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E43: Geraldine MacCarthy, CRO of Oyster HR, Demystifies Distributed Sales Teams

80m 12s

E43: Geraldine MacCarthy, CRO of Oyster HR, Demystifies Distributed Sales Teams

The podcast discusses managing distributed sales teams, emphasizing that the remote vs. in-office debate is often a false binary. Most companies naturally have a blend, especially when scaling. The key is to assess which roles and seniority levels benefit most from co-location versus remote work. Junior roles, such as SDRs, tend to thrive in shared spaces for mentorship and rapid skill development, while senior specialists and functions like engineering often perform better remotely due to deep focus needs. The primary advantage of distributed teams is access to talent that is not locally available, enabling faster and cheaper market entry, such as hiring a native German speaker in the Bay Area to target the German market without setting up a full office. However, success hinges on having the right infrastructure: collaboration tools, clear norms for asynchronous communication, and explicit expectations around response times across time zones. This reduces anxiety and improves efficiency. Ultimately, distribution is a strategic choice driven by talent access and business growth needs, not a moral stance.

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[MUSIC] Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host Kyle Norton, CRO at owner.com. And every Wednesday, we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes. This episode is brought to you by Pavlov. I'm excited about this one because as a customer of myself, I can tell you it's a game-changer for revenue. We all know acquisition is critical, but how much revenue opportunity are you missing post sale? Pavlov's AI agents plug directly into your entire GTIM staff to find opportunities and take actions that grow revenue from your existing customers, whether it's accelerating time to value, driving expansion, or proactively addressing term risks. For us, Pavlov cut our customer time to value in half and increased our revenue activation from 70% to 90% plus. This product is insane. Learn how Pavlov can accelerate your NRR growth at trypavlov.com/kyle. That's trypav.gov.com/pyle. Today's guest is Geraldine McCarthy, who is the Ciro at Oyster, which is one of the premier remote employment platforms in the market. Previously, she was the Ciro at Personio from Series C to Series E, and they are one of the biggest HRIS players in Europe. That was after six and seven-year stints at Dropbox and Google and increasingly senior roles, and she started her career in management consulting at Accenture, actually. An interesting career arc. Today, we are going to talk about how to manage distributed sales teams. We're going to talk about distributed sales culture as a competitive advantage. Who it's right for? How to approach doing this really well. Obviously, Geraldine has a ton of experience doing this from previous roles, and this is Oyster's business. I'm really excited to dig into this one and appreciate you joining. Thank you, Kyle. It's great to be here and looking forward to a great conversation. Yeah. What did I miss in your background for folks? What do they need to know about your career story as we dig in? Yeah. Thanks. I think you hear a lot of names, probably that are high-soul names that people know. I think what's interesting about the companies that I joined were very small companies at the time. When I joined Google, we were really just getting started in Europe at the time. Equally, when I joined Dropbox, I joined on the B2B side. We had just launched the B2B product, and at the same time, we were just launching Europe. Very, very safe businesses that I was able to support the growth both from an international perspective as a new product perspective. That's kind of what I love to do. Most of the companies become big over time, but I love to go in and have throughout that growth early stage. Very cool. Swashbuckling and market building, who's a lot of money. A bit of that, yeah. Or as I like to say, putting the train track same as the train is coming along. Yeah. There is something really unique about that role in being the leader of a non-core market, trying to bring a, especially, US company to other markets. You've clearly been good at that. So a bit of a warm-up question. What do you think are the key things that you need to do great as an in-market leader, bringing something from somewhere else to Europe, APEC, like what are the things that you think you did well that led us to that success? Yeah. Thank you. We could probably spend an hour talking like that already, but I'm very sure. That'll be fine. That'll be fine, I guess, too. Yeah. I'll try to be as brave as I can and we can dig in more if needed. So I think first and foremost, if you're bringing a product that's been developed in the US into another region, first is to be aware of how that product is going to be used in that region because it's not always the same. Sometimes there's different cases, which can be good on about it. I think, secondly, it's understanding sometimes as local competitors that you're playing against, which actually might have enough around because they're local and they understand the local market better, at least early days. And then I think the third thing is really about understanding as you get the market dynamics, bringing those dynamics back into HQ to help the teams understand what's happening in the region and how you can help to stare for even better performance in the international markets. And I think that's probably one of the most challenging things to do, depending on the stage and maturity of the business. And so if the business is early stage and internationalizing, most international markets are pretty complex when you compare to the US. So obviously, you have a lot of different states, but it's a relatively homogeneous market. Everybody speaks one language. Everybody uses one currency. When you go into Europe or APAC, there's many languages, there's many cultures and so cultures. There's many different currencies and many different legal systems. And so as an international leader trying to synthesize that information back in a way that's coherent because you won't be able to do everything for all of the market. And just on what are the really big needle movers in the very kind of heterogeneous market and versus what are the things that are kind of more nice to have or that you can solve at a later stage and so that you can help the HQ teams understand where to prioritize and drive impact. Yeah, that makes a lot of sense. I had a bit of this experience in my first tech role having teams in Amia and APAC and spending time there and just starting to get an appreciation of just how different the market is. Because as a Canadian, it's not just that the US is homogenous. Canada is basically the same market. More or less. We're a little more risk averse. We pay in USD for software. So that's almost all the same. So it was a very different experience trying to manage at the time. It was BDRs in Paris and Cologne, London and each of those teams having very specific ideas how they thought things needed to be managed. And this will transition into our remote topic. I'm going to come back to the, we're going to weave in this internationalization theme because I think it's important for a lot of companies that are going overseas. Because that is inherently remote now. More than 100%. Yeah, and I think actually doing it, we can talk about remote in more detail. But whether you decide that it's a remote way that you do it and I think oyster does a great job doing that. That's one of the reasons why I came in to help all these companies to scale internationally with their businesses. So whether you're doing it in a remote first way or whether you're doing it in office culture effectively your ways of operation will up remote at least in the early days until you've reached scale in those international markets. Yeah, for sure. So you've led international teams across many markets now across Google Dropbox, Personio, you had a bunch of markets, correct? Yes, we were across most major markets in Europe, yeah. And now oyster is everywhere, sort of by nature of the platform. And I'm curious, what are the biggest misconceptions about scaling remote teams and specifically scaling remote sales organizations? Yeah. So I think first and foremost when you think about scaling remote teams, I think particularly now, I think during COVID we were in a certain phase. So right now there's a lot of talk about returned to office and I think for a lot of businesses that make sense that that's what their culture requires and what they need to do. And it almost feels like you're sitting in these two separate categories. You're either fully office based or you're fully remote. And in general there's a lot of companies that have made a very principal decision to be one or the other. And that sounds really clean. But in reality the vast majority of companies have some blend where they sit somewhere in the grey zone where there's a certain number of people that are remote. And so I think there's this kind of misconception that you either have to be one or you have to be the other. And that's the only way to be successful. But actually I would challenge a lot of companies when you go in and look at it to say, okay, well it's 100% of all of the talent that you can find. Can they be based in that specific location that you live in? And honestly I think when you ask people they say, oh and actually that's true because this person with very specialized skills sits over here in the stage that we don't have an office in or this person over here who's setting up a new market force. Yeah, they're by themselves over there, but the rest of us are all in the office. So I think any company that is growing, and particularly growing fast, is going to continue to have some level of ambiguity or greatness in how they structure. So I think for me I would just challenge that kind of conception that everything has to be one or the other and actually it can often be quite in between the two. And rather than not being a disadvantage if you accept that for what it is, it can really play to your advantage as well. And so we're going to get into how to do it well because I very much agree with you. I think this is such a silly false binary. that people like to present, especially on LinkedIn because it's good for clicks. I won't name any founders or CEOs of remote management companies who are prone to do this, but there's like this click-bady thing on LinkedIn where people make it like a moralistic argument. Like in person, if you are making people come to an office like you are a bad leader, or if you are doing remote, you are letting people like work from the beach and basically not do their job. And it's sort of, it's just like a nature of social media and engagement farming. But I very much agree with you that in reality, every company has some level of variance. It could be a cross team like we, for example, we are fully remote in terms of engineering, like we'll hire developers anywhere. Sales is now consolidating in our Toronto sales hub, but we'll likely graduate people out of fully in