E18: Confessions from a First-Time CRO with Catie Ivey of Walnut

And today my guest is Katie Ivey, who has almost a 20-year career in tech sales across some of the biggest names that everybody knows— Meltwater, Pardot, Marketo, Demandbase, and Pendo. And that ranges all the way from star individual contributor through first and second line leadership. And she is now the CRO at Walnut, who provides interactive demo solutions for companies like Medallia Adobe, and I'm excited to dive in. Thanks for coming on, Katie.

Yeah, thanks for having me, Kyle. Looking forward to the conversation.

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com, and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes.

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Cool.

So, uh, we are gonna talk about 2 topics today. You've got a really interesting background in absolutely crazy competitive industries. MarTech is one of, uh, one of particular note. It is a knife fight. And now you are in this interactive demo category, which is also crazy competitive. So you have some love for doing the hard thing. And so we'll unpack what it means to win in these markets in terms of positioning, go-to-market strategy, all that good stuff. And also you're over a year into your first CRO role. And so I'd love to unpack some lessons because there's tons of people who are going into that role, who are aspiring to that role. And so we're going to have fun and get your lessons transitioning, hearing about the things that you wish you knew before you took it. And so I think that'll be an awesome conversation.

So sounds like two very fun topics for sure.

Related as well, trying to, trying to figure out positioning as a first-time head of it all. So before we dive in, just give people a little bit of the background that I missed. Talk about your journey. A little bit about your team today, and then we'll dig in.

Yeah, sure. It's always hard to answer that question in a really succinct way. I feel like most sales or revenue leaders, I stumbled into sales very accidentally right out of college, thinking it would be this short-term stint. And, you know, as you mentioned, almost 20 years later, gosh, it was like the luckiest, you know, accidental stumble into an interview that ever happened. And I've really just, you know, fell in love with tech sales pretty much from day one. I think I fell in love with business from day one and solving problems. I wasn't actually very good at sales out of the gate. I learned and got better. Consider myself really good now, but it took me a long time, I think, to really feel like I had a handle on the craft of selling, the art and science of selling. But I love leadership and people leadership from day one. So there's just been a lot of fun twists and turns, and like most of us, some lucky breaks along the way, but have led some incredible teams, as you mentioned, at some really, really cool companies. Had the opportunity to learn a lot, failed many times as well. But now in my first-time CRO gig at an incredible company called Walnut, feel very lucky to be there. A lot of learnings. And that's one of the things we're going to unpack today. You know, just, just really fun ride, but feel very privileged to be where I am for sure.

Very cool. How many acquisitions have you gone through?

That is a great question. 2. I'll say 2 and a half.

Multiple.

Yeah, well, it depends also if we consider the Marketo years 1 or 2. So I joined when Marketo was public, went through a Vista acquisition and then got bought by Adobe before I left. So I guess that was technically 2. And then I joined Pardot and then was acquired by ExactTarget and then was acquired by Salesforce. So went through two there as well. So I guess we'll call it four.

Four. Yeah. I was listening to your conversation with Alex and I was like, man, there's a lot of transactions along the way. This is good. This is either great fortune or very challenging.

I mean, both, but I would say mostly great fortune and a lot of happened to be in the right place at the right time, for sure.

Very cool. So let's start with lessons as a first-time CRO. So you were, you've been at some iconic companies, like you've certainly had a knack for choosing, choosing wisely and have gotten to see a range of stages and a range of different ways of operating. And so now as a first-time CRO, I want to start with what was about what you expected it to be, what wasn't a surprise, and then I want to get into some of the surprises.

Oh, that's, that's an interesting place to start, or a good place to start. Well, it wasn't a surprise. I certainly— so Walnut's the smallest company that I've ever worked for. So, I knew that I was getting into a lack of process, a lot of foundational work that needed to be done. Obviously had great conversations during the interview process. So, had some clarity in terms of what I was walking into in terms of opportunities to optimize across marketing, sales, and post-sales, but even down to getting tighter on refining our ICP and really nailing the persona and just the problems that we're solving, who we're solving them for. So, a lot of that was very much as advertised in terms of the, where we needed to start and some of the layers that we needed to dig deeper into to solve some of those fundamental kind of foundational pieces. Yeah, I would say that was pretty much as advertised or not a huge surprise compared to what I was expecting.

So lack of process, needed to figure out documentation. I would imagine just a lot of fact-finding and wayfinding at the beginning. Anything else that was about what you expected as a first-time revenue leader?

The other thing that I think I was expecting and very much kind of checked the box is I knew that there was some incredible people on the team, but that it would be somewhat challenging to pattern match because like many startups, they had hired different profiles, different personas. Walmart also sells into a variety of different company sizes. So we have everything from a relatively transactional SMB motion to a, you know, much more enterprise-ish motion upmarket. So I knew that there was some complexity there, and I would walk into a variety of different types of people doing things different ways. That was also very much as expected. Some really fun surprises in terms of just like incredible individuals, but at a company that small, the, the lack of consistency I was expecting and was certainly there when I walked in the door.

Okay. Now, what about surprises? What was different than your expectation going in?

So, I think one of the things that was really surprising to me, or maybe that I just wasn't expecting at the level that I experienced, was the number of things that had been built on a foundation that wasn't really there yet. And I know this happens in startups where, especially startups that raise money and move really quickly in the early stage, or maybe feel like and discover we've got phenomenal product market fit, we want to move quickly. There is just, you know, you buy a bunch of tech, you hire a bunch of people, you do a lot of things and make a lot of decisions. And I think because I knew that there were some foundational pieces that we needed to really nail around ICP and persona and just some of those core business decisions, I was a little bit surprised at how much we had tried to build on top of that, of not being there. So We had a lot of technology that we weren't using particularly well, a lot of systems that weren't really optimized. We'd grown certain teams without really nailing just core fundamentals of what great looks like and what we're running towards. So, there was a little bit more, I'll say, misalignment than I expected at a company so small. And not because like the individuals didn't work well or didn't communicate well, but a result of running really quickly in those early years. It's also probably partly a result of Having an Israeli-based company with most of the go-to-market base in the US, I hadn't experienced that directly of having just two very different time zones and different cultures. And I also signed my offer letter the day before October 7th. So, there was some other—

Wow.

—over the last year that have, you know, added to that walking, working across a lot of differences, a lot of time zones. Also, people that would get called out into reserve duty and other things that kind of just added extra layers onto some of that. But I think that piece of not the lack of clear, clear alignment at all levels. I expected that to be easier at a really small company than what I walked into or what I experienced.

So, what were the most important things to get alignment on? We're going to transition a little bit into this concept of foundation building, but what were some of these foundational pieces that you needed to get cross-functional folks rallied around?

