The Exchanges

Q 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.

A Yeah, absolutely. Oh man. I could talk to you about outbound for hours and hours. So good outbound. Let's talk about actually cold outbound because cold outbound is kind of the thing that people, you know, are scared of say it doesn't work. Does it work for me? Cold outbound. Your single biggest objective there is to build a marketing machine and build your brand awareness with cold outbound. The main reason that you are doing cold outbound is to Educate your 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, 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, you know, total piece of crap. I need a new website. Huh? I remember that sales rep from Webflow reached out to me six months ago. I'm going to go take a look at this and I'll tell you actually a really funny story that happened pretty recently. Uh, we recently bought a PLG tool, you know, to sit on top of our database and surface up insights…

AI assessment note: “Your single biggest objective there is to build a marketing machine and build your brand awareness”

Q 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 B to B marketing, but there's many different ways, whether it's, you know, Instagram videos, Facebook videos, short form, you name it. Like, is this not the blurring of marketing and sales? And how do you think about that?

A They need each other. I mean, marketing and sales should be working hand in hand and that's. Why so often you see them rolling up to a chief customer officer or wherever. So marketing, think about that is, you know, the bigger, broader awareness, the, I don't want to call it billboards or articles or whatnot, but marketing is really out there just trying to get the name recognition. And then you think about sales outbound. That needs to be personalized, targeted, directly tied with a hypothesis to you, to what I think you, 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 kind of our, our rule of philosophy, um, for how we do our outbound prospecting. We call it the 1080 10. So 10% personalization within this email needs to be about, Hey, Harry, I saw you live, you know, in London. Here's some common things that people like you struggle with. You know, I saw you were over in Uh, Finland last weekend, or whatever it might be. All right. And then I've got the 80% of content, and that's usually the very, you know, 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, a…

AI assessment note: “There is no way that a marketing team could get so hyper targeted”

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

A Yeah. You actually asked for examples. Tell me about a time that 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 needed, that you identified needed to be changed? What did you do? How did you spot it? You know, 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, uh, you know, gonna take the bull by its horns? Or are they going to wait for all of the process to change on their own and just kind of go with the flow?

AI assessment note: “You actually asked for examples. Tell me about a time that process changed”

Q Yeah. Uh, tell me, you mentioned being a mother there. Parental leave in twenty-twenty-two. What can be done to keep mums in work?

A Man, how much time do we have? Just kidding. Uh, so I actually helped to change our parental leave at both Slack as well as Webflow. This is something that I'm really passionate about. And a pretty horrifying stat is that last year in 20, 21, there was more women that left the workforce than any other time in the last 35 years. Horrible. There was eight hundred billion dollars in lost wages to women that happened in 20, 21. So let's let that sink in. Number one thing that companies will actually do things. That companies can do, but the number one thing is support your working parents. You know, of course there's the whole big talk about time off of parental leave and here in America, it's absolute shit. I think everyone knows that compared to the rest of the countries in the world. Um, but it's actually support them. It's give them benefits. It's give them, you know, all these different resources from mental health to. Coaching. Give them support groups. Actually at both Slack and Webflow, we have a pregnancy support channel that is the freaking best. It's a whole bunch of moms and they're being like, what's happening today? I don't understand this. Can someone help me? And it's making women and parents feel like they have a community and that they are no longer alone. And that is the single most important thing that you can do to support parents is, is really give them that, …

AI assessment note: “the number one thing is support your working parents... It's give them benefits”

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

A Unless you are someone who has really done sales and marketing before as a founder, I probably wouldn't expect that. So, uh, let's take an example. I don't know if you're familiar with Jolly. 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 kind of go build this, you know, I know I'm sure we'll talk about playbook, but kind of this V one 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. Um, 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, you know, their close friends, friendlies being their portfolio sibling companies. Like, can you truly go out there and get people to be interested and to buy your product outside of your already existing close network? So 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 to a sales team.

AI assessment note: “Unless you are someone who has really done sales and marketing before... I probably wouldn't expect that.”

Q That is Such a good marketing tool. I like that packaging. 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?

A 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're probably, and you know, 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, I have, so I've now built over the last year, our sales dev team, it's world-class from zero to 19 people. So really quickly spun up two different teams, two different offices, and 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 are Harry, you come and you create an account on webflow.com, right? And my sales dev team, you know, 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 th…

AI assessment note: “dependent on your company size and how much money you have to put towards outbound”

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

A Unless you are someone who has really done sales and marketing before as a founder, I probably wouldn't expect that. So, uh, let's take an example. I don't know if you're familiar with Jolly. 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 kind of go build this, you know, I know I'm sure we'll talk about playbook, but kind of this V one 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. Um, 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, you know, their close friends, friendlies being their portfolio sibling companies. Like, can you truly go out there and get people to be interested and to buy your product outside of your already existing close network? So 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 to a sales team.

AI assessment note: “Unless you are someone who has really done sales and marketing before as a founder, I probably wouldn't expect that.”

Q Yeah. Uh, tell me, you mentioned being a mother there. Parental leave in twenty-twenty-two. What can be done to keep mums in work?

