Joining Marketo

Alex Kracov: I'd love to start today's conversation talking about Marketo, which is such an iconic company in the world of SaaS. Can you talk a little bit about the state of Marketo when you first joined?

Catie Ivey: Sure. And yes, I agree, one of the all-time iconic brands I think in SaaS. It was such a privilege to have the opportunity to join. My only regret is, I wish I had been there earlier in the journey and had probably an even longer set there. So I joined Marketo as a mid-market sales leader when they were still a public company, so pre-Vista acquisition but obviously very much a mature business at that point. Marketo had opened an HQ or an East Coast HQ where they are running part of the commercial business out of Atlanta, which is where I live. So I was the first round up hires that joined to lead the team in Atlanta.

Alex Kracov: Very cool. Then what's been market sales look like at Marketo? What was the sale like at the time? Who are you selling into? Can you kind of take us behind the scenes of what it was like at the time?

Catie Ivey: Sure. Well, it changed a little bit during the time that I was there because I went through the whole Vista ride until the Adobe acquisition. So there was a couple of iterations. When I joined, they did have a true SMB motion that we didn't touch. But basically, everything from about 25 million in revenue up to 500 million was our cutoff. That's how we defined mid-market. In terms of who we were selling to, obviously, marketers within those organizations. It was still very, very inbound heavy. We were working hard to build a more structured outbound motion. Because Marketo, like many of the early marketing automation days, had grown up very much in this. They kind of created the world of inbound, and then their sales organizations were birthed out of that. So we were about 25% outbound when I joined, and we got that up to about 35% in the two and a half, three years that I was there.

Marketo's Private Equity Acquisition

Alex Kracov: What was it like? You mentioned these different stages of Marketo going through the Vista acquisition and then ultimately the Adobe acquisition. Can you take us maybe starting with the private equity turn into Vista? What is that like? What is that like for you sort of personally going through something like that?

Catie Ivey: So I don't have anything to compare it to, because this is the only PE ride that I've ever been a part of. I was at Pardot much earlier in my career as a rep, and then I went to the Salesforce acquisition there. So obviously, that was quite different or a very different type of experience. I learned a lot going through the Vista ride. There was clearly a number of inefficiencies that they identified and lots of reasons that they felt like they could optimize and improve some of the fundamentals of the business, which I think they very much were able to do. I mean, even just in terms of how we looked at renewals and who owned what for our retention, expansion, where we split off the net new versus the expansion motion, all of those things. This has got a pretty clear playbook, at least they did at the time. This was quite some time ago, but a pretty clear playbook in terms of how they optimize those things.

They also introduced some really impressive frameworks around outbound motion from an AE perspective, sales leadership. So I was a frontline sales leader morphed into a second-line leader towards the end of my time there. Really, really clear playbooks and expectations in terms of what great looks like. I mean, down to the details of, here's exactly how you run a forecast call. Here's, if you're on a monthly cadence, here's what you roll up week one, week three, week four. Here's what it looks like. Here's what the notes need to be structured as. So it helped to add a lot of predictability. Obviously, I'd worked at some great companies before that, but this was certainly the most rigor in terms of just commercial rigor that I'd experience. So I have tons of positive learnings there.

Alex Kracov: Super interesting. So it's really that tactical. Because I've never been through a PE acquisition, but it was literally like these are the notes you should do on a forecast call. Because I always think of it as like, all right, PE comes in. All right. Let's fire these people. Let's get some efficiency over here. But it was really like super tactical go-to-market advice.

Catie Ivey: At least for us and the experience in the commercial business, it was incredibly tactical. And that just points to part of the fact that Marketo had been a bit of the wild, wild west, been growing really, really fast, a victim of its own success in certain ways. And so they clearly saw opportunities to create more structure and predictability even just in terms of how we looked at lead flow, how we carved territories, who did what, what was considered inbound versus outbound, all of those things. I don't know if it's part of their standard playbook, but they just certainly had an opinion on those things and I think made as a much tighter, cleaner business as a result.

Alex Kracov: Yeah, super interesting. And even on the first example you gave around the renewals, what did they say to do? Was it separated out from a customer success person to like an account manager role, like add a more salesy person?

Catie Ivey: Yeah, they built out a whole renewal coordinator role, a team that was also based out of Atlanta during the season that I was there. It was literally just high-volume SMB to mid-market renewals, and that was their entire job. So they're very focused on how do we eliminate inefficiencies, where an AE might be spending unnecessary amounts of time on paperwork or documentation. Same thing on the CS side, like looking at things that have the ability to be more scalable or automated.

Alex Kracov: And who's actually doing it? Is it just like a Vista associate, or somebody comes in and starts sitting in meetings and doing stuff?

Catie Ivey: We could probably unpack like 60 minutes on nothing but Vista, but I feel like I'm so far removed from it that I'm going to get some of the details wrong. But yeah, they definitely - I mean, there was a team. There was a team that they brought in. And again, I was kind of a mid-level manager, so I wasn't like an executive running massive organizations at the time. So I was exposed to some but not in all of the conversations. But yes, there is a team that is tasked with some very clear deliverables along the way and come in and roll out the playbooks.

Alex Kracov: Yeah, so interesting.

Catie Ivey: They've got a whole team of trainers as well. So we went through as sales reps, and then people managers as well went through some pretty detailed training in terms of kind of the - there was a whole-phased approach over the first 12 months where we learned a lot and were expected to implement things pretty quickly.

