Becoming a Fixer

Alex Kracov: So, normally, we focus on a guest experience at one or two companies. But your career has taken a different shape. It seems like you're kind of more of this fixer, where you come into a scaling company, revamp the revenue team, improve results almost overnight, and then move on to a different challenge after a couple years. And so, I'd love to kind of start there. Why do you love this role of fixer so much, and kind of how did you end up in this career path?

Wynne Brown: It's such a great question. My mind is voracious, and I'm an adrenaline junkie. And so when you put those things together and add in kind of the core of who I am, of being very people centric, whether that's customers or staff, it all ends up to, like, give me a really complex problem to solve and I just want to get at it. You know, when I started my career, it was kind of when tech started. I went to San Francisco in 1999 after grad school. Because that's where everything was happening, and it was this totally unique opportunity to be part of a new industry from the start. You know, all of us who were the first people in tech will readily admit we had no idea what we were doing, and so we made big mistakes. And so coming in and having kind of sense of and a thrill with the framework of how you unravel problems that got into the system, kind of into the works from the start, just became really fun. Glutton for punishment, I guess.

Alex Kracov: Yeah, it's funny. As you're talking through your answer, I think I might - I guess, historically, I've been a little bit more of the opposite. Like a builder, right? It's like starting from scratch and then kind of going from there. But I guess I was a consultant at one point. And that's kind of more of like that fixer type of seeing what's messed up, auditing, talking to people, and then kind of running your own playbook of trying to figure out, all right, how do I solve this problem? So it's kind of building when something is already started, is maybe the way to think about it.

Wynne Brown: Yeah, and it's such a cliched thing that we all say. It's like, oh, we're building the airplane while we fly it, or changing the tires on the bus as we drive it. But startups are, by their nature, extremely rapid in cadence. And often, what happens - and maybe you've seen this at other places or, certainly, over a beer with friends. You've probably heard this as people talk about, "Oh, my gosh. This is a really successful company from the outside. But once I was hired, I can't even get data that's clean." And so what's really important is to know that every company has skeletons in the closet. But you need somebody to come in, get the skeletons out of the closet, bury them in the ground, burn some sage, and move on. But you have to fix the fundamental mistakes that were made when the company started, and that's because humans made the company. That's not like somebody made a massive error or was stupid. It's just the nature of how fast these companies develop.

Alex Kracov: Totally. And I think about what I did at Lattice. It's like things that worked for us in the early days would break later. Then you maybe didn't have time. It worked at one point in time. And so it wasn't that we were stupid at the time. But then when you look back on it, it clearly wasn't working. Then there's often so much baggage, too, as you're in the company that you forget why something is done a certain way. It really takes kind of like that fresh perspective to come in and be like, "Okay. Wait. This is silly. We got to do this now, and this is a better way to go about it." So, yes, we need more fixers at companies.

Wynne Brown: I agree.

Introducing CS at Military.com

Alex Kracov: So, for this episode, I'd love to kind of walk through a few of your career stops. We can talk through about how you fixed different problems. Maybe let's start with Monster. Because I think you joined there in 2008, I believe. You were a top AE at Monster and then promoted to director of sales. And you really quickly expanded Monster's revenue. But it sounds like you did that mainly by implementing a customer success program back before CS was really a thing, and it was established as it is now. As a sales leader, why did customer success become such a focus? Can you kind of walk us through that change at Monster?

Wynne Brown: Yeah, and so to put a kind of finer point on it, I was part of a division of Monster called Military.com, which was a separate startup that they acquired. We came in, and we had the advantage of being still that startup spirit in San Francisco versus the kind of HQ of Monster as like a job board behemoth at that time back in Massachusetts. I think this is even true today, and it's why I am consistently obsessed and talking all the time with folks, posting so much on LinkedIn and networking so heavily, is that even back then, when we were doing the new things that created customer success as a program and really put the customer in the center and true customer centricity, people still don't do that consistently. What we did was, it was actually a book of named accounts. So it was in kind of the renewal and expansion space before any of us were really calling it that. What I did was shut up and listen to the customer. A great example of that is, because we were Military.com, the named accounts where all the recruiting agencies for the military recruiting commands, so typically, stereotypically, conservative kind of, you know, they had a playbook that they would run for all of their outreach. That was really what it was with these vehicles to find leads. It was way back during the first war on terror, as they called it, and there was a huge recruiting need. If we had just gone in and done the traditional things with them that we thought that they wanted, we would never have innovated for them, and it would have not solved new problems.