A Man, how much time do we have? Just kidding. Uh, so I actually helped to change our parental leave at both Slack as well as Webflow. This is something that I'm really passionate about. And a pretty horrifying stat is that last year in 20, 21, there was more women that left the workforce than any other time in the last 35 years. Horrible. There was eight hundred billion dollars in lost wages to women that happened in 20, 21. So let's let that sink in. Number one thing that companies will actually do things. That companies can do, but the number one thing is support your working parents. You know, of course there's the whole big talk about time off of parental leave and here in America, it's absolute shit. I think everyone knows that compared to the rest of the countries in the world. Um, but it's actually support them. It's give them benefits. It's give them, you know, all these different resources from mental health to. Coaching. Give them support groups. Actually at both Slack and Webflow, we have a pregnancy support channel that is the freaking best. It's a whole bunch of moms and they're being like, what's happening today? I don't understand this. Can someone help me? And it's making women and parents feel like they have a community and that they are no longer alone. And that is the single most important thing that you can do to support parents is, is really give them that, …

AI assessment note: “the number one thing is support your working parents. You know, of course there's”

Q and a half months pregnant going for a role? You go. That's fucking awesome. In terms of parental leave, how do we think about, um, parental leave? So, let's think, like, specifically, how have you navigated this, because it is a challenging topic, also knowing that you're inevitably behind due to, kind of, I feel bad saying it, but like, your career being on pause while everyone else does progress.

A Yeah. So career pause, I think sadly can be a very real thing. You essentially step out of the business for four to six months and the business is still moving forward without you. And that's why I actually think, and this is a bit counterintuitive, but it's so important for companies to have equitable parental leave for both parents, for the birthing parent and the non birthing parent. So it shouldn't just be the female that is getting the bulk of the parental leave. And, you know, typically the male or the other partner Um, it really needs to be both. Need to have pretty darn near equitable leave. Because if you don't do that, it actually puts women at a disadvantage both financially as well as in their career if they're taking far longer than their non-birthing counterparts. And this is going to happen multiple times if they have multiple kids. So in my case, I've now gone out and leave twice in the last few years. And then actually speaking on the home front, studies show that With a non-birth and parent or a partner's increased involvement in baby care can mitigate maternal postpartum depression. And actually one in seven women get postpartum depression, which is something that is not talked about enough publicly and enough out there. It can be really, really hard to come back to work and to focus on your career if you're also battling postpartum depression at the same tim…

AI assessment note: “So career pause, I think sadly can be a very real thing.”

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

A Man. Okay. We can talk about, I'm actually leading a whole big discount training, which I'm happy to share with you on Tuesday for our entire sales org. Love, love thinking about all the nuances behind discounts, but discounts for testimonials. Yes, but you need to make sure that, I mean, 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 a discount should be used is to control the close date of the deal. To tie a discount and say essentially like, 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, if this company of 20 VC decides to close by, you know, if they can commit to closing by December 15th, will we give, will we honor for them this 50,000 dollar price point? Outside of, you know, bringing it all the way down from 80,000 dollars. Harry, will you commit to me that you can sign by December 15th if I go make this case internally for you?

AI assessment note: “discounts for testimonials. Yes, but you need to make sure that”

Q I view it as supporting the economy. My therapist has unwavering demands on his time, so I'm really a net additive to GDP. Uh, Maggie, uh, I want to move to you on an inspirational story. Hit me. What's the first that comes to mind for you?

A Yeah. First off, Stevie, thank you for always just being so real. There's, like, fewer people I know that are just more real and out there than Stevie, and I believe is yours, and, and really anyone. We have a duty for those Out there to set this kind of standard and set the stage of how we want to show up and we're going to be setting this mirror and those who potentially look up to us or all of us are leading orgs, um, are going to mirror what it is that we're putting out there and we're going to show that it is okay to act and kind of behave and share these stories. So thank you, Stevie, for always being so open and honest. Um, yeah, working parents are just some of the toughest that are out there and I think it's really important for me to never hide that I'm a parent. So, obviously, I realize it's kind of coming from a place of privilege, but for my teens, I want them to know that I am a working parent. I am a working mother. When I am pregnant, that I, you know, I'm not having the best days, and sometimes I just need to cancel that meeting or go off camera. And actually, speaking of being pregnant, one of the biggest things that happened in my career was actually when I was eight and a half months pregnant. There was a role that opened up at Slack for an enterprise leader, and at that point in time, I was a senior manager of mid-market. And there was this new role to help…

AI assessment note: “one of the biggest things that happened in my career was actually when I was”

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

A Man. Okay. We can talk about, I'm actually leading a whole big discount training, which I'm happy to share with you on Tuesday for our entire sales org. Love, love thinking about all the nuances behind discounts, but discounts for testimonials. Yes, but you need to make sure that, I mean, 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 a discount should be used is to control the close date of the deal. To tie a discount and say essentially like, 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, if this company of 20 VC decides to close by, you know, if they can commit to closing by December 15th, will we give, will we honor for them this 50,000 dollar price point? Outside of, you know, bringing it all the way down from 80,000 dollars. Harry, will you commit to me that you can sign by December 15th if I go make this case internally for you?

AI assessment note: “discounts for testimonials. Yes, but... if you don't have to discount, don't discount.”

Q So we know now that we need embracing chaos and ambiguity. Now we need to actually engage in the hiring process. How do we structure the process? Just walk me through it. Like, is it one meeting and then job offer? Is it one meeting, qualification? How do we actually structure the process?

A 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, if that's of interest. 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 one million dollars. And that's because of all of the time it takes to interview candidates, to write the job offer or 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 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. And they've brought in nothing, and now you're firing them, and you have to start that whole cycle all over again. That, all that time lost, time savings, you know, also just bad morale. When people are getting fired and, you know, or laid off, it's, it's always bad morale. 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…

AI assessment note: “recruiter phone screen, hiring manager phone screen, whole panel of what we call a chronological interview”

Q Woohoo! That's a party day. Can I ask you though, um, 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 five million a year and a much more broad approach?

A So I can't give you an answer there, and here's why. It's gonna depend on who you're selling to, right? Are you, you know, are you a Vanta of the world where you're kind of 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, uh, 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 be, it's 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. And so it's really important for these founders to have kind of a reality gut check and figure out who, who, 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, um, 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 because very few people ever want to be the very first mover…

AI assessment note: “So I can't give you an answer there, and here's why.”