E56: Becoming a CFO Whisperer & Revenue Architect (Allison Metcalfe, CRO @ Zenoti)

Alison Metcalfe is the CRO at Zenoti and was previously an SVP at LiveRamp, where she helped the company scale from $30 million to $500 million. But she'll be the first to admit she is not the typical sales leader.

I think the skills that make me strong are less about my own personal sales skills and more about my architectural way of thinking.

She shares why she's such a believer in multiplier leadership and why you should assume your team is judging your strategy.

Everyone's weighing in on what you're doing as a leader, whether or not you're inviting them to. So you may as well give them an opportunity to, to weigh in.

Alison also breaks down exactly how to manage 2026 planning season and manage your CFO relationship.

Don't bring your feelings to a data fight. You have to prove your thesis. The onus is on you.

From utilizing an alter ego for tough conversations to the exact feedback loops she uses with product teams, Alison opens up the playbook.

The people that grow the most really focus on—

Welcome to the Revenue Leadership Podcast. Here's a familiar scene. A deal's in commit and the buyer says, can I talk to somebody like me? Next thing you know, sales reps are asking CSMs after hours. 5 people are in Slack trying to remember who helped last time. And that one customer who always says yes is getting burned out after 3 requests in a week. That's why this episode's brought to you by User Evidence, the platform that turns customer proof from chaos into a repeatable GTM system. With advocates, references, and real customer evidence all in one place, your team can share credible proof instantly and keep deals moving forward instead of stalling. Companies like Gong, Ramp, and Workato already use User Evidence to capture customer proof, build buyer confidence, and shorten sales cycles. See how at userevidence.com. That's userevidence.com. Today's guest is Allison Metcalfe, the CRO at Zenoti. And Allison spent the first 10 years of her career in customer success, where she was eventually a senior director of CS at Demandbase, then VP CS at LiveRamp. And, uh, she moved into revenue at LiveRamp where she spent 7 years, eventually becoming the SVP field strategy, productivity, and partnerships. Then followed by stints as CRO back at Demandbase, Cloudinary, and now Zenoti. And today we are going to talk about. Executive relationship management, executive collaboration. It is 2026 planning season, so it is a very topical thing to dive into, as I'm sure many listeners are deep into a number of disagreements that hopefully we can help them work through. So thanks for joining us, and I'm really excited for this one.

Great to be here, Kyle.

So you had a nontraditional path to CRO. And, uh, you've said oftentimes being a successful CRO, uh, has very little to do with personal sales acumen. And so I'd love for you to unpack those things, like how much of a non-traditional, uh, journey informed that opinion and what does that opinion mean?

Yeah, I mean, so I think it's a couple things. I think, you know, in the same vein that the best IC salespeople do not always make the best sales managers, I think that the same the same kind of logic applies. And I think the two roles that I've had that have made me what I— hopefully people think I'm a good CRO, the two roles that I feel like make me a stronger CRO are actually my time in go-to-market strategy and operations, as well as my time being a GM, where I had to have very broad purview of the business. I always had a revenue focus when I was doing customer success, in the old days, I always had renewal, upsell, cross-sell. So, I always had a revenue responsibility, had a lot of empathy for customers. But I think the skills that make me strong are less about my own personal sales skills and more about my architectural way of thinking, the fact that I always think about the entire customer journey, 'cause I've had to think about all of it from soup to nuts. I've had to be very data-driven in building those types of models. And so I, so no, I don't think, I don't think I'm the best salesperson at Zenoti by far. And I think my skills that are, but I'm probably better than others at what I do uniquely well.

And would you say that the architecture skills are going to be increasingly important as we are in this AI age?

Yes, because I think, I mean, we've always, as CROs, especially this type of, this time of year when you're doing the planning, The number one thing CFOs are typically gonna ask and board members are gonna ask is how much can you increase productivity and efficiency? How can you, you know, 10%, 15%, 30%? And AI is really making that very confusing. How much should AI increase productivity and efficiency? And I am definitely a believer in AI and I, I use, you know, ChatGPT all the time and I'm still trying to, to to, to get better at my use of AI in general. I don't think it's at a place where it's increasing productivity 30% or anything like that just yet, but I think it's gonna be really important for CROs to have a strong point of view. You can't say zero. You know, I don't think that's defensible or, or credible, but, but yeah, I think like sprinkling the AI dust on top of your organization and figuring out how it can increase that efficiency is gonna be really critical when you think about models of the future.

It's definitely my opinion that the CROs that will win are systems thinkers and revenue architects as the act of acquiring revenue is less about people and more about this revenue factory. You know, AI is leverage. It's just leverage on anything. So if you can think in scale and leverage, I think it is going to be a distinct advantage. Yeah.