So, again, the most important thing was we went and listened to them. So we would show up that timeless kind of value of being in front of people and creating relationships. That was really the play. That's always the play. So I would go, for example, and talk with the representatives from the Navy and would just have lunch with them, listen to them. One of the things that they shared with us was how difficult it was to recruit for the SEALs. It was at a time when, it was one of the only times that they were recruiting not from the Navy. You could come into the SEAL program from a different armed service, or maybe not even having been in the armed services. It was a totally unique opportunity. And the base of who we could reach, with the incredible reach of Monster, could fit the demographic profile that they were seeking. So we had to make a new product that was super cool that attracted those folks. So we built this new, essentially a website where people could come in and play games and look at gear and all the things that would really appeal to that type of person. We ended up actually being a Webby honoree for this innovative at the time. It seems kind of old fashioned now. But at the time, having your mouse look like a machine gun, for example, was kind of a new thing. It was this very innovative thing. And ultimately, it gave the customer, the Navy, what they really needed and couldn't find anywhere else.

Alex Kracov: Super interesting. I did not realize at all about your experience that you were working with these military guys and trying to get them more online and things like that. So you show up. You meet with them in person. You get this feedback. How do you think about being the voice of the customer and working back with the product team? And getting that Webby award-winning website built, or whatever it is, how do you sort of think about translating? Because I assume that they're just like, "Hey, I want more SEALs." They probably aren't very technically advanced, so you have to be like a great translator, right, of what they're actually saying to what you want the product to build?

Wynne Brown: That is actually so astute of you. Yes, absolutely. One of the primary things, and I kind of consistently will talk with teams or leaders or individual contributors about this to this day, is that you have to have authenticity and be in integrity about why you care about your customer. And if you can't find that hook within you, it's never going to play out to the point where you have extreme success. You can meet your quotas or your metrics. You could still have a successful career. But to go into that level where you are an A player, where you win a Webby Award, it has to be on a foundation of shared passion or connection. For me, in this specific circumstance, it's my husband who - he has a whole other podcast of probably not this form, but he was really foundational in how the metrics work in SaaS. He looked at success factors very early. But before his career in tech, he was a lieutenant commander on submarines in the Navy. And it formed who he was in his character. And so when I had the chance to work at Military.com, all of my other tech friends were like, "Oh, you should go work at these hot startups or what have you." I said, oh, my goodness. No, I'll just support the military. I'm not the usual demographic that comes out with that kind of level of patriotism, especially at the time when it was somewhat controversial. But it was a huge passion hook for me. So when I had to go to my engineers and say, "Guys, I have the best idea," not only is it going to help fulfill the customer's mission, but this is the revenue that it represents. And when you carry the torch of passion into your organization, it is contagious. And so being able to have that hook of why it should matter so much to everyone. I didn't care if the teams like hooks. It can be making lots of money. It's whatever, however they needed to translate that passion for themselves. But when you connect and share a passion with the customer, that's when the magic happens.

Joining GitHub

Alex Kracov: I love that story. I try and do that as much as I can. Because I think when I'm working with the engineers at Dock, it's like, it can get so just in the weeds around features. We need to make this cut in blue, in blue or whatever it is. But you need to say why it matters to the customer, and how this is going to impact their business, and how this is going to change lives. The more you can connect that, the more it inspires engineers and just other people in the organization to do great work. So I love that story. It's such a great cause to work on. So I'd love to jump forward, I guess, five-ish years to when you joined GitHub as Director of Customer Success. Can you kind of talk about the state of GitHub at the time? What was your mandate when you joined?

Wynne Brown: Yeah, so, obviously, GitHub is super well-known. I joined when it was way before the Microsoft acquisition. It was when the lobby was still a full-size replica of the Oval Office. I don't know if you've ever heard that story.

Alex Kracov: I didn't know that.