Martech Trends

Alex Kracov: You've basically spent, I mean, most of your career working in revenue tech and martech. I mean, obviously, Marketo was part of this huge martech boom that sort of shaped how we all do. Think of marketing today and marketing automation. I'm curious how you think about, like looking back on that era, taking it forward to today, what's your take on the martech landscape today? Is marketing automation still sort of the core centerpiece of it? Does everyone still need to buy a Marketo system today? How do you sort of think about how this whole industry has evolved? I don't know. What's your recommendation for marketers thinking about their tech stack today?

Catie Ivey: Oh, that is such a big question and a loaded question.

Alex Kracov: Yeah, fair enough.

Catie Ivey: The other thing I would say is, probably it's changing faster now than it's ever changed in my career. AI is just driving so, so, so much change. And I think we're all asking some really fundamental questions in terms of how will we be using CRM in 5 to 10 years? How will we be using marketing automation? How will we be thinking about email or the lack thereof? There's a lot of pieces that, at the moment, I think still are very much core to how we do our jobs as sales and marketing leaders. There are questions in terms of whether those will continue to be core. One thing that I think did change my perspective, I consider it such a privilege to have lived through and sold through those early marketing automation days. Because I remember. Some of this was at Pardot, so even earlier. But I remember the magic of, like, people could go to a website and put their email address in, and then they'd show up in the CRM. That wasn't common 15 years ago. You would walk a marketer through that workflow and it'd be like minds blown. Oh, my gosh, we could use landing pages to do this and emails to do this. Then we can track this layer of anonymous activity. And so I'm constantly thinking, what are the things that today we're just starting to get exposed to, that maybe in 5 or 10 years will going to be like, obviously, we should be able to use technology to do that? Obviously, it should work that way. And I think having some of those, like living through some of those big pivots, kind of maybe help shape your thinking in some of that.

Joining Demandbase

Alex Kracov: Totally. I mean, it's amazing how much the industry has evolved from like the, all right, let's submit your form for the e-book, and then we'll run the drip campaign. That's just going to magically bring in all the MQLs. That era seems to have kind of drifted away from, how to say, now it seems to be way more signal-based and sort of different to that. Then after Marketo, you moved on to, I guess, Jon Miller's next company which was Demandbase, right?

Catie Ivey: Yes, sort of. So Jon Miller actually left Marketo and started Engageo. Engageo is sort of a competitor of Demandbase. I actually went to Demandbase, and then Demandbase acquired Engageo. So then Jon came in as our CMO for a season, I think a CPO as well. So an executive at Demandbase for quite some time. So I got an opportunity to work with him at two different companies.

Alex Kracov: Then what was your role at Demandbase? I think you were still in the mid-market segment.

Catie Ivey: Yes, so I was an RVP. I owned the East Coast mid-market when I joined. Then that transitioned into more of owning the East and West Coast. But always mid-market was my entire focus at Demandbase.

Alex Kracov: What is it like managing mid-market reps? What is the secret there, like when you're not just in the deals themselves? What's the difference between managing, let's say, a mid-market rep or maybe an enterprise rep versus like a commercial rep? How do you sort of think about the difference?

Catie Ivey: Well, part of it is just the nuance of how you define them. Every business and even the TAM that you're selling into has its own nuance in terms of what makes sense. I love mid-market, specifically how we defined it at Marketo and Demandbase. There was a lot of similarities. At Demandbase, it was companies that were larger than 25-million annual revenue but smaller than a billion. So just similar to how we broke it down at Marketo. Those are some of my favorite types of deals to do as a sales leader and some of my favorite types of customers to support on the post sales side. Because they're big enough to have some complexity and to be interesting and to have real business problems that they're solving and to have figured some things out about product-market fit, who they're selling into and the ICP. But they're still small enough for the most part, be a little bit more nimble. So you're not talking 18-month procurement cycles and like the true enterprise slowness, which I just do not have a ton of patience for. And so at least, for me, personally, in terms of my personality and my skill set, that upper end of mid-market or lower end of enterprise is definitely what I enjoy the most because of those two factors.

Alex Kracov: Totally agree with you. I think at Dock, we've been experimenting with, all right, which, where do we sell into? We started super SMB, but it wasn't that interesting because they don't even have a sales process. There's not that much to work with. They're still even figuring out their own business model. But as you start to drift into mid-market, all right, they have product market fit. They have something that's working. They're going through all the scaling challenges of a company. That's where technology like Demandbase can get really helpful and sort of put, I don't know, supercharge that growth that they're trying to make happen.

Catie Ivey: And that's why I would say it probably is even SMB really interesting depending on the product that you're selling or the problems that you're trying to help them solve. Because if you're helping them nail product-market fit, or pricing and packaging, or what should we build based on this persona, there's really interesting things that happen in those first 50 employees. But I think in the world specifically of martech, sales tech, revenue tech in general, yeah, things start to get interesting once you get to that 25 to 50 million threshold. I don't know. There's some real scale momentum.

Alex Kracov: Did you feel like Demandbase was creating a new category, a new type of software? Were you sort of leading the way, or do you think of it more as like you were, all right, account-based marketing kind of already existed, and you were a solution to help supercharge that? How did you think about kind of structuring the sale and the positioning?

