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

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.

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Today's guest is Geraldine McCarthy, who is the CRO at Oyster, which is one of the premier remote employment platforms in the market. Previously, she was the CRO at Personio from Series C to Series E, and they are one of the biggest HRIS players in Europe. And that was after 6 and 7-year stints at Dropbox and Google in increasingly senior roles. And she started her career in management consulting at Accenture, actually. So, an interesting career arc. And today we are going to talk about how to manage distributed sales teams, and 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, Oyster's business. So really excited to dig into this one and appreciate you joining.

Yeah, thank you, Kyle. It's great to be here and looking forward to a great conversation.

Yeah. So, uh, what did I miss in your background for folks? What do they need to know about your career story as we, as we dig in?

Yeah, thanks. So look, I think you hear a lot of names probably that are household names that people know, and I think what's interesting about the companies that I joined, um, were very small companies at the time. So, uh, when I joined Google, you know, 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 was just launching Europe. So very early-stage businesses that I was able to support the growth both from an international perspective as a new product perspective. And yeah, that's kind of what I love to do. And most of the companies become big over time, but I like to go in and help drive that growth early stage.

Very cool. Swashbuckling and market building is a lot of fun.

A bit of that, yeah. Or as I like to say, putting the train tracks in as the train is coming along.

Yeah. There is something really unique about that role in being the leader of a non-core market, you know, trying to bring a, especially a US company to, to other markets. You've clearly been good at that. So a bit of a warmup question. What do you think is, 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, to Europe? APAC? Like, what, what, what are the things that you think you did well that led to that success?

Yeah, thank you. We could probably spend an hour talking about that already, but that'll be podcast too. Yeah, I'll try to be as brief 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 use cases, which can be good and a bad thing. And I think secondly is understanding sometimes there's local competitors that you're playing against, which actually might have an upper hand 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 steer 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 in internationalizing, you know, most international markets are pretty complex when you compare to the US. So obviously US, you have like a lot of different states, but it's a relatively homogeneous market. Everybody speaks one language, everybody uses one currency. And when you go into Europe or APAC, there's many languages, there's many cultures and subcultures, 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 understand what are the really big needle movers in a very kind of heterogeneous market. Versus what are the things that are kind of more nice to have or that you can solve at a later stage, so that you can help the HQ teams to 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 EMEA 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 homogeneous, 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. And 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 sort of 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.

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 an office culture, and effectively your ways of operating will look remote, at least in the early days until you've reached scale in those international markets.

Yeah, for sure. So, um, you've led, uh, international teams across many markets now, across Google, Dropbox, Personio. You had a bunch of markets, correct?

Uh, yes, we work across most major markets in Europe.

Yeah, 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, like, I think during COVID we were in a certain phase, but right now there's a lot of talk about you know, return to office. And I think for a lot of businesses that makes sense, that that's what their culture, 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, you know, fully office-based or you're fully remote. And in general, there's, there's a lot of companies that have made a very principled 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 gray 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 I actually, I would challenge a lot of companies when you go in and look at it to say, okay, well, is it 100% of all of the talent that you can find? Can they be based in that specific location that you are in? And honestly, I think when you ask people, they say, oh, well, actually, that's true because this person with very specialized skills sits over here in a state that we don't have an office in, or this person over here who's setting up a new market for us. 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 grayness 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 can often be quite in between the two. And rather than that 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, there's like this clickbaity 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 like basically not do their job. And it's sort of, it's just like a, it's the 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 across team. Like, 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 5 days a week into the office. That's silly. But an SDR, what we've seen in the data, just tremendously benefits being co-located to their manager and others. But the— I'm glad that we're already getting here because what I wanted to tease out of the conversation was nuance. Because it's completely missing from this conversation. And so, and so, uh, I want to talk about like a framework for that decision. How do you advise companies when colocation and an in-person presence is advantageous versus when you should be primarily remote? Across what functions? Just walk people through a maybe a decision-making framework or the heuristics that you've used and, and you help advise your customers on?