I think some of the things that you maybe take for, or at least I had taken for granted working at larger companies or coming out of somewhere like Pendo, which is just phenomenal in so many different ways, is we had a really clear company operator, operating rhythm that trickled down to every team. And planning was really operationalized and communication was super, super clear. And the cadence of town halls and what's communicated and how often things are repeated. It's again, all things that now saying it out loud, of course, that happens at large companies, or at least good, great large companies, like have some of those things nailed. And you, at least for me, coming into a lot less experience with a true startup or someone that early stage, I took some of those things for granted that, oh, we don't really have a clear cadence for how we run this type of meeting. We don't have a clear structure in terms of how these types of decisions get made and than how the information gets trickled down. So some of the, I'll call it lack of alignment, but some of it, some of it just manifests itself as inefficiencies because you actually have the same meeting 3 different times, or you're saying the same thing in 3 different forums and then realizing, "We actually could have done that in this forum," or just with a little bit more kind of operating structure or rhythm, these things could have been both more efficient, but then also communicated really clear so that everyone understands Here's exactly what direction we're marching in. Here's the decision that we made. Here's who's responsible for making that specific decision. I think that was some of the, that foundational work that happened really over, I don't know, the first 3 to 6 months of uncovering. Nothing's perfect. So it's not that we have it all nailed or perfectly fixed now, but uncovering what those things needed to look like. So we at least ensure that we've got the right channels, we've got the right structure, we're hosting the right number of meetings with the right attendees, at the right times. Again, stuff that I think I just assumed would naturally be really easy because we're talking about a small company versus a larger company. And some of that actually has to be even more intentional when you've got a small company because you sort of take certain, or at least I take some things for granted, like, well, we said it one time, of course everyone heard the thing. No, like you still have to say things multiple times in multiple different channels. People learn differently. They absorb information differently. So some of that has been, has been a big focus for me, for sure.

Yeah, we usually say 3 points of contact. It's a rock climbing term. Yeah, give it to people 3 different ways, 3 different times. Uh, this whole idea of operating rhythms is a bit of an obsession of mine. And, and the interesting thing is it needs to change at a bunch of different company stages. We had one way of doing things, and now we have second and third line leaders in my revenue org And so we're updating everything. I'm rewriting this document called my operating methodology where I clarify exactly the principles we should be using to define how things are communicated and how do we build a process and how do we structure one-on-ones and team meetings. It is a never-ending state of evolution, but it can be such an excellent—

kind of your operating rhythm or model a few different times. And I love how process-oriented you are. I feel like I I've learned a lot in listening to you unpack that in different layers, but you're 100% correct. Like, and that was one of the big learnings or early learnings for me that some of the things that have worked, nothing's plug and play. Like no matter how good your playbooks are, no matter how good your structures are, like every company's different, company size is different, the nuance is definitely different. So yeah, because you've been so wildly successful over your, what, 2, 3 years as an owner, like it's changed a lot because now you're growing and you have to do it at a whole different scale.

Yeah, I can't remember who said this, but some of the most successful companies are the worst managed because they don't need it. When you have extreme product market fit, I won't call out companies as they're in my head, but, you know, there's a bunch of companies that they're just like grabbing demand and then taking deals at such a rapid pace that you don't need to necessarily build that same sense of discipline and you can get to $100, $200, $300 million in ARR and things can sort of still be a mess because it doesn't matter. Like it doesn't really get in the way.

Look at those same companies and think, oh, but how much more could they have done? Like how much more could have been accomplished just maybe with a little bit of that framework or the framing or the process that might have been missing?

Yeah, it's hard to make that decision because ultimately that probably means it needs a change in leadership or a change in operating style. And, you know, the opportunity cost at that point is pretty significant. It's like, oh, but we're growing 120% year over year. Why would you rock the boat? And so you see that happen a lot.

But there's always that trade-off of perfection versus velocity, like how quickly do you want to move? And yeah, you're You're 100% right too. There's that trade-off of if you're willing to— sometimes it requires that slowing down and being really purposeful at creating those types of rhythms and may or may not be worth it depending on the opportunity you're operating in.

And so what are the other foundations that you had to put in place? So operating rhythm is a foundation. You referenced ICP and personas. Like, I would love to hear your thoughts on both of those. But what else did you have to put in place as sort of the baseline scaffolding, the foundation of the team?

I mean, there's, there's quite a bit, but if you think of just like the big buckets, because marketing, sales, and CS all roll into me. So this, all of the things that you would expect from a marketing perspective of understanding just at a high level, the whole demand gen waterfall, where does our demand come from today? What are the different breakdowns? Trying to break down and understand that funnel, the various different channels and how do we optimize? Some of ours were very efficient and some were very inefficient. So understanding what those breakpoints were and in no way attempting to solve all of them, but at least making sure that we had an aligned understanding in terms of particularly our inbound motion, which, which Walnut was primarily built around the inbound motion and then has grown and scaled into more of an outbound or split there. Making sure that I understood that. So we were at least in the short term prioritizing the right key pieces from a pipeline build and demand gen perspective. The other big component that fell into marketing was this whole concept around positioning. So positioning and messaging, understanding Not just ideal customer profile, but what are the various segments that we serve? Who are the, you know, core personas within each of those? In our category, it's still so new and there's a lot that people buy interactive demo platforms to do. Like there's 14 core use cases that we support. So pattern matching across our customer base and understanding, okay, we can do a lot of things, but where do we really, really, really want to win? Where do we believe that we're the best? So all of that factored into, you know, those, those really deep dives and tiger teams around positioning and messaging, which I call, I called that out in the marketing bucket, but that's, it's the whole thing. It's a company initiative. So it's not just about marketing, but it's spending time really unpacking those pieces. And then that trickles into how you look at sales. So for us, I already mentioned we sell small companies up to really large companies. So there was a lot of questions around the segments that we serve. Where do we want to focus within that persona and the ICP? The reality is we have customers that are 10-person startups and we have customers like you called out, like Adobe, got big brands that use us. So we've got to figure out how to serve each of them well, which then morphed into, so that's how do we want to close the deals? I mean, something as simple as are we a bottoms-up motion or a top-down motion? Like those are two very different sales motions, very different go-to-market motions. And guess what? We actually, turns out we do both. And so figuring out what fits into each of those categories and then how do we want to build process around each of them was probably the most important fundamental thing that we're still solving for in sales. So we're still very early in that journey, but identifying kind of where we want to go and how we win the different types of deals within our category has been, you know, the biggest focus for us in sales. And that ties directly into how we support those customers as well. So we have a mix of high-touch customers that pay for ongoing support, have dedicated CSMs that we spend a lot of time with, and then we have a scale bucket that's much lower touch as well. So breaking all of that apart, understanding the product signals that we're listening for, and then how do we provide the guidance, not just of how to use the platform, but what, what should you be doing and thinking about with a platform like ours that's very new? Those are— that's probably the biggest bucket when we think post-sale. It's not just about how to use our product, but it's what does great actually look like across our best customers so that we can go build, you know, playbooks for the rest of our customer base in terms of how to do it well.