Wynne Brown: Yeah, this is like old school GitHub days. Really fun and really loved. I mean, there's, I don't know, many brands that are as loved by their users as GitHub is. The challenge was that, as the user base grew, which was really organic and really by individuals, and as they then were leveraging into real commercial engagements, we were kind of coasting on that love. And the mechanics, really, the fundamentals of how you treat really mid-market up to enterprise customers, isn't just fun and games. So I love having fun at work. I love loving my colleagues, but I'm very serious about my work. And so what they really were curious about is, hey, here we have these very loyal customers. Retention was not an issue. What could it look like if we were giving ammunition to our customers to help us get into the other pockets of dev teams? At the time, a lot of dev teams were just able to choose their own tools. And so, if GitLab was in the other group, or the other division, or what have you, there wasn't a lot of momentum to change that. So that was the big question is. Could we stop just resting on great retention and look at potential growth?

So when I came in, there was already a really talented team focused on mid-market in place. There was no enterprise team, and that's kind of another interesting story. Really, for me, it was about, how do you stop just checking in with your customers and making sure that they love GitHub, and talking about how to make customers heroes by being bold enough to take the GitHub goodness and take it to the other teams that could be captured in the footprint? I call that pull mechanics, where you are not just checking in on your customers. Because we all know if you're checking in on your customers, you're trying to make sure, are we okay? Is there any risk here? Is my revenue at risk? But that's not why customer wants to spend time with you. Even at GitHub, with all the love we had, when we would reach out, our CSMs would get meetings maybe half the time. That wasn't a good connect rate, a good engagement rate. So instead, what we did is we took a big step back and said, "Let's center the customer." What do these personas, a director of engineering, or a CTO, what do they care about? What do they want to learn about? Because GitHub is seen rightly so as this Mecca of developer collaboration. And so we came up with, every quarter, the CSM team would crowdsource. These are the five main topics. And now I'm going to like each CSM, either in pairs or individually, would develop a whole curriculum, just a slide deck, a talk track on brown bag lunch. But it was content we knew that they desperately needed to learn about. And so then the campaign every quarter was, "Hey, how are you? Here's our latest and greatest of what we think you'd care about. Which do you want to talk about? Which do you want me to present? Do you want me to present to leadership, to your ICs? How do you want to do it?" Then we went to an engagement rate of like 85%, 90%. And then we bring other teams. Then we were like, "Hey, how can we bring this goodness to other teams as well?" All of a sudden, we had an expansion footprint, an expansion motion, happening across many of our customers. It was really exciting.

The other interesting thing, and this has become the kind of like, hey, you know, you're looking good if you do this, was early renewals. So, usually, people will just renew on time. But we were creating this cadence where we saw our customers to their benefit on a quarterly basis. We were pattern spotting that every now and then. People would be so excited, like, "Oh, let's just get the renewal out of the way." And so, predictably, about 30% of our renewals would pull forward into the quarter before. It was astonishing.

Alex Kracov: It's amazing.

Wynne Brown: Yeah, it was a really great, just positive sign something magical is happening here.

Alex Kracov: I'm taking notes as you're talking, because I think we definitely fall into this trap at Dock.

Wynne Brown: Get this thing in recording.

GitHub's Customer Education

Alex Kracov: Yeah, where it's like, all right, we want to renew our customers. We want to stay on top of them. But oftentimes, we fall into this trap at Dock too. Our outreach can be more like, "Hey, just checking in. I want to see how it's going. Let's talk." And it's like no one wants to just talk for the sake of talking. You need a touch point. You needed an education touch point. And I'm curious. Like, when you're doing this at GitHub, was the customer education you're bringing, was it about like new GitHub features and ways they could unlock GitHub? Or was it more about the market and developer? Then maybe a follow-on question to that is like, who's the audience? Are you trying to get to the CTO and the highest people in the org, or was it sort of teaching everyone? How did you sort of think about the persona on the other side?