Yeah. So, look, I think there are some roles that are naturally more— 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 distraction of those that sit around. So, actually, remote work or work from home can 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 everybody together tends to work better because it speeds up 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, BDRs in particular, I think is a good case study to have people together and to learn from one another. So, I think if 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 there. They're in demand, but there's a lot of them around. There's a high supply. There's also a lot of people that have done similar roles before. But if you're starting up a business somewhere that has less of a built-out tech ecosystem, whether that's either somewhere else in the US or in EMEA 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 talent 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 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 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. 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. And so that's one on the infrastructure, but also working norms for how you work together. So if you are a globally distributed team So right now, Kyle, you and I are talking, it's afternoon for me and it's morning for you. So if I was to send you a message first thing this morning when I got up and expect 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. That means sometimes that some regions get up a little earlier and finish earlier. Some start later and finish later, or it might be about 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 without being able to look at people and then you haven't heard a response and you don't know why. So, but if you know that they're not going to get back to you for minimum 4 hours until they're in their time zone, it kind of relaxes your nervous system. You're not concerned. Okay. 'Did that not resonate? Like, do they not care what I wrote?' You can say, 'Okay, they'll be on it once 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 want to come back to infrastructure and norms and go, and go a lot deeper there. Because it's just simple stuff like leaning into asynchronous. Like if you're gonna 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 whatever. Okay, well, tell me more. And then like that back and 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, 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, uh, approach, or types of sales team? Because obviously enterprise is, 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, if we're talking about sales leaders in general, and I think revenue, like 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 sits within 10 blocks of each other. Why not? Like, what's the point in all being, you know, distributed? You know, we're still humans by nature, still like to be around other people. So 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 help 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 into. It's 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, but you may not be ready to set up a whole office with 50 people yet 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 teams 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 that unicorn German speaker who sits in the Bay Area and is a perfect fit for your product and your culture, having the folks who sit in the region are often, they're much more often much closer to the cultural 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, um, 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, it's working. It's usually a 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, you know, all of the things that are required to do that, including bank accounts and legal documents and all of that. So you can go much faster by, um, having a distributed worker and also setting that up through a system like an employer of record.

Yeah. It, 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, we are for SDR and BDR, new, new hires, 5 days a week, fully in person. Like that's the requirement, but then half the company is fully remote. I've 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? Like this—

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 and where you really have everybody collaborating together live versus which are 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 and based on the teams that are working through it.

Yeah. And life is about tradeoffs. Like there's tradeoffs to everything. There's, there's not one thing that's better. You know, we're bringing these teams these sales teams in person and there's significant advantages like we've, we've seen ramp is much faster, productivity is, 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, you know, like we've had people decline not BDR offers, but, uh, AE offers because they got a competing remote offer. And they, they, that was important to them, which I understand. Um, but the going into any of these things with like, with an understanding that nothing's perfect, I think is important. Um, so let's talk about how to do it well. Um, so in, in my heuristic here is similar to you. Like, I think all companies are going to have some variance of in-person versus remote. There's, there's Far fewer companies now that are fully, fully remote. There's the Automatics of the world, the GitLabs of the world, some great examples, Oyster, great examples of people doing that. But for the most part, I think people or 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 the default should be remote work with the principles of a remote company because then that is like 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 a remote team or a remote company in your mind?