And I think if you, if you can think like all the way through and not just about one part of the journey, and actually you made a joke before I went live about be being a journalist. And I actually studied journalism. That's what I wanted to do when I went to college. And I actually find that is another element of my skill toolset that helps me, because I do think like an investigative journalist. I'm like very why, why, why focused. I can go really deep into things. So that applies to everything. But again, as it applies to AI, you know, I get very frustrated when these kind of broad platitudes are thrown around about like, it's going to do this or that. And then it's just like, how and why and what do you mean by that? And practically what what's going to happen. And, you know, I think getting that kind of pressure and being able to, you know, not react defensively, but being— but reacting with curiosity, um, is going to be very important for CROs and all of us going forward.

Yeah, if you don't have good curiosity and you can't smell BS, you'll buy a lot of the wrong things today.

Yes, yes, that's true. Not always true, but especially today.

Yes, especially today. Yeah, for sure. Okay, that's a great framing. So I wanted to spend time talking about how you manage executive relationships. You, you've mentioned this as a strength. I messaged a bunch of folks that have worked with you closely, and this is a thing that came up repeatedly in, in everybody's feedback, uh, about sort of your superpowers and what, what they saw you do and build. And so I think it's a, it's a conversation I've wanted to have, and it feels like I got the perfect guest for it. So, I mean, no pressure, but, uh, I'll fix all your problems, relationships, Kyle. So you mentioned that oftentimes you see the role of a revenue leader as more therapist, mediator, driver of collaboration than like salesperson. And, and, uh, I would love to just hear you unpack that and then we can talk through some examples.

Yeah. So I think, okay, so let me, let me go back a little in time. Um, because I think a lot of this started for me when I was working at Salesforce for a while. This is a million years ago, 2010 or something. Liz Wiseman, who wrote this book called Multiplier Leadership, she had just published— it's a great book. So get this story if you're a fan of this. So she had just published that book and she was friends with Benioff and she was, you know, um, just moving into that realm. And she had just published the book and she wanted to trial a multi— like a workshop. And my company had just been acquired by Salesforce. So I had this like distinct honor in retrospect. It was like incredible luck to get invited to participate in this 3-day workshop of, um, it was like her inaugural multipliers workshop. Yeah. And it changed everything for me. It changed my whole entire way of thinking about leadership. And I, and like the practical example I'll give is I had just been promoted and I was taking on about to take on a kind of distressed team. Um, we had just been acquired by Salesforce and it was pretty rocky. It was their first ever acquisition, which is also story— Jigsaw was? Jigsaw was, yeah.

Cool.

Yeah. First ever acquisition, $110 million. And it was like front page news. Um, and Silicon Valley.

I loved Jigsaw as an early—

It was amazing. It was amazing.

Hoover up all my data, scrape all you want. Like, let's, uh, just get—

I don't think it would work. I don't think it would work today. Um, but it was very, it was a very cool concept. Very cool. Garth and Jim and Kevin were all really smart. But, um, so I'm about to take over this distressed team. And prior to the workshop, the way I was thinking about this was I, the, the team was in Spokane, Washington, and I was like building out this presentation and I was like, I need to go up there and I need to present my vision and my thoughts and, you know, don't worry, I'm here and I have a plan and everything's gonna be okay. And after I went through these 3 days, I ditched the entire presentation. And, you know, not to be like all Pollyanna or whatever, but I went up to Spokane and I put everyone in a room with a whiteboard and a marker and I facilitated a discussion and I had ideas, right? I had things that I thought, but I was, but I was way more taking the role of leading people to, to present, to coming up with those ideas and, and bringing them there. And so one of the biggest tenets of multipliers is like, A, everyone's weighing in on what you're doing as a leader. Whether or not you're inviting them to. And so you may as well give them an opportunity to, to weigh in and, and hear them out because, because they're doing it anyways, right? So, so, so just do it. Just, just give them that forum. That's one of the, the one big thing. The other big thing I learned is, you know, that in multipliers, there's this concept of multipliers and diminishers, and those are the two types of leaders. And diminisher's a tough word. I, I, I don't think that people that are diminisher leaders are bad people or jerks or anything. I think that they fundamentally misunderstand their role as leaders. I think that they believe that like, I'm the boss, I'm the leader, so I should have all the answers, and that's what people expect of me. But in fact, the best leaders, or the people that people like working for the most, really do ask a lot of questions and facilitate and treat you like you have all the answers and try to elicit that from you. So, this is often what I do when I, you know, when I, and I should say, and by the way, the other thing that's kind of been my superpower that you'll appreciate Frankly, I think is being Minnesotan. I'm, I'm not from a coastal, but maybe you're from Toronto, so maybe you are coastal elite, but no, no, no.

