YouSaid · the spoken record

Maggie Hott

lines on the record: 65
first: 2022-12-14
most recent: 2022-12-14
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Do not super rep. Single biggest mistake I see new sales leaders making is they go super rep their team steals 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 rep 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. 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, my entire likeness sales, though, it literally is like bribing me last night. I was trying to try on a pair of shoes for my daughter to see if they still fitter 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, my mom used to put these shoes on and see if they still fit. Guess what? Now we know that shoes don't fit anymore”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 place where they know where to go, seek advice and help.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 thirty-five years. Horrible. There was eight hundred billion dollars in lost wages to women that happened in 2021. So let's let that sink in. Number one thing that companies watch two things that companies can do. But the number one thing is support your working parent. 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. 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I do and I don't I still get a great high going out there on purse 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 different times a week anymore”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 going to care more about the actual product that you're selling than the lunch that you're buying them.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“You didn't think to look into it right. The other thing is equity. 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, 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Is that you see candidates chasing OTE in 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 question is 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 quota to OTE ratio behind the scenes. Oh, I don't know what the quota is going to be. Well, you could have a 300 KOT, but if you have a $5 million quota and nobody is bringing in more than two million dollars, you're not going to get anywhere close to hitting your number. And goodbye to any chance of getting accelerators.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 ten person company that ends up oftentimes going nowhere. It is so important to choose that rocket ship, and was it hits your wagon to it, hit your saddle and join on with that rocket ship. I started at slack as essentially no SMB midmarket 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. 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Quite a bit. Yeah, but usually people will be like, I was hoping you would ask me about the craftiest I ever got in a deal and how I ended up earning the customer trust. And then I'm like, cool, tell me all about it. And then they go tell me all about it.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“implement whatever X mistake was. The other kind of magical question that I really like to ask people is 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 prep 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 SE, I had a bad SDR, whatever. Take ownership of your destiny. That'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 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 seal deal cycle and uncover all the different rocks. And then that actually allows me, Harry, to go in many different layers deeper and uncover it. Why did they make these mistakes? How are they thinking about at the time? How would they then implement that now? What are examples of what they've done now?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“or 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 are on your team? Oh, there were 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. So were 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 was spend her first hour prospecting next hour customer calls and that's why she was the top rep. So again, are you blaming?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 is 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. Or are you taking ownership for why you lost this deal? So are you actually saying I was not multi-threaded enough? 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. What I'm looking for again here is like, are you taking ownership and responsibility?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 T's, dot your I's.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 hypergrowth, hyper scaling company, and 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 because what I'm going to whether it be offered 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 you're 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”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh boy. So I'm going to take you back on a little bit of a journey to two weeks in to my management career where I had probably the biggest learning lesson that I will ever have that just to this day 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. I can do whatever I want. So I gave the authority to approve a two hundred thousand dollars 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, 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?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 for curiosity. We're looking for research. We're also looking for coachability at the end of the mock discovery.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. You need to be able to understand pain. You need to be able to articulately pitch what web flow is and the problem that we solve. We're also looking for things like are you wrapping in a relevant?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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? Because the assumption is you're probably not passionate about Webflow just yet. Hopefully you'll be there someday, but you are darn passion 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, about all these different areas, and I want to see how you are teaching me as your perspective 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“There, oh, you miss this thing, you miss 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. 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. This 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Also just bad morale when people are getting fired and so it's 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 issue where you're just meeting different members of the team. Then you have a final round. One of the most common things that 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. When 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 different.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 higher 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 one million dollars. And that's because of all of the time it takes to interview candidates to write the job rack 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 to then only have them be crap and not bring in any revenue and then 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 loss, time savings.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Jobs within my six years there. It's been very similar at Webflow one day. Hey, can you take on your SE or can you go build out sales dev? Go build out partner dev. Cool. We're going to build out enterprise and 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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. 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”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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,”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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, a hundred hours getting them up to speed, enabling them, coaching them. If you bring in four sellers, you're probably going to have to spend a hundred and twenty 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 night 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 solo and alone. So if you can quite literally afford to hire multiple people, you should.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“of experience, that's right, the other type of person you can hired 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 is 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Super, super junior in 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 go to go to teach someone how to write an email or teach someone how to put together a price and 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 hypergrowth 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. The sales force 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 customers here, but you don't really know just yet who you're selling to, what's your deal size ahead 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 ahead 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. So everything I just talked about really points to me that ahead 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”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“That payment term's normal as net thirty, and my mind we will go up to net forty five, maybe even net sixty 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? 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 you simply just asking for this as a point of pride 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 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, biennial 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. But people are going to ask for everything they can get.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Thank you. Great. So then here, what I would do is I'd follow up with that in writing. But now, of course, 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Harry, will you commit to me that you can sign by December 15th if I go make this case internally for you?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“That's exactly right. In this case, get the friendlies in because you want to show that you have people that are using your product successfully. And 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It's going to depend on who we are selling to. Are you a vanta of the world where you're selling to maybe smaller SMBs in mid-market? Or are you a five tram 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 staff a company like Walmart? Probably not. It's really important for these founders to have kind of a reality gut check 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“On the website. So, again, you were 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 give us your phone number, we pick up the phone and we call you. And this actually works. We actually just closed the single largest deal the company has ever had over a million dollar TCV by doing this exact method.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 sales dev team, it's world class from zero to nineteen people. So really quickly, spot up two different teams, two different offices. Their single biggest charter right now is to respond to our self-served signups within seconds of the person signing up.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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, was hyper personalized, hyper specific for you, but really me is 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“They need each other. So marketing, think about that, 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. 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 webflow or marketing speak that's written by the company.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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, Calixa. 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, sign the contract. We're all set here. And this founder said to me, can I ask?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 perspective 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, 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. But 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 really ever started dialing up this outbound motion. It 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.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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, portfolio, sibling companies, 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 one to two million dollars in ARR, as well as sell outside of the friendlies, that's the time that it is to start building an enterprise product as a sales team.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Jolly. She's the CEO of Muni. One year ago.”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yep, great question. A couple different things. First off, you need to have some ARR. This needs to be essentially not only 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?”
2022-12-14 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source