Yeah. And especially with those smaller customers that churn at such a high rate. How do you get them to impact without needing to hold their hand? Will you think about— when I hear SMB to enterprise, 14 different use cases, are you thinking about narrowing focus at all? That seems like a ton to juggle.

Yes, it is a ton to juggle. The short answer is yes. We have already gotten more focused. It's an interesting tension though. And it actually goes back to one of your earlier questions in terms of like what surprised you or didn't surprise you. One of the things that actually drew me to Walnut is I loved the fact that I saw a real potential. When you think about the total addressable market of who should be using our space, I loved the fact that I saw real product market fit across small companies, real need for the technology. And then that morphs in theory all the way up to much larger, much more complex organizations. And part of that's just selfishly, I love that internal model of being able to go, Higher entry-level folks, you know, have they cut their teeth on a more transactional model? They're able to morph and grow and evolve. Like, it's just phenomenal when it's done well. I know you guys do that incredibly at Owner, but it's definitely something that's really exciting to me when I think about building kind of over time, a more mature revenue organization. But with that, and so our category definitely fits into that where there's such an opportunity on both ends. But to your point, it's a lot to juggle and there's so much work to do to figure out how to nail each one of those. So there have been plenty of missteps, plenty of lack of direction, probably some of the wrong decisions along the way. I think we have, we've refined a lot in terms of where is like the tip of the spear, like where's the core focus, and then knowing that there are things that are downmarket and upmarket from that core focus. But we've certainly aligned on what are the companies that we are building for, what are the companies that we're optimizing for and building the right process around, and then from there, understanding what needs to to morph or change depending on if we're serving further downmarket or further upmarket. So it's helping a little bit, but we still have a lot of work to do around continuing to evolve that focus for sure.

This is the advice I give to founders a lot when people want to go after multiple markets. You don't have to say no all the time. You just have to be clear about what you are and what you're not. And so what I heard you say there is this is who we're building for. Like, that's the bullseye. And if there are people that are smaller than that that can put in the resourcing to use the product as it is without needing to have their hands held the whole time. Or if there's a larger customer who are okay with some of the product tradeoffs that exist today, you can say yes to those customers, but you just have to be transparent. You just have to say, like, this is the solution because it's tempting. You have like a $150,000 deal and you want to, you want to, you like you just think about the impact on ARR and you want to persuade and cajole them into saying yes and leave out some of the rough edges of maybe what they're going to be disappointed by. But it never works. And I think that's one of my lessons for the last bunch of years. I've owned new customer onboarding, CS and support sort of on and off in different varieties for sort of like the last 6 years. Maybe a little more. And you really get a great— it's such a great learning as even just a core sales leader to have to deal with all those post-sales problems because you never really appreciate it as a VP of sales. You never really appreciate the downstream impact until you're the one cleaning it up. That pressure, I think, is very productive for revenue leaders.

That's another thing I should have called out to your earlier question of like one of my surprises and it had nothing to do with the company itself, but one of my surprises walking into my first time CRO gig was how long it took me to pattern match across some of that because I hadn't experienced, I didn't have as much post-sale experience. I of course had owned a retention and expansion number in pockets, but because our customer base was so diverse and we were supporting so many different use cases and different personas and different company sizes, It took me a lot longer than I expected to be able to really effectively pattern match across those and be able to find that bullseye of, oh, here's where we're really great. Here's what we actually need to be optimizing for. Here's who we need to be building for. And then of course you uncover, there was a lot of times that we didn't make those decisions or we said yes to things that we shouldn't have said yes to, which kind of compounded some of the challenges. But we've, we've made a lot of progress there in the last 12 months, but we still have continued progress to make for sure. Yeah, makes total sense.

So what feedback would you give yourself? You're now a year and change into the role. If you could go back and give Katie on day one a bunch of advice, what would you tell yourself?

That's a really good question. Overarching feedback, I've done obviously a lot of reflection at the end of year one in the role, and there are certain key areas where I wish I had moved quicker. And I highlighted the fact that I knew that I was walking into a relatively disparate team with different skill sets and different strengths. And the reality is there's some incredible individuals that I work with and that work as part of my org. And I think because there were some really great strengths and a lot of really good building blocks, I took way too long to make some decisive decisions about some of those foundational pieces that we've been talking about. So even just identifying, What are the core pieces of certain aspects of the playbook that we've got to get written down, that we've got to get on paper, that we've got to ensure are crystal, crystal clear and being overcommunicated? I think I did too much crowdsourcing or consensus building. And back to my point around it taking longer than I expected to pattern match. And I'm sure some of this is just like the nature of the first time you're doing anything. So, it was the first time I was owning the entire numbers. First time I was having marketing rolling into me. And so you underestimate some of the areas where you have things to learn. But I also just underestimated how long it was taking me to figure some things out. And I think I was expecting to get to a place where there was just more crystal clear. I know exactly what to do here, or I know exactly, you know, based on this one conversation with this one person, great, we're going in this direction. And the reality is some of it still isn't crystal clear. Some of it, like, The best leaders make decisions clearly and quickly. And I think in reflecting, there are definitely some opportunities where I could have moved a bit quicker or been more decisive that would have probably had, you know, positive impact on where we, where we are right now.

So how, how are you trying to operationalize that now? Like, what's your rubric for deciding how fast to move on a decision? How much information are you collecting? What does that look like in practice?

Yeah, I don't know if I have a clear or concrete answer. Like one example I'll give is, so I was like a month and a half in when we ran our first revenue kickoff at the beginning of this year and covered a lot, great team building. It was a super successful event from my perspective, like learned a lot, anchored the team around a lot of principles, learned a lot from each other, but we tried to cover way too much because there was so much to do and there was so much to rebuild and there was just a lot of foundational things. We tried to attack way too much in a really limited window. That's just impossible for a group of people to really ingest, really understand, really operationalize and make actionable. So we're in planning mode now for our revenue kickoff, which will be mid-February. And so we're making some very purposeful decisions. One, to be crystal clear in terms of like, what are the two things, like what are the most important things that we've got to get out of this? And then what are the 15 things that we're going to deprioritize? So being really, really clear on How much repetition? How many times we want to go over it? What's the output that we're going to align on so that we know that we've got the right level of documentation, the right level of follow-up, and exercise? We're working on some things around command of the message and golden pitch. Oh, cool. Yeah. So what do we do in person while we're together? What does the workshop structure look like? But also then what's the output that is expected? Phase 1, Phase 2, like how do we actually reiterate? I think it doesn't really actually answer your question about moving quicker. I think it's more of a question of being really decisive and clear and prioritizing the right things over and over and over. So we make sure we get the right outcomes. Yeah. Now that I'm saying it out loud, it's definitely not an answer to your question. So it's more about being more decisive versus moving faster. But that's one of the examples that comes to mind in terms of, at least for me, how I'm tackling some of that year 2 versus year 1.