Wynne Brown: These are perfect questions. Often, it would be hot topics. Like disaster recovery was really hot at the time. We would then try to hook it into, if GitHub could be helpful in those areas, then we would say, "Hey, do you want to follow on training? Because this is how you could actually leverage the platform to help support what you just learned." But it was really trying to be, especially, it was unique to GitHub, because GitHub is such a leader in this whole world of how developers work and collaborate. And so we had the advantage of automatic status as thought leaders. So just us providing information that was helpful to their teams was a huge win for us. It varied where we were targeting. We did a lot of account planning. Each CSM, we kind of rebalanced books of business so that everybody could have an account plan. Who do I want to penetrate to? Am I more concerned in this engagement with users who seem to be falling off are not using us as much like what's happening? Or, hey, we have nailed the director level. Do we need to rise to the VP level? So then we're going to suggest topics that are more about, how do you leverage your developers in a more effective way? It could be more of a business-oriented or efficiency gain-oriented topic.

And I will say this. Often, unfortunately, many, many organizations reach out to just touch base. And it isn't even just a neutral. It's not like, oh, bummer. They're not going to engage with us. It actually erodes trust. Because it's noise. Everybody has a million things coming at them all the time. And if a software tool that you really enjoy using and you hear from the CSM, "Hey, just want to touch base," you're like, oh, I like this tool. But why did that even occupy my attention for the 30 seconds it took me to read the email? Every touch counts. The whole pull mechanics idea is that every touch should give value to the customer. And if you're writing an email like, "Hey, just want to touch base. Do you have time," don't send it.

Alex Kracov: Yeah. And even worse, if you get on the call to touch base, and then you get on the call and this is like, "Hey, how's it going," then there's no value-

Alex Kracov: Do you want funds with that?

Alex Kracov: Yeah, exactly. And you're even wasting more time. Then you lose trust, so you can't even get on the next call when it's more important than things like that.

Wynne Brown: That's right.

Enterprise CS at GitHub

Alex Kracov: Yeah, it's really, really interesting. Then also in GitHub, you sort of established an enterprise success motion. Is that very similar to what we're talking about now, or did that look very different? How did you think about the difference between mid-market CS and enterprise?

Wynne Brown: That was really fascinating. And in fact, one of my happiest things in my career is about the first hire there. He's still there in that role. He was a super senior kind of strategic thinker. But backing up to your question. So when I came in, I was actually really, really surprised, like foundationally shook, that there were no CSMs assigned to the largest accounts. It was really interesting, and it was really odd.

Alex Kracov: So this was all pooled CS?

Wynne Brown: No, it was the AE. And absolutely correctly, the very, very largest strategic AEs had just two or three accounts. So they were kind of maybe they do a new business sale once or twice a year, but they were really keenly focused on like, say, Apple, just as an example for conversation. And so they were really playing the role of CSM and AE, which worked for a time. One of my most important and, thankfully, successful internal campaigns was getting my point across to those strategic AEs of why they should want a CSM - we call them field CSMs - a field CSM partner, what it would alleviate for them in their workload, and how it would unleash revenue. Because at their core, those people were salespeople. They had very high quotas. They were meeting them, but I just started to just pretty relentlessly paint a picture of like, why do you want to do the CSM work? I mean, you can go to all their meetings. We're not trying to cut you out of the relationship. Quite the opposite. The only way enterprise or strategic accounts actually thrive forever is multithreading. And you are a single person. You are the only person talking to Apple. We cannot do that. So I got the strategic AEs on board and then made the case, the business case, to my leadership team, and we were able to establish that new team. And it still is thriving so that makes me really happy.

Alex Kracov: When you're hiring for enterprise CSMs, what do you look for? Because it's definitely a really, as you're kind of describing, it's very different than SMB, mid-market. You're really long-term oriented. What type of character do you need to hire into that role?

Wynne Brown: So, for all CSMs, I'm always going to hire people who are curious, who are very human-centric. Because that customer centricity, like we've been talking about, is absolutely required for everything to be successful. When we look at the really top of the pyramid CSMs who are working with a handful of strategic accounts, they also have to understand business. They have to understand the strategic, long arc of what an engagement could and should look like. So things like we've already talked about, like multi-threading, understanding how to map an org. It's very similar to how you will want to hire for that strategic AE. People who really understand how to extract from public filings, from interviewing senior people, from news articles, what are the corporate goals, stated and unstated, that are happening in this account? And how does my solution consistently support those goals? So they're always tying everything back to the business case, to making VPs or C-level people into heroes.