I'm, I'm a mid, like Toronto is hardcore Midwest vibe.

Okay. Okay. Okay. Um, we can have a Midwestern off later, but I, you know, I grew up this, this life that I have in this career that I have was never part of the plan. I moved to San Francisco because I thought it'd be cool to live in California. I did not go to an Ivy League college. When I first got here and I started having success in the tech industry, I was, you know, people were, had gone to Harvard and Stanford. I didn't think I'd ever meet people that went to these colleges and they're like working for me. So I have a lot of ingrained humility slash, you know, shame or whatever you want to call it. But like, I don't have a really big ego. And so I come in and I can kind of work with anyone. I can collaborate with anyone. I don't think I'm better than anyone. I know that I'm not. And so I, I do often approach things by asking people what they think I should do. Um, it's always a really interesting question is because everyone's got an opinion for better or worse, especially for CROs. Everyone has an opinion on the sales team and how they sell and marketing and how they're marketing. Everyone, everyone thinks they can do it. So may as well ask them and collaborate with them and, and, and bring them on your journey. And I have found those tenets of multiplier leadership to be as equally effective for me leading my teams as it is leading my, you know, not leading, but having my peer-based relationships and even working with the CEO. It's always been really, it's always in the back of my mind, the multiplier stuff.

I think the everyone is always weighing in is like an underrated takeaway. Do you want to just explain that a little bit more? You buzzed by it, but it's such a good framing for folks.

Yeah. I mean, and I, it's so funny. I even remember It was so impactful to me when I first heard the framing. I can, I'm right back in that conference room in Salesforce's, like, you know, initial building. She was like, people are at the bar and they're talking about, they're having after-work drinks and they're talking about how you presented. They're talking about your plan. They're talking about how stupid they think you are or whatever, most likely. Like, they're talking about what you don't get, you know, they're complaining about it or, Most likely people tend to commiserate more on negative stuff versus being like, you know, Kyle's so amazing. But it's that, especially if you're leading, you should not be under any idea that you're up there presenting your plan and everyone just turns off their camera or leaves the meeting and just goes, she's, that was a great plan. Perfect. 10 out of 10. No notes, right? They're all gonna go and talk about it, right? And So, and if they don't like it or they don't really believe in it, like they're, they might not feel comfortable telling you, right? So this is, then I'm gonna jump into the, another thing I learned extensively. I had, I had an executive coach, Leslie Higgins. I'll give her a shout out. She changed my life as well. And the, the thing that she taught me that's also in parallel to this concept of everyone's weighing in, so let them. And now I sound like Mel Brooks or not Mel Brooks. Um, I sound like Mel Robbins with the let them.

Yeah, yeah, yeah.

Uh, but like, She really taught me this concept of advocacy and inquiry. So advocacy meaning, you know, whenever I give an opinion or make a decision or roll out something, I really try to show my work in terms of like, let me just help you understand how I got here, right? I started here and then I, you know, I made this assumption, I made this assumption and da da da da da, and then ultimately in this data, and then ultimately I got here. And it's the, a similar concept on the other side because what I try to coach my team to do is if I say something you don't understand or if I, or if anyone else does, we've all had this experience, right? We're like, I don't know why this person thinks this or why they're doing this. This is crazy. The, the power of the question, can you help me understand how you got there? That's the inquiry, right? And so I will, I try really hard to invite people to give me feedback. I also try to create opportunity for them to jump in when I'm practicing advocacy by showing my work so then they can say, ah, there on point 3, you made an assumption that I don't agree with, and can we unpack that a little bit more? And that's, that's really, really, really helpful. I will say I've seen companies go too far on the letting people weigh in thing though, and LiveRamp did this for a while too. We were like, in the early days, we were like super, you know, not hierarchical. Yeah. Yeah.

Great.

And then at one point, do you remember holacracy? Do you remember that concept? The, oh, look it up. It's like, I still get like, we never did it, thank God. But it was this concept. I think it was like, um, the Twitter founder, not Jack Dorsey, but the other guy, Evan, whatever. And it was like, there's no leaders and there's no management. And it's just these like circles that people, it was just, Chaos, chaos. But we didn't actually do it, thank God. But we did over-index on this. So then everyone had a chance. So you have to, as you know, right? Multiplier leadership is also, I might, I try, I try, I'm gonna always say I try 'cause I know I don't always do this perfectly, but hey, I have a decision to make and I'm gonna ask for your feedback, but this is not a, this is not kind of like a democratic vote or a consensus. I'm just soliciting. I'm just curious, right? It doesn't mean I'm gonna listen to you or I'm gonna survey everyone, but I'm ultimately, it's my decision. You gotta be clear about that. Consensus-driven decision-making does not always work or scale. So I think there's a way for you to like create space to hear people out, but not be beholden to like the opinions of the entire group. Right? Like, that doesn't work after a while either.