That makes sense. And so that's an, that's a sales team, revenue team kickoff, or that's your leadership meeting in February?

The whole revenue team. So sales and post-sales.

Yeah. Very cool.

So I have some work to do on the pre-work going into it. So that will be the revenue leadership team. But no surprise, we're a little bit behind. So we have a lot to do over the next 6 weeks or so.

And were you originally introduced to Force Management through Vista? Okay.

Vista. And then we used it pretty heavily at Pendo as well.

Okay. Yeah. I think Vista uses force management and command of the message. And what's their other one called? That other big module in almost every single one of their acquisitions.

Now, I feel like the Vista playbook is like so incredibly well known, but I'm forgetting like the acronyms and what they call it. We spent a lot of time in there, like Vista creating demand model. Because we didn't really— at Marketo, we didn't really have an outbound motion at all pre-Vista. So that was one of the big focuses across sales. But yeah, there's an overarching thing that they call everything, and I'm forgetting what it's called.

Was any of that relevant? Vista obviously acquires much bigger companies. Was there anything from that Vista playbook that helps you today, or is that not relevant yet considering the company size?

I think so. And it's always, you know, you've been in a lot of different roles, and I feel like everything morphs together a little bit where I'm like, Salesforce, Or was that like a Pendo thing? And so some of it in terms of even what specifically came through the VISTA playbook, but a lot of just even the super simple rigor around how they expect frontline leaders to run their team meetings and roll up forecasts and what goes in Salesforce and how their various systems work together. For sure, they're creating demand, outbound kind of model of how they expect even really entry-level or more junior reps to think about the problems they're solving and And it's funny actually how relevant some of that is now in a very, very different time where outbound looks very different than it did 8, 10 years ago. But still, like, how you orient yourself around real business problems as a salesperson, I think that piece is super relevant and definitely ties into some of the things that we're building. So, so yeah, in short, I would say there's, there's a ton of it that's still super relevant even at a much earlier stage company.

Yeah. It's funny hearing you say that. I have this like career FOMO all the time. I've done the early stage thing a bunch, and then I spent time at Shopify, which was a large-ish public company, and I learned so much different stuff there. I learned so much about, in particular, product management. And it was such an interesting way to round out a lot of the skills I had acquired. And then I hear about people going through big Vista acquisitions. I was like, man, I would love to get bought by Vista at some point in my career just to like see the experience. Would you really, Kyle Norton? Well, yeah, I just want the learning. I want to go through that experience and see the playbook. And I just hear about these experiences. I'm like, oh man, you could take a lot from this, that experience. Today's business landscape is full of uncertainty.

And succeeding as a go-to-market leader has never been more challenging. Pavilion is here to provide you with the education, support, and resources you need to grow, learn, and unlock your full potential. Join more than 10,000 of the world's leading go-to-market executives in a private membership community designed specifically to fuel your success. Visit joinpavilion.com and use the code Topline20 to get 20% off your membership. That's joinpavilion.com/topline20. Pavilion.com and the code is TOPLINE20 to get 20% off your Pavilion membership. And now back to the show. I think that's true. And I love that perspective for sure. I just think that's true in almost any job. Like if you have the right mindset, like, gosh, there's so much to learn. Great companies, super shitty companies, like everything in between. Like there's so much opportunity to learn. Um, and you're, I mean, you're right for sure. I've accidentally stumbled into some things that became really great learning opportunities like Vista. But I think we can probably learn a lot more than we give ourselves credit for in a lot of different roles. Yeah. Learning FOMO.

Yeah. Arguably some of the most valuable lessons I've learned in my career from my worst boss. I worked for a guy who was just like an old school, top-down authoritarian. Everybody hated this guy and it was my job to sort of stick handle him constantly. Try to prevent my team from quitting and just being miserable. And that experience, I was working with an executive coach at the time. I had to quickly build a bunch of new tools in my toolkit, and I came out of it such a better leader. It seems cliché, and people are sick of me talking about Stoicism and Ryan Holiday, but it really is those experiences that challenge you, that, that force you to learn and develop. Yeah, absolutely. Cool. Well, okay, I want to, I want to move back to some of this lessons as a first-time CRO. So playbook building, obviously that's one of these big foundation pieces that we all have to endeavor to piece together. Where did you start? Like, how did you try to stitch together from all of the chaos that you that we all walk into, into something approaching repeatability?

Oh, gosh, is that a bad answer to say I still, a year later, feel like I'm still starting in some ways? I feel like I'm still starting. It's very much an area we have a lot of work to do. One of the things that I did is hired a head of go-to-market enablement who's been just an incredible business partner. Even though we're really small, it's like mission critical for us. At least it was a mission critical role to get on board.

Not for you only. Everybody should be investing in enablement way earlier than they do. I say this all the time.

I've heard you talk about your structure and the enablement team that you have in place, and I think you are just crushing it and really nailing that piece. It wasn't in place when I joined. And I also am a little bit of a different bend than you. I have different strengths, and I'm not as operationally wired and process-oriented naturally as you are. So I need a partner that works with me that is working on documentation, getting things in the right place, or like we, the whole company is basically oriented out of Notion. So, we started day one of dissecting everything that exists and then trying to build really simple frameworks of, because there was lots of stuff, but it was way too much stuff. So, it was more where do we start again for those fundamental building blocks? Like what are the core things that we need to make sure people know? And that led to lots more discovery around parts of the process that weren't optimized, things that weren't working as well. I mean, even something that feels simple and obvious now of talking about a bottoms-up versus a top-down motion, like we didn't really have clarity that we were running those two motions and how different they were. And so, getting things on paper, here's exactly how we expect you to run a process when it's bottoms up, like when we're starting with the core user and we're moving fast and we're minimizing friction and we expect the deal to be small, here's how you do it. Even like really sophisticated reps were struggling to like pack, to see the signs early enough of, are we going top down and wide and broad here? Or do I need to move fast and make it really easy? So, getting those types of things documented and practiced and oriented around over and over were some of the kind of foundational things we focused on.

Nice. And that would have been a very different experience building from scratch versus what you would have been doing previous is a lot of optimizing, I would imagine. A lot of optimizing.

Yeah. Almost every other job that I've had has been more a version of optimizing, walking into something that's either working well or parts of it are working really well. So, it's very easy to see like, oh, here's where we double down. Here's the things that are not working and that we need to, you know, lean in and fix. But even like when I joined Pendo, it was to lead their commercial segment. And then I moved into owning enterprise and a piece of commercial as well. But there were such clear signals of what was working well, both on the net new side, as well as on the customer side of the business, because we had a really healthy expansion motion, specifically in enterprise. But it was, you know, very much about optimizing and making things better. Quicker driving velocity, improving win rates, all the things that felt predictable and easier to see. And that is, or at least for me, has been harder and taken longer to take a step back and not try to force things into a, you know, a model that's worked in other places, but how do we really want to build this thing, you know, from the ground up.