Yeah, yeah, I think there's a couple of things. So, um, we mentioned tools and technology earlier. I think it starts with that, and I don't think you can, you can really scale a company unless you've got the right tools and technology. So you need to make sure that you have— it's an individual choice, but what are the tools that you would select to, um, help your company grow? And actually, for anyone that's interested in what that looks like, we've written a full open source document. It's on our website, and it's called The Reef, which you'll find on our on our website. And it goes through what we have used as what we view as best in class for a tooling and technology perspective and how we've used 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. And 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 know, you're not just having these really long threads where all your knowledge just sits in Slack, where you can do that deeper level of collaboration, thought-through form processes where you can work through stuff. And then you need, yeah, obviously communication, whether it's Google Meet or whether it's Zoom or something else that you're using. But there's a lot that you can use that's— they're kind of like 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. And secondly, I think what you need is the norms around how people work remotely and whether that's around expectations around hours that people are working so that people know when to get a hold of you or when they can expect to hear back from you. And or the people understand, you know, what's the urgent thing that needs to be handled versus, you know, something that can be left till later in the day. And 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 kind of filtering through, okay, 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 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 steadfast, this is my working time zone and that's all that can happen. But As in any business, when something goes wrong, like the rules can always be broken. So, you know, if, you know, product breaks or if something goes really wrong somewhere, you need to be able to say, okay, 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 making sure you have the structure to allow for that, but also that it's not so firmly set in stone that people can't move around from it. And then I think the last piece, particularly for distributed work and for folks who are working from home, 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 external 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 if you're as old as me, you know how to do that because you've had enough back injuries and blahdy blah over the years because you haven't done it properly 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, your home working environment. And ideally you're not just hunched over a laptop and become like stooped over at the end of 6 months working in one business, that you have the whole setup 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 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 bit more intentional about it. One, to remember not just when to take 5 minutes for lunch and grab like a pack of chips from the press to eat them and to keep you going. But, you know, of course, if you need to do it on a busy day, to do it, but that you have that intentional break. You know, 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 1 or 2 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, work when you're, when you're working from home as well. And that probably sounds silly. And it's not something certainly that impacts people on day 1, but over kind of 3, 6, 12 months, it can, it can add up. And studies do show that people who work from home have a higher chance of burnout if they haven't put those rituals in place. So, it's not about 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 wellbeing perspective.

Yeah. Up until recently, 90% of my team was not co-located with me. One of my directs lives like 3 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 2 meetings a day will be 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 because I can plant myself in this seat. I have a standing desk and all the stuff, but you can plant yourself and not move for 8, 10 hours. So, I agree with you there. The other thing I think I want to double-click on 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 think where I see a lot of companies go wrong is none of it's written down. Like, the— their working norms are not documented. And so when, uh, 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 like, just get past that. And I had forever worked in sales environments where it was like a bullpen, and I've got almost my entire team with me. And this was a shock, like a very rude awakening, and I 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 Mullenweg 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.

There.

But there's a lot of norms that take intentional decision-making. Like, what do you use Slack for versus a phone call versus writing a Notion document? You know, response time expectations. You know, like, the default should be, you know, if you need an answer, don't send a Slack. Pick up the phone and call somebody if, you know, it's deal-related or whatever. But unless these things are unless you sit down and think thoughtfully about it and actually make those decisions, then you just end up in, in chaos, I find. Are, are, what are the parts of those working norms that you think people need to give the most attention to? Like, where do we need to make intentional decisions about what norms we're establishing? You've talked about following the sun, which I think is a good one. What else?

Yeah, yeah, I think that's a really good one. So I think one is about 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, 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 bulleted and that people understand what it is that you need to do. And 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 it's going to understand that there's not these kind of cultural nuances that maybe don't translate?

Analogies.

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, like, if you need me for a deal, don't wait until the end of your day. You just Slack me. If you don't hear back from me in Slack and you need it straight away, you message me. And if I don't get back to you within 15 minutes, then you call me. So, you know, there's kind of escalation paths that you can use for that. I think the other piece on that that you didn't talk about— so there's a lot that you can do kind of systematically about where and how you communicate stuff. But the other piece is about about how you build trust with the people that you work with. And it's much 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, you know, whereas 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 upfront as you get started. Often what I've seen work really well is a work with me document, which I know a lot of companies use where you describe, okay, this is who I am, this is how you get the best out of me. And you can link in whatever studies you've done, whether it's your Enneagram or whether it's whatever other kind of personality studies you've done. So people know, okay, this is the framework for how I can deal with this person and then and also more details on how to get the best out of that person. That can really work in terms of building trust.