Yeah. We, we like this approach for hiring as well. We are a champion-based hiring environment, not a consensus-based hiring environment. So the hiring— yeah, like ultimately it's the hiring manager. You get feedback from other people in the interview loop, but like you are making the call. And I don't even really veto people. Like it probably comes across as a veto when I'm like giving critical feedback and I'm like, I don't, I don't like them, but there will be reps or there will be managers that are like, I hear you and I still want to take the bet. And we let them. And there's a, there's a, there is a rep who one of my youngest, newest managers, not youngest, one of my newest managers wanted to hire. I was like, good. I like everything about him, but like SDR, not BDR. He doesn't really have like enough of the experience. And that very new manager was like, I hear you. He's like, I absolutely believe in him. I'm betting on him. And this is like a stud BDR now, clearly didn't need the SDR. I was like, I was wrong.

Yeah. And, and that's good.

He, he put a 90-minute, he put a 90-day reminder in both our calendars to be like, you know, reflect on it because we talk a lot about Ray Dalio, like pain plus reflection equals progress. And so I wanted a, a reflection point to be like, okay, what, like what did we miss? And like that was a great, like we got to the right answer because the manager had spent 90 or 120 minutes with that person. I spent 30. So ultimately, like my feedback is one input. And, and so I think this, you can go too far in being flat is a good warning for folks.

I think it can be, 'cause you, it can be very paralyzing, right? And like, I, I remember even at one of the companies we had the more consen— and I remember getting like, someone, you know, having negative feedback about a candidate that I really wanted to hire. And it was like stuff I just didn't care about, you know? Like, I just, I was like, great. I don't care. Like, this, my, my, he's now like a great friend. My friend Eric Chernoff was like, we would always fight. He'd be in my hiring committees and he was really big on asking people their 5-year plan. And I was like, I just, I couldn't care less. Like, I've never had a 5-year plan and it's not important to me. Critical to his success. And so it was just one of those things where he would, you know, ding someone because I didn't have that. And I would just drive me crazy cuz I was like, it doesn't matter to me. Right.

So I think he still won most of the time, but anyway, I also don't have a 5-year plan, so, uh, power to the chaos, right? Yeah. Yeah. So I go back to like, so people are always weighing in, people are always judging. And so then your feedback is like, you might as well let them share it. Share it publicly? And what's the, the outcome for you sort of like after you give them the opportunity to share?

Well, you mean like how do I, what do I do next? Or you mean like how does it work for me? I guess.

How does it, so you, so give them the opportunity to share because why?

So yeah. Okay. So the, the main, one of the main reasons, this also goes back to multiplier, is people are way more likely to be heavily engaged and bought in on a plan or an idea if they felt they had a chance to participate in the creation of that plan or idea, right? If they have, if they feel some ownership of it versus this top-down thing. And so I, I'll do that all the time, right? I'll come in and again, similar to my Spokane jigsaw example, I will typically have some at least rough idea of where I wanna go with this, but it's so much more effective if the group collectively participates in creating that because then they feel like it's theirs, right? They feel like it's their idea and everyone likes their ideas the most, another tenet of multiplayer and leadership. So I do feel that from a kind of emotional perspective, people are way more bought into the success of a plan and driving towards that plan if they feel it was theirs just as much as it was yours versus being pushed something, you know, having something done onto you. And I think they also feel like, they feel like pride or at least some, you know, recognition when they see their, you know, their concept in your plan, then they're like, I did that. And they, you know, they're way more invested.

Yeah. Liz doesn't talk about this in the book, but it's the endowment effect is, is sort of the psychology behind it. It's like anything you put your effort and time into, you automatically endow a piece of yourself into that, into that thing. And so you're, yeah, if you feel like you can see, especially your language, in the proposal or your idea, or you get referenced, like you're, you're gonna be so much more likely to support that thing. And then ultimately, like our job is about adoption. A job, our job is, is like not pretty plans. It's about driving behavior change. I think people, people miss this so much of the time and there's a lot of great stuff in Multipliers and, and like all of her work.

Yeah. I'm so excited you're a fan. I, it's like my number one thing I recommend to people. But I wish, I don't know that I would've gotten as much from Multipliers had I just read the book. Like having it be this like 3-day workshop. And by the way, my, one of the things I love about Multipliers is, have, have you ever done the 360 under the Multiplier umbrella?

No.