person as they hit a certain as they hit a certain sales level. Like, you know, if you're a, I'm not going to make an enterprise rep come in five days a week into the office, that's silly. But in SDR, what we've seen in the data just tremendously benefits being co-located to their manager and others. But I'm glad that we're already getting here because what I wanted to tease out of the conversation was nuanced because it's completely missing from this conversation. And so I want to talk about like a framework for that decision. How do you advise companies when co-location and in-person presence is advantageous versus when you should be primarily remote across what functions? Just walk people through maybe a decision making framework or the heuristics that you've used and you help advise your customers on. Yeah. So look, I think there are some worlds that are not really more and trend more towards remote. You mentioned engineering. I think that absolutely is a role that tends to be more remote focused. And it's by way of the type of work that people are doing, which tends to be very much, you know, deep focus and actually often even in companies I've been in where we've been very office-based. The engineering teams tend to not just like the the distraction and the the system. It's a rant actually remote work or work from home can really help them from that. So I think that's probably one to think about. And then there's other areas. In general, I think where folks are more junior, I think having having everybody together tends to work better because the speeds of the learning between each other. You mentioned onboarding and ramp time. That's something that's really important as well for more junior folks if you're hiring more on the kind of grad level, media hours. Yeah. In particular, I think is a good case so to have people together and to learn from one another. So I think it really depends, yes, depends kind of unit by unit, but it also depends on the structure within your business as well. So actually, you know, you can imagine probably if you're sitting in some parts of the universe, you have really great access to talent no matter where you are, like no matter what roles you're looking for. So, you know, if you're sitting in the Bay Area, there's probably great engineers. They're in demand, but there's a lot of them around. There's eye supply. There's also a lot of people that have done similar roles before, but if you're starting up a business, you know, somewhere that has less of a beltage tech ecosystem, whether that's somewhere else in the US or in a maya or APAC, you may want to think about having a much more distributed team because that distributed team allows you to get access to talent in a way that if you were sitting in a small city in northern England that you just wouldn't have that access to be able to get them all together. So, I think that's probably one thing to look at. Interestingly enough, our data shows that, you know, when you think about where you're accessing talent, the vast majority of people that are in these distributed roles tend to be on the more senior end, and that's because they're, it's talent that people are looking for out in the market, and probably doesn't sit near them. So, kind of validates the point that I just made about how we think about the structure of, you know, how you think about where you would, how and when you would hire, like, for a very locally based versus more globally distributed. And so, that's the kind of second area to think through. And then the last is, you know, as you're going in to think about, if you do want to have a more distributed workforce, making sure that you have the infrastructure to be able to do that. And by infrastructure, I mean lots of different things. One, of course, is the tools and technology that everybody can work together, whether that's about your messaging, emailing, collaboration tools, but also about how you can communicate together. So, that's one on the infrastructure, but also working norms for how you work together. So, if you are a globally distributed team, and so right now, I'll call you and I are talking this afternoon for me, and it's morning for, for you. So, if I was to send you a message, first thing this morning, when I got up and expected an answer from you straight away, you would be like still asleep and blissfully unaware of the message that had come through to me. So, helping people to understand the time differences where they work through and what that means. That can look very different for different companies. Some companies like to have like dedicated time where they all work together. And that means sometimes that some regions get up a little earlier and finish earlier. So, start later and finish later, or it might be like being very clear on your calendar or on Slack, when you're available. So, people know when to expect responses back, because I think there's nothing worse than sitting in front of your screen with I've been able to look at people. And then you want her to response, and you don't know why. So, but if you know that they're not going to go back to for minimum four hours until they're in their time zone, it kind of relaxes your nervous system. You're not concerned, okay, does that not resonate? Like, do they not care what I wrote? You can say, okay, that'll be on I want to say they're in work and I can move on to mine. So, lots of things to work through, but I think making sure one that you understand why and how you're hiring, two, the types of folks that you're hiring for, and then three, if you do decide to go global, make sure that you've got the right infrastructure in place to ensure that it's going to be successful for you as a business. Yeah, I'm going to come back to infrastructure in norms and go a lot deeper there. Because it's just simple stuff like leaning into asynchronous. Like, if you're going to have people all over the world, you can't run a synchronous culture where you're getting work done via slack back and forth. You need to write fully, fully formed thoughts that somebody can pick up on their own time and give you a fully formed response. So, there is a one pass back decision making process as opposed to many of us. It's, hey, I got a question about this thing. Okay, what is it? Well, I got this deal that wants it, wants whatever. Okay, we'll tell me more. And then like that, that back in forth doesn't work remote. But we'll come back to the best practices. So, in terms of who remote is for? So that's the type of role, the type of seniority would be informative. What about the type of business? Are there certain businesses that lend themselves more to a distributed approach or types of sales team? Because obviously enterprise is naturally going to be fairly remote by default versus SMB. What are the other sort of key indicators that would tell a founder or revenue leader how they should be thinking about building their team? Yeah. And so specifically, we're talking with sales leaders in general. But revenue in general. Because we've got lots of CS and marketing leaders who listen. Great. Yeah. So I think specifically for revenue as a whole, it's really about, for me, I think it's about access to talent. And you can get access to everybody locally and everyone is, we were talking about everyone, this is in 10 blocks of each other. Why not? Like, what's the point in all being distributed? We're still humans by nature, still like to be around other people. That seems like a waste of time to not be together and to spend time together. But really the opportunity for distributed work is getting access to either different types of talent or talent that you cannot get in the location that you're in to make sure that you can have your company grow. And that might look like, for example, let's say if you're a US company and you've decided Germany is the target market that you want to go to. The biggest economy in Europe. So it's probably one of the places that you might want to land first, actually to find a native German speaker who does sales who sits in the Bay Area. Yeah. Which you may not be ready to set up a whole office with 50 people either. So getting that balance right between the two, I think is important. So that's really how I would get folks to think about distributed sales scenes and distributed revenue teams and how they think about it. And on the other side, I think distribution can be really helpful as much as you talk about enterprise versus SMB. Even if you manage to find out like unicorn German speaker who sits in the Bay Area and is a perfect fish for your product and your culture. And having the folks who sit in the region are often much more often much closer to the culture and achievement of what's actually happening there in that moment in time. And so they resonate and they're much more relevant to the customers that they're talking to at the time as well. So I think there's probably lots of reasons to do it. Often it starts off as something small and as an experiment. And then they see that it's working. It's usually much cheaper and faster way to go out into market rather than having to do all of the complexities about setting up new entities. And all of the things that we're required to do, that include in the bank accounts and legal documents and all of that. So you can go much faster by having a distributed worker and also setting that up through the system that can afford record. Yeah. It's like we need a different word for that. Because when people say hybrid, it generally means people are working some days a week in office, some days a week at home. But then there's this other organization type, which could be-- like for us now, we are for SDR and BDR, new hires, five days a week fully in person. That's the requirement. But then half the company's fully remote. I have got big teams in Latin America, our developers are all over. We have an executive HQ in San Francisco. Do you guys have a word for that? This small-- I don't have an official word for that. But I really like the way you're describing it because I think it's really thoughtful about what you've done and that you've decided what roles need to be-- what roles need to be in person, where you really have everybody collaborating together live, versus which of the roles that can be much more distributed. And I think what you're also highlighting is that it doesn't have to be like in many companies they think about it's kind of like it's A or B. But actually, often there's much more nuance in that in terms of how you think about it based on the teams that are working through it. Yeah. And life is about trade-offs. Like there's trade-offs to everything. There's not one thing that's better. We're bringing these teams-- these sales teams in person. And there's significant advantages. We've seen ramp as much faster productivity is really high. But there's going to be implications for a bunch of team members who aren't in that office, who may feel left out. Or we've had people decline-- not BDR offers, but AE offers, because they got a competing remote offer. And that was important to them, which I understand. But going into any of these things with an understanding that nothing's perfect, I think, is important. So let's talk about how to do it well. So in my heuristic here, similar to you, I