Catie Ivey: It's an interesting question. Because depending on the day and the customer, it felt like we were doing a little bit of both. So there was certainly the element of ABM was just the next phase of what marketing automation needed to grow into. So acknowledging that there's a different way to go to market, that we need to be much more focused, more relevant, less scale, all of those things. Part of that was just sort of where the need for ABM came from. But on the flip side, there was a lot of conversations that felt much more, at least how I think conversations are in category creation would feel in terms of, like, they were actually challenging you to think about how you go to market differently. Yes, you've created this that functions a certain way. But if you want to do ABM well, then you're actually going to have to unpack some of that and be willing to approach the problem in a very, very different way. That, to me, is what felt much more like the category creation mode. It wasn't just making what you're already doing better. It was being willing to think about something quite differently. We'd have folks, especially smaller companies would come to us and just think that ABM was like the silver bullet they needed to layer into their tech stack. We would tell them very honestly. Like, you're not actually going to be successful with us. You're not thinking about this in the way that we actually are enabled to make you successful. And so we got really good at sniffing that out. Because we owned the net new and the retention number, so we had to sell good deals. It was really important, at least in the early days there.

Alex Kracov: And so what is the right way to approach ABM? I think a lot of people see these buzzwords floating around. They're like, "Oh, I should be doing that." What's the right type of business segment or ICP that you should employ an ABM strategy? How should companies go about building out an ABM strategy at their company?

Catie Ivey: You're taking me back to my roots. I haven't talked about ABM in depth in quite some time, although I do own marketing today. So it's one of the topics of conversation that we're having at Walnut. The first place that I would always hope people to start is, regardless of whether you're an entirely inbound motion and you're trying to build some sliver of the business that's outbound, there's got to be a data layer that you get in place, that there's some commitment around actually getting it right. So it sounds super, super basic, but you've got to actually be committed to a target account list. Then as a company - so end to end, not just your CMO. The company has to be committed to, hey, there's a certain subset of our ICP, and we are willing to double down and spend money and resources on going and building awareness and building brand there. Because we're committed to. We believe that they're going to be bigger deals and stickier deals for us. That's the real fundamental simple thing that so many of those early customers, whether it's Demandbase or other players in the space, that they would miss that. It was literally like, "Well, we've got a list of a thousand companies, and we're going to upload it into some system. You guys are going to do magic and get us deals out of that list." That's not really how it works.

Alex Kracov: Yeah, I think we tried to do this at Lattice a few different times and had a bunch of false starts, where I was like, "Let's have our list of 20,000 accounts. Then let's have our list of 10,000." It's hard to do. I was doing, I'm in the marketing seat trying to - I was like, "Okay. I can run ads at this segment." I can do some things. But I think we sort of got better at it as we actually made the list smaller, which was maybe more unintuitive. I was like, "Okay. Let's start with 100, and let's really focus on these 100 and go after them. We know that these are perfect." That's sort of what we're trying to do now at Dock, too, with our own sales motions. Let's keep it really small and tight, and then build out there as we get more sophisticated and better as an organization.

Catie Ivey: Yeah, every company is different, obviously. The product that you sell is different. But as a general rule, somewhere between 500 and 2,500, depending on the size of your go-to-market organization. You try to figure out some subset of that and then start there.

Winning in a Hyper Competitive Market

Alex Kracov: And then I think of Demandbase in a super competitive market, with like Demandbase against 6sense. I don't know if that's exactly what it was like when you were there. But what's the secret to winning a super competitive deal?

Catie Ivey: Well, yes, it was very hyper competitive. I think today the market is still pretty competitive, even though I've been removed for a bit. I don't know that there's one single secret to winning a hyper competitive deal. I've sold in some really competitive industries. And honestly, the category that I'm playing in today is pretty competitive as well and getting more crowded by the day. If I had to pick a couple of things, I would say one people buy from people. So this is not rocket science. If you build real relationships, which usually starts with genuine intellectual curiosity, you've got to care about the person that you're talking to and the company that you're selling into, and genuinely be interested in the problems that they're trying to solve and what makes them successful. Usually, from there, you can build out a plan that is going to feel slightly more thoughtful, robust, strategic than almost anyone that you're competing up against.

Demandbase is probably not the best example, but there was clear examples during the time at Marketo. For example, we knew our product was much more complex than HubSpot at the time. So there was some very clear, in our SMB deals, we knew if we were competing with HubSpot. Like the angle that we talked about was, "Hey, this is going to look harder on the surface. You just need to be prepared for that. You need to be very, very clear. But if you want to mark it with the big boys, if you're looking for the right long-term solution, then I'm going to help you get there, and I'll help you put it together along the way." You found the things to anchor around regardless of whether your product was less robust, more robust, all of the things. To me, that's the secret in winning in a competitive space. You have to understand. You're either better or your simpler generally, or you're better or your way less expensive. And neither one of those is right or wrong, but you do need to understand clearly where you sit so that you build a plan around that and then you sell to your strengths.

Alex Kracov: So it's like being super authentic about what your product is actually good at and your strengths and weaknesses, and then just mirroring that back to the customer. Hopefully, they care about your strengths more than your weaknesses. That's where you win deals. Or you can learn to take that product feedback back to the team and say, "All right. We got to cover up some of this stuff."

Catie Ivey: And as basic as it sounds, to say like people buy from people. Yes, of course, you tell a sales rep. You never lie. You never lie to a prospect. You never lie to a customer. But take that a few layers deeper, just be authentically human and real with the feedback that you're giving. Like, "Hey, yes, one of the things that you highlighted, it's not a massive strength of ours. Let me talk to you about two other things that, based on what I know about your business, I think they should really matter. But you tell me if I'm wrong. You know your business better than I do." And so just being really, really honest and transparent and then being able to do that while you still kind of have that art of spin, if you will. I don't know. It's hard to teach. But when a seller has that, it's a super power for sure.