With so much surface area in terms of segments and use cases, how did you decide where to start? What, what did your prioritization look like?

The two things that I spent the most time on early on was spending time with customers or with people that work directly with customers. So, I was really trying to understand not just what our customers said they wanted to do with our product, but th— what they were actually doing with our product and all the ways that they were using it, as well as things that weren't working or any negative feedback that we were getting. So, I spent a lot of time with our CSMs and my head of customer success, and then with customers live. And then I spent a lot of time with reps, but more so focused on how do we use our own product and how should we be using our own product. Obviously, it's— if you don't sell into go-to-market or you don't sell into the persona that you are, it's very different. But for us, we are building and selling tech that is applicable across essentially an entire go-to-market team. And so I wanted to understand exactly how we were using our own product and then the feedback loops, how we're getting that information to product, like all the ways that we're working together to build the absolute best technology that my team would be obsessed with so that we can then obviously build that playbook for our customers. So, those are the two core areas that I spent a lot of time on early on. And that's something I wouldn't have changed. Those were the right focus areas. There were some things that got missed or that I, again, I should have ideally been able to see quicker or move faster on making decisions out of those exercises, but prioritizing customers and then our own usage of a product that sells into our persona was absolutely the right two focus areas for, for me at least.

So then you download a bunch of this data from the customer and team, and then how did you pick where to start? Like, how, how did you, how did you think about picking the first things to start putting resources against?

So the, well, the two big things that came out of kind of that first quarter or so of learnings was one, we codified our, the use cases that we support across our customer base, um, and we identified some things that were not particularly aligned, like simple things, the dropdowns that you have in Salesforce not matching the dropdowns that customers select in the product and not 100% matching the different CS technology that we were using. So, getting everyone speaking the same language in terms of the specific use cases that we're supporting and then how we're documenting that then translated into the success that we're seeing, what's working, what's not. So, there was, there was a whole, like, waterfall of exercise that started with spending time with the customers, then marrying that with product data and then getting systems aligned so that we had the capacity to track the right information. And then that fed into, okay, so I've been spending time with reps and understanding we actually had some huge gaps. Like we weren't using our own product particularly well. There was like really good things happening in pockets, but it wasn't consistent. Like we didn't have a consistent, okay, before someone ever talks to us, here's exactly how they interact. Again, we, we build demos. So like there's a very clear way that If you're buying from me, like you should have interactive demos in your inbox before we ever have a first conversation. And you have your own journeys that you go through and you're learning a little bit about the product. And then as a salesperson, I can see, oh cool, Kyle spent time on this specific demo and clicked through this click path. And now I incorporate that in my first conversation. And then here's what the sales process looks like using that. And then here's the follow-up using again our product, like through the whole funnel. And that wasn't, uh, playbookized, playbookized, not an actual word, but we didn't have that documented. And so, when you then look at a seller and identify, I've got one person that's doing really well and one person that's not doing well, like we weren't, we think about like a sales process. And of course, like, here's how you run great discovery. Here's what good follow-up looks like. Here's what multi-threading looks like. But for us, it had to anchor around using our own product really, really well because we're selling a product that makes go-to-market teams more efficient. And so, we spent a lot of time then starting to document what we thought great looked like, what our best sellers were doing in terms of how they were using our product, and then incorporating that into kind of what became the framework around what the sales process looked like.

Makes sense. I want to go back to something you said, the feedback loop to product. So time with customers, looked at product data. How did you establish that feedback loop? What does that look like today? What were the big lessons learned on how to partner with the product team? Because I think that's a thing that a lot of new CROs struggle with.

Yeah, we've, I mean, thankfully we've got a head of product that I really enjoy working with and have gotten to spend some time with. He's based in Tel Aviv, but I've spent some time with him in person. So some of it already existed in terms of how we were ingesting data through Salesforce. Like there's a really clear, there was already a clear process where sellers and CSMs would submit op gaps if they were hearing feedback or things that they needed or ideas that they had. The next thing that we did that didn't exist before I was there was create, we created a, essentially a Slack channel. There's a few other layers, but where we provided internal feedback based on our own usage. So once we got that structure set up in terms of, okay, reps, okay, CSMs, here's how I want you to use Walnut. Now, of course, you're going to uncover like, oh, this actually doesn't work the way I thought it did here. Or we'd love for this folder structure to actually exist over here. Like, Being the best users of our own product should in theory lead to us having a really strong opinion about what we think great looks like for a sales use case or CS use case. So we created different channels to be able to feed real-time information, which then incorporated into, in some segments, biweekly or monthly sessions where we sit down live and unpack it further and ask additional questions and make sure that we are understanding things correctly on the go-to-market side, but also that they're getting real-time feedback from, like, we all talk about voice of the customer, but like voice of the customer zero, primary customer being us using the own product. Like, we definitely put by quarter, end of quarter 2, we had really clear structures around how we were orienting around that process.

Must be nice to be a customer of your own product just from a customer empathy and a product literacy perspective. I've never had that.

Oh, it's amazing. I've actually had that most places that I've worked. So Pendo, not, but almost everywhere else I've been either a primary or a secondary persona, which I will tell you is like, it's pretty amazing.

Yeah. Yeah. We've been lucky at Owner because for the most part, I've been really aligned with what's being roadmapped. We haven't had to get into a lot of big challenging disagreements around where things are going. It's been fairly natural, but I've definitely had other experiences where that product advocacy has a lot been, been much, much more challenging.

You guys have a built-out either customer advisory board or user advisory board or like some, some core like subject matter experts that are driving your, your roadmap? Yeah, we have a customer advisory board now.

Uh, honestly, this has been pretty deep-seated in the company from the two co-founders, CTO and CEO. They just spend a lot of time with, with customers. They text Adam. My founder has a great line. Anytime he's in front of a customer or he gets like pulled into a big demo, he goes, take out your phone, I'm going to give you my cell phone number. You can text me anytime. Christmas Eve, New Year's Eve, my birthday. He was like, I will always answer you. And he means it. Like, this is not a shtick. He will literally answer anyone at any time and help them out. And so he just naturally— he and Dean both just naturally are very intertwined with customers. They both have a group of customers in their local area that they're stopping in and shopping from. One of our customers in Palo Alto where Adam used to live, I swear he was there like twice a day, almost every day. And so because she has this, like, it's called The Toss. This is amazing salad place.

I was going to say, it must be really good food or a really good drink, one or the other.

