asking these questions on the deal lost, is I'm looking for, are you blaming people? Are you taking responsibility? It's totally okay to lose a deal. We all lose deals, but what I want to know is, are you saying, I lost the deal because of the product? I lost the deal because of the competitor? I lost the deal because my SE screwed up? Up or are you taking ownership for why he lost this deal? So are you actually saying, I was not multi-threaded enough?

• 49:50Speaker 00

  I made a big mistake where I didn't get in front of the buyer as fast as I should have. Or I just assumed that the person I was talking to was the buyer and I didn't realize there was a whole separate buy-in committee. And what I'm looking for again here is like, are you taking ownership and responsibility? Or are you blaming someone else? The next thing that I love to dive into is stack ranking. So Harry, you're coming to me from the sales team at Asana. How many people were on your team? Oh, there was eight people. Cool. Out of those eight, where did you come up on the leaderboard? Maggie, I was at four. And what I'm looking for here, it's actually okay if you were at four. But what I want to know is what is it that those top three people that beat you did differently than you? What I'm looking for here is self-awareness, but I'm also looking for blame.

• 50:34Speaker 00

  So are you saying, I actually had someone pretty recently be like, oh, they had a better territory than me. And it's like, control what you can control. That's not a good excuse. Like territories are always going to be all over the place. Or is it, you know what? Lauren, she was our number one rep. She was so diligent at managing her time. She would wake up and first thing she would do is spend her first hour prospecting, next hour, customer calls. And that's why she was the top rep. So again, are you blaming or are you taking ownership and sharing what other people could have done better? You get all excuses all over the world that people get. I had a bad manager, I had a bad SC, I had a bad SDR, whatever. Take ownership of your destiny. It's the only way you're ever going to be successful. So the next question that I like to ask is if you could go back in time 10 years

• 51:18Speaker 00

  and coach yourself on something that you wish you knew now, what would it be? Same themes here of what I'm looking for. First off, is this person, are they thoughtful? Are they very introspective? Are they saying, I made this mistake or I made this poor company choice? Or I did this thing wrong. I used to push through deals way too fast. I would tell myself to have a better attitude or to slow down the deal cycle and uncover all the different rocks. And then that actually allows me, Harry, to go in many different layers deeper and uncover. Why did they make these mistakes? How were they thinking about it at the time? How would they then implement that now? What are Examples of what they've done now to implement whatever X mistake was. The other kind of magical question that I really like to ask people is,

• 52:00Speaker 00

  what is something that I didn't ask you that you were hoping I would ask you? First off, that just gives you a chance to brag. Maybe you prepped some incredible story and you didn't get the chance to share it within your interview. It lets you open up and brag and share presumably a really big success and highlight that I probably want to hear about it. But secondly, it also lets me see how much did you prepare for this interview? Did you think through different stories and different patterns? Did you get ahead of what potential questions and objections might come at you? Because very often, people who we will almost certainly never hire will say, nope, you asked everything all good. And like, no, no, not all good.

• 52:40Harry Stebbings?

  How many, okay, that on that one, how many people actually say, no, I'm good. That was great.

• 52:45Speaker 00

  About 25%.

• 52:46Harry Stebbings?

  Oh, wow. That's quite impressive.

• 52:48Speaker 00

  It's quite a bit. Yeah. But usually people are like, I was hoping you would ask me about the craftiest I ever got in a deal and how I ended earning the customer trust. And then I'm like, cool, tell me all about it. And then they go, tell me all about it. And now everyone's really happy and laughing.

• 53:01Harry Stebbings?

  Final one before we move into a great fire. And so that's all from the employer side. If we take on the hat of the candidate, 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?

• 53:16Speaker 00

  Yep. 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'll start with the problem statement here. I so often see people chasing VPs of sales titles at a 10 person company that ends up oftentimes going nowhere. It is so important to choose that rocket ship and was it hitch your wagon to hitch your saddle and join on with that rocket ship. I started at Slack as essentially no 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. Choose that rocket ship and you will ride it far.

• 54:00Speaker 00

  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. We have had so many AEs come to us and saying, I have this counter offer from this other company for $50,000 more. Can you match that? And my first questions are going to be here. Well, how many people from that other company are actually attaining? Well, I don't know. What's the quota that you're going to be given for this 300K OTE? Because usually there's always a quoted OTE ratio behind the scenes. Oh, I don't know what the quota is going to be.

• 54:45Speaker 00

  Well, you could have a 300K OT, but if you have a $5 million quota and nobody is bringing in more than $2 million, you're not going to get anywhere close to hitting your number. And goodbye to any chance of getting accelerators.

• 54:57Harry Stebbings?

  And then that also shows you actually have anything. Like it's a bit of a self identify of like, really? You didn't think that?

• 55:02Speaker 00

  You didn't think to look into it? Right. The other thing is equity. That 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 going to be very different than $200,000 at maybe a small company that doesn't have a good chance of success and is probably either going to 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,

• 55:46Speaker 00

  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.

• 55:54Harry Stebbings?

  I love that. God, you're a font of wisdom. I love this. So I'm going to do a quick fire round now and then we're going to do a part two. 60 seconds per one. What's the sales tactic that has not changed over the last five years?

• 56:07Speaker 00

  Curiosity, empathy, personalization. Every step of the process should be personalized from the first outreach to the actual demo that you do. Incorporate in their name, their logo, their branding, everything. So important.

• 56:20Harry Stebbings?

  So often I have founders like DM me on LinkedIn or Twitter and they're like, oh, this is perfect for, and then the name of my old fund or old funds. And I'm like, literally you just have to Google it. Like Google me, number one page you'll see.