Fixing Churn at Seal Software

Alex Kracov: So let's switch gears and talk a little bit about Seal software, which was like an AI contract analytics platform that was eventually acquired by DocuSign. And I think when you joined, they had a big churn problem. But you flipped around. And so how did you go about identifying, all right, what was the cause of the churn? Then how did you go about actually trying to, okay, now that I know what the problem is, how do I actually fix it?

Wynne Brown: So, in hindsight, I always feel like I tell my stories a little bit weird because I want everybody to think I'm a genius. But I don't think any of these things are genius. I think that the real differentiator between mediocre, good, and great is execution. Because I think anybody would look at the situation at Seal and have the same conclusions. But then it's the big, what do we do now?

I actually was a fixer twice at Seal - first for the CSM function and then for the learning services function. Seal software is a fascinating story. They were a first mover in the contract analytics space. They were doing machine learning and AI before everybody apparently does machine learning and AI. And it was a really incredible opportunity. All the customers were large enterprise, which is like the playground I love to play on most. It's the most complex and most challenging. And we all know, if you have a leaky bucket, if you have a retention problem, it makes the burden on new sales at times seemingly impossible. When I went into Seal software, we were in an impossible situation. It had to get fixed, or the company would die. So we had 65% net retention. So the leaky to buckets, the company would die. And so it was clear they had incredible logos. The CS team was basically non-functional, and I was brought in to rebuild it completely. I was extremely supported by the sales leadership and the CEO. They understood that the problem was dire and that they needed help. And so that's thing one. It's that, a lot of times, people know they have a retention problem. They bring in a CS leader, and the problem is leadership, or the problem is the product.

We did not have a problem in leadership. We did not have a product problem. We actually had an overabundance problem. Our platform had a list of 120 use cases. So your Google or your Kaiser Permanente. And you buy the platform. CS is weak. You have no idea where to start. And so you don't. And so you become shelfware. So that was the situation when I came in. Looking at that, I was like, "This is awesome. This is so fixable." So very quickly - I always lead from the front, so I always had my own customers amongst my own CSMs having the bulk of everyone - we did some very simple things. First and foremost, the AES, who were super paranoid understandably about, like, "My god. I had this incredible sale, and it's dying," they were able to rekindle the relationships and introductions. We could kind of get everything back to conversational with our customers. A lot of customers had gone completely silent. Then we did - it's going to sound familiar to our conversation about GitHub. We created persona-based pull mechanisms where we said, okay, you're the head of procurement. You're the CPO, or you're the GC. You are going to worry about these three things in your contracts. Where do you want to start? In the meantime, we've already looked into the repository and have a good sense of what we should recommend. But instead of saying, "Okay. Great, have you purchased Seal's software," here's 120 use cases. Good luck. And so I'll kind of anonymize a little bit here just to respect the confidentiality we had, even though it was years ago. So we had one customer who had gone dark. We rekindled the relationship. We brought them three likely use cases. They chose one of them. And within eight weeks, we returned, through the savings they could identify, $15 million to them in two months. That's 2,000% ROI.

Alex Kracov: Unbelievable.

Wynne Brown: So we just kept blocking and tackling. We only had about 50 customers at that point, so it didn't feel like a mountain, like that was impossible to scale. We could block and tackle for 50 accounts and do this and that and do for everyone what we did for that one customer. It was really exciting.

Alex Kracov: Yeah, it's an amazing story. Then how did you think about onboarding, too? Because I assume you figured out this problem on the churn side. But then as your onboarding customers, I assume it's like, all right, you got to identify which out of the 100 whatever use cases that they should start with. And I think you're able to increase or shorten time to value from like six months to six weeks or something like that. How did you think about onboarding, and how did you overhaul that?

Wynne Brown: Well, it was really a holistic effort, first and foremost. When our partners in sales and the AEs started building confidence in us when we were fixing all these problems, right? And so then we could go to them and say, hey, we want - especially at the C level, they needed to understand the robustness of the platform. But when you're talking with a sponsor, the business owner, the champion, the users, we need a specific use case. So in the sales cycle, just agree with them on one thing. During implementation and during onboarding and training, we'll focus on that one thing. And so, again, it's like, I want to seem like a genius. But it's just logical, right? Don't confuse them with 8 million things we can do for them. Just pick that one thing that's going to make somebody hero, and then we win. And then we have access, and then we can just keep doing it over and over and over again.