Especially for leaders. Like, I think every leader— I call it my— my document's called my blueprint. But yeah, the work with me doc, or what's the other? Oh, a README, people will call it. But, you know, this is who I am, what I'm about, hobbies, like, you know, personal stuff so you can build relationships at scale. But then, And like 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 like, hey, I'm probably going to have a response. I'm going to have a bunch of questions. And unless I've explained that I'm going to feel opinionated, but I'm actually really open-minded and I'm drilling you with questions. Not to, not to poke holes in your idea, but because I'm like pretty curious, but I'm open and I'm, I want to be proven wrong as long as you bring me like ideas that are well thought through and backed by data, uh, where possible, and, uh, holistically oriented. Because people will bring me ideas, I'm like, this sounds great for sales and this sucks for everything downstream of sales, right? And so So in the doc, when I explain people opinionated but open, it's so that they are pre-warned 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 6 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, like, 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 questions. Yeah. Yeah, I think that's great. And I think that the team know who you are really helps. 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 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 basis of trust in the first place, that can be really hard. And so building the trust is the foundation, but that 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 place, builds even further trust within the team because people know what they'll get from you, what to expect. So, I think they're probably some of the key things that I focus on and that we focus on in Oyster. In general, we try not to have meetings for meetings' sake. Anything can be done You know, 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 it, let's do that. But let's not spend an hour talking through it ourselves as well. We only have a small number of hours that we work together in the same room.

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. Meeting. 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 skim through it. We don't need to find that cross— those crossover hours. But, uh, very few companies have this written down. Like, this is when we use meetings, this is when we— this is how we write documents, this is how we make decisions. This is the other thing that's in our, in our doc, you know, for decision-making. Like, don't call a meeting to brainstorm. Storm. Don't bring 7 people onto a meeting to grind out from scratch an idea because there's really good stuff in Annie 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 templates for this stuff. So, when you create like a project, it walks you through, this is the problem we want to solve, these are the desired outcomes. Then 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. I love that. That's great.

But it's got to be written down.

Yeah, and 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, but I think it benefits everybody.

Yeah, especially because writing is thinking. Like you, you quickly understand how, uh, how strong your ideas are or how like clear you are about the problem you wanna solve once you're forced to put it on paper.

Yeah.

And see it there and look at sort of the, the ontology of, of that idea and how things connect. You're like, oh, well that's sort of a mess. Or 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, 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 me had, in the way that you've described, had really well documented it. So I was able to pick up, you know, 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 about it 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's, you know, 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. Yeah, yeah.

And meetings are so costly for like, oh, like, let's, you know, let's, let's get together and like hack this out. Okay, well, that's 7 people at a whatever, $100,000 salary. And whereas like one person could have sat down and done the work to, 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 readout 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 really actively discussed and debated. And you get get so much more done that way.

Yeah, I agree.

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I want to go back to building trust. Are there any ways that you have found— so you've talked about spending more time with people to get to know them upfront, a README 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 I think being very straight up and honest people, it does actually by default build trust. I think often people are afraid to kind of really touch on the stuff that you really want to talk about. But the other way is is just about calling out what you see. So for example, you know, 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 in that is to say, hey, like, maybe it's just me, like 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. Do you want to talk about it? And sometimes people might say, I just had a really bad night's sleep last night. I'm like, just tired. So let's say there's a whole lot of personal stuff going on and I do or 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 I had a really bad interaction with somebody else and didn't go my way, or something's going on in my personal life and, and it's— I need some support to figure out how to manage that and work as well. And so actually just being very proactive about that stuff. I think people know that you care about them and that you notice. And I think the easy thing is to say, oh, 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 sounds obvious, but I think you should say 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 6, whatever number of pieces of feedback from, from you over this week. These are the 3 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, folks think stuff goes up the chain and they're like, well, where did it go? Did anyone even hear me? 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 discussed, why we're not going to do those things. And look, if you see it 100% differently, come back and challenge me on that. But I think Usually, people say, "Okay, I get it. That seems reasonable, and 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 zip through 10 meetings in a day, and there could be a variety of small deliverables or just, like, things I need to do and the little things fall through the cracks. And I, 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.

