Hiring, Firing Fast, and AI Reshaping Marketing Teams (Full Transcript)

[00:00:00] Speaker 1: There's nothing like entrepreneurship, putting everything on the line, including like your home, your family's financial health, and also having to write the paychecks of the people that work for you.

[00:00:10] Speaker 2: Was it hard transitioning from running your own business to working for other people and having some of those decisions out of your hands?

[00:00:18] Speaker 1: Oh my god, yes. All of my deepest scars from my time running my own business are financial. Hope is not a strategy, and it didn't work for me. I really do believe in firing fast.

[00:00:37] Speaker 2: Hey everybody, it's Sam Jacobs, CEO of Pavilion. Welcome to Revenue Blindspots, powered by Otter.ai. It's a podcast where we explore the pivotal moments in the careers of top revenue leaders. Our focus is to dive deep into the blind spots that have shaped leadership strategy and growth, uncovering lessons that can help the next generation of revenue executives. Of course, it's brought to us by Otter.ai, an incredible AI-focused company that we use every day at Pavilion. And of course, Otter helps you uncover those blind spots. Today on the show, we've got Kathleen Booth, someone that I know very well, who is near and dear to my heart. She's the SVP of Marketing and Growth at Pavilion, the company I run, a 10,000-member private global community of go-to-market executives. Prior to joining Pavilion, Kathleen was founder and CEO of Quintane Marketing, a digital marketing agency. After selling her company, she held marketing leadership roles at VC-backed B2B tech companies, including Attila Security, Clean.io, and Tradeswell, and continues to serve as an advisor and fractional CMO to early-stage B2B SaaS startups. She's been named one of the top 50 B2B marketers to watch by TopRank and six global marketing advisors who are rising stars by USA Today. She's also an active influencer on social media, notably LinkedIn. Kathleen, welcome to Revenue Blindspots.

[00:01:58] Speaker 1: Thank you, Sam, for that very gracious bio reading. I feel very important right now.

[00:02:05] Speaker 2: Well, my friend, you are important. Didn't you recently cross 30,000 LinkedIn followers or maybe 40,000?

[00:02:12] Speaker 1: I've come up on 36,000.

[00:02:14] Speaker 2: Let's go. Let's go. So there you go. That's a testament to your importance. Now, anything I missed in the bio, by the way, anything you wanted to call out? It's always interesting to know a little bit about how you got here. So when you think about formative experiences, tell us a little bit about Quintane, tell us about some of your experiences at other companies, and then tell us a little bit about what you do at Pavilion.

[00:02:36] Speaker 1: Sure. I think I've had a sort of strange career trajectory, to be honest, because I spent the first 10 years of my career working in international development consulting. I was actually a USAID consultant, may it rest in peace, working on clean water in the developing world. And I had done two graduate degrees, one of which was in marketing. The other was more aligned with what I was working on at the time. But it became clear when I was doing that, that there were real strategic communication problems with those projects and governments weren't building support for reform. So it created this opening for me to move back into marketing. And then when I wanted to have a family and kids, it also created an opening for me to build a different kind of career that didn't require me to travel all over the world, even though I loved that when I was single and in my 20s. But the reason that that's important is that I transitioned away from doing that work and directly into starting a marketing agency with my husband. And I did that for 11 years. And I would say in terms of formative experiences, that really is the top of the list, because, you know, you know, this while you're an entrepreneur, there's nothing like entrepreneurship, putting everything on the line, including like your home, your family's financial health, and also having to write the paychecks of the people that work for you and bearing the weight of responsibility of that there's there's nothing like that to like cause you to learn faster than you've ever learned before in your life. It's a lot of pressure. And I think I did learn the most in that 11 years. But I also made a lot of mistakes, because, you know, I had never run a company before, and I was learning it while I did it, or some people like to say building the, you know, plane while you're flying it, and sometimes we crashed a little bit. You know, and I think that experience really has informed the rest of my career, because some of the mistakes I made, like left really deep scars that I never wanted to repeat again. But also, there were some like really beautiful things that came out of it, where some of the people that work for me are many of my closest friends and collaborators still today. I learned a lot about leadership. So that that gave me a different lens. Then when I wanted to go back in house and be ahead of marketing, I think it gave me an appreciation and some empathy for what it means to be a CEO and the weight you do carry and the difficult decisions you have to make. It's sort of popular sport to attack CEOs for things like laying people off or, you know, a few years ago, especially that was like a big thing on LinkedIn. And I remember seeing that and thinking like, there is another side to this story, and not a very popular one that anyone wants to hear told. But that really made a mark on me and changed how I then thought about being a revenue leader in the years after that.

