The Exchanges

Q I love that. Maggie, it's so good to see you again. I mean, we do message very frequently, so you've probably had enough of me by now. Uh, but, uh, tell me, who are you, and what's the best part of being a working mum?

A Hi, Harry. Great to see you again. I'm Maggie Hott. I recently joined OpenAI and previously before that I was leading sales over at Webflow and as well as at Slack for spent about six and a half years there. Um, this, so I'm a mom to a one-year-old and a three-year-old and the single best part about being a working parent is being an inspiration to my daughters and really showing them that you can do whatever it is that you put your mind to. It's just been really awesome to kind of see how they've adjusted their mindset over the past Couple years of their lives and that they have really no fears and go after whatever they want.

AI assessment note: “the single best part about being a working parent is being an inspiration to my daughters”

Q I love that. Maggie, it's so good to see you again. I mean, we do message very frequently, so you've probably had enough of me by now. Uh, but, uh, tell me, who are you, and what's the best part of being a working mum?

A Hi, Harry. Great to see you again. I'm Maggie Hott. I recently joined OpenAI and previously before that I was leading sales over at Webflow and as well as at Slack for spent about six and a half years there. Um, this, so I'm a mom to a one-year-old and a three-year-old and the single best part about being a working parent is being an inspiration to my daughters and really showing them that you can do whatever it is that you put your mind to. It's just been really awesome to kind of see how they've adjusted their mindset over the past Couple years of their lives and that they have really no fears and go after whatever they want.

AI assessment note: “the single best part about being a working parent is being an inspiration to my daughters”

Q The only thing is, I think they were, like, far more impressed than they were with her than they were with me, which is, you know, a challenge in itself, but I, I love that, and I'm so grateful for that. Maggie, tell me, in terms of actually getting granular and improving situations, how can we create a more inclusive and supportive environment for working mothers in sales leadership roles?

A Totally. So, I think similar to what, to what everyone said is to normalize having children, you know, back in the day, so, you know, it wasn't normal for, for children to be around, to be talked about. My mother-in-law was, um, Lieutenant Governor of Colorado, and she went back to work I think it was something like two weeks after having both of her sons. Um, and it just wasn't a normal thing back then. And we're so fortunate to be in a day and age now where it's perfectly acceptable to be a working parent and to be a mother and to have a career. So first off is to normalize it. And some really easy ways to do it is bring your kids on calls. If your kids are running around in the background, pop them onto a call and have them say hi. Honestly, everyone's going to love it because it's so fun and it kind of breaks things up. Be honest when your kids are sick or when they have, you know, their preschool or their daycare or their school is closed. Don't try to hide it. Say, hey, there might be a visitor that's gonna jump in to our call or have them over in the background. Your companies and teams, again, are gonna look up and mirror what you do. And then the other thing you can do is create resources and kind of support an affinity group. So something that, um, we had at Slack that I then brought over to Webflow and created was a pregnancy support channel. And this is where People…

AI assessment note: “some really easy ways to do it is bring your kids on calls”

Q I, I do just have to ask final one before we do a kind of quick fire on advice. I made it like mandatory that we're all back in office again. Um, I just think we're so much more productive in office. We're all in London anyway, but is that bad of me? And like, is remote just so much better in terms of being the best in this balance?

A It's going to be different to every single, um, company. I, uh, you know, I just went from Webflow, which is fully remote and now to open AI, which is more of a hybrid model. Um, so it's going to be, every company is going to have its different choices. The one thing I wouldn't say though, is still always remember to be flexible while in office may be a requirement. Again, doctors, uh, preschool or like different school events or outings, soccer games, parent teacher conferences. In a remote world, it is so much easier to just kind of, like, slip off and go do those things. In a in-office world, it's really hard to do that, so just continue to normalize that. The expectation is that you are in office when you can be in office, but if you need to miss being in office for some other reason, you know, family event, sick event, whatever it might be, it is totally ok.

AI assessment note: “It's going to be different to every single, um, company.”

Q Like, I mean, you, 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 terms?

A Net payment terms normal is net 30. In my mind, um, we will go up to net 45, maybe even net 60 with approval. Um, the main thing that I actually want to know though, Harry, if you're asking me, you know, hey, I want net payment terms of net 90, I want to know why. Is it a cash flow thing? Do you need help? Like, do you not have enough cash in the bank? Are you maybe doing another raise? Are you waiting for other contracts to pay you so that way you can pay me later on down the road? Or are you simply just asking for this as a point of pride because you want to get all you can get because You know, why not shoot for the stars and ask for it?