Yeah.

Because, you know, so much of the time the, there's like 6 action items and 3 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 gonna test out Notion's, um, call recorder. But you need it because I don't have a system. Like, I need a system, uh, for it, uh, or else you just— stuff drops. Like, you sort of need systems for 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 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. And I agree on the AI note-takers. I think they're still improving day by day, but actually, I think what happens is you get the macro notes out. On a very basic level, I just take stuff out. I have different colors, Post-it notes, which sounds very old-fashioned. Different color means different thing to me. And that's how I categorize what needs to get done at different stages. So, until I find something better, that continues to be 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 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 some of the best practices that you've used to scale communication across, you know, broad teams?

Yeah, so I think there's a couple of things, and 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, you know, very clear and making things as transparent as possible. And so that doesn't always work. There might be, you know, 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. And all Google Docs, all of your working docs are by default open to everybody. And 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, if stuff needs to be locked for any particular reason, that it can be done. But the default is it goes one way rather than the default is it's locked and then you have to ask for access to get it.

And defaulting conversations to be in channels and not DMs. I 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. Don't have this conversation here.

Or if it needs to be something new, if it needs to be 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 like it's very easy to do. It's just the defaults that you set, but it allows no matter 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 touched 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 communicating with the other teams. Sometimes 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 communicating 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 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 bullet format because some people would prefer to read than listen to my awful voice for like, you know, 5 or 10 minutes update about what's going on. So they can they can listen to it that way and they can absorb the information that way instead. So 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 2-minute chat about something and something's decided, but that impacts somebody who sits in one of the regional teams. So just having that thought pattern about updating the teams about that conversation has happened and that it impacts them. You can never make it work 100% of the time, there'll always be a certain amount of, you know, oh, sorry, 'Oh, I forgot.' But as much as possible thinking, 'Oh yeah, that other person also needs to know.' So you get that communication out to them rather than one month later there's a change in the product and they 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 talk and decisions, but actually systematizing some of that.

And AI plays such an important role here too. 'Cause you can do the video, get the AI transcript, or get the transcript, dump it in ChatGPT, it'll structure it into the right bullets and you ship it with the update. That flow I think is so important. It's funny 'cause 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. 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. The AI recorder pin or whatever it is.

Yeah, 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 remote 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, you know, sometimes you need to share very detailed information. So if you're in, for example, a Google Sheet or an Excel document and you need to show someone, you know, this is like the information where it sits somewhere very detailed in a, in a calculation, doing that in a way that's recorded and you can point to it and actually show them how to use something can be really helpful as well. So you can record on Zoom, you can use Loom 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 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. A 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 leader's 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. Out. But also just having like a consistent way that you do stuff is so critical in communication. Even the way we communicate stuff to the team, we've got this traffic light model. There's green, yellow, and red changes. And a green change is like something small. You can just blast out a Slack update. But a red is, okay, we need 3 points of contact, got to have a video. The managers have to talk about what their reps in team meetings, It's got to get updated in Notion and Guru, and there's a system for it. And building those foundations takes a lot of time upfront. 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. And I do agree that it takes investment upfront, 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, yeah. The other mistake I see people make on communications is too many surfaces. You've got some information that's in a Google Drive or a Docs, 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. Like everything, everything you need to know about doing your job about as an, 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, in Guru. You can get to Guru through Slack. And then Notion is internal docs and planning and, and project management. But, but we try to really limit that. Surface area creep. Because people come in and they like to write Google Docs. That's what they're used to. That was me. Shopify was all Google. And then I was like, oh, now I got to learn Notion. Now I love Notion. But it's like—