[00:05:18] Speaker 2: The empathy is definitely one perspective. And as a fellow CEO and founder, as you were, I appreciate it, of course, was it hard transitioning from running your own business to working for other people and having some of those decisions out of your hands that used to be in your hands, regardless of whether they were, you know, they went, they ended up good or bad?

[00:05:39] Speaker 1: Oh, my God, yes. I mean, you know, that's like, it's probably the hardest thing of all, you know, having the freedom. And I would say, like, even before I started my own company, I was a person who, who felt a lot of frustration with some of the, I think, leaders that I worked for over the years who I saw do things sub optimally. And I know when I went to start my company, I had strong opinions about like, behavior, I didn't want to repeat. And so there is that great side of being an entrepreneur, we were like, I can do all the things that I think should be done well, in the way that I believe is good. But you know, you get used to making all the decisions you are, I think it was George Bush, who called himself the decider, right? You are the decider when you're the CEO. And, and everybody has to kind of live with that at the end of the day. And so transitioning to not being the decider, or certainly not being the decider on everything, like if you're in a leadership role, there's things you decide, that's a difficult transition. And I think, and I think the other complicating element in there is that I always worked in startups. And in startups, things move fast, right? And especially pre product market fit, like you're, you're testing, you're doing things, you're moving on to the next thing, as soon as the first thing doesn't work. And like that pace, combined with being used to being the decider creates a certain like working style that that is very comfortable with momentum and quick decision making. And so I think part of what was difficult was learning to give space for other people to be deciders, but also learning to slow down. Because if you spend enough time in startups, it can almost feel like terrifying, and like physically uncomfortable to slow down in that regard. Because when you do that in an early enough stage company, it can mean death in a way, whereas in later stage companies, it can mean death to go too fast. So it's just been a really interesting journey. And I think in many respects, I'm still working on that. But, you know, work in progress.

[00:07:40] Speaker 2: Me too, for sure. Well, let's talk about the topic of the show. So, you know, the prompt to use a refrain that is very common in the modern world. The prompt is think of a time in your career when you had a significant blind spot in your approach to revenue leadership, go to market strategy, or operational execution. What was the blind spot? How did it reveal itself? What were the short and long term consequences? How did you course correct or adjust? Share with us what were the blind spots? What'd you learn?