Alex Kracov: Yeah, I've also found too, especially if you're a startup and sort of the smaller player in this space, it's really hard to compare apples to apples. Like Dock competes against Seismic, right? Comparing our feature setting and Seismic, of course, we don't have every single bell and whistle, but you need to make the comparison more like apples to oranges. It's like, hey, both of these are good. I like apples. I like oranges. Pick which sort of fruit or which approach you want to go with more. That's how we're able to kind of wiz our way into some of those deals with Vita and incumbent, which is way trickier.

Catie Ivey: Yeah, for sure. And I think also, as you start to figure out the person that you're selling to or the team that you're selling to, some people really care about being an early partner. Your voice is going to be so, so amplified here. Like, I want to work with you. I want to learn from you. We think that the feedback you're going to have on our product and our roadmap is going to be massively impactful. That doesn't resonate with everyone, but I guarantee there's people that your team is selling to that love that messaging. They want to partner with an early player because they feel like they're going to have a different seat at the table in terms of influencing that roadmap.

Joining Pendo

Alex Kracov: I'm curious about your next sort of stop in your career. You went to go work at Pendo. Was that very different for you? Because I assume it's a really different ICP or maybe selling more to product managers outside of the house.

Catie Ivey: Very, very different, yes. It's the only place to this day that I've ever worked where I wasn't a power user of my own product. So I wasn't selling to more of me or teaching people how to sell to me. So yes, that definitely, honestly, it was one of the things that drew me to Pendo. I had actually used the product. So at Demandbase, we used Pendo and it sent great signals around retention and expansion opportunities. So I was familiar with the analytics enough to understand the value and the reputation and just the quality of the product itself. But I was partly interested in, can I actually teach someone to sell to a different persona? Can I teach someone how to think about solving problems that aren't just for a CRO or a CMO? So that felt like a really fun challenge/opportunity. It was also an opportunity to take on a much larger team and a broader scope than I had up to that point in my career. And so, for a lot of reasons, it just felt like something too good to say no to.

Alex Kracov: And I guess what's the biggest difference selling to a product manager or something like that versus somebody, a marketer who's just like, all right, I got to grow, grow, grow sort of thing?

Catie Ivey: Oh, there's a lot of differences. Certainly, I learned a ton about products, and I got a ton of new respect for product managers and product people in general in terms of how they think, how they're oriented. They definitely are - it's just a different breed in terms of what keeps them up at night. It's very different than a marketer that's tasked with a really large growth number or a sales leader. They're thinking about seven layers deeper and not always connecting those seven layers deeper with the ultimate business impact. So we had to help with that a lot. Like understanding the things that we're solving for, why do they ultimately matter and then who cares the most? Pendo was interesting because it had, I think it still has very much a combination of both the bottoms-up sales motion. So you would start selling to relatively small deals to those in power users, but there was also a top-down motion. You could have a pretty inexpensive subscription that would ladder up and get to a critical mass essentially where executives cared. And so you're teaching reps to do both of those motions to sell to the end user and then figure out how to sell up internally into the customer base and then also those larger land deals that we're starting at an exec. Those are two very different motions. And I would say selling with top down had a lot more in common with all of my experience selling into martech. The bottoms up was definitely a new motion for me.

Alex Kracov: Yeah, bottoms-up gets tricky. When I started Dock, I was like, all right, I want this to be just pure product-like growth. I'm going to make money when I sleep. I don't need to hire a sales team. And it doesn't quite work like that.

Catie Ivey: It's a dream, right?

Alex Kracov: Yeah, we did make some money while I slept, but it was like 2K ACV. Not exactly where I wanted to be playing. And so I think the way we think about it is like, that's just like more of a lead-gen machine for us. Then we take that momentum and it's like, okay, let's take whatever progress that end user has made and present it back to the actual, the CRO, or whoever is the actual person making the decision. Then it starts to look more like your traditional top-down sale at the end of the day to get those big contracts.

Catie Ivey: Yeah, 100%, and you have to figure out what those critical masses are at the different pieces of the segmentation. Once you've got 10 people actively in the product, is that enough for someone to care? Or what is kind of that tipping point to work into a broader customer conversation?

Alex Kracov: Totally. There's so much opportunity to waste your time too, I find. Like, all right. This looks good, but they have no buying power or whatever it is. And so it can be really, really tricky to figure out that.

Catie Ivey: Isn't that true in most, at least in my experience? The smaller the deal, the more challenging it is to close. And the smaller the customer, the more challenging it is to retain.

Alex Kracov: 100%, yeah. I have so many stories of that, of just these small companies who are quite the pain. But the big ones are pretty easy. It's funny how it works. I'm curious, what's your leadership style? How do you think about managing a big sales team? You mentioned Pendo is sort of like the biggest team you've ever managed. I assume, were you managing managers? Was it that sort of level?

Catie Ivey: Yeah.

Strengths-Based Leadership

Alex Kracov: How do you think about inspiring a bigger sales team when you yourself can't be involved in every single deal? How do you think about that challenge?