I agree with that. Yeah, that people know where to go to find the right information and that they have confidence that where they're going is the right place. Maybe a subcomponent, because I've been talking about a lot of stuff that goes right, but a subcomponent of that that goes wrong that I see companies doing is is in Slack where they post the same thing either multiple channels or you have two people posting kind of similar updates. And because from a communication perspective, people want to know, they want to get it, get it once, know that that's it. And if they're getting it like 3 or 4 times in different channels or in different formats, they actually switch off, you know, 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 and there's new stuff in there, then you've missed it. So yeah, being really Being intentional 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 as first-line sales leaders, I really like them on a, particularly on a Friday to wrap up the week and 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 the 3 or 4 boxes for the must-haves? And then, you know, everybody has has at least the minimum threshold of information that they need to do their job on that week.

Yeah, my enablement leader 2 companies ago, uh, 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. Depends how well informed. But that was like, that was an important drumbeat 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, to, cause Slack can be, you know, an insane Christmas tree of overwhelm. You know, I've been, this will be, this is a 90-minute recording by the time I open my Slack after, it's just going to be like bleeding red, my Slack. But the stuff sales, if it's like, I would love that for me. Stuff Kyle should know.

Yes. Yeah, I love that for sales teams. 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. Um, and that's true, there's, there's obviously some, 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. And 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 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 yet again.

No, it is such a critical piece.

It's the foundation. Yeah, but with a 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. View 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 100 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 100 calls set up in the first 2 weeks? Yeah, yeah, it's impossible to make that work in ways that would have been effective for me to learn. So I would challenge that piece around like onboarding and enablement, that it 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 rep's 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 funk is, you know, to have somebody else that you're going to 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 in, hey, it looks like you're a bit stressed, or you look like you're irritated, you know, or I saw you in that meeting, like, was everything you really need to check in much more proactively and have those proactive conversations because you can— I do it too. Like, you can wallow in your own thoughts 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, I just want to challenge your thinking a little bit on it as well because I see it a bit differently.

Yeah, that's interesting. So this was my— this was sort of the journey I went 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, 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 suck at enabling people. There's no structure, and so they're just defaulting to return to office because they're not doing the difficult thing, which is setting up the right structures. And so, I would say our onboarding and coaching structures are, I mean, probably better than 99% of companies at our stage in— I spend a lot of time benchmarking, and I think that are— 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 mocks 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 it remote. And I— and 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 Soraya. They're like, hey, like, I'm confused on this thing. And it's just that, that pace of question and answer. You don't have to be like, hey, can we hop on a Slack in like for 15 minutes? Or the, the like access to answers from folks around them and the, the pace of iteration I find, I think is the differentiator there.

Yeah.

Because I, I went through this whole thing where I was like a, I, I was really resistant to, to doing in-person again because I didn't want to give up hiring, uh, 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. 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, this was only a pilot to begin with, but it only took 4 months before the numbers, like the, the ramp productivity is literally 3x in person versus the remote, the remote teams going through basically the same programming. And so there's, there's something there, not that it can't be replicated. I think maybe bringing people 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 kind of like one week a year or specifically for onboarding, that they get that time together. I think probably for— it probably depends like business for business, like what are you selling and what does 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 going to work for us? Like, can we do it in a distributed way 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, for other reasons, can you make that work in a scalable way in the long run as well? So I think, yeah, lots to 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, your business. And depending on the circumstances you find yourself in.

Yeah, for sure. And so what are, in your mind, the the key principles for just enablement in general? I won't even say remote enablement, but what are the things that people need to get right?