Alex Kracov: Yeah, I think there's such a good lesson there. I find people just over complicate business so much. I mean, my backgrounds are marketing, and people try and make it so freaking complicated. It's not complicated. It's simple, but it's hard. It's like, actually, doing it is hard, but the roots of what you need to do are fairly straightforward and simple. It's like people over complicate too much. It's just, I don't know, too much weird advice on LinkedIn about what you got to do, and so on and so forth. It's a funny state of business advice.

Wynne Brown: Yeah, and I wonder if it's like machine time in people's careers. Because I definitely remember earlier in my career, I boiled the ocean. I tried to do everything for everyone. And I feel like as much as you want to as a leader in part and take out of your brain and put in everybody else's brain what you've learned, I feel like human development requires people to make those mistakes. I mean, one of the things that is so important that I learned as I matured in my career is, you say no and you prioritize. And that's good. You're not letting anybody down. You can definitely explain your process so that people understand why something is a higher priority than not. And going back to the CSM work, one of the most important things is for a CSM to be able to take a feature request. Run it up a five pool product, and come back to the customer and say, "No, we're never doing that." To have such a trusting relationship, to close the loop and say, no, that's just, nobody else has asked for that feature. It's just not going to be on the roadmap ever. But let's focus on the things that do make a difference.

Being Acquired by DocuSign

Alex Kracov: The company was eventually acquired by DocuSign. What was that like? What's it like going through an acquisition as a CS leader, and what's it like to work at DocuSign?

Wynne Brown: DocuSign is awesome. If I wanted to be part of an 8,000, 6000-person company, it would be very high on my list. But my DNA is early stage. And the more problems, the better. So coming into DocuSign, all of the senior leaders, we all stayed for the year that we promised. Some stayed longer. Some really found a good niche to fit into. That year was really about focusing on the transition and making sure all of our people are taken care of, making sure that the products were well-integrated. The landscape of DocuSign now, it's like Seal is part of the core of their offering now. It's really exciting. I loved the team that I landed into and got to do this transition work with, but it wasn't a fit for me. My cadence is adrenaline junkie, right? And so they are very wonderful, methodical organization. I thought that I was moving slowly on a project, and I was about to apologize to my boss one day. She spoke first, thank God. Because she was like, this is moving so fast. I was like, this is just not my water I swim.

Alex Kracov: Yeah, it's so funny.

Wynne Brown: I can't say better things about them. Yeah, I mean, there's just, know thyself and be at the stage that works for you. For the good and the bad, early stage has been where I've sat. I'm now focused a bit more on taking a lot of my learnings and applying it to later stage companies. But fully-established companies is just not on my list.

Scaling Fable and RocketReach to Series A

Alex Kracov: Totally. I think there's such a difference between the DocuSigns of the world public company, then even there's the startup and then the scale up. Scale up can feel fun and building and all of that and move fast too. But then after DocuSign, it seemed like you went even more early stage, a seed stage company, with Fable, and tried to do that again. I think they were digital accessibility. And you, I think, had a broader role. Not just CS but just general revenue. What was that like? What was that like taking the company from seed stage to series A and sort of building up? This was maybe more of a building situation. What was that experience like?

Wynne Brown: Yeah, that one was super exciting. It was so much fun. And it was the first time that I've really been part of a mission-based company, using the platform that we had to make sure that the digital world is more accessible to people who live with disabilities. It was just such a joy to work on something that really mattered. I mean, we all joke about, like, if software is down, nobody is going to die. In certain startups, actually, - not that anybody would have died - but to think of how Fable empowers people to, you know, we don't even think about being able to use digital products, right? It was just a really exciting place to be. It was really like the step in my career really leveraging the things I've learned. There's a certain point where you hopefully have had enough success and failure that you feel like, I just want to leverage all of this and put it to work for my colleagues and for my customers. I have always, you know, I cut my teeth as a salesperson. And so I've always loved the combination of customers plus revenue. I've managed sales teams off and on, sometimes just the customer base, sometimes new sales. And so it was a really great opportunity in a very early stage company to have a huge impact on how they did business. To really craft everything from the first touch at the top of the funnel by creating a BDR team, all the way through, how do we do the first sale? It was really a land and expand motion in a lot of ways. How do we then fulfill that promise of that first sale by delivering value and then, like you've heard me say, spreading that goodness across other areas of those organizations?