Catie Ivey: First of all, I'd say it is very different company to company. Any CRO that tells you they've got a playbook that's like plug-and-play from one place to another, I would say is just full of shit. Because I just fundamentally don't believe that that's how it works. Even when I think about my management style at Pendo, I think it's different in a lot of ways to how I approach the role at Walnut even though the team sizes are similar or the scope might be broader today. Probably, to me, the most important thing, I think a lot about strengths-based leadership. So how do you figure out? Every individual has a unique set of things that they're really good at. Well, I call them superpowers. There is something. And just about anyone on your team, if they legitimately want to be there and have some sort of buy-in to the business, there is something or multiple things that they're really good at. And the flip side is, there are some things that they are not good at. I think us, specifically those of us that came up in the old days of sales leadership, we were taught so hard to harp on everything that's broken, everything that doesn't work, to criticize and critique everything that goes wrong in a sales process. Even back before, we had call recording and all the different AI ways to power it. We were poking in at all of the things that might be making that rep a D player versus a C player or a C versus a B, like all of the way up. And I think if we can flip that on its head - and of course, you've got to be willing to give critical feedback, challenging feedback. But if you can identify at the end of the day what is it about this individual that they're uniquely skilled for, they're uniquely set up to be successful, that usually also ties into having some sort of understanding of what they care about on a personal level.

Of course, career ambitions, like what they're working towards. But you've got to know what they ultimately want to accomplish and what really matters and drives them. If you can connect that into some of the things that they're good at, and then figure out how to double down there, then I think that's going to waterfall, whether you are leading a sales organization of 8 or whether you're leading a revenue team of 80. There's layers of that all along the way. And of course, the larger the organization, you have to figure out how to tap into vision and inspiration and some of the big picture pieces without having the same depth of personal relationships. You're certainly not in every deal, and you're certainly not in the nuance of the business the same way that you are if you're managing a team of six reps directly. But I think that the same skill sets and the same values really still pervade the entire way up in terms of that strengths-based focus and figuring out how do you unlock greatness at every layer of the organization.

Alex Kracov: I love that idea of focusing on people's strengths. I mean, I think what's so surprising to me about just like sales rep persona is, there's so many different styles of sales reps who are successful, right? There's like the big personalities who are talkers and can just kind of get it done all on a call without doing all of the hardworking activity, follow-up. Then there's the ones who maybe don't sound as good on a call or maybe not as charismatic but then get it done just through really rigorous process and sort of being maybe more academic in their sales process. And so yeah, it's I don't know. The psychology of a sales rep is so interesting, because I've seen both be really, really successful.

Catie Ivey: Yeah, it is so fascinating. One of the things that I do today at Walnut is, I try to get 15 minutes with every new customer that signs on with us. They don't always take me up on it, but I offer a conversation, where a part of it is just welcome to the fam, really. If what approval, you just have an opportunity to work with you. But then I ask for some feedback. Hey, I would love to know what stood out in the sales process. You'd be amazed people will give you much more trends they've already bought from you. So if there was something that erupted that got under their skin, or they didn't like, or they didn't think was very well executed, they will also share that piece of feedback. But the thing that, to your point, so interesting, you will hear very, very different things. The thing that this person loved about Audie is very different than something that so and so loved about Leslie. Very different approaches, very different styles. But for whatever reason, part of why they won the deal is because, oh man, I loved my rep manager. I just loved working with this person. They did very, very night and day approaches. But trying to then marry those two and figure out, okay, how do we build a repeatable process that is scalable but then also allow reps to really flourish and do the things that they're great at, it's hard. It's hard balance for sure.

Alex Kracov: And I'm curious. Like, how does that impact hiring, like hiring AEs? Because you can have two very different types of AEs that are both successful. But what are the through lines? When you're looking at hiring sales reps, what are the things you're looking for, regardless of those different approaches that you're sort of prioritizing to bring them into Walnut?

Catie Ivey: Yeah, for sure. And that does vary a bit depending on the segment that we're talking about. Because we have both an SMB motion that's much more transactional, and we've got a pretty robust enterprise motion as well. So obviously, different skill sets. And even just the ability to work long-term customer relationships is important in enterprise, not important in SMB. So there's some of those nuances for sure that changes. To me, the one thing that's foundational for any sales rep that has to be there is intellectual curiosity, like someone that is genuinely curious about other people and about business. I just I don't think you can fake that. I don't think that you can teach that. If this is someone that doesn't read books, or Google things, or listens to podcasts, or get up and watch CNBC out, there's got to be something where they're just a little bit wired for business. And I think that's even more important in a startup where things move fast, things are changing fast. You just have to learn pretty quickly. I don't think there's any amount of structure that you can put in place as a leader, certainly as a frontline leader, to force that element of learning. So there just has to be intellectual curiosity. And I think coupled with that, they got to be good listeners. Curious people tend to ask good questions. But then, do they listen and digest the information? If they can do those two things, and they can probably learn just about any product, they can certainly learn most personas. If those two things are there, if they're not curious, or they're not good listeners, it's just really hard to come back from that.

Alex Kracov: And so it makes them like a good consultative seller too. Like actually listening to the problems, anchoring on whatever the customer is telling you, and hopefully anchoring and recommending an authentic solution that's actually going to help them reach their goals. So yeah, very important. I think regardless of the segment.

Catie Ivey: I was about to say it. I think about like whether we're talking about a 5K inbound transactional deal that's a really small company or a 500K enterprise deal. That same skill set is needed on both. It may manifest itself differently in a one call close versus a 12-month sales cycle. But that level of curiosity, pattern matching, building different relationships with different people, that matters to both of those. And the dream is, you want to hire someone relatively junior that you can then grow into the next segment, the next segment, or the next leader. That's obviously what we're all hoping for and working for.

Joining Walnut

Alex Kracov: Totally. And so now you're the CRO of Walnut. I think you joined a little over a year ago, like right after they raised the Series B. Can you talk about sort of like the state of Walnut when you joined? Why did they need to hire a CRO? What were you sort of focused on over the last year and maybe, yeah? Because I don't know if it's a good question. But yeah.