Yeah. And 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, is around, okay, generally, we're working in tech 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 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. And It hasn't given the right results, it doesn't necessarily mean it's a failure. It just means that we've learned something from it, either, you know, 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 what's happening in the teams is really helpful. And then, for me, there's probably two other things to talk through. One is where with how enablement works with the leadership teams. And I've often seen in early-stage businesses, managers— so we get, you get an enablement team, the managers suddenly go to enablement and they're almost using them like a service desk. They have a problem, I need you to fix this. Hey, I have this problem, I need you to fix it. Actually, for me, when enablement works best is when they are able to work in true partnership, which is able to take a step back and say, okay, I've heard all of these pieces of feedback. I'm also looking outside in at your business. And I think these are 5 things that we need to do this quarter to really help drive the business forward. And it's done in true partnership where they're the thought leaders and they're really able to drive it. I think it's normal in early stage businesses that it's 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, um, 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 about how teams work with enablement and where, you know, they kind of say, oh, enablement, they're going to do everything for me. They're going to do all these things. I really believe that the best managers are also enablers and coaches. And so it's their job to make sure I call it like the last mile of enablement comes from the managers. So, it's the manager's job to make sure, okay, enablement have created all this content. Have you digested it? Have you absorbed it? You know, like at the end of the week, has everybody taken this on board? These are the important things for you to look at. You know, enablement can do things like create your sales methodology, create your onboarding, but it's still the manager's job at the end of the day to be on calls with the sales reps to say, okay, actually, I feel like you missed part of, you know, part of whatever sales methodology you're using. Yeah, exactly. That you can pull that in. You say you missed that part. Like, 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 like not working here. Like, this is what I would suggest that you do. So whatever the specific is, you know, you can't outsource that. That is still your job as a manager. Your 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. Like, 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, like, I'll ask, 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 like 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 IC-focused and sort of doomed to fail.

Yeah, I 100% agree with you. And actually, in the last 3 businesses I've I've been in, I've brought in specific training for first-line leaders because I think they often don't get enough attention, you know, 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, you know, so long as you have a good manager, you're fine. But if you don't have a 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 IC looks like. It's, you know, what are your activity metrics? What does your funnel metrics look like? But actually creating some of those for the sales leaders, I think, is 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. As well. And yeah, so it's something I spend a lot of time on with, with my teams as well. I 100% agree with you on manager enablement.

If you want your managers to coach, you want your managers to participate in sales calls, do you measure it? You know, I, I, uh, 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 performative.

100%. Yeah, as much as you ask the reps to be on customer calls, what are the managers spending their time on, which should also be on either customer calls or listening and coaching calls?

Yeah. All right, let's move to the quickfire before we close. So, what do you think separates a good CRO from a great one?

I think good CROs focus just on revenue results. I think great CROs 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 about TA, hiring great talent, you know, maybe marketing reports into or not working with marketing for great pipe builds and positioning, working 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 stuff straight away. And then, they're kind of 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 be 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 lot, usually a long one. Hopefully it's going to be a long and, and really fruitful career. So don't waste it on like the first, you know, 15 or 30 days. Give yourself that time to really get into 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?

Oh, uh, that's a really good question. Um, 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 that, 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, if things aren't going well, they'd rather hear them upfront rather than than too late. I think I've definitely had some, yeah, difficult situations from not being straight up enough in, in the first place.

Yeah, makes sense. Um, last question: what's the best thing you've read in the last 12 months?

Oh my goodness, I read so many books. Um, let's see, in terms of— oh, in terms of non-fiction, I've read a great book called Breath, which is all about how you breathe.

James Nestor.

Jane's Nestor. 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, you know, how much you sleep and how much you eat. And then we rarely think about like how we're breathing, which is actually much more fundamental to what we're doing on a moment-by-moment basis. Yeah, that's a great book. And I got a lot out of that. And one book I recommend to all my sales team to read is The Qualified Sales Leader, because I think that's a great book just for like first-line leaders to read. So, that's probably another 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 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 So I think I've got some 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. 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 of 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 I know.

We need to come up with— you're absolutely right. We need to come up for a word for it, 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 have been doing it for a while.

Yeah. But actually how you describe it, because we don't describe it really. Yeah. Yeah. I agree.

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