It's like, here's the question that she asked. It's so amazing. The question is, okay, you work for Kyle, uh, you know, on a scale of 1 to 10, how much of your intelligence do you use working for Kyle? And the— isn't that an interesting question? Because the idea being, if you work for a diminisher, you're using very little of your intelligence because whether you realize it or not, you're like, Kyle's just going to tell me what to do. So I don't really need to think about this that much, right? But if you're working for a multiplier, you're like, okay, I do know I have to come up with this answer myself, or I'm going to be expected to really know my stuff. And, you know, so it's like a really Really interesting question that, um, I think about all the time. I want to be a multiplier. I want people to say that when they work for me or on my teams, that they're using a high degree of their own intelligence.

I, I'm slacking this exact quote to my RevOps leader. The next time we do a pulse survey, I want to, I want to ask that.

Good question.

Yeah, it is a great one. And, uh, I get too excited by new ideas and I want to do it all. I'll have like we have an external engagement in February, but I'm going to pin Multipliers for a future like workshop engagement. Yeah, they'd be great. You know, it's funny, one of the last, like, uh, one of my favorite authors I talked about on the podcast was Michael Jervais, and then he, they, he saw it and reached out and came on the podcast, and I was like, oh my God, I could have like my favorite authors on the podcast. And now I'm like, why didn't I reach out to Liz Wiseman? Like, this would be—

you should That'd be amazing.

Yeah, we read, we read Impact Players as a leadership group when I was at Shopify. That was, 'cause that was like right in the middle of COVID I think. And that got me into, then I, then I went back to Multipliers. I hadn't, I, I didn't catch Multipliers when it was first written.

Interesting.

Yeah. So I wanna go back to this concept of like, okay, you're in an executive team. Most of the listeners, this is, this is sort of their role. How do you assess whether or not there is healthy relationship, the right amount of conflict. Like you can go back to Lencioni and sort of like trust, conflict, accountability, like whatever framework you want, but how, what's your rubric for understanding like executive relationship health?

What an interesting question. Rubric for understanding. I mean, I think that there's little signals that I look for and one would be how often is the team having debates that get even a little bit testy altogether versus how often are people just talking to the CEO one-on-one. And when I've been in unhealthier situations, you, I could always tell if the CEO is coming to me and he's like giving me feed— he or she is giving me feedback or asking me questions or something, which I'm like, this is clearly not coming from you. This is clearly coming from somebody else. And I can tell who it's coming from. And I don't understand why they didn't just come and talk to me about this, like, first, you know? That's a sign of bad health is when we can't just all talk to each other and ask each other questions and you have to feel like you have to go. And frankly, this is why, this is another way when I've taken over teams, I've always, I've like, ah, there's an unhealthy situation going here when everyone only wants to talk to me about everybody else and they cannot seem to, and they all have opinions about each other, but there's not a culture of giving feedback and just talking. And I hate the word feedback. I think we need to rebrand. That word because it sounds so formal, you know, like I've actually heard someone say, rather than say, can you give me some feedback? It's just, can you give me advice? Because feedback does, it just sounds so like formal and HR and like, I have feedback for you. And it's just like, why does it have to be? And I think that's created this, like, it feels scary or intimidating to say you're going to give feedback, but it's not. It's just like, I just want to talk to you about what you're doing. I want to understand why you're doing it. And I, you know, I maybe have some questions or I maybe have some advice or an idea or something like that. And I think that This concept of feedback gets people really tripped up sometimes, and that's why you can tell if they're not talking to each other. Or again, another big thing would be like, if I go and talk to you and I give, give you advice or ask you advice or run ideas by you and, you know, I might get head nods from you and then later, you know, the behavior does not match what is being said, said, like that's also a pretty, that can be a tough That can be a tough sign. I think the other thing that would be, you know, it's funny, I actually just got off a call before talking to you. I was talking to a CEO, giving a reference for a CFO that I worked with in the past. And I said, you know, one of the key reasons I worked so well with this particular CFO is, is we had a, we had some personal connection too. We could talk about life outside of work. We could talk about skiing. We could talk like, we, we do have to be like whole people. And I have like the one culture that I was in that was not good for me was when it was like, it was just all business all the time. And you were just not allowed to show any of your own self, um, at all, which for jobs like the ones that we have, if you're an executive at a tech company, like for better or worse, you're working a lot. Uh, I think I've seen you talk about this, right? We work a lot. We have, we're together a lot. Um, it's exhausting if you can't be at least a little bit of your authentic self and it's exhaust— I, I find it very difficult to collaborate well with people if I have no vibe with them that is beyond just professional.