think all companies are going to have some variance of in-person versus remote. There's far fewer companies now that are fully fully remote. There's the automatics of the world, the Git Labs of the world. Some great example, oyster. Great examples of people doing that. But for the most part, I think, most companies have some level of in-office now, but still lots of remote. And the danger is that you can work as a remote company and support people in office. You can't really work as an in-office company and support remote people well. And I think you basically-- I think the default should be remote work with the principles of a remote company, because then that is a higher floor for communication, training and enablement, all of these things. And so I think the lesson-- because especially for people listening who are primarily in-person, I think the conversation is still very relevant, because it's harder to manage a remote team, it's harder to manage and build remote companies, because you can't just swivel a chair. So I think these are primitives that all companies should be implementing. So we mentioned it a little bit. So infrastructure and working norms were a piece of it. What are the building blocks of a high functioning remote team or remote company in your mind? Yeah. Yeah, I think there's a couple of things. So we mentioned tools and technology earlier. I think it starts with that. And I don't think you can really scale a company unless you've got the right tools and technology. So you need to make sure that we have-- it's an individual choice for water, the tools that you would select to help your company grow. And actually, for anyone who's interested in what that looks like, we've written a full open source document. It's on our website. It's called The Reef, which you'll find on our website. And it goes through what we have used as-- what we view as best-than-class for attooling and technology perspective and how we view those. Often, it's probably most of the tools people have already heard of. So we're using Slack for internal collaboration and for messaging. We still use email every now and then, but not so much mainly Slack. And then you're using tools like Notion to make sure that you're not just having these really long threads for all your knowledge or your sits and Slack production. So you can do that deeper level of collaboration, thought through form processes where you can work through stuff. And then you need obviously communication, whether it's Google Meesh or whether it's Zoom or something else that you're using. But there's a lot that you can use. That's their general specific ones. Then you need to have the ones that you need per team as well to make sure that the teams can work together within their individual departments as well. So I think that's first and foremost in terms of what's needed. Secondly, I think what you need is the norms around how people work remotely. Whether that's around expectations, around hours that people are working. So the people know when to get a hold of you or when they can expect to hear back from you. Or the people understand what's the urgent thing that needs to be handled versus something that can be left till later in the day. Because actually often, depending on where you are in the world, you're picking up stuff from folks who've been working during the working day and you're filtering through, OK, what's the most important or the most urgent stuff I need to get through first while somebody else is still in working zone and then that they can wrap up. So we call it as follow the sun to make sure that you have the right process for how you can pick up that work. The one thing I would say about that though is sometimes you find that people hold really like steadfast. This is my working time zone and that's all that can happen. But as in any business, when something goes wrong, the rules can always be broken. So if product breaks or if something goes really wrong, somewhere you need to be able to say, OK, well, I understand these are like, this is what we should be doing 90% of the time. But we need to have a 10% exception for when something goes wrong that we can come together and maybe you need to work a little earlier, a little later, same as anywhere. You know, if you were in the office, that's true too. But I think you need to articulate that as a business when you're remote because you have already set structures around kind of working norms for when people are available and when to access and when you can get in touch with people and so on. So I think hope, making sure you have the structure to align for that, but also that it's not so firm recession zone that people can't move around from us. Yeah. And then I think the last piece, particularly for distributed work and for folks who are working from home is, which is really important, is to make sure that there's a really good home working environment. And so what you see, like often in offices, they're by default already set up to work really well. People have, you know, usually seats that kind of swivel, which is like good for your back, they usually have a second-year in a monitor when you're working from home. That's up to folks individually to do that. And lots of us know how to do that. Like it is, "Olders may, you know how to do that because you've had enough back injuries and bloody blood over the years because you haven't done a problem and you've learned from experience, but ideally you don't get to that stage and you can help people with best practices on what all of that looks like." So that includes, yes, one having the right structure in place for how you set up your home working environment. And ideally you're not just hunched over a laptop and become like stooped over at the end of six months working in one business that you have the whole set of that you need in the same way that you would have in an office. But also with that is making sure that you take enough micro breaks during the day. And studies have shown that people who work from home actually take less breaks. So you need to be a little more intentional about it as one. To remember, not just a quick to take five minutes for lunch and grab like a packet chips from the press to eat them and to keep you going, but of course, if you need to do it on a busy day to do it, but that you have that intentional break, if you were in the office, you would probably take a couple of minutes as you're walking from meeting to meeting to talk to somebody you would have to go from a different meeting room to a different meeting room. You'd probably at least one or two days a week have lunch with some of your coworkers and sit down and have a chat so that you think about how you make those structures for your work when you're working from home as well. And that probably saying silly and it's not something certainly that impacts people on day one, but over kind of like three, six, 12 months it can add up. And studies do show that people who work from home have a higher chance of burn out if they haven't put those rituals in place. So it's not by getting it perfect, but it's about making sure that you have enough in place that it works for you for the long run from an overall energy and well being perspective. Yeah, up until recently 90% of my team was not co-located with me. One of my directs is the lives like three blocks away, which was great. But other than that, everything is on a screen. So as much as possible, before a meeting starts, I'm like, do you need a screen share, or can we walk and talk? And just having enough, usually it's like two meetings a day. We'll be like walk and talk. And I've got the notion app on my phone with the stuff we want to talk about in the meeting. And that's just an important way to move your body. I can plant myself in the seat. And I got a standing desk and all the stuff. But you can plant yourself and not move for like eight, 10 hours. So I agree with you there. The other thing I think I want to double click on is like, is working norms. Because there are some of these principles that especially in an office are just part of the culture you see and hear around you. But I see a lot of companies go wrong as none of it's written down. Their working norms are not documented. So when the pandemic hit, I was at Shopify. And Shopify was one of the first companies to announce, we're going fully remote. We're not going back to an office. So just get past that. And I had forever worked in sales environments where it was like a bull pet. And I've got almost my entire team with me. And this was a shock, like a very rude awakening. And I was not excited about it. And so I had to go study, basically. And I studied all the best remote companies. And luckily, there's guys like Matt Mullinweg, who write a whole ton about it. And I could learn. And so out of that, I wrote this digital by design, working guide for our business unit. And you don't realize it until you're in there. But there's a lot of norms that take intentional decision making. What do you use Slack for versus a phone call versus writing a notion document, response time expectations? The default should be, if you need an answer, don't send a Slack. Pick up the phone and call somebody if it's deal-related or whatever. But unless you sit down and think thoughtfully about it and actually make those decisions, then you just end up in chaos, I find. What are the parts of those working norms that you think people need to give the most attention to? Where do we need to make intentional decisions about what norms are establishing? You've talked about following the sun, which is a good one. What else? Yeah, I think that's a really good one. So I think one is by being intentional, where something needs to be. And I think the other piece is about just being very clear in your communication as well. So actually sometimes when we talk, we kind of the words come out and the thoughts are getting formed as they're coming out. But actually, when you're writing something, and you're expecting someone else is going to read it, making sure that that's really clear. So much more abolished and the people understand what it is that you need to do. Whether, I think particularly for globally distributed companies, often a lot of folks English won't be their first language. So have you written it in a way that no matter where you are in the world that is going to understand that there's not these kind of cultural nuances that maybe don't translate? Knowledge is the right. Yeah, language by language. So I think that's a big one to make sure that you have that right. And then I think depending on where you sit within the organization, making clear how and when people can contact you for different things, I think you're absolutely right. And I say to my team as well, if you need me for a deal, don't wait until the end of your day. You just slack me. If you don't do that, you slacken. You need to straight away. You message me. And if I don't go back to you within 50 minutes, then you call me. So there's those kind of escalation paths that you can use for that. I think the other piece on that that we-- you didn't talk about it. There's a lot that you can do systematically about where and how you communicate stuff, with the other pieces of how you build trust with the people that you work