AI assessment note: “Net payment terms normal is net 30.”

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

A Yeah. Okay. So I'm actually going to tell you what our prompt is. Uh, so for anyone listening that someday is going to interview at Webflow, here you go. You have some insight into our prompt. Um, okay. So here's our prompt for the mock discovery call. Essentially, you know, myself or our panelists 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, you 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 Webflow is and the problem that we solve, We're also looking for things like, are you wrapping in relevant, you know, 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. We a…

AI assessment note: “We are going to pretend to be a company... run a very thorough discovery”

Q So, okay, question. What are your favorite questions to ask? What are most revealing of great quality candidates?

A Yep. So I'll walk you through some of my more tactical ones. And, and really the thing I'm looking for here is a lot about accountability. So first question that I'm going to ask you, you know, as a, as a hiring leader, as you're, let's pretend you're an AE coming the, in the door. The first thing I want to know from you is what, tell me about a deal that you've lost within your career. And I'm looking here within asking these questions on the deal loss is I'm looking for, are you blaming people? Are you taking responsibility For this deal that we, that lock was lost. It's totally okay to lose a deal. We all lose deals. But what I want to know is, are you saying, you know, I lost the deal because of the product. I lost the deal because of the competitor. I lost the deal because my SC screwed up. Or are you taking ownership for why you lost this deal? So are you actually saying, you know, 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, you know, assume that the person I was talking to was the buyer and I didn't realize there was a whole separate buying committee. So am I looking at 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 know, you're coming to me fr…

AI assessment note: “tell me about a deal that you've lost within your career”

Q pricing, but then they layer on traditional sales and that business model does not work. I hate to say it, you know, Harvard grads, um, but clearly you missed HBS because you would have studied the business study there. Um, but it doesn't work to have the hundred dollar a month product with the CS team, with the sales team. Do you see this too? And does that worry you?

A Yes. And I would actually say, um, it's, it's something that I advise all founders, and I realize we're kind of getting off track here a bit, but it's something that we, that I advise all founders to really think about that product differentiation early days, because it's really hard to get that right as the company gets bigger over time. So what I mean by that is if you are building a PLG or a self-serve model, think really hard about what you can do to make that model scale over time. So if I, you know, someday want to be selling into the Fortune, 500, Fortune thousand, what is a different product that my sales team will be able to sell them? Because the single biggest thing that I see PLG companies do wrong Is they have their, essentially their self-serve or their lower end product cannibalize what could be their future enterprise product. We ran into that at Slack. We run into it at Webflow all the time where there has to be a huge product differentiation outside of just security. You know, actually something that Xenia talked about whenever you interviewed him, I think earlier on this year is, was, was this idea of. SSO and security at Dropbox, where they weren't selling a ton of differentiation, and that's very, very common for early stage PLG companies, but that's really where it's so important for the founder to get this right early on, because otherwise, if you make yo…

AI assessment note: “Yes. And I would actually say, um, it's, it's something that I advise all founders”

Q I am totally with you. I'm trying to think now. I don't know if Calendly does, but they would probably be the first that comes to mind, but I, I, I'm totally with you. Okay. So that's for the leader, for the sales rep, say I'm coming in fresh and bushy eyed and ready to go. Is there anything that I can do to make new relationships cross functionally?

A Yep. And it's actually starting from the very beginning when you start, you know, a lot of times companies will have these random, we actually do. And so did Slack, these random donut meetups were essentially kind of like virtual coffee chats and you just need to put yourself out there. You need to be in different Slack channels. And if somebody posts a question that maybe you want to know something more about message them, introduce yourself to them. Also really think about, you know, as a sales rep, how you're showing up, you know, your, like Essentially your business is your brand. Are you coming out legal saying, Hey legal, I need this right now, right away, get this over the line, or are you approaching it in a way saying, Hey legal, you know, I know you're so slammed. I know things are busy. We're really hoping to close this customer by X date. I was wondering if you would be able to spend some time and potentially prioritize this this week. Let me know if you have questions. Thanks so much. I really appreciate you. And if you look at those kind of two different ways of how I approached it, One makes you feel like a partnership. The other makes you sound like a total jerk.

AI assessment note: “these random donut meetups were essentially kind of like virtual coffee chats”

Q Like, I mean, you, 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 terms?