Yeah, definitely agree with that. Like I, I don't have a problem being myself. I probably do it to a fault and I say what's on my mind and, and I, I've been given the feedback in, in the past at especially at bigger companies, it's like, oh, you should like, you know, think about your messaging and na na na na na. I'm like, yeah, I would just rather be myself and, and like have a direct conversation. And I've learned to do that in like in, in different ways, but I find it difficult to, to work with somebody where it's like there's, there's so much corporate veneer. I was like, just say the words, just like, yeah, whatever's behind there, behind those words, just like say the words. And we're actually a couple weeks into doing trust and conflict training at Owner. My like enablement team built an awesome program built around Dare to Lead and Crucial Conversations. And so we're like deep into this now and trying to build more of a culture where we can, you know, like really openly disagree and get to the heart of our our problems because I find remote makes it difficult as well.

I agree. I agree. Very, very, very hard. Um, I agree with you though too. I think there's something at LiveRamp in particular when we got really, 'cause when, when I left LiveRamp, it was like $500 million and I'm laughing 'cause it's like so embarrassing to say that out loud, but it was suggested to me that like I should, there was like, um, this like corporate like makeover person and they was like showing me before and after pictures and I was like, here's the thing, if I have to look like that, I don't want to do this job. Like, this is not for me. Like, I, so I, I feel that deeply. Like, I have to be, I've had to polish it up, right? Like, to a certain extent, for sure. I, you know, but, um, it's almost impossible for me to not be able to be like, it just comes through. It's too strong, you know, like it's, it's going to overpower it. So yeah, power, power to those that, uh, can, that can tone it down, but I can't.

Yeah. How do you think people should deal with this in a remote setting? Like when, you know, if there is so much value to a personal relationship, I don't know about you, like I don't really want to get on a Zoom and like have a gab. It's like just, it feels forced and I just found it the time investment and payoff is like not really like, I don't actually feel like we really have a relationship. Versus like go out for a dinner, get coffee, go for a walk. Uh, what are your thoughts on doing this well remote?

And I, I totally agree. I even find when I'm on, you know, and we're on Zoom calls all day long, so the last thing I wanna do is do another Zoom call that's like, and I find it difficult enough sometimes to not multitask. I don't know. Do I, I don't know that there's any other answer outside of you just need to get people together in person. I mean, you just, you just have to. Um, and you have to, you have to almost kind of mandate it. I, I'm going to India in January. I'm going to Manila in December. I was in Austin, I think this week. I don't know what day it is, but, um, you know, there's ways that, and I have found, by the way, like I have, my kids are a little bit of a naysayer. I have a 10-year-old and a 13-year-old who do not like me traveling. Uh, I try to do it in bite sizes. Like I will fly to London on a Monday, land. Have 2 days of meetings and get on a plane and come back. So you just, you do have to kind of sacrifice yourself to a certain extent. But I mean, I don't know, there's really no other way. I value remote work and I want to continue to allow people to do that, but you have to have regular touchpoints that are in person. And they, they're, to your point, I think there has to be something that you're doing that is not just working to, to build those to build those connections. I mean, what else is there, Kyle? I don't know.

I, I don't know.

I, I think you don't have the great answer either.

No, it's, it's certainly not like coffee chats, like Google Meet coffee chats. Like, I, I don't feel like I've ever built happy hours.

Yeah.

Oh God, like, miss me.

Yeah.

I think the time in person makes sense. I do think, you know, like, we, we had this 90 minutes with my SLT and our core, like our core stakeholders, biz ops, marketing. And we had like a really open conversation built around the Braving framework and getting into some Crucial Conversations stuff. And that did very much like move the ball forward. So I think if you're going to try to, if you're going to try to do the relationship building thing in a remote setting, it has to be like very structured. And you probably need a facilitator. And you know, we're lucky because our enablement leader is, I think, Crucial Conversations certified and is like very, very ingrained in, in this stuff. And so his team facilitated and it worked great. But I, I don't see, um, I don't see another way.

I think that's actually a great point, the structure of it. 'Cause like, you know, one thing that I've, in addition to multiplayer workshops, the other thing I'm really passionate about is Enneagram.

Yeah. Shop will buy his hardcore Enneagram. Oh, take one guess.

You're an 8.

Yeah. Oh, competitive achiever. Whatever. Competitive achievers. A 3.

No, you're not. Okay. You're a 3. Okay. Okay. That's interesting. So I'm a 2. Um, which is the helper. Yeah. I'm a, I'm a 2 with a strong 8, which is the challenger. And I have some challenge.

I have some 8 in me for sure.