with. It's easier to build trust with somebody when you've met them in person, when you've got to know who they are and even at a very basic level, when you meet them in person, what height they are, when you're remote, you don't have those pieces. And so there's much more requirement early days in any relationship to set up some of that trust. That can be done in lots of different ways. It can be done through, first of all, spending more time getting to know the people up front as you get started. It can often-- what I've seen work really well is a work with me document, which I know a lot of companies use for you describe. This is who I am. This is how you get the best sides of me and usually you can link in whatever and studies you've done, whether it's your like anyogram or whether it's-- Yeah. --their library, whatever other kind of personality studies you've done. So people know, OK, this is the framework for how I can deal with this person. And then also more details on how to get the best sides of that person. That can really work in terms of building trust. Especially for leaders. I think every leader, I call it-- my document's called my blueprint. But yeah, the work with me, doc, or what's the other-- oh, a read me. People will call it. But this is who I am, what I'm about, hobbies, personal stuff. So you can build relationships at scale. But then for me, one of my principles in there is opinionated but open. Because I'm a pretty opinionated person. I think a lot about sales and revenue and leadership. And so people will bring me things. And I have to warn them that, hey, I'm probably going to have a response. I'm going to have a bunch of questions. And unless I've explained that it's-- I'm going to feel opinionated. But I'm actually really open-minded. And I'm asked-- I'm drilling you with questions-- not to poke holes in your idea, but because I'm pretty curious. But I'm open. And I want to be proven wrong as long as you bring me ideas that are well thought through and backed by data, where possible, and holistically oriented. Because people will bring me ideas. I'm like, this sounds great for sales. And this sucks for everything downstream of sales. And so in the doc, when I explain people opinionated but open, it's so that they are pre-worned against what I find to be the things that make working with me sometimes challenging. Or people will get intimidated by that. And so you can crystallize that stuff. So you don't have to go through six months of, oh, by the way, this person doesn't bring me ideas anymore. Then you have to catch that and explain, oh no, Geraldine. I'm not second-guessing you. I just-- this is how I engage with ideas. And so I think it's really important that people, again, remote or in person-- all of these things translate-- do that work. Yeah, I agree. And that you ask the questions because you care ultimately. If you didn't care, you wouldn't ask the question. Yeah. Yeah, I think that's great. And I think that the team know who you are really helps. I think whether you're in person or remote. And then I think with trust. So once you've built that trust, it's much easier to be much more straight up and honest with the folks. And I think having-- sometimes like all of us, we have to have tough conversations or crucial conversations with different people on our team. If you haven't done that from a base of trust in the first base, that can be really hard. Yeah. Building the trust as a foundation without actually helps to then move to the next level of what you want to work on with the team. And then actually those very straight up conversations if it's done from trust in the first base fails even further trust within the team, because people know what they'll get from you, what to expect. So I think there are probably some of the key things that I focus on. And then we focus on in oyster. In general, we try not to have meetings, for meetings, sake. And to where anything can be done, either through email or Slack or another format, whether that's notion or other format, let's do it that way. And then if we need to get on for 15 minutes to talk through, let's do that. But let's not spend an hour talking through it ourselves as well. And we only have a small number of hours that we work together in the same team. And again, you have to be thoughtful and clear about those norms. And so one of the norms we have, because I'm really like anti-meeting. It's meetings are poorly run, and they can be a waste of time. So in our operating methodology, so I have this big long document that's like, this is how we operate as an organization. One of the principles is like when to hold a meeting. If your meeting is going to be 90% you talking at people, it's an update or you're explaining or it's data, that is not a meeting that's a recording, or that's a document. Because then I can listen to it on 2x speed and slow down on the important parts. You can flip-- you can skin through it. We don't need to find those crossover hours. But very few companies have this written down. This is when we use meetings. This is how we write documents. This is how we make decisions. This is the other thing that's in our doc. For decision-making, don't call a meeting to brainstorm. Don't bring seven people onto a meeting to grind out from scratch and idea, because there's a bunch-- there's really good stuff [BLANK_AUDIO] Duke's book, How to Decide on why group brainstorming isn't a great approach. But if you need to make a decision, you write a document, be clear about your problem statement and in notion we've got templates for this stuff. So when you create a project, it walks you through, this is the problem we want to solve, these are the desired outcomes. When you take the first pass at drafting this thing, people can read it, respond, comment, then we generally come together to go through comments and have that like valuable synchronous conversation. Yeah, that's great. But it's got to be written down. Yeah, but you know, I think what you're talking about, I think as a, when you're a company that have people that are not all in the office, you have to be very intentional about it, but I think all of these principles, if you can apply them in a fully in office culture as well, actually they benefit from it as well. So again, we're talking about it's not one or the other, it's the same thing as well. It's maybe kind of a gradient of what you need for I think it benefits everybody. Yeah, especially because writing is thinking. You quickly understand how strong your ideas are or how like clear you are about the problem you want to solve once you're forced to put it on paper. Yeah. So I think that's the way I look at the sort of the ontology of that idea and how things connect. And like, oh, well, that's sort of a master. These are actually two problems that I've mashed together in one or I'm solving a symptom and not a root cause. Writing is the ultimate equalizer for that. Yeah. And I have to tell you I had a great example of that this week where I'm picking up a program that we looked at a year or two ago and then we kind of let it slide. It was before I was in the business and luckily the person who had looked at it before we had in the way that you've described it really well documented. It's always able to pick up a Google Doc which was extremely well written with a lot of research already in there that I was able to pick up and say, okay, this is what has already been done. So rather than me having to start from scratch and rebuild everything and do the research again, it's already ready to go and I can now bring it to the next level. And so I think if you're thinking of edges from that perspective, whether you're office-based or whether you're distributed, it's a really helpful way to make everybody more productive. You leave behind something that could be used again in the future. So yeah, I 100% agree on the writing over brainstorming and then leaving it in people's brains and then when they've left the business, it's gone with them. Yeah. And meetings are so costly. I feel like, oh, let's get together and hack this out. Okay, well, that's seven people at a whatever $100,000 salary and whereas one person could have sat down and done the work to think something through. I find myself pressing on this a lot. Write it down, put it together. We do our monthly business review and one of my constant pushes is to all of the updating and read out is all done ahead of time. We do all the comments and then we should be pulling out only the things that need to be like really actively discussed and debated and you get so much more done that way. Yeah, I agree. Are you ready to level up your go-to-market strategy for 2026? Then don't miss GTM 2025, the only B2B tech conference exclusively for go-to-market executives. Join a thousand other revenue leaders this September 23 to 25 in Washington, DC for an exclusive executive only experience. This three day event is hyper focused on connection, strategy and execution. Expect hands-on workshops, in-depth strategy sessions and curated opportunities to build relationships with BPs, CXOs and founders facing the same challenges you are. You'll stress test your GTM approach, align your team and leave the real actionable insights from top performing leaders. Don't miss the Must-A-Ten conference designed to help you boost go-to-market results in 2026. Visit attendgtm.com. That is att.edgtm.com to secure your spot today and don't forget to use the code top line for 10% off your GA ticket. I want to go back to building trust. Are there any ways that you have found? We've talked about spending more time with people to get to know them upfront, read me document, any other key ways that you can boot up trust or accelerate trust building in your experience? Yeah. I think there's, so first of all, I believe in radical candor and being very straight up and honest people, it does actually by default build trust. I think often people are afraid to really touch on the stuff that you really want to talk about. But the other way is just about calling out what you see. So for example, sometimes you're looking at someone on your team and you're thinking, they look kind of stressed or they don't look very happy right now, but they haven't actually said it to me. So my general approach is to say, hey, maybe it's just me. Maybe I'm completely misreading the situation, but you look like you're pretty stressed or you look like you're not very happy right now or whatever that thing is. You want to talk about it. Sometimes people might say, oh, I just had a really bad sleep last night. I'm like, just tired. Sometimes people might say, there's a whole lot of personal stuff going on and I do where I don't want to bring it up. But the majority of the time people will actually appreciate that you have noticed that about them and say, thank you. Actually, I wasn't going to bring it up, but we got interaction with somebody else and didn't go my way or something's going on in my personal life. And it's, I need some support to figure out how to manage that and work as well. So actually just being very proactive about that, if I think people know that you care about them and that you notice, I think the easiest thing to say, well, that person looked a bit stressed, if they have a problem, they'll come and talk to me, but I