Catie Ivey: Yeah, sure. I was going to say it's a big question. How much time do you have? It has been just - I just had my one-year anniversary. So it has been an action-packed year. I had definitely learned more this year than in any other single 12-month window of my career. So that's a huge positive, obviously. It's one of the reasons that I took the role. It's because I felt excited about the product and the category but also excited about the scope and the opportunity to learn new things. So I lead marketing sales and customer success. So obviously, three very different motions. In terms of why, I think one of your questions was why they need a CRO. On paper, one, it would probably be a little bit smaller than some companies that would bring in a CRO. We have a bit of a unique set up in that we were founded and headquartered initially in Tel Aviv. Then almost all of our go-to-market and our customers are based across North America. So it can feel at times a little bit like two different companies. So most of product and R&D is in Israel, and then most of go-to-market are here in the US. I think that's probably one of the big reasons, that for Walnut specifically, they needed a relatively senior leader to own that broad purview, to function a little bit more as like how you think of it as a GM or someone that's connecting lots of pieces of the business into the headquarters in Tel Aviv and driving really strong alignment. Specifically, revenue and product was really important for us.

Alex Kracov: What's been the biggest thing you've learned? I mean, maybe we'll start with the marketing and customer success side of things. I assume marketing was maybe easier for you because you've had such a long career in marketing tech. But maybe I'm getting that wrong in assuming. Yeah, I don't know.

Catie Ivey: I love that that was your assumption. Of course, because I've sold into martech, I could obviously manage marketing. No, I would say there's been a lot of learnings there. We've done some rebuilding. We've done some hiring. I've got a small but mighty team that's doing some really good work. But to boil it down to one, I mean, I'm in the weeds of the business down to like what we're solving for on SEO, how we're optimizing our demand gen and our paid strategy? What's our influencer marketing strategy? Which conferences are we sponsoring? Actually, thank goodness, I have an event marketer finally. But I was literally doing booth set up and tear down and renting TVs, all of the tactical sort of on the ground pieces of running a small marketing team. So that's been really fun, but definitely a lot of learnings around just project management and efficiency and dividing up the tasks. There's always more to be done, of course. Any marketer knows, like, whether you've got a team of 3 or a team of 33, there's more that you can be doing. So trying to figure out the levers to pull to optimize that small but mighty team has definitely been fun learnings there. It felt like you had a follow-up question. I could see in your face.

Alex Kracov: I was thinking about my question. And I was like, actually, that's pretty stupid. Customer success feels more like sales in some ways. It's building relationships, talking to people, managing renewals, all that stuff. Then yeah, marketing is kind of this other weird witchcraft, this other separate thing. So yeah, it was probably, my assumption was stupid. I was reflecting on that, yeah.

Catie Ivey: Not a stupid assumption at all. Because I think I naively went in with some of the same assumption that I've worked with so many amazing marketers, both as partners in terms of working directly with CMOs at great brands, but then also selling to really, really smart marketers and being able to advise and consult and help to build fundamental parts of the business. But as you know, running that business day-to-day is very, very different than swooping in for a couple hour conversation and solving a few things and then swooping back out. So that's definitely been big learnings for me.

Sales and customer success, obviously, I've done those things before and had more in the comfort zone on both of those sides of the business. But I would say the startup dynamic, because I only ever worked for one true startup much earlier in my career, so this is certainly my only experience at the executive level of a company so small. Startups move fast, change fast. You've got to be nimble. So trying to strike that balance of ensuring that you're building the right long-term rigor in process and playbooks and all the things that us as sales and CS leaders we know. Of course, we need to nail our sales process. We need to make sure we've got the right methodology. What are we tracking in sales scores? How do we make certain things predictable? Doing that in an environment that is also very, very fast moving and needs to be quite nimble. It's a healthy tension but it's definitely, that was a new piece for me of balancing those two, the short-term and the long-term balance. At Pendo, we had quarterly planning and annual planning. It was just a much more mature, predictable process that was in place. That's certainly different at a company as small as Walnut.

Alex Kracov: How do you think about driving Walnut's growth? Where is it coming from? Is it from inbound? Is it outbound? Is it ABM? Are there specific channels that are really working for you, or is it a bunch of little things? How do you sort of think about where's the growth coming from?

Catie Ivey: Historically, most of our net new sales have come through the inbound motion. We have done just a really good job on the marketing side of optimizing. It was clear that that pivot was already happening before I joined. So there was already a lot of conversations around how do we optimize outbound? What do we build there? But there wasn't really the foundation in place to do it just yet. So that's been a big focus over the last year. It's yes, how do we optimize and make sure that we're still really good and smart at how we think of top of the funnel and paid? But then how do we add the right layers and the data layers? Even that we talked about in terms of nailing our ICP, getting really tight on the personas that we sell into, and then whittling that down into a clear target account list that we feel really bullish on. Because for the foreseeable future, we are going to continue to have reps that both work inbound ops and then also are expected to source a specific percentage of their own pipeline. Those are different motions and different skill sets, so we need to enable them to do both of them well.

Alex Kracov: Yeah, that's my preferred setup as well. It's what we're trying to do at Dock, although it's hard. It's easy to get distracted with the inbound leads and focus on the things that are going for you and not carve out the time that you need to with the diligence, with the outbound. And so yeah, it's tricky. Tricky.