We all, we have to, there's no way we could survive if we didn't. And I'm like very, I have so much experience managing 8s, but I think the one thing about 8s, the classic thing about 8s is they don't believe that it should matter how they come across if what they're saying is right. So it's like, it shouldn't matter if I'm being a total jerk. It's like, I'm speaking the truth. And it's like the biggest management challenge with 8s is like, but no one can hear all your goodness because you're coming, you're such a jerk. So I have a lot of experience with that, but, um, I, I have used Enneagram facilitators in a lot of different settings and I've done it on, I've done it remotely too. And you're right, it really does work because it's like, it's so interesting. Like you, when you start to understand other people's Enneagrams and like what it means, it starts to make so much more sense. And then you like, interesting. One time I had a facilitator that was just like, okay, like what do you do when you go to a hotel? Do you unpack? What does your hotel room look like right now? Like, is it unpacked, immediately put away? And like, I was like, no, mine looks like a tornado went off in it and I need everything. It's like chaotic. And then everyone's looking at me like, what? Like, like it's really like interesting questions that to your point with the facilitator can like, it's like, now what does this mean about these people? And you know, it's fascinating to me. Um, that's interesting. The Top of Fire is a big Enneagram shop. I'm such a fan of it.

Yeah. They had internal coaches, like they had coaches on staff that all they did with this was this. So they would do executive co— they would do executive coaching, they would do like Enneagram stuff one-on-one with teams. So I just tapped into their resources. Interesting. I was super skeptical about this internal coaching thing at first. I'm like, man, like, I can't really like open up if this person is talking to all the other, all like all these other folks. And I had an amazing exec coach at the end of my time at League which I wanted to work with, but, but couldn't. But I really found that the coaches there had so much Shopify context on how that place works, cuz it's real quirky as, as maybe you might know, it, it's a very unique place and they like really live their own culture, which I loved. But, uh, the coaching and the facilitation was, was good. And like they would share enough specific feedback about like, okay, well you're working with this person and like, you know, this person is like this and and just the, the embeddedness actually, uh, was genuinely helpful, although I was very skeptical going into it.

I'm skeptical of all of that stuff. And then, and then it like emerges that it's incredibly, incredibly helpful. But Enneagram for me is the most helpful in dealing with people that are struggling to get along or struggling to connect and struggling to work together because you're right. It can be like, oh, Kyle's a 3. This means his big, and it gets very vulnerable and emotional. Kyle's a 3, so I for— I didn't, I forget what the 3's like biggest fear is.

It's, it's looking good to others.

That's, well, what is it? What's your biggest fear? So your biggest fear is looking bad to others.

Yeah. Yeah.

Yeah.

Okay. 3s look for external validation a lot. We are achievers. And so like oftentimes it's about, it's about like looking good on a scoreboard and like the, the metrics, like in a bank account, like that, that's where threes have trouble.

Got it. Okay. That's super interesting. And then like eights need to be in control and, and then, um, like I think it's nines are very conflict averse, very conflict averse, like really they struggle. So it's like, it's, it's very helpful to understand these. And then what I also love about Enneagram is it's like, it's I use the stuff I learned from Enneagram in my personal life. Like a big thing for twos is struggling to ask for help. Like, like I'm the helper. I don't need help, you know? Like, so it's like, but, uh, I really need a lot of help. Right. And so, um, I'm like, oh, and I had these flashbacks, like being in college and my best friend telling me like, you are such a difficult person to help. And I'm like, this has been a problem for my whole adult life. And I'm learning this in executive coaching right now. Okay. This is very surprising. But so helpful.

Yeah, very cool. So I wanna zoom out a little bit and just ask, so what do you think are the sort of bedrock criteria of a strong executive relationship? So like personal, like a personal out-of-work relationship seems to be one of them. What are, what else are the things that you think people need to build?

I think a lot of empathy and understanding. I try really hard. I work with, you know, I, I, a very important role for us as CROs is product, right? Chief product officers. Yeah. And, um, I think that it's un— and that's interesting. Like two of my best friends are chief product officers, uh, at different companies. And so I talk to them all the time about stuff. And I think, I think being in product is really hard. Like if you think about go-to-market, I don't know how often product hears from go-to-market, great job, we love this product, it's perfect and it's on time and everyone loves it. And like no notes, you know, it's like, Where is this? Too slow. It's too slow, right? It's not— it's the— and I love when people say, oh, it's just not very user-friendly. Like, that's so not actionable for product. What are they supposed to— the UI, the UI. So I try to really practice kind of radical empathy and understand. I like to— I really like to know what kind of pressure they're under. I like to know what they're getting yelled at about because it's like very clear what I'm getting yelled at about. And by the way, a CRO, We are, there's, and there's pros and cons to this. Our work is objectively graded in public by other people, right? We can't really spin it. It is there in black and white and every quarter. And if you're in the board meeting, we're probably doing the most of the talking and hopefully being saying, they're hopefully saying good job, but you know, the last couple years have been hard and it's, it's, there's some difficult conversations there. Product is under a lot of pressure too. It's just not necessarily visible. I don't think. But I also feel like, you know, there's pressures that product is under to like ship things really fast. And so you, you might be super frustrated as CRO that this product is shipped and it doesn't seem to be ready for prime time. And so you're like, this chief product officer is out of his mind. Or, and then it turns out that he or she was forced to do that or really pushed very, very hard to do that. Like it wasn't, they, they would rather not. So I really, I really do try to understand like, what is it that's stressing you out? What is it that's making you, You know, yeah. What, I don't know how else to say it. What are you, what's, who's yelling at you and what are they yelling at you about? I think that really, that really helps. And then, yeah. And then also understanding what their motivations are. Like, what are they trying to, what is it that they're trying to accomplish? Again, it's obvious for us, but it's not necessarily obvious for, for others. The other person I love to dig into deeply with is finance. Like, I love to understand, like, you know, what kind of part, because every, I think everyone thinks that that's it's just spreadsheets and reporting and it's so much more than that. But I don't know, I guess I would summarize with radical empathy as much as you can.