think you as a leader proactively bringing it up, I think is important. And I think that's kind of in one-on-ones. I think when you're working with like a wider group, and this probably says obvious, what I think you should stay what you're going to do and then you should do what you're going to say. And I think there's a lot of leaders that say, oh yeah, that's great. And they take feedback on board, but they actually don't come back to say, okay, I heard like these six, whatever number of pieces of feedback from you over this week. These are the three things I'm going to work on and here's the reason why. And these are the things I'm not going to work on and here's the reason why because I think often in organizations, you know, folks think so goes up the chain and they're like, well, where did it go? Did anyone even agree? So just closing out those feedback loops, I think can be really important for people. I think sometimes leaders were so busy just going and delivering that you forget to close out the feedback loops to say, these are the reasons why we're not like, of all the things we discuss why we're not going to do those things. And look, if you see 100% definitely come back and challenge me on that, but I think usually people say, okay, I get it. That's that's the reason why it's a good reason why we haven't done that. So across the organization, I think that's an important way of building trust with the teams as well. This is a key, this is a big weakness of mine because I'll, I'll zip through 10 meetings in a day and there could be a variety of, of small deliverables or just like things I need to do and the little things fall through the cracks. And I keep trying to build a system around me to catch more of it. And I haven't had a ton of success with the AI note takers like properly getting the right action items because, you know, so much of the time that there's like six action items and three of them are not totally, not actual action items. They're not things that I committed to doing and they don't go into my notion task manager. And so I'm, we're going to test out notions, call recorder. But you need it because I don't have a system like I need a system for it or else you just stuff drops like you sort of need to do everything. Even going back to, you know, radical candor as a foundation. Well, then you need to be clear with people up front. Hey, by the way, I believe in radical candor. I believe in this like conscious style of leadership. And so that's what it means. You should go read the book because that's how we're going to operate as a team. But unless it's explicit, it's tough. I agree. I agree on the AI note takers. I think, you know, they're still improving day by day, but actually I think what happens is you get the macro notes that on a very basic level, I just take the bait on a different color post-it notes, which seems very old fashioned. Yeah. Different color means different thing to me. And that's how I categorize what I need to get done at different stages. So until I find something at better, my organizational system. I might have to do it. What about communication systems? This is another part of building remote teams that I think people struggle with. You hear so frequently the non-HQ teams feel like they're like, I just never know totally what's going on or I'm always like a week behind on things. What are the best practices that you've used to scale communication across broad teams? Yeah. So I think there's a couple of things that some of them are culturally that you need to figure out that's going to work for you. One thing. that I really like, particularly in early stage businesses, is very clear and making things as transparent as possible. So that doesn't always work. There might be for legal or financial reasons stuff that you cannot share, like with everybody in the company, but my preference is by default, everybody's calendars are open, so everyone can see what you're working on, all Google Docs, all of your working docs are by default open to everybody, and it's unset similarly with Slack groups that by default they're set to open so that they're discoverable for anybody that needs anything on a particular topic. And of course, this often needs to be locked for any particular reason that it can be done, but the default is a goes one way rather than the default is it's locked and then you have to go for a list to get it. And defaulting conversations to be in channels and not DMs, I'd probably say this twice a day. I'm like, somebody will send me a message with one or two other people in a DM and my response is send this again in XYZ channel. Yes. Don't have this conversation here. Or if it needs me something new, if it needs me a new channel, that's fine too, but I 100% agree on that as well that it's open and that folks can get it. So yeah, that's a big one for me, and it sounds probably, it's very easy to do, it's just the defaults that you set, but it allows them, out of where you are, that you can get the information that you need at any one space and time. I think the other piece that you kind of touch on is like HQ versus non-HQ. So when you're in HQ, you kind of have that center of gravity around you, people are around. And I think the onus is on the leaders in that location to really make sure that they are openly communication with the other teams. That might mean that there's specific communications that only go to them so that they get updates on what's happening, or it might be that you're very intentional about when you're communication to the wider team. So I don't believe in just having like a monthly all team and that's when everybody gets the updates actually, I think you should be sending at least weekly pulse updates out to your team and that's how they can get information. It's also true that different people like to pick up information in different ways. So when I'm sending out, I will send out a video, but I will also send it out like a summary in like, well, a format because it'll be prefer to read than listen to my awful voice for like, you know, five or ten minutes update, a very fast going on. So they can listen to it that way and they can absorb the information that way instead to making sure that there's multiple ways that they can get the information that they need and in a way that works for them. My job as a leader, whether I sit in HQ or whether I'm a leader of the organization, is to make sure that my team can get the information in a way that works for them, not in a way that works for me. And so I think helping the HQ teams to understand some of that can be really helpful. I think the other thing that often happens in HQ teams versus kind of regional teams is sometimes things happen. A sales leader bumps into a product leader walking down the corridor and they have a two-minute charge or something and something's decided, but that impacts somebody who sits in one of the regional teams. So just having that thought pattern of updating the teams of age, the conversations happen and that it impacts them, you can never make a work 100% in such a time. They'll always be a certain amount of, you know, sorry, I forgot, but as much as possible thinking, oh yeah, that person, the other person also needs to know. So you get that communication aid to them rather than one month later, there's change in the product and weren't consulted on it. So having the right rituals for some of that I think is important as well, so it's not just about like water, cooler, torque and decisions, but actually systematizing some of that. And AI plays such an important role here too. Because you can do the video, get the AI transcript or get the transcript of Dumpin and Shabby TBT. It'll structure it into the right bullets and you ship it with the update. The that flow, I think is so important. It's funny because all every single one of my internal meetings is recorded with the transcriber. Now that I'm having some meetings in person, my instinct is to be able to go back and query my meetings and I was like, oh, damn, that was an in-person meeting. I don't know. Like I don't have a place I can go back to. And then I start thinking I'm like, this is why the pendant is going to be great. AI recorder, pin or whatever it is. Yeah, exactly. We all need it. Yeah, you were going to say something else there. I was just going to say we kind of spoke about tooling earlier on, but I think it's also important to think about the tools that you need, whether it's like fully or most or whether you're like HQ into other teams and how you share information. So yeah, a lot of stuff you can, if you need to share stuff that you can share it and sometimes you need to share very detailed information of your, for example, Google Sheet or an Excel document and you need to show someone, you know, this is like the information where it sits and we're very detailed in a calculation, doing that in a way that's recorded and you can point to it and actually show them how to use the community as well. So you can record on Zoom, you can use Lume or whatever works for you as a way to do it. It doesn't always have to be this kind of like, I'm going to send something out and then I'm going to send the supporting document, but actually show them where to point to in the documentation as well. Yeah. I think the other thing here about communication that's important is just having like consistent rituals. Like for us, my leadership team all fills in this weekly maple, which just stands for metrics, like the metrics of their business. It is advanced. What did they do that week? P is planned for next week. L is learnings and E is emergencies, like things that you really need my attention on. And everybody writes their updates in the same place so you can see every single other leaders updates. You can tag other leaders in it. They can comment. This is sort of the default to open thing, which I really like you're talking about, but also just having like a consistent way that you do stuff is so critical on communication. Even the way we communicate stuff to the team, we've got this traffic light model. There's green, yellow and red changes. Like something small, you can just blast out a Slack update, but a red is okay. We need three points of contact. We've got to have a video. The managers have to talk about what their reps and team meetings. It's got to get updated in notion and guru and there's like a there's a system for it and building those foundations takes a lot of time up front. Like it has not been easy and we've invested significantly in enablement to be able to do these things, but worth the effort for sure. Yeah, 100% worth the effort. I do agree that that it takes investment up front, but actually longer term makes everybody much more productive and also builds trust because everybody has an expectation of what they can expect and when and where it sits in a framework for them. Yeah. The other mistake I see people make on communications is too many surfaces. It's some information that's in a Google Drive or a doc. Some information is in guru. Some information is hidden in Slack and so building the muscle to try to bring everything back to one or two places. Everything you need to know about doing your job as an individual contributor owner is in guru. If you have a question about the approval matrix or