And very healthy. For Adam. And, you know, he was getting product feedback from her every day, sometimes twice a day. And so it's, it's been fairly naturally built into the DNA of our business. I still get on demos myself. I'll deal with customer problems. Like, I was on a demo this week, a churn call last week. Like, I don't do nearly as much of it as I would like to do today, but it's been— I spent a lot of time in front of customers for the first 2 years, and it just if you have that naturally built into the organization, everything's easier. Everything is easier if you set the clear expectation and it's led from the top that, like, you just expect people to be in front of calls. Even my managers—

Focus area for us over the next year in particular, like, we've certainly oriented around us as customer zero and got a lot of great channels where we're collecting information and we've got some amazing customers. But part of the challenge of having that really broad scale of SMB, enterprise, all this mix in between, has made it a little bit tough for us to really solidify customer advisory board and just the right processes for getting consistent feedback. I feel like we've got some really noisy customers, of course, that are very vocal, but there's some others that we need to be doing a more consistent job of really putting at the, just the center of our universe.

Yeah. So going back, we, I asked, so what feedback would you give yourself if you could do it all again? We talked a bunch about moving quicker. What other advice would you give to yourself on day one?

Probably the other advice I would give myself is that it's okay not to have the answer, that there's going to be a lot of things that I don't know, and to be decisive where you can, but very, very honest or transparent when you don't have the answer.

That makes a lot of sense. Yeah.

And not that I haven't been transparent, but I think there was— I can definitely identify some scenarios in my head where Goes back to the not being decisive or not moving quickly enough. But I think because I was having this expert— oh, surely I'm going to figure it out. Surely I'm going to know the thing to do. That I wish I had just sat down and been really clear of. I don't have a solution here. I don't have experience here on how to do this one thing. Like, let's get a few people around a table and make a decision. Like, if you need me to make a call, I can do it. But let's just move quicker, but identify that this is not one of my core competencies or an area where I have expertise. So we just need to be aligned and clear on that.

Yeah. Bezos has a great framework here. He's like, you should have roughly 70 to 80% of the information you want to have to make a decision. Any more than that, you've probably spent too much time in analysis. And then Elon has one from his book. I'm going to, I'm going to paraphrase it and probably butcher it, but you should be making decisions at such a rapid pace that you have to go back and change something at least 10% of the time. If you're not making mistakes 10 to 20% of the time and having to go reverse course, then you're probably going too slow. Obviously, there's a one-way door, two-way door thing. Things need more consideration if it impacts every customer or every rep. But I like—

But most of the decisions we make are two-way doors. Like, very few of them are really the one-way doors that are that impactful. Yeah, 100%.

Any talent learnings that, you know, hiring in a true startup versus like a later stage, more mature company? I don't know if I would call it a learning.

I think I innately knew this, but you underestimate when you've got a more mature go-to-market or motion, like, you know exactly what you're looking for, or, you know, 90% of what you're looking for. And you know, it's very different for SMB than it is for mid-market, than it is for net new, that is compared to customer. Like you just kind of know, because you've got so much data and so much, like so much information to tell you what reps are going to be great versus not in the various roles. In a company as small as Walnut or such early stage startups, you know that you need this little mix of art and science. So like, I'll talk about our enterprise motion. Like we knew we were building a lot in enterprise. We didn't have a lot of frameworks. I needed someone that had enterprise experience, that knew how to think about enterprise deals, that knew how to work with complex buying committees, that knew how to get an MSA and legal and security done at a company the size of Cisco. Like, there's certain enterprise chops that needed to be there, but it definitely couldn't be the profile of what a lot of us would consider a—

And your Oracle Salesforce seller. Yeah.

Certainly, that was not what we were looking for. So, it was like this special snowflake that we needed that could think a little bit like a startup guy or gal that was willing to be creative, that didn't expect to have a really clear playbook, that was willing to take some risks and maybe try two different deals, two different ways, and figure out what worked and like think like a business person and map it together enough. And so, I think that was maybe just, it was a reiteration, but it was probably a learning as well of there's just some special sauce that you need, I think, to thrive in startups. And I'm still figuring out what that means across various different roles. But someone that's like that growth mindset, like solution-oriented, really decisive, and like will move and make decisions, but like is okay with some ambiguity and doesn't have clarity on every decision. Like, it's a really unique person, I think, that is thriving in I don't know, we'll call it a sub-200-employee-size startup, you know, or less than 10 years old, less than 5 years old. Um, and so there's, there have definitely been some learnings along the way as I've gone through, you know, interviewing. We haven't hired a ton since I've joined. We're not in mega growth mode yet. Uh, but some of the people that I brought on and the processes, um, yeah, they haven't been as clear-cut as some decisions that I've made earlier at other stages in my career.

It is such a threading the needle exercise to find an enterprise rep that wants to go early stage. They're almost mutually exclusive. You know, you've decided to be an enterprise rep for the long term, which means you're optimizing for earnings a lot of the time and a certain lifestyle. And going to a startup, like, both those things are such major question marks. So it's tough. I have found most of the success I've had Hiring early stage enterprise reps is taking a former mid-market rep who has a little more sophistication and this being their first crack at real enterprise. And then you just have to surround them with the training because it's tough. You're like a—

We're actually doing it with two right now. We hired one from the outside who is doing amazing. He's just been such a breath of fresh air and really helped build a lot of the structure. And then we had a kick-ass mid-market rep that we promoted as well. So it's really fun watching them build and figure things out together. And they're learning from each other and of course making mistakes as well. But having those two kind of on the ground level building it together, at least for us, has been really fun.

Yeah, very cool. I have completely mismanaged time because there's so much good stuff here. But let's— so I want to transition. You know, we talked a lot about figuring out positioning, and you have had a ton of experience trying to figure out messaging in and go-to-market in extremely competitive markets, just like knife fight markets, as I call them. So what have you learned about what it takes to be successful in these markets? And let's start strategically first. Like, how does the company need to think about positioning and go-to-market strategy? And then let's get into, like, what does a rep need to execute in a deal to win hypercompetitive deals in these markets with so many different vendors.