[00:08:11] Speaker 1: So I think all of my deepest scars from my time running my own business are financial. And the the mistakes that I made, well, one was taking on too much company debt, and not thinking about what it would mean to have to service that debt. But we'll put that one aside. I think the one that's more the one that's more relevant for this conversation, and that I think has broader applicability is really around hiring and firing. And, you know, it was interesting because I ran a professional services business. And so your ability to scale is directly linked to when you know when you're billing people's time, it's directly linked to the people that you hire and have available. And it's challenging in the agency world, because your people and the experience that your customer has with them are essentially the product, even though they're like doing marketing, and they're creating artifacts, really, the relationships are what your contracts live and die by. And so the challenge was, you know, if I know I'm going to have three more clients coming on with retainers in the next three months, you know, logically, it would feel like I need to hire ahead of that, so that I'm not putting someone whose first day on the job it is to work with a new customer. And I think logically, that makes sense. But it also kind of doesn't make sense, because you hire a head of demand and not not like a head of in charge of but in advance of demand, and you're paying somebody for time, they're not available. And so I there were a few moments when I own my company where I saw momentum, and I saw pipeline growing. And I like took these risks and staffed up so that we'd be ready. And it would be a smooth transition for those new customers. And in some cases, they didn't come or they churned and then I was left with people who were senior. And you know, again, this was my first time running a business. And I think I suffered from some of what Kim Scott would call ruinous empathy. And I really didn't want to have to fire people who were excellent, like they were really good, but not doing it was terrible for my business. When I had too many people and not enough, you know, revenue coming in, not enough monthly recurring revenue. It was also terrible for the other people who I needed to keep in the business because it put us in a financially precarious situation as a company which jeopardized all of them. And it was terrible for the ones that needed to be fired because it just delayed the amount of time that the inevitable happened and that they needed they could have been going out and looking for another job. So it was bad for everybody. And I think I didn't realize that at first, like my first instinct was I want to do right by these people, I want to keep them on, I'm going to try to find the business to make it work. But like hope is not a strategy. And, and it didn't work for me. And it really put us in a terrible position. And so I think that has changed how I think about hiring and firing now. I really do believe in in firing fast, especially when it's, it's related, well, under any circumstance, but definitely when it's related to the financial health of the company, I think you need to do it as quickly as possible. You know, and there's ways to do it that are compassionate and, and fair to that person. But, you know, I think the interesting thing about this conversation is like, it also, I just got off the phone with somebody this morning, who's at a large company, who's having to fire a lot of people, not because of financial problems, or because of performance, but because like AI has changed the landscape. And a lot of these companies with bigger teams, they just don't need that many people anymore. And so I think like, as I think about revenue leadership today, I'm asking myself this question of like all the different dimensions of how we think about staffing a company, and those are changing. And we as revenue leaders, I think need to, to be able to, to like see that coming and make quick decisions to get ahead of it. Otherwise, the outcome will be the same as the outcome that I suffered from, which will be you'll have a bloated team, you'll be spending too much. And that's a downward spiral that's difficult to recover from.

[00:12:14] Speaker 2: How do you manage morale in those situations, particularly when it's a small team, and everybody knows everybody. I imagine this was at a time when people were probably in office, you know, today, it's a remote, it's a remote world, which things which makes things maybe more weird, I think when people depart an organization. So how do you think about morale management and comms when you're having to make these difficult decisions?

[00:12:40] Speaker 1: So interestingly, this was in 2015. And I had actually hired remotely back then. I had some in office people, but my some of my best team members were, you know, I was in Maryland, one was in California, one was in Florida. And I, you know, a I think when you let people go, you need to just get directly to it, you have to get on a call with them and immediately just tell them what's happening, because nobody wants the soft lead in and to be wondering what it's all about. And, and it's ripped the bandaid off quickly. That's the most compassionate thing to do. But with the people that are left, I think it's, it's about transparency and explaining like why it happened. I know that the team I had at that time, really craved transparency around the company's financial situation. What saved us after I finally let those people go was taking very much like an open book approach and reporting weekly on the financial health of the company, showing them what our bank balances were, what our cash flow was, because, you know, they needed to plan for their lives too. And I did lose one person who I wanted to keep through that experience because she was pregnant with her first child and her husband was like, you can't stay there. I don't feel like it has enough financial stability. Ironically, she wound up coming back a year later and working for me again. But, but I you know, and I don't blame her, she needed to do what she what she had to do for her family. But I think that had I communicated more transparently earlier, I don't know if she would have left. So that's a big change that I would make.

[00:14:13] Speaker 2: That's, um, I mean, that transparency is hard. I think, how do you manage it? It's one thing when you say, hey, we're in a financial position, we have to do a layoff. But how do you manage it to the rest of the organization when it's performance related? Do you make that clear? Or do you try to be diplomatic? What are your best practices there?