the DQ criteria, like that's all in guru, you can get to guru through Slack. And then notion is internal docs and planning and project management, but we try to really limit that surface area creep. People come in and they like to write Google docs. That's what they're used to. That was me. Shopify was on Google. And then I was like, oh, now I've got to learn notion. Now I love notion, but it's like. I agree with that. The people know where to go to find the right information that they have confidence of where they're going is the right place. Maybe it's subcomponents. We talk about a lot of stuff that goes right, but a subcomponent of that that goes wrong that I see companies doing is in Slack where they post the same thing, either multiple channels or you have two people posting similar updates. Because from a communication perspective, people want to know, they want to get it, get it one note that that's it. And if they're getting it like three or four times in different channels or in different formats, they actually switch off. Because they think, oh, that update, that update that I get from Carl over there every week. He always duplicates stuff that I'm getting over here. Well, you know what, the week that he doesn't, there's new stuff in there, then you've missed it. So we intentionally about who communicates what and what gets communicated where really helps the team to understand what they need to absorb. And that, you know, particularly for a slide sales leader, I really like them on a, particularly on a Friday to wrap up the weekend to point their teams to all of the things that they need to be on top of. And if you can say, have you done this Slack channel? Have you watched this enablement video? Have they ticked, you know, the three or four boxes for the most halves? And then, you know, everybody has at least the minimum threshold of information that they need to do their job on that week. Yeah. My enablement leader two companies ago used to have stuff sales should know. And every week there was like the stuff sales should know. And as long as you went through that document, it might point you to Slack channels or a document or a release or like a release page, like those were the things that we expect you. It's like, this is what you have to have read as a sales rep. Everything else, there's lots of noise. And you can read it or not. It depends on how well informed. But that was like, that was an important drum beat for us to make sure that as a baseline, These are the things, like, if you're a sales rep, you have to know them, you have to read them, like, please, like, just check those boxes to, 'cause Slack can be, you know, an insane Christmas tree of overwhelm. (laughs) - That's all right. (laughs) - You know, I mean, this will be, this is a 90 minute recording, by the time I open my Slack after it's just gonna be like bleeding red, my Slack. - Yes. (laughs) - But the stuff sales, if it's like, I would love that. For me, stuff Kyle should know. - Yes. (laughs) - Yeah, I love that for the sales, I think, so it really helps keeping them focused, yeah. - Yeah. So the other big challenge that I think people have with remote is enabling and training reps. The default is, it's, you know, much easier to do that in a co-located environment. If a manager's there, they're learning from their teammates. And that's true. There's obviously some truth to that. But what are the key foundations that you think companies should be building to enable their teams and train and develop as quickly as we can? And what are some of the best practices there? - Yes. So actually, interestingly, I disagree with that. I think that's kind of like, I think it was historically a thing, and I think it's kind of still like almost like urban myths that that's the case. I think if you have your onboarding flow really well documented and it's really clear what people need to do, that should not be the case in terms of how you onboard and how you coach and enable your team. And I think particularly with tools like Gong, you know, when you talk about some of those use cases, you're, I'm sorry, we're going back to tools and technology. Yes, again. - Oh, it is such a critical piece. - It's the foundation, yeah. But the, with the solution like Gong, actually you can learn much faster because you're not just dependent on who is sitting to the right and to the left of you and who you happen to get on well with and that you're shadowing from their perspective, but you can get a whole historical library of what you need to onboard. So for example, when I started a couple of months ago, I was given a hundred calls to listen to and they're all historical calls. There's no way I could have said to the reps, "Hey, I'm starting. Can we get a hundred calls set up in the first two weeks?" - Yeah, yeah. - It's impossible, like, you know, to make that work in ways that would have been effective for me to learn. So I would challenge that piece around like onboarding an enablement that can't happen as well remotely. I think if you do it right, it can actually happen even better. What I do think though is more challenging in a more remote environment. I always say, when the times are good for sales, everybody's really happy, but when times are tough, and particularly if a reps had a bad, whatever it is, day, week, month, quarter, and they're sitting at home by themselves, you know, often the best way to get out of that phone 'cause, you know, to have somebody else that you're gonna spend a bit of time with and talk through it, that I think is the more challenging thing for folks when they're remote. And I think with that, there's a real requirement on first line leaders to make sure that they're really proactively coaching their team. We spoke a couple of minutes ago about me proactively checking and, hey, it looks like you're a bit stressed or, you look, like you're a pro-seritated, you know, or I saw you in that meeting, like, was everything cool? You really need to check in much more proactively and have those pro-active conversations because you can, I do it too. Like, you can wallow in your own - Yeah. - Much more than when you've got somebody kind of, like other people around you to kind of bounce some of that off you. So yeah, just not to challenge. You're thinking a little bit on it as well 'cause I see it a bit differently. - Yeah, that's interesting. So this was my, this was sort of the journey I went on with remote. Like, Shopify went remote and we went all in. Big enablement investment, all the tooling, really thoughtfully done. Same thing with owner. Like, we hired a senior enablement leader way earlier than you would in almost any company. We have a big enablement investment for the size of team we have. And I was a big proponent of remote. I'm like, companies just suck at enabling people. There's no structure. And so they're just defaulting to return to office 'cause they're not doing the difficult thing, which is setting up the right structures. Now, and so I would say our onboarding and coaching structures are, I mean, probably better than 99% of companies at our stage. And I spent a lot of time benchmarking. And I think that those structures are world class here already. And but when we brought SDRs in person, they're going through this same training program that is like with all the calls, we've got this Avara AI sales simulator. They've got a buddy system. They're doing Mox with their manager. Like there is a lot happening. And the speed at which those SDRs are coming out of the gate is still just so much higher than when we were doing a remote. And I, in the programming is the same now. The pro, and there's not a lot of like, oh, new in-person stuff that we've tacked onto it. But I think a lot of it is they sit beside their manager when they get stuck on something. They just like, they just go to Sari, they're like, hey, I'm confused on this thing. And it's just that pace of question and answer you'd want to be like, hey, can we hop on a slack in like for 15 minutes or the access to answers from folks around them. And the pace of iteration, I find, I think is the differentiator there. Because I went through this whole thing where I was like, I was really resistant to doing in-person again, because I didn't want to give up hiring broadly. Because I can just go pick off President's Club performers from wherever they happen to be and people like remote. And so we ran this as a pilot side-by-side, like remote hires versus in-person hires and the metrics just sort of jumped off the page. And it was after I talked to people that were doing these experiments. But I think that's unique to SDRs and BDRs. Or earlier career folks. Because I went into it with a really open mind, like this was only a pilot to begin with, but it only took four months before the numbers. Like the ramp productivity is literally three acts in-person versus the remote teams who went through basically the same programming. And so there's something there. Not that it can't be replicated. I think maybe bringing people in-person for some period of time could be a way to counteract that. But yeah, there's some magic there that I can't put my finger on yet. Yeah, definitely sounds like there is. And I think getting people together for a certain amount of very focused time can be really helpful. So whether it's one week a year or specifically for onboarding that they get that time together. And I think probably for, it probably depends like business for business. Like what are you selling and what did your motion look like as well. And probably something to unpack for sales leaders as they're thinking about, okay, well, if something is working in the US market and we're thinking about internationalizing, is this gonna work for us? Like can we do it in like, we didn't distribute it away or do we need to get everybody together to make this work? And then if you do need to get people together and you have a globally distributed team either because you're starting to scale internationally or for other reasons, can you make that work in a scalable way in the long run as well? So I think lots of unpack and probably lots of, interesting to hear, I think your view, which is different to mine. And probably just highlights that there's a lot to unpack as an individual sales leader, how you make it work for your business. Yeah. Depending on the circumstances you find yourself in. Yeah, for sure. And so what are in your mind the key principles for just enabling us to maintain general? I won't even say remote enablement, but what are the things that people need to get right? Yeah. Yeah, enablement for me is one of the most important parts of the team. And I think for me, it's by taking the broad lens around enablement. So first of all, as a brand, okay, generally we're working in tech companies. So working really closely with product marketing to understand what needs to, what is happening, what are the changes there, what we need to bring in to the team and then making sure that we have, they're kind of like the gatekeepers into the organization. Like it can be great. A product are actually delivering tons of stuff, but it may not always be the right time to release it into the market. Maybe the sales teams aren't ready for it or maybe we want to wait and package stuff up together. So I think having