Catie Ivey: The other piece of your question, you asked just in general, where does our growth come from? We also have a healthy number of customers. But because we have, I think, pretty legitimate product-market fit across really small companies up to really large companies, figuring out that ICP and really nailing, okay, where do we want to focus and double down our efforts not just on the net new side but also within our customers. Because we definitely have a subset of customers that want to spend more with us and do a lot more with us and then others that are much more hands-off and more transactional. So that's also been a big focus area of ensuring that we build the right structure on the CS side of the house so that we can, out of that subset of a really large number of customers, narrow down on where we're pretty bullish, that there's four or five, six X growth and lean in to support them really well. Because we feel like there's a lot of growth there as well.

Alex Kracov: And when you think about those expansion opportunities, is it just like other use cases for interactive demos, like other parts of their product that could be showing off or things like that?

Catie Ivey: And that ties into a seat-based model as well. There's a couple of different components. I won't get into the weeds on all of it. But generally, our customers typically start with, they're trying to do one or two things with an interactive demo. It might be as simple as we want a product tour on our website, or we want an interactive demo that gets sent out via email before our first call happens with a sales rep, like just two super simple use cases. They tend to start small and then realize like, oh, we should be using - basically, how do we unlock the magic of our product at more phases of our go-to-market? Like earlier, often, more often, post-sale, customer training. Every time we release a new feature, there's use cases for interactive demos in all of those pieces. So as we see them roll out more and more, that tends to mean more of the organization is actively using Walnut's, our interactive demos, which over time leads them to spend more with us.

Alex Kracov: Makes sense. Then on the sales side, do you try and go in with just one, like win one use case? Or do you go and say, "Hey, here's 10 different things we can help you with"? Because I assume the 10 different things, you're going to get a bigger deal size. That's beneficial for Walnut but might add complexity in the deal. How do you think about that tension?

Catie Ivey: So it is one of the very first questions we started wrestling with when I joined. So a year ago is, are we a fast land in an expand or are we a top-down slightly larger sale? Because we have customers that have bought both ways. Frankly, customers that have been successful both bottoms up and tops down, what we have settled on and I don't know that it's the perfect solution but the reality is right now that we are still both. So we have built playbooks for, we call them volume and value. But basically, we have volume deals that are going to start typically with one use case. Our goal there is to remove friction, be really easy to do business with. Obviously, we want to win the deal and maximize win rates, but we want to make it a pretty simple process, come in relatively competitive on the pricing side, and then be able to build value over time. We have different deals that come in typically at a more executive level where they've got broader business challenges that we're trying to solve for. Our goal there is, "Okay, let's slow down for a minute and let's actually unpack your go-to-market end to end and figure out where you should start. And generally, that will mean more people, more use cases and slightly bigger deals that take us a little bit longer to do.

Interactive Demos

Alex Kracov: And for people who are just thinking about setting up an interactive demo, where's the best place for them to start? Obviously, use Walnut. But is it on your website? I go to a bunch of websites, and I see that there. Is it using it more in the middle part of your funnel? What's the best place for people to start as they want to explore interactive demos?

Catie Ivey: So the easiest low-hanging fruit that I'm still shocked at how few companies are doing it or how often I come across websites that aren't doing it, just get a product tour on your website. Get a clickable interactive product tour. There's really, really inexpensive ways to do it, but literally something where someone has multiple different path links. They can click through some version of your product. That would be my first piece of advice, just because it's so simple and so inexpensive. All of our buyers are self-educating before they talk to us. So whether we like that or not, they are going to go out and do a lot of research. So I would rather be in the driver's seat and try to give them exposure to our product earlier so that we are helping drive some of that process.

The other thing that I continue to be shocked at how it takes some more of the customers a minute to get to this place, but you absolutely should be leveraging interactive demos asynchronously in your sales process. So like for us, even if it's just an inbound motion. So relatively transactional or straightforward, we'll say it's an SMB or a mid-market customer. When someone schedules a first call with a rep, the day before that call happens, we send out a playlist that has some micro demos included. So they have the opportunity to self-educate a bit before the call. Then we're looking at that data to understand where they spent time. Then we incorporate that into the first and second call. There's some pretty simple unlocks that you can do there that definitely help just minimize friction in the sales process itself.

Alex Kracov: I assume like one objection you probably hear, and I remember hearing this at Lattice when I was right at marketing, it was like, I wanted to put like a demo video up on the website, even pre-interactive demo. Just a video, right? You have to put your email in and whatever and see it. But the objection I would get from the sales team is often like, "But I want to talk to them. I don't want to give it away. I need to structure that conversation." I assume there's probably some tension like that with interactive demos, where salespeople want to be involved. They want to talk. Are we giving it away too much? Like, why is that the wrong mentality?

Catie Ivey: Anyone that has that mentality, one, I could tell you they must be a certain amount of age or older. Because they grew up in my generation of, you don't give a demo away. Like, make people work for it. Everything is about really, really good discovery. Of course, there's principles there. Like yes, you absolutely don't want to show up and throw a bunch of features of your product without doing adequate discovery. But I guarantee, regardless of how complex or simple your product is, there are certain things that are going to be aha moments every single time. There are certain things that I guarantee when you're showing Dock, like there's a couple of places where people light up when you're talking about it. And there's ways that you can craft a version of a demo or a micro demo that's highlighting enough of those to add interest and anticipation without - there's certainly best practices around how many clicks, how long of a flow, where people's attention span is, which, guess what? Their attention spans are getting shorter and shorter and shorter, so that's going to continue. But if anything, you should be leveraging interactive demos or technology to help you figure out what you actually want to be showing in your product. When you get that live golden 30 minutes, or hour, or two hours with them, it's all about making that more efficient, I think.