Yeah, for sure. I will say there's, there is some nuance or some difference compared to much more mature markets that I've been in that were hyper-competitive. You called it martech. So I've got experience in the Pardot and the Marketos of the world. It is a little bit different than what we're experiencing today, just being such a new category that's still very undefined, but obviously a lot of the principles still are very much plug and play or very, very applicable. It was another thing that really excited me about the opportunity at Walnut because I felt like a lot of my learnings from those hyper-competitive knife fight type deals that you describe were certainly going to be, you know, applicable in this new role, which is for sure been the case. I think to answer your question in terms of starting strategically, like, what does the company need to figure out? Like, this sounds so obvious, but you very much need to know, am I going in as the low-cost, great to work with, like, where do I sit in the landscape? And then how do I double down on that in a way that's going to resonate really well with my customers. Like even using the example of Pardot, Pardot in the early days compared to Marketo, they were very different. The way that we talked about the products, the way that we positioned them to the prospects that we were selling to was very different. We anchored on really different things because at the company level, we were really clear. Here's the things we're great at. Here's the areas where we do either do not play well or we're just not as good as other players in the market. And it's okay to be really transparent and really honest with those things. Of course, in sales, there's always some element of spin and, you know, we're, you know, overenthusiastic and energetic about our own product. But in order for a seller to be really successful in a hypercompetitive environment, one, they've got to be super trustworthy, and they can't be trustworthy if they don't really understand, like, here's the stuff we're great at, and then here's the things that we're not quite as good. And maybe here's the things that don't matter. Like, there's things that buyers may think really matter. You've got to come in as a subject matter expert and help educate them on what are the things that are really, really going to be impactful to them as a customer year 1, year 2, as they scale and grow into more complex use cases. And as a seller, as a, you know, at the various levels across the organization, if you're really clear on those things, then you generally are equipped to be really transparent with the prospect or the customer, which builds a ton of credibility. At the end of the day, when we're talking about competitive markets, like the biggest competitive differentiator you have is your go-to-market motion and your rep. Like, products are commoditized or commoditizable. Like, yes, you can have the best product, and I've been lucky to sell some incredible products, and I think I sell an incredible product today. But at the end of the day, like, technology is technology, and things are changing really quickly. And I— it's going to get easier and easier and easier to build and code. And, you know, someone's going to be able to copy a lot of what I've done at just about any other company. Like, technology is getting easier to build. The thing that is not going away is folks are desperate for really clear direction, some best-in-class thought leadership, like, oh, help me understand how to think about this market or this category. Maybe they're not even asking those questions, but reps and, you know, CSMs and folks that are able to come in with that level of perspective, I think that's hands down the biggest differentiator in most sales motions, but certainly if you're in those hypercompetitive type markets like what we are today.

Yeah, I say this about AI all the time because everybody's like, oh, sales is going away and BDR is going away. And I thought this was a contrarian take, and then I saw it in an Andreessen Horowitz article. So I'm like, all right, well, it's not a unique opinion anymore, but clearly learned it from you. Yeah, hopefully. But I'm very much of the opinion that sales will become more and more important. The craft, the craft of sales will become more important as AI becomes more prominent in both the go-to-market experience and in sort of the broader venture capital ecosystem, making it easier to start companies, easier to scale, less money is needed. That means more salespeople are needed. And I think ultimately people still want to talk to people to make decisions. And the differentiation will make so much more sense. Like there are, I wish I had counted how many companies there are that do call transcription and meeting notes. There's like 40 of them. And so the only thing that matters in that space, because it's impossible to really do feature-to-feature comparison and a technical evaluation, nobody's doing that. But it's just what is the brand story What is the community that they're building? What is the sales experience that they can offer? Like, that's really what's going to determine winners or losers. And there's an argument to be made that, you know, the pendulum is swinging away from the technical person to the go-to-market executive in terms of what's going to really define success.

Yeah, I'm 100% aligned in that perspective for sure. I love that you call out community as well. That's something I didn't mention. Like, and obviously there's companies that are doing that phenomenally well right now. Clay comes to mind, but like even thinking back in time, like it was one of our biggest competitive differentiators at Marketo was Marketing Nation. Like Marketo had built a sense of community and CMOs wanted to be a part of it. And so we leaned hard into that. Like at first we were very honest about the fact, look at our product compared to others in the market. It's going to look harder to use. Certain things are going to look a little bit different. Yes, certain things are going to take longer. It's going to be way more powerful over time. We will help you. But don't you want to be part of Marketing Nation, man? Like, there was just this brand that smart, amazing CMOs wanted to be Marketo customers. So we leaned into that. And that's not anything that sales did, but like the company built that sense of community and identity. That was just an incredible tailwind.

Very cool. I wanted to actually ask about that. So you mentioned Pardot and Marketo were very different and knowing what you are and doubling down. So what was the differentiation? How did you explain what was different about Marketo?

Well, Marketo was by far the more powerful of any of the solutions on the market. So like the UI was quite dated and I think to this day still is a little bit dated and it was harder to learn. So you typically had to hire a Marketo admin and they required a team to do it well. You had to spend more money to get it up and running. But the outputs of what you could do, I mean, just to get really nerdy, like the level of automation that you could build in and the variety of triggers and all these things that you could build into the background. Which are probably much more commonplace today, but back then they were really sophisticated compared to what you could do with like a Pardot or a HubSpot. So we would lean into that, hey, certain things are going to take longer. It's a little bit harder. But when you think long-term of what you want to be doing with the platform in 6 months and 18 months, like down the line, like here's where we're going to get you. So we sold on roadmap, not product roadmap, but like the roadmap of what their marketing team was working towards and scaling and building. And that's ultimately why often folks would choose Marketo over others in the market.

Use the big girl tool. Yeah. Step up into the big leagues.

I mean, even being willing to acknowledge, hey, like if you, if you need the cheapest tool on the market, it is not us. Like if that's what you're looking for, I can make recommendations. And being willing to say that, like no one wants to acknowledge like, oh, of course I want the cheap. No, I don't want the cheap. I want the good tool. I want the best tool. And so like empowering reps with that level of confidence too, like, hey, we're not going to be the low price vendor in the if that's true, you may be the low price vendor and that's a great thing to compete on if you are.

We were clear that that wasn't us. I've been teaching what I call a radically transparent sales methodology for, I don't know, 7 or 8 years now. And I was on the Sales Loft podcast that I like talked about this forever ago now. And it seems obvious to me, but it, and yet it doesn't happen. Like I buy a lot of technology and No, I never have this experience as a buyer where somebody can say, this is what we're good at, this is where we fit into the market, this is what our competitors are good at, good at and not good at. And if you believe these things, then choose us. Like, that's all I want. That's all I want as a buyer. This is what I try to teach our sales reps. It's like, look, owner gives you much less customization. If you want all the customization and all the stuff, go somewhere else. But if you want to make money, As long as you're willing to give up some of that, some of that control in order to use all of our best practice, like, just use us. And people quickly put themselves into two camps. They either—

Do you feed that to— I love that. I'm going to go back and listen, find that podcast and listen to you talk through it in more detail. But what format do you teach that to your reps in terms of, like, how are they presenting that on a first sales call?