the sales enablement team being very close to the sales team, but also working closely with product marketing to work effectively, I think is really important. And the second for me with enablement is being really clear about what you want from their role. Because I think often with enablement, it can be too fluffy. And so what that can look like is just a lot of programs, but there's no measurement on actually has this driven the right results. It's not necessarily mean it's a failure, it just means that we've learned something from it. Either it wasn't the right time or it wasn't the right structure or something else. It wasn't the biggest thing that we needed to go and to work on with the team. So I think really making sure that you have that measurement, not measurement at all costs, but making sure that the measurement of and what's happening in the teams is really helpful. And then for me, there's probably two other things to talk through one is with how an Aidman works with the leadership teams. I've often seen in early sage businesses managers. So we get you get an enable team, the managers suddenly go to enable them, and they're almost using them like a service desk. They have a problem. I need you to fix this here. I have this problem. I need you to fix it actually. For me, when enablements work best is when they are able to work in true partnership, which is able to take a step back and say, OK, I've heard all of these pieces of feedback. I'm also looking outside in at your business. And I think these are the five things that we need to do this quarter to really help drive the business forward. And it's done in true partnership. We're there, the thought leaders, and they're really able to drive it. I think it's normal in early sage businesses that is this kind of reactive mode, but it's really important for businesses. And I think for the CRO to guide it, that they get out of that motion fast so that you can start to drive strategic impact within the organization. And then the last piece for me is around working with how you work with the sales leaders. And again, I think it's a maturity thing but how teams work with enablement, where they kind of say, oh, enablement, they're going to do everything for me. They're going to do all these. I really believe that the best managers are also enablers and coaches. And so it's their job to make sure-- I call it the last mile of enablement comes from the managers. So it's the managers job to make sure, OK, enable to have crazy all this content. Have you digested it? Have you absorbed it at the end of the week? Because everybody's taking this on board. These are the important things for you to look at. Enabment can do things like create your sales methodology, create your onboarding. But it's still the managers job at the end of the day to be on calls with the sales reps to say, OK, actually, I feel like you miss part of whatever sales methodology. You use a part of the-- Like traumatic, or yeah. Exactly. You can pull that in. You miss that part. Make sure you go back for the next call that you're doing that, or as part of onboarding. Hey, you know, I've noticed some of your cadences are not working here. Like, this is what I would suggest that you do. So whatever the specific is, you can't outsource that that is still your job as a manager. Your job to drive results, actually, a core part of it is enablement. And having managers who really want to do that is really important. So it's enablement will get you so far. And then the managers will get you over that last hurdle. And part of that is we significantly under enable our managers. We don't have a train the trainer set up before we take something to the reps. And so a manager is learning things at the same time as the reps. And then they're invariably going to get questions. And the answer is, I don't know. I'll ask that question. And then now the trust is diminished. So we've been trying to be really intentional about if we're deploying something new to the team, we're going to teach even at the director level to the managers. So we redeployed my coaching mastery methodology, which is like, this is how you have to coach-- this is how you have to coach your reps. But first, we had to go to all the directors and make sure that they could live and breathe these coaching mastery principles and knew it cold. So we were doing that in a group like a week or two in advance of then doing it with the managers. And then the directors were part of the delivery mechanism. They were teaching some of the content. But so frequently the enablement programming is just I see focused and do the fail. Yeah, I 100% agree with you. And actually, in the last three businesses I've been in, I've brought in specific training for first-line leaders. Because I think they're often don't get enough attention. And they're kind of just learning by watching the person who's more senior than them. That's like the equivalent of saying to the sales rep. So just talk to your manager. And so long as you have a good manager, you're fine with your job for good manager. You're not in good shape. So really making sure that you systematize what great sales leadership looks like. And ensuring that the sales leaders know that we've set criteria for what great sales leadership looks like as much as you talk about. You have all the metrics for what a great I see looks like. It's what are your activity metrics? What is your funnel metrics like? But actually creating some of those for the sales leaders, I think it's super important as well. And it's really important for the overall efficiency and productivity within the organization. But it's also really important for those sales leaders as individuals for their own professional development that they get to learn and grow as well. And so it's something I spend a lot of time on with my teams as well. I 100% agree with you on that amount of your own. If you want your managers to coach, you want your managers to participate in sales calls, do you measure it? You know? I do this fairly ad hoc and we need a better system for it. But I'll go into our call recorder. So I'll go into momentum and look at how many calls people have participated on. And it's very informative. 100%. Yeah. As much as you ask the reps to be on customer calls, what are the managers spending their time on, which has showed also be on either customer calls or listening and coaching calls? Yeah. All right. Let's move to the quick fire before we close. So what do you think separates a good CRO from a great one? I think good CRO's focus just on revenue results. I think great CRO's understand in all humility that a lot of what the sales team does is at the bottom of the value chain. And you need to go right back up through the rest of the organization to influence all of it for great results for the long run. So whether that's the base, TA, hiring great talent, and maybe marketing reports into your not working with marketing for great pipe bills and positioning, work with product and really working on what you hear is in the market and how you position that. So I think that's the difference for me between good and great. That's a great one. What is the most common advice you give to new leaders? So people taking their first VP of sales role, their first, second or third line, what's the most common advice you find yourself giving them? Yeah. I think often folks want to come in and they just want to start doing self straight away and then they're 30, 60 days into the role and they're like, oh, I've got too much on my plate. I haven't spent enough time actually learning about the role first. So sometimes you need to just go a little bit slow to go fast in the long run. So just your career is a usually a long one. Hopefully it's going to be a long and I'm really fruitful career. So don't waste it on like the first 15 or 30 days. Give yourself that time to really get in to seat and make sure you understand what you're doing first. Makes a lot of sense. What's the hardest career lesson you've had to learn? Ooh, that's a really good question. And I think early on in my career, I was afraid to give people bad news and maybe to be as straight up with folks, you know, in terms of if their performance was not at the level or to have just to be very straight up and honest. And what I realized was the more I did that, actually the more I was respected, you know, because people want to hear that. They want to have those conversations. And if things aren't going well, they'd rather hear them up front rather than too late. I think I've definitely had some, yeah, difficult situations from not being straight up and often in the first place. Yeah, makes sense. Last question. What's the best thing you've read in the last 12 months? Oh my goodness. I read so many books. Let's see. In terms of, oh, in terms of nonfiction, I've read a great book called Breath, which is all about how you breathe. James Nester. James Nester, yes. And I've become a little bit obsessed with it. But it's for me, it was just like, I love the idea behind it. You think so much about how much you sleep, and how much you eat. And then we rarely think about how we're breathing, which is actually much more fundamental about what we're doing on a moment-by-moment basis. Yeah, that's a great book. And I got a lot out of that. One book I recommend to all my sales team to read is the qualified sales leader. 'Cause I think that's a great book. Just for like first-line leaders to read. So that's probably the recommendation for first-line leaders over the next while. So yeah, they're my nonfiction books, I would recommend. That's great. Yeah, Breath is a great one. I've read it pretty soon after it came out. So I've been taping my mouth shut, sleeping for years, and I try to do one run a week where I'm predominantly nasal breathing. And it's hard. I boxed and wrestled for years. So I think I've got some like not great nose stuff going on. But try to go for a run and not open your mouth. Oh boy, is it tough? I know, it's super hard. I've tried it. And it's like respect for anyone that can do a whole run like that. Yeah, yeah, yeah. Well, Geraldine, this was great. I'm glad that we could go super deep on the topic here. And I'm hoping people that, I'm hoping people who are not just remote managers take a lot from this because I think all of these principles can be applied to any sort of configuration. And now we need to name the company type that is not just hybrid, everybody in person versus at home a couple days a week, but like this new type of company that is a bunch of in office, a bunch of fully remote, a bunch of hybrid, there's some new thing. I know we need to come up with your absolutely wise. We need to come up for a word for us for sure. Yeah, that's the thing that people should be really understanding is this is not this false binary. There's something new. Well, it's not even that new people in doing it for a while, but. Yeah, but actually, how you describe it? Because we don't describe it really. Yeah, yeah, I agree. Thank you for listening to the Revenue Leadership podcast. If you enjoyed it, don't forget to subscribe. and you can find a link in the show notes. And be sure to leave a five-star review, share it with your network, and please join me next Wednesday for another great conversation.