Alex Kracov: I also think sales people today have so little time actually talking to the buyer. Like if there's some stat, I think it's like from Gartner, like 17% of the buying cycle, they're actually talking to sales people. That's your competitors included. So you have like 5% of the entire buying cycle to actually get on a call and talk to people. And so I think of interactive demos or things like we're doing at Dock as a way for you to help influence the deal like when you're not in the room. Because they're going to do your research regardless. They're going to go out there and learn about your product. And you might as well control that a little bit more with something like an interactive demo.

Catie Ivey: That's been the big evolution or one of the evolutions we've seen in our category. Because I think three, four or five years ago, it was very much we thought we were solving the live demo. Demos generally suck. Let's build technology to make them better, more personalized, more customized. And yes, interactive demos can help with that. But what we have found is, the market has very clearly pulled us to what really matters is all of the ways they are going to interact with your product when you're not in the room, to your point, and trying to make that process better.

Alex Kracov: So this interactive demo space is super competitive. We touched a little bit on competitive dynamics before, but I'm curious how you think about winning in such a competitive market. I don't know too much about where all the different players sit. Maybe some work for enterprise, some work for SMP. But how does Walnut win this category? I think you are actually kind of already the category leader, at least in my mind. I don't know the exact numbers. But how do you think about winning in such a competitive category?

Catie Ivey: It's such a good question. I would say it's probably the question or one of the questions that keeps me up at night, if you will. Because I don't think that anyone really knows yet. It is absolutely a category that's blown up. We definitely consider ourselves part of the key creators of the category. So it's, in a lot of ways, a privilege and honor. How exciting to see to be at a product marketing alliance event and look around and see nine other interactive demo platforms? That validates we're onto something. There's just a lot of momentum and a lot of energy. But to your point, I think one of the things that we're constantly obsessing over is trying to be hyper aware of what's going on, both at the top end of the market as well as the low end of the market. Because there's pieces of what you do with an interactive demo platform that are super simple. Even if something as simple as just taking screenshots of your product and making like PowerPoint 2.0, that's not where Walnut plays. But we need to understand because there's new players in that space daily, weekly a lot. And so trying to understand who's doing interesting things there. Like, are there things we need to be paying attention to that would be at the low, low end of the market? And then also the flip side on that more complex, there are people that are solving different problems than we are that are very much only focusing on large enterprise. That's not our intention, but we do certainly want to understand what's working there, who's finding success. They're trying to figure out how much to obsess over our customers versus our competitors. At the end of the day, we're always going to skew. We've got a lot of great customers. So the more we can be leaning in, learning from them, understanding what they care about and what they're looking for in a product, I think that's going to be the single biggest thing that keeps us ahead.

Alex Kracov: I'm sure AI throws a fun wrench in all of this too, of like, all right, how do you actually build interactive demos? Yeah, probably there's lots of really interesting ways you can leverage AI to actually just make it easier to set that stuff up.

Catie Ivey: Yes, so there's that end of how do we leverage AI to drive just a more seamless AI-driven demo creation. But then it's also, a lot of companies that sell AI products, and they're trying to figure out how do they demo it. The experience of showing AI-driven workflow is very different. So both ends of the spectrum, we're trying to solve for it.

Alex Kracov: Yeah, that's really interesting. Because a chatbot sort of experience or something like that probably wouldn't work in the first version of interactive demos. Yeah, that's really interesting. Yeah, fun.

Catie Ivey: Fun problems, for sure. Fun opportunities. I won't call them problems. Lots of opportunities.

Alex Kracov: Yeah, champagne problems, I like to say.

Catie Ivey: Yes, or first world problems. We're just certainly in the thick of that, for sure.

Career Advice for Young Sellers

Alex Kracov: I'd love to end today's conversation just with some advice for sellers younger in their career. Because I think you've had this dream career as a sales person, going from an AE all the way up through the ranks at multiple companies to becoming a CRO. What do you think made you successful in your career? Why were you able to sort of move up and have that dream sales career? What advice would you give to someone who's just getting started as an AE and has dreams of being a CRO one day?

Catie Ivey: I love that you called it a dream career. It doesn't always feel that way in the thick of it. But I appreciate the fact that, at least on paper, it looks that way. So I'll take that as flattery for sure. In terms of advice to folks earlier in their career, honestly, an advice that I would give even to myself if I can go back in time 10, 15 years, I think one of the reasons that I've been able to be successful is, if you remember my comment around like strengths-based leadership. I think relatively early on, I was able to figure out some of the things that I was uniquely good at and honestly a lot of things that I'm not that great at. Early in my career, I wasn't a superstar seller. I became really good over time, but I wasn't one of those hit the ground running, always at the top of every leaderboard. I had to work really hard in the early days. Some of it didn't come quite as natural to me as it did other people, but I had a lot of conviction that I could learn just about anything. I was willing to be uncomfortable. And so at every stage of my career, there certainly had to be this willingness to step outside your comfort zone. Maybe it's, take the job that you might not be qualified for, or put up your hand and say, "I'll take on this deal, or this team, or this opportunity," with some element of conviction that I'm smart enough to learn. I'll ask good questions. I'm humble enough to recognize what I don't know. I think, at least for me, when I look back, that's going to be unlocked for me at a couple of different really key pivotal moments.

Alex Kracov: Well, thank you so much for the time today, Catie. If people want to follow up with you or learn more about Walnut, where's the best place to find you?

Catie Ivey: Oh, thanks for having me, Alex. What a fun conversation. The easiest place to find me would be on LinkedIn. So I'm one of the few Catie's with a C. It's just Catie Ivey. You can easily find me on LinkedIn. Yeah, I'd like to connect there.

Alex Kracov: Awesome. Thank you.

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