A Net payment terms normal is net 30. In my mind, um, we will go up to net 45, maybe even net 60 with approval. Um, the main thing that I actually want to know though, Harry, if you're asking me, you know, hey, I want net payment terms of net 90, I want to know why. Is it a cash flow thing? Do you need help? Like, do you not have enough cash in the bank? Are you maybe doing another raise? Are you waiting for other contracts to pay you so that way you can pay me later on down the road? Or are you simply just asking for this as a point of pride because you want to get all you can get because You know, why not shoot for the stars and ask for it?

AI assessment note: “Net payment terms normal is net 30.”

Q You know, you mentioned kind of building out SDR teams and we've mentioned kind of different outbound. Do I, I'm the founder, you're advising me, do I hire a head of sales, a seasoned leader, if I can get them, um, or do I hire junior sales reps early and start smaller? How do you advise me on that first sales hire? Which profile do I go for?

A Yep. I will rarely ever advise you to hire a head of sales, especially early on. And here's why is you don't, you know, 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, you know, really, really down on the ground, cold calling, cold emailing, of course, a bit here and there, but they're probably pretty far removed from it. So everything I just talked about really points to me that a head of sales is 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 go to go to teach someone, you know, how to …

AI assessment note: “I will rarely ever advise you to hire a head of sales, especially early on.”

Q Games style of competition where one eventually praying mantis style eats the other at the end of the quarter. Yeah. That's really, that's really, 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. Um, so like, should you do two by two, or should it be one at a time because resources are constrained?

A Yeah. First off, that sounds a great way to get an HR violation on you, but, uh, in all seriousness, the only reason, so you should always hire in multiple sets of sellers, not for competition, but because it's actually not, not that much more work to teach people, you know, 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 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, you know, 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, you know, like early days at Slack. I mean, it was nights and weekends. We couldn't even handle the load of inquiries that were coming in. And it was always best to be able to do it in groups versus to be kind of solo and alone. So if you can quite literally afford to hire multiple people, you should always do that.

AI assessment note: “you should always hire in multiple sets of sellers”

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

A Yeah. Okay. So I'm actually going to tell you what our prompt is. Uh, so for anyone listening that someday is going to interview at Webflow, here you go. You have some insight into our prompt. Um, okay. So here's our prompt for the mock discovery call. Essentially, you know, myself or our panelists 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, you 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 Webflow is and the problem that we solve, We're also looking for things like, are you wrapping in relevant, you know, 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. We a…

AI assessment note: “So here's our prompt for the mock discovery call. Essentially, you know, myself or our panelists”

Q So, okay, question. What are your favorite questions to ask? What are most revealing of great quality candidates?

A Yep. So I'll walk you through some of my more tactical ones. And, and really the thing I'm looking for here is a lot about accountability. So first question that I'm going to ask you, you know, as a, as a hiring leader, as you're, let's pretend you're an AE coming the, in the door. The first thing I want to know from you is what, tell me about a deal that you've lost within your career. And I'm looking here within asking these questions on the deal loss is I'm looking for, are you blaming people? Are you taking responsibility For this deal that we, that lock was lost. It's totally okay to lose a deal. We all lose deals. But what I want to know is, are you saying, you know, I lost the deal because of the product. I lost the deal because of the competitor. I lost the deal because my SC screwed up. Or are you taking ownership for why you lost this deal? So are you actually saying, you know, 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, you know, assume that the person I was talking to was the buyer and I didn't realize there was a whole separate buying committee. So am I looking at 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 know, you're coming to me fr…

AI assessment note: “The first thing I want to know from you is what, tell me about a deal that you've lost”

Q You clearly never saw cheaper by the dozen, but I'm sure that I managed to get in a plug for Slack there. Maggie, you should be so proud of me. Uh, you mentioned, Maggie, that America's worst parental leave policy. Tell me, how can you advocate for parental leave if the existing policy isn't up to parlet? What can we actually do to change things?