Podcast Summary

Key Points:

  1. Distributed teams are not a binary choice; most companies operate in a gray zone with some remote workers even if primarily office-based.
  2. Remote work is more suitable for senior roles and functions requiring deep focus (e.g., engineering), while junior roles like SDR benefit from co-location for faster learning and onboarding.
  3. Access to specialized talent that is not locally available is the primary driver for adopting distributed sales teams, especially for entering new markets.
  4. Successful remote operations require proper infrastructure, including collaboration tools, clear working norms, and asynchronous communication to manage time zone differences.
  5. Distributed work can be a faster, cheaper way to enter international markets compared to setting up full local offices with legal entities.

Summary:

The podcast discusses managing distributed sales teams, emphasizing that the remote vs. in-office debate is often a false binary. Most companies naturally have a blend, especially when scaling.

The key is to assess which roles and seniority levels benefit most from co-location versus remote work. Junior roles, such as SDRs, tend to thrive in shared spaces for mentorship and rapid skill development, while senior specialists and functions like engineering often perform better remotely due to deep focus needs. The primary advantage of distributed teams is access to talent that is not locally available, enabling faster and cheaper market entry, such as hiring a native German speaker in the Bay Area to target the German market without setting up a full office.

However, success hinges on having the right infrastructure: collaboration tools, clear norms for asynchronous communication, and explicit expectations around response times across time zones. This reduces anxiety and improves efficiency. Ultimately, distribution is a strategic choice driven by talent access and business growth needs, not a moral stance.

FAQs

One major misconception is that you must be either fully office-based or fully remote, but most companies have a blend. Another is that this gray area is a disadvantage, but it can actually be a strategic advantage if managed well.

Consider the role type: junior roles and SDRs benefit from co-location for faster learning, while senior or specialized roles often work better remotely. Also, assess talent access—if you can't find local talent, distributed hiring is a key advantage.

You need the right collaboration tools and clear working norms, such as setting expectations for response times across time zones. This reduces anxiety and ensures smooth asynchronous communication.

Distributed work is ideal when you need access to specialized talent not available locally, or when expanding into new markets quickly without setting up a full office. Enterprise sales teams often work well remotely, while SMB teams may benefit from co-location.

Establish clear availability on calendars or Slack, and set norms for when responses are expected. Leaning into asynchronous communication—like fully formed written updates—helps avoid the need for real-time back-and-forth.

You must understand how the product will be used locally, be aware of local competitors, and synthesize diverse market dynamics (e.g., multiple languages, currencies, and legal systems) to help HQ prioritize effectively.

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