Alex Kracov: Then after Fable, you went to go work at RocketReach. I think there you had a similar situation, where you started maybe on CS and then expanded into sales, and then were running kind of the full revenue or both the full customer journey there. Maybe one question we haven't talked too much is like, how did you think about managing this broader team? How did you think about managing not just sort of the frontline folks, AEs and CSMs, but also managing managers and inspiring a bigger team to go out and go get revenue and retain customers and all of that?

Wynne Brown: Yeah, I love that question so much. It's one of the most humble things you can do as a leader, is be a first-time manager's mentor. Because it kind of makes or breaks people. You hear from friends who had an awful first time being a manager who got no guidance, who felt like they had to make it up as they go along. There are great tools like Lattice, where I used to work, that can really support people. But if you don't have somebody who's basically like your consigliere behind the scenes, you can really fall flat, and it can leave a bad taste. Usually, first-time managers have been waiting for that opportunity for a few years, maybe even longer. And it is this potentially magical moment in their lives.

I love having first-time managers be promoted from within. The thing that you have to have - as a manager, we all know this - is that your people know that you know inside and out what the role requires for success. It doesn't mean that there's great sales leaders who are not the best salespeople. You can do that, the whole coach-athlete thing. But you have to know the product, for example. So, in the situation at RocketReach, the folks who were those first-time managers were internal promotions. It was delightful to see them really step into the role. Being open to coaching is something that, no matter how old or young we are, we always have to have. So having that open learner's mindset is absolutely essential. Folks who come in and think that they know everything when they're a first-time manager is obviously a future flag. That's like, you know, what are they up to? Are they trying to power grab? The motivations have to be there in order to be successful. RocketReach was really interesting too. It's really my first time in SMB. It was one of my main reasons to go there. It's that there's so much happening in plg motions, even on the enterprise side of the CS world, that are at scale. And so I really wanted to go there and dig in deep on that long tail. It was fascinating, and I learned a ton. It was a really fun ride.

Alex Kracov: What was different about the SMB and product-led motion?

Wynne Brown: When you're dealing with SMB, or even DSMB, or any of the plg type motions, data is obviously king. Making sure that, kind of two things, data has to be clean. So things that haunt us like duplicate accounts, right? Like the things that you talk to anybody in tech or the things that haunt everyone. Being able to have a clean data set is so important. And then not boiling the ocean. You can ask your data set 20 questions. And if you get 20 answers back, you're going to get stuck. You're not going to know what to do. So knowing how to ask the right questions of that data and then giving it enough time to evolve so you can see if the things that data is telling you, those two or three North Stars you're setting, have a positive impact or negative impact, and just iterate, iterate, iterate.

Alex Kracov: The other stuff I'll add there because we deal with this at Dock. It's like segmentation and prioritization. It's like we have so many different types of customers, one-person users, big companies, everywhere in the middle. It just becomes so overwhelming. And so thinking through, okay, which we basically have an unmanaged segment, and managed and super managed. How do you think through that, and how do we sort of structure our day as CSMs? It gets tricky, because there's just so many people reaching out to you, so many potential avenues to go in the plg, SMB land. And different levels of user too. Some are totally self-sufficient and don't need your help, and then others desperately need you in there to help them. So yeah, it's tricky. It's tricky.

Wynne Brown: Yeah, I'm fascinated by a user as a user as a user in the sense of how you onboard people. So that's one of my huge takeaways, was even very large enterprises, now people want just to do on-demand or group live webinars. You don't have to do white glove training all the time for everyone. That was really hugely impactful for us. So we started doing at-scale offerings that we'd offer everyone - our SMB, our mid-market and our enterprise customers. Because there we still had some on that other kind of end of the segments, and we have plenty of people who just wanted to show up or watch the recording. Because RocketReach is a pretty simple tool. And so, in that case, it was easy to try and see how much we could not do one-on-one with our customers. And it was, yeah, it's a huge takeaway for me, for sure.