A Yeah, absolutely. Great question. I think about it in a force kind of four-step structure or framework. So first I'll start off with the number one thing that's important to do is to educate your company. And I've found that oftentimes policies just haven't been formed. They're outdated. They haven't been reviewed in years. It wasn't actually a bunch of folks up at the top being like, let's make some really bad policies. It was just something that maybe was never worked on, or maybe was really never thought through. So it's a great time to really come together, and I'll walk you through the steps, but to really educate those at the top who are the key decision makers on why it matters to go change these policies. So the first thing that you should really think about doing is pull together data and research of comparable companies and comparable, you know, kind of companies within your industry. So, you know, if we are Webflow, who are kind of the maybe Tots different fund companies and really compare ourselves to as we think about top talent and then really go and look at what are their policies? How are they treating this? Is there anything that we can learn from them? The second thing that's really important to do is to meet with leaders and peers from the company, ideally parents or people who want to be parents or people who are really kind of like allies to families. So re…

AI assessment note: “I think about it in a force kind of four-step structure or framework.”

Q Julie, you mentioned kind of game time decisions there. Maggie, if there's anyone who can absolutely crystallize like the plan, I know it's you, uh, with your kind of strategic thoughts, which you've outlined to me many times before. Um, tell me when we think about like strategies or tools specifically to help maintain that balance, To allow for those game time decisions. What advice would you have there?

A Yeah, my biggest advice is that nothing is more valuable than your time. So work and life these days, especially with so much of a shift to remote work from home, they're so intertwined. I think probably most of us on this call work some variety of hours from seven AM to 11 PM, but this is really flip-flopping between work and personal life back and forth, just like how Julie was saying. So there's been two Big tips that have worked really well for me that I've kind of had to figure out over the last few years. The first one, again, going back to nothing is more valuable than your time. It's ask for help. It's ask help from your friends, your family, your neighbors, uh, whether that's something of, Hey, can you watch the kids for half an hour or asking for help from your partner? Um, it's also, if you are, if you have the means and are able to afford it, Spending some money on things, maybe like grocery delivery. So rather than going and spending two hours back and forth in the grocery store, bringing the kids back and forth to it, just have Amazon prime, spend that nine 99 and get it delivered to your house. And all of a sudden you've got two hours back in your day or cleaner, same thing rather than, you know, spending hours clean. If you have the means to do it, maybe once a month, have those cleaners come and then you all of a sudden start getting hours back. The other strat…

AI assessment note: “two Big tips that have worked really well for me that I've kind of had to figure out”

Q Julie, you mentioned kind of game time decisions there. Maggie, if there's anyone who can absolutely crystallize like the plan, I know it's you, uh, with your kind of strategic thoughts, which you've outlined to me many times before. Um, tell me when we think about like strategies or tools specifically to help maintain that balance, To allow for those game time decisions. What advice would you have there?

A Yeah, my biggest advice is that nothing is more valuable than your time. So work and life these days, especially with so much of a shift to remote work from home, they're so intertwined. I think probably most of us on this call work some variety of hours from seven AM to 11 PM, but this is really flip-flopping between work and personal life back and forth, just like how Julie was saying. So there's been two Big tips that have worked really well for me that I've kind of had to figure out over the last few years. The first one, again, going back to nothing is more valuable than your time. It's ask for help. It's ask help from your friends, your family, your neighbors, uh, whether that's something of, Hey, can you watch the kids for half an hour or asking for help from your partner? Um, it's also, if you are, if you have the means and are able to afford it, Spending some money on things, maybe like grocery delivery. So rather than going and spending two hours back and forth in the grocery store, bringing the kids back and forth to it, just have Amazon prime, spend that nine 99 and get it delivered to your house. And all of a sudden you've got two hours back in your day or cleaner, same thing rather than, you know, spending hours clean. If you have the means to do it, maybe once a month, have those cleaners come and then you all of a sudden start getting hours back. The other strat…

AI assessment note: “two Big tips that have worked really well for me that I've kind of had to figure out”

Q You clearly never saw cheaper by the dozen, but I'm sure that I managed to get in a plug for Slack there. Maggie, you should be so proud of me. Uh, you mentioned, Maggie, that America's worst parental leave policy. Tell me, how can you advocate for parental leave if the existing policy isn't up to parlet? What can we actually do to change things?