It's the opening line. So before, before— so I teach what's called staggered discovery. So I don't want the rep to be like, great, here's the call. I'm going to interrogate you for 15 minutes and then I'm going to talk at you for 15 minutes. That's not a conversation. The scripting is written so that it goes back and forth and back and forth. And I want to give value first before I ask for value, because buyers, especially if you're going outbound into the market, aren't taking a call for you to then, like, rip off a bunch of questions. So the first thing that we get into on the call, it's, hey, Katie, thanks for taking the time. Let me just like give you the lay of the land and then I got some questions for you and then I'll talk. We'll show you the product. So in terms of this, where Owner fits in and then we give the customer a landscape, you know, there's a bunch of customers, there's a bunch of vendors that look exactly like us. They say they do the same things, but like, let's, let's architect what this actually means. And you can use our direct competitor and you'll have a prettier website and you have more control over how it looks. But we believe that the control is not good for you. You need proven templates, proven playbooks. And because our websites look the same across thousands and thousands of customers, we can test and learn things and then deploy it on your behalf, which means you're always getting the expertise of the best restaurant marketers in the world, as opposed to you trying to out-market your competitors. Like, you know, you're a, you're a chef and people, either it clicks and they're like, yeah, I don't want to do this. I don't want to learn to be a digital marketer. I want you to give me the answers. Or they go, no, but like my brand experience is everything. People need to like see things in the same way. Awesome. I will. And the reps are trained to do this. Let me refer you to the right vendor. And they'll say like BentoBox is one of our competitors that's like very aesthetically driven, is very like very design-oriented, if they care a ton about their brand and they have a custom font they want to use and they want, you know, the whole page to be a video and this and that, be like, good, you should go use BentoBox. They're awesome. They will give you the most aesthetically looking site possible. And you're fine dining, like, use them. And we send customers to our direct competitors all the time. But then that builds massive trust. But and if they What we're doing is it's called point of view positioning. I'm just pitching my point of view to the customer. You decide if you like my point of view, which is you should partner with an expert and take their expertise, or you want to learn to be a digital marketer and you want control and you want design and aesthetic, then like go choose these other things.

I love that because you're not only— you're being really transparent, you're positioning yourself well in a lot of different ways. You're leaning into something that you're very, very good at, the data, the learnings, the everything that you described around, you know, thousands of websites, and we're going to empower you to do all of those things. But then you're also disqualifying folks that are ultimately going to waste your time and not end up buying from you. Absolutely.

A win-win on all sides. Yeah. I introduced a bunch of this at Shopify and what you notice is time to lose went way down. So win rate stayed about the same, but we were using, we were spending way less time on deals we ultimately lost. And this is how I want to buy. I want somebody to have this level of transparency. So execution, biggest differentiator is GTM experience and rep execution. Anything else in terms of winning these hypercompetitive deals that have been big lessons for you?

I don't think anything that we haven't already talked about or unpacked in a couple of different ways.

Yeah. Yeah, that like honest, know where you sit in the market, I think is so much of it.

Radical candor. Love the transparency.

Yeah. All right. Quickfire before we wrap.

Okay.

What do you think separates a good CRO from a great one?

Oh, I love that question. I think that great CROs and great leaders are able to identify superpowers in the people around them that maybe even those people haven't identified in themselves yet. And then you find ways to bring out those strengths or those superpowers. Yeah, that's the first thing that comes to mind. Like all of us as sales leaders and revenue leaders, like we're, I'm all about like identifying strengths and trying to amplify those superpowers. But in, I certainly don't, don't have the experience to classify myself in the great bucket yet, but it's certainly something I'm focusing on. Of how do I identify that unique thing that that person doesn't even know that they're good at yet, or where they just come alive when you see them operating there and finding ways to amplify it. Yeah.

Much easier to amplify a strength than to buff out a weakness. Oh, 1,000%. What's the most common advice you give to your frontline leaders, your mentees? What do you find yourself sharing with them most frequently?

We've been recently talking about asking better questions, asking more questions. Just because we identified some opportunities where that wasn't happening. We were doing a lot of managing and not enough coaching. And again, it's different at different kind of segments of the business or different levels of experience, but great leaders are usually really good coaches. So that's one of the most fundamental things that I'm working with, especially newer leaders or younger folks of just core principles of being a good coach and identifying what coaching even means. And most fundamental thing is asking good questions.

Absolutely. I published a document I wrote for my managers called Coaching Mastery on my Substack, and that's one of the principles. Great coaching is questions-based.

You've read Trillion Dollar Coach, my favorite books.

I have never. It's funny you say that. I keep meaning to put it in my to-dos, but that is a good one.

I just started rereading. I read it a long time ago and I was like, I need to reread it coming out of this conversation I just mentioned.

I just made a note.

What's the hardest? What's that? You're good at multitasking.

I can tell. Well, I take notes as I go because I do the podcast because I'm— for my own learning. And so I didn't take notes for a couple episodes and then because I wanted to just focus. Then I was like, oh, but I want to remember what that person said. And so now I take notes again because I read an article after as well. So It's helpful for that. What's the hardest lesson you've had to learn?

You can't do everything. You're certainly not going to be good at everything.

That's a great one. And what's the best thing you've read in the last 12 months?

Well, I just said I was rereading Trillion Dollar Coach. There was a recommended— oh, Pattern Breakers. AJ recommended it on Topline. I just finished it and it was a while back that you recommended it. It's really good. You have it sitting next to you. Yes. There you go. So great. So great.

I now quote Maples frequently. His whole choice versus comparison thing actually dovetails exactly with your positioning around know where you are and force the trade-off.

That is one of the best things that I took from him and just pulling the future forward. I don't know, there's, there's a lot in there that I, I feel like I need to go back and read it a second time, but it was really good.

I've recommended it to a lot of founders. Um, yeah, this is awesome. So we, we got through a ton of stuff. I have a whackload of notes here. This is a great conversation. I think people are really going to, uh, take a lot away. There's so many folks that are either in the early stages of this journey or aspiring to get to this journey, and I think this is going to be a really helpful, uh, playbook for people to, uh, to use. So where can people find you and what are you hiring for? How can people be helpful? Like, plug whatever you got.

LinkedIn's the easiest place to find me. I'm one of the few Katies with a C that you'll find. So Katie Ivy is usually pretty easy to track down on all social channels, but LinkedIn is definitely where I'm most active. If you've got— if you're working aggressively to try to figure out how to make your whole go-to-market motion more product-oriented, product-centric, which includes interactive demos as a piece of that, then we would certainly love to talk to you about that. But I love talking all things go-to-market, go-to-market efficiency. So I'm happy to connect there. We are hiring for mid-market and enterprise reps. I just hired a head of marketing that's about to start. So we've got a few other roles that are open. So feel free to go to the website as well, walnut.io, if you want to check them out.

Yeah, awesome product, trailblazer in the category, and it's an important category. We talk about we call it sell between, you know, what's, what's the experience in between the calls and how do you shape that? I would be a walnut customer if we didn't sell to restaurant owners who will not visit a website or go through an interactive product. Now we have to do— we're like text messaging and sending them PDFs and all. It is a, it is a very different market.

But you guys are not at the core of our ICP.

I will acknowledge that we are definitely not. but it is a space that I look at from the outside and it's like, I, I so wish I had a solution like this, uh, at Shopify, at League. Like, this would have been great. So people, if they're not—

things that resonated with me early in the interview process, I'm like, oh, this tech is cool.

Like, it's a no-brainer. Yeah. Yeah. Uh, well, this was great. Thank you for joining, Katie. Appreciate the time. Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe, and you can find a link in the show notes. And be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.