Customer-Centricity and Buyer 3.0

Alex Kracov: I'd love to end today's conversation talking about customer centricity, which I've seen you talk a lot about, and sort of this concept of buyer 3.0. Can you explain kind of what you mean by that concept, and how should revenue teams adopt this mindset?

Wynne Brown: Okay. So I'm super obsessed with this. And I wrote a whole series of seven articles over the summer because I just think it's fun to put ideas out there and see what people think. So Buyer 1.0 was way back when I started in tech, where people, all of a sudden, weren't buying software and putting it on their machines, in their own closets, or colos, or what have you. They were renting it, right? And so we have this whole SaaS thing. Nobody knew how to buy it. All of the power was in the vendor side, where people would show up and you do whatever demo you want. People were just like wide eyes trying to figure out this new world, extremely vendor-led sale. Then we had 2.0 which was about, like in my estimation, about 12, 10 years ago where there was so due to crowd and all social sharing of information - LinkedIn was a huge part of that as well - where the buyers came in much more informed and what I think people use the rule of thumb, like they're coming in 80% informed. And it became much more of a dance between the vendor and the customer.

Now enter 3.0, and so many companies live in that world. Plg, people are using your product before really even committing to it. Right? There's so much transparency of information that I posit that 3.0 means it's all in consumer, the prospect, the customer side. The power is on their side now. And the implications for that as sellers is that you have to come arm for bear. You have to know your prospect. You have to have really good, informed research guesses on what they care about. You absolutely cannot do spray and pray outbound. You absolutely cannot do the kind of dog and pony show you want to do in a demo. You have to show them what solves their problems, and you have to understand that the control is more on their side. This is all about like, again, every interaction you have with a prospect or customer has to give them value. So this is why I'm actually super excited about the buyer to 3.0 era. Customer centricity is not optional anymore. It will be a differentiator between companies if you are not customer centric. There's so much competition. ChatGPT can probably write the code to be your competition. And so how we execute and how we treat people is the differentiator. And I will say this, too. Shameless plug for Dock. My whole career, I wanted something like Dock. Deal rooms are made for lawyers. They're ugly, and they're transitory, and they're not user-friendly. To have a place where you could do what I think is required, absolutely capture what the value is the customer is purchasing on first purchase, have mutually agreed success plans that name not only what the goals are, but on what timeline and how you will mutually measure it, all of these things as transparency is what this era of buyer 3.0 is all about. And shameless plug for Dock. You've solved a problem I've been complaining about my whole career.

Alex Kracov: Thank you. I really appreciate that. I mean, everything you are talking about, obviously, we are huge believers of it in Dock in sort of why we see this category of software taking off. And sort of one way I like to think about it is like, we're shifting from this world of sales enablement where it's all internally focused. How do we train the sellers and the sales team to buyer enablement? How do we better support our buyers? How do we be more consultative in the sale? How do we be like an authentic partner to them and collaborate around business cases, and actually recommend solutions that will solve their problems and not just kind of jam your software, your solution down their throat? We think it's positive, right? We think this is a good power dynamic shift. People don't want to just be sold stuff that they don't actually need. They want to buy things that actually solve their problems. People have been burned too much, and so you really need that transparency in sale and to be really consultative. So that's where we see Dock fitting in. It's a good shift in the world, we think.

Wynne Brown: I love it.

Alex Kracov: Well, thank you so much for the time today, Wynne. This was an amazing conversation. I'm going to immediately go send this to our head of CS, so we could start taking some of these learnings and applying it in our own CS function. If people want to go read those essays you wrote or follow up with you, where is the best place to find them?

Wynne Brown: LinkedIn. So you just go. I've pinned some of them, but it's a series of seven that I released weekly. So you can pretty much come to my profile on LinkedIn. I would love to have anybody message me, chat about it. I love this stuff. I'm a total nerd for it. So, yeah, that's where folks can find it.

Alex Kracov: Awesome. Thank you.