A Yeah, absolutely. Great question. I think about it in a force kind of four-step structure or framework. So first I'll start off with the number one thing that's important to do is to educate your company. And I've found that oftentimes policies just haven't been formed. They're outdated. They haven't been reviewed in years. It wasn't actually a bunch of folks up at the top being like, let's make some really bad policies. It was just something that maybe was never worked on, or maybe was really never thought through. So it's a great time to really come together, and I'll walk you through the steps, but to really educate those at the top who are the key decision makers on why it matters to go change these policies. So the first thing that you should really think about doing is pull together data and research of comparable companies and comparable, you know, kind of companies within your industry. So, you know, if we are Webflow, who are kind of the maybe Tots different fund companies and really compare ourselves to as we think about top talent and then really go and look at what are their policies? How are they treating this? Is there anything that we can learn from them? The second thing that's really important to do is to meet with leaders and peers from the company, ideally parents or people who want to be parents or people who are really kind of like allies to families. So re…

AI assessment note: “I think about it in a force kind of four-step structure or framework.”

Q I love that. I totally agree with you in terms of understanding the incentive structure there. Uh, final one for you. What one company sales strategy have you been most impressed by recently?

A There's a lot actually out there. There's a lot of bad sales strategies. There's a lot of good ones. Uh, one company, a tool I had mentioned this earlier that we recently bought was Clary. It's a forecasting app, uh, which, you know, doesn't sound necessarily all that sexy and exciting. This is probably the tool that I'm the single most excited about because it gives me about 10 hours a week back, you know, 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've just been so obsessed with.

AI assessment note: “one company, a tool I had mentioned this earlier that we recently bought was Clary”

Q I am totally with you. I'm trying to think now. I don't know if Calendly does, but they would probably be the first that comes to mind, but I, I, I'm totally with you. Okay. So that's for the leader, for the sales rep, say I'm coming in fresh and bushy eyed and ready to go. Is there anything that I can do to make new relationships cross functionally?

A Yep. And it's actually starting from the very beginning when you start, you know, a lot of times companies will have these random, we actually do. And so did Slack, these random donut meetups were essentially kind of like virtual coffee chats and you just need to put yourself out there. You need to be in different Slack channels. And if somebody posts a question that maybe you want to know something more about message them, introduce yourself to them. Also really think about, you know, as a sales rep, how you're showing up, you know, your, like Essentially your business is your brand. Are you coming out legal saying, Hey legal, I need this right now, right away, get this over the line, or are you approaching it in a way saying, Hey legal, you know, I know you're so slammed. I know things are busy. We're really hoping to close this customer by X date. I was wondering if you would be able to spend some time and potentially prioritize this this week. Let me know if you have questions. Thanks so much. I really appreciate you. And if you look at those kind of two different ways of how I approached it, One makes you feel like a partnership. The other makes you sound like a total jerk.

AI assessment note: “put yourself out there. You need to be in different Slack channels.”

Q 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 hyper growth. What was a big lesson or takeaway for you from that experience that really shaped how you think Maggie?

A 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 is essentially sales is very often, you know, on an island on their own, but the reality is no sales team will ever be successful. Without the support of their cross-functional partners. So finance, marketing, ops, tooling, executives, product, engineering. I mean, there is the entire company has to swarm around sales in order to make sales to be really successful. So it is so important to nurture and foster these relationships and really show deep appreciation to them. I think that's something that I learned to do quite. Yep. Sorry.

AI assessment note: “cross-functional relationships and showing appreciation.”

Q You know, you mentioned kind of building out SDR teams and we've mentioned kind of different outbound. Do I, I'm the founder, you're advising me, do I hire a head of sales, a seasoned leader, if I can get them, um, or do I hire junior sales reps early and start smaller? How do you advise me on that first sales hire? Which profile do I go for?

A Yep. I will rarely ever advise you to hire a head of sales, especially early on. And here's why is you don't, you know, 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, you know, really, really down on the ground, cold calling, cold emailing, of course, a bit here and there, but they're probably pretty far removed from it. So everything I just talked about really points to me that a head of sales is 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 go to go to teach someone, you know, how to …

AI assessment note: “I will rarely ever advise you to hire a head of sales, especially early on.”

Q So when we say done this before, what's more important that they've sold to this type of customer, or they've sold this size of deal?

A That they, actually neither, that they, what's most important is that they have built from the ground up before, or they have seen it very closely. They've been a spectator sport in building, in setting up tooling, in setting up pitch decks, in practicing how to tell a story. I actually don't mind, you know, obviously bonus points if you can hire someone that 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, you know, the persona, the ICP, your product, but what you can't teach is hustle, and grit, and drive, and what it looks like to be down on the ground building again.

AI assessment note: “actually neither, that they, what's most important is that they have built from the ground up”

Q 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 hyper growth. What was a big lesson or takeaway for you from that experience that really shaped how you think Maggie?