• 56:33Speaker 00

  Yep. Yep. I mean, that's when you just unsubscribe or you just say, no, thanks. And we're done here.

• 56:38Harry Stebbings?

  Yeah, totally. What sales tactic has died a death?

• 56:40Speaker 00

  You no longer need to be onsite 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 doesn't need to be that way anymore. Maybe one or two onsite's 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 going to care more about the actual product that you're selling than the lunch that you're buying them.

• 57:11Harry Stebbings?

  Do you miss the in-person interactions?

• 57:13Speaker 00

  I do and I don't. I still get a great high going out there in person. So 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 with my children. I'm exercising. I'm focused on other things. I just have so much time back in my life that I'm not boarding United a couple of different times a week anymore.

• 57:32Harry 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, was she happy? I hope so, but I have no idea. Tell me, you mentioned being a mother there. Parental leave in 2022, what can be done to keep mums in work?

• 57:46Speaker 00

  Man, how much time do we have? Just kidding. 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. 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. Of course, there's the whole big talk about time off of parental leave. And here in America, it's absolute shit. I think everyone knows that compared to the rest of the countries in the world, but it's actually support them. It's give them benefits.

• 58:29Speaker 00

  It's give them 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 really give them that that place where they know where to go, seek advice and help.

• 59:00Harry Stebbings?

  I love that in terms of the channel. I didn't know that, but that's really special. And I totally agree in terms of them not feeling alone, from something very wholesome and meaningful to back to the world of sales. One piece would, sorry, I didn't mean that rudely.

• 59:11Speaker 00

  No, no, no.

• 59:13Harry Stebbings?

  Just moving from children to sales seems a little bit.

• 59:16Speaker 00

  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 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 and said, I literally held the cookie in front of her and said, do you want a cookie? Yes. Okay. I mom used to put these shoes on and see if they still fit. Guess what? Now we know that shoes don't fit anymore.

• 59:34Harry Stebbings?

  Bribery work as well. The trouble is my mother used to bribe me with Almani jeans. So you got off lightly with a cookie. So at least appreciate the light expenditure. And tell me, what one piece of advice would you give to a sales leader today, starting a new role?

• 59:47Speaker 00

  Do not super rep. 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 into part two here, is to understand the why and what motivates your teams. So I'm a new leader, you're my AE. Harry, 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 going to know exactly how to coach and how to motivate them.

• 1:00:23Harry Stebbings?

  Final one for you. What one company sales strategy have you been? Most impressed by recently.

• 1:00:28Speaker 00

  One company, a tool I had mentioned this earlier, that we recently bought was Clary. It's a forecasting app, which doesn't sound necessarily all that sexy and exciting. This is probably the tool that I am the single most excited about because it gives me about 10 hours a week back to do other things. And the way that this was presented in the sales strategy that this team did was really understanding what is our pains with 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 very recent top of mind one that we purchased that I have just been so obsessed with.

• 1:01:08Harry Stebbings?

  Maggie, as I said, we did the worst job at getting through this schedule. I mean, it's my fault. I'm the interviewer. This is all on me, but I am thrilled because it was fantastic conversation. We're going to do a part two next year on actually post hiring, but thank you so much for doing this with me. I love doing this and you've been a star.

• 1:01:25Speaker 00

  Thank you so much. Really appreciate it.

• 1:01:29Harry Stebbings?

  As you heard, we had so much fun on that show. If you'd like to see more from us behind the scenes, of course you can by going on YouTube where you can see the full video for this episode. Search 20 VC and you'll find that very easily. Or you can find us on 20vc.com. We always love to see you there. But before we leave you today, planning sales force capacity and successful quota management can define the trajectory of your business. That's why you need Pigment. Pigment is an integrated planning platform that helps sales leaders bridge the gap between strategy and execution by promoting those golden conversations between your sales planning team and the leadership of the reps out in the field. From capacity planning and quota management to accurate territory plans and increased visibility on pipeline health.

• 1:02:11Harry Stebbings?

  Pigment's intuitive interface lets you focus on what matters, driving that revenue. Integrate all your sales data, your CRM, HRIS and financial data into a single platform for trackable, predictable success. Introducing an entirely new segment, unsure if your team is even set up for success this quarter. Well, with Pigment, you can make changes in minutes and overcome the disruption that moving heads can have on your plans. That's why companies like Figma. Gong, Deliveroo, Carter and more, trust pigment. Visit gopigment.com/20vc to request a demo and grab a free copy of the report. What's more, if you use that link in the next 30 days, the team has promised me they'll run a personalised sales planning audit for you and you will get an exclusive discount on the product.

• 1:02:56Harry Stebbings?

  And speaking of incredible products, SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify and Stripe all love and use SalesLoft and so can you. It's the new way to sell. Find out more at salesloft.com. And finally, we have to talk about Chargebee. Chargebee is the subscription revenue and billing management platform that streamlines your revenue operations like never before. Chargebee automates the lead to ledger workflow across your revenue stack so you can dream,

• 1:03:40Harry Stebbings?

  deploy and enjoy the breeze while the MRR just keeps rolling in, baby. But don't worry, Chargebee goes so much further beyond just billing. One example, pricing alterations. They allow you the ability to change pricing models with one click. Grandfathering old pricing has never been so easy. That and for hundreds of other reasons is why the likes of Freshworks, Okta and Envoy all love and use Chargebee. Head over to chargebee.com and find out more. As always, I so appreciate all your support and we have an incredible episode with Hattie Potovi coming on Friday.