[00:14:32] Speaker 1: Um, I think you have to make it clear, but I don't think it's necessary to go into details. Meaning you can just say it was performance related. And, you know, you the to everyone who remains, you all are working really hard. And you deserve to be surrounded by people who are going to work as hard and as effectively as you are. And that's what we're doing here. And I think most people will appreciate that context. But I don't think it's necessary to go into and here's this thing that person did wrong. And that thing, like, I don't think that's required.

[00:15:04] Speaker 2: Agree. Last question. You know, to your point about org chart and org design, you're a career marketer. How do you see AI impacting the structure of marketing organizations? What does it look like? How is it different? Besides, you know, maybe the glib answer might be fewer people, but what are those people doing? Where do you see the dire need for humans? Where do you see machines rising up to take some of the work off our hands? What do you see as the marketing work of the future?

[00:15:34] Speaker 1: So this may be somewhat controversial, but I do think there will be less people like, I don't know what I would tell somebody going to college today about majoring in marketing, for example, I, I just sent my son off to college, and he's going to do mechanical engineering. And I'm saying a huge sigh of relief, because I feel like you can always fall back and be a plumber and electrician. And that's not going away anytime soon. It's, you know, I don't think any of us really knows what's going to happen. But here's how I'm thinking about it. In the past, like I talked to a lot of pavilion members about their careers, and the jobs they're applying for. And I think in the past, when you would talk to people about what they wanted in a new company, they would use, for example, like VC funding rounds as proxies, because it's easy to be like, I want to go to a Series B company. And what they really mean is, I want a company that has a certain amount of money, and that I will have a team of a certain size supporting me, that proxy is no longer valid. You know, if you go to a Series B company, there's more likelihood that you're going to be given the resources and team or maybe not the resources, but the team that is more akin to what a Series A might have had five years ago, because that company doesn't need as many people. So you know, as I talked to people looking for jobs, what I'm hearing more and more is like, this transition from company size as the barometer to does this company have product market fit, you know, being more important, because with that as a raw material, if you're an AI forward go to market leader, you can really push the limits in terms of what AI is able to do in substituting for a team. And I'm not saying you won't need anyone like I think we still need people. But I think AI is going to slow down our need to hire dramatically. And it's going to change the nature of who we have to hire. I do also think though, that and I talked to somebody this morning who's at a pre IPO company, who's having the opposite problem. And what that person told me is, it's almost equally as if not harder to come into a bigger company today, because what you're inheriting is a very bloated team that dates from before AI was really mainstreamed. And the challenge there is you're effectively going to have to lay off swaths of your team, not for performance, but because truly AI is going to eliminate their role. So like, I don't know, I don't know which situation is better. Like I personally, I'm leaning into AI. And I think it's exciting to think about how can we let these machines and these algorithms do some of the day to day things that maybe weren't the highest value adds and focus the humans on the creative part, because like, you know this about me, I'm very much a believer in brand. And I think that's the thing that's going to set us apart in this age of AI. So we have to like, let the AI work on the stuff that that isn't as differentiated, and focus the humans on how can we connect more deeply with customers and prospective customers? How can we build relationships? How can we truly differentiate and stand out and, and build a voice for ourselves that that is compelling and that people feel a connection with?

[00:18:52] Speaker 2: I love that. Agreed wholeheartedly. Kathleen, it's been great having you on Revenue Blindspots. If folks, you know, want to reach out to you, what's the best way to get in touch? They want to ask questions, they want to pick your brain as a mentor, maybe they want to join Pavilion. How do you prefer people contact you?

[00:19:10] Speaker 1: Well, if they're interested in Pavilion, they can go to join pavilion.com. And there's a little button in the top right that says join now. And it's pretty easy to do. But you're also welcome to just connect with me on LinkedIn. And if you do have questions about Pavilion, I'm happy to answer them or connect you with someone on the team. And always happy to connect with anybody who heard me here.

[00:19:29] Speaker 2: Thanks so much, Kathleen. And folks, if you're listening, thanks for listening to Revenue Blindspots. Give us five stars on the iTunes and Spotify stores, and we'll talk to you next time.