A 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 is essentially sales is very often, you know, on an island on their own, but the reality is no sales team will ever be successful. Without the support of their cross-functional partners. So finance, marketing, ops, tooling, executives, product, engineering. I mean, there is the entire company has to swarm around sales in order to make sales to be really successful. So it is so important to nurture and foster these relationships and really show deep appreciation to them. I think that's something that I learned to do quite. Yep. Sorry.

AI assessment note: “cross-functional relationships and showing appreciation”

Q I want to unpack there. You mentioned kind of, you know, 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?

A You can, but I wouldn't fully recommend it. So what I would actually, and this isn't going to quite be as blank as a yes or no, but what you need to do is you need to be able to understand, you know, who are you selling to? What is your market? What is your ICP? What is your persona? And that's 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 up their outbound sales motion. And I'll break down a little bit of what this looked like at Slack, as well as what we're doing at Webflow. And then actually it's okay. If it's okay, let's kind of talk about pure, true to form cold outbound, because I think the word outbound, it's really big. It's really broad. You know, what is outbound? The hallmark of PLG is really reaching out to self-serve signups or small credit card teams with the goal to either upsell, expand, you know, go wall to wall within a company. But then pure cold outbound, which is kind of that, you know, traditional sense in non-PLG companies is a completely different animal with very little similarities. So first let's start with PLG and let's start with kind of this self-serve notion. As I mentioned, when I came into Slack, there had been absolutely no reach outs ever to anything proactive. Everything that we were doing, our single biggest goal, our single biggest cha…

AI assessment note: “You can, but I wouldn't fully recommend it.”

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: “The main reason that you are doing cold outbound is to Educate your perspective buyer”

Q Miss, what's the hardest bit of feedback you've ever been given?

A 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, um, 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 pretty quite a bit easier. So I was early on management career and I thought, you know, coming in Maggie, I'm a new manager. I have all the authority in the world to approve Big old pricing discount. You know, I can do whatever I want. So I gave the authority to approve a 200,000 dollar credit to a customer at Slack that my team was selling into. Oh yeah. Your face right now. Yikes. Right? So went, 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, Christina Kosmowski. 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,…

AI assessment note: “Maggie, what the bleep did you just do? And what did you offer to this customer?”

Q I, I do just have to ask final one before we do a kind of quick fire on advice. I made it like mandatory that we're all back in office again. Um, I just think we're so much more productive in office. We're all in London anyway, but is that bad of me? And like, is remote just so much better in terms of being the best in this balance?

A It's going to be different to every single, um, company. I, uh, you know, I just went from Webflow, which is fully remote and now to open AI, which is more of a hybrid model. Um, so it's going to be, every company is going to have its different choices. The one thing I wouldn't say though, is still always remember to be flexible while in office may be a requirement. Again, doctors, uh, preschool or like different school events or outings, soccer games, parent teacher conferences. In a remote world, it is so much easier to just kind of, like, slip off and go do those things. In a in-office world, it's really hard to do that, so just continue to normalize that. The expectation is that you are in office when you can be in office, but if you need to miss being in office for some other reason, you know, family event, sick event, whatever it might be, it is totally ok.

AI assessment note: “It's going to be different to every single company.”

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 important for companies to have equitable parental leave for both parents”

Q I want to unpack there. You mentioned kind of, you know, 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?

A You can, but I wouldn't fully recommend it. So what I would actually, and this isn't going to quite be as blank as a yes or no, but what you need to do is you need to be able to understand, you know, who are you selling to? What is your market? What is your ICP? What is your persona? And that's 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 up their outbound sales motion. And I'll break down a little bit of what this looked like at Slack, as well as what we're doing at Webflow. And then actually it's okay. If it's okay, let's kind of talk about pure, true to form cold outbound, because I think the word outbound, it's really big. It's really broad. You know, what is outbound? The hallmark of PLG is really reaching out to self-serve signups or small credit card teams with the goal to either upsell, expand, you know, go wall to wall within a company. But then pure cold outbound, which is kind of that, you know, traditional sense in non-PLG companies is a completely different animal with very little similarities. So first let's start with PLG and let's start with kind of this self-serve notion. As I mentioned, when I came into Slack, there had been absolutely no reach outs ever to anything proactive. Everything that we were doing, our single biggest goal, our single biggest cha…

AI assessment note: “You can, but I wouldn't fully recommend it.”