Yeah. Radical empathy, understanding of the motivations and pressures, and then that personal relationship. I also think one of the other big building blocks, and this is top of mind because of the Brené Brown stuff, but it's like boundaries. Like what are your boundaries? What are you cool with? What are you not cool with? And like making the unsaid things said. Because going back to the Enneagram stuff, like me understanding how a 2 and a 9, how they tick, I was like, my God, like I didn't know, I didn't know like that was going on up there. Like, like, I don't know, like I'm just like, I felt like a totally different sense of understanding of like how a different person's brain works.

Works.

I'm like, sort of know that. You're like, yeah, everybody's different. But then you like really unpack, like the, the, um, that hotel room thing is great. The other, a similar one is like somebody's airport routine. Like, what's your, like, like how early? This was a, like an icebreaker. This is an icebreaker question at a dinner I was at. Like, what's your airport routine? How early do you get there? What do you do? And I like heard people explaining their answers. I was like, you're out of your goddamn mind. Like, yeah, that's so crazy. It like, somebody was like, yeah, I go and I check in. I'm like, wait, you don't check in on your phone? It's like, no, I usually just go walk up to the thing. And like, yeah. And I was like, I, that broke my brain more than it really should have. But just like everybody's living in their own skin and mind and reality and, and like until you until you like get under it and make the unsaid things like more explicit, it's hard to understand. Like, you know, I tell people, it's like, I'm going to Slack you late because my kids go down and I crack open the laptop and I'm just going to rip away on stuff. But like, if you don't like getting messages late, pause your notifications. And like, I'll never be like, Alison, like waiting for your, waiting for a response here at like 9 o'clock. Like I won't do it. I need to be like, for me to get my job done, I need to be able to work from 8:30 to 10:30 at weird times because like, I, you know, I, I, whether or not I like it, like 5:15 is happening and that door is like coming bursting open and like my kids are here now. And so, yeah, but, but some, but if you don't explain that, because I had to explain this because people told me that they were stressing them out and I was like, why don't you just turn off your notifications? Like you don't have to answer Slack. Slack is asynchronous. It's an asynchronous platform. Answer when you can answer. But, and then I was like, all right, like I guess I am 2 or 3 levels more senior than this person and they're gonna want to like answer the CEO.

Scary.

Yeah. Yeah. And, and, and so, so like making that thing explicit I think is, is, and, and setting a boundary. is the other thing now I'm like thinking more about as we go through this.

But you also just said something really important, I think, which is the like sharing context. So, the other thing that I do, and I've done this in every, I got this advice when I first got into my first CRO job, is I have a presentation that is like, it kind of explains some of the key elements of my background and my personality that's kind of like, this is why I am this weird, this is why I am this way. Right? I talk about when I join companies, how I'm the oldest, um, and I had a brother who died when I was 6 and he was 4. And I talk about that, that has made me really, I'm very irreverent about life because it's like, I've like, I have this mentality. I, I'm not one of these people that when I see bad things happening, I think, oh, that'll never happen to me. I assume everything is going to happen to me. And so that, that makes me that because like the worst things have happened to me, you know, in terms of. My brother dying and things like that. So I feel it gives people context about what I care about, what's important to me. And then it's kind of fun. When I've done this presentation, other people have then— when they wanted to introduce themselves to me, I've noticed them putting together a few slides about themselves and be like— and I love hearing people's backgrounds. My favorite type of book is a biography. I just think it's fascinating. All of us are driven by— these unique experiences that we have. So as much as you can share context about like why you are who you are and why your values are what they are, like, I think it really helps people understand you.

Yeah. I have the same thing. It's my blueprint, uh, blueprint presentation.

Yeah.

And like one of the things I'm like is, uh, opinionated but open. So like, look, like I'm very opinionated. I like, I love ideas. I like to unpack. And so if you bring me something, I'm gonna like rip questions at you because I'm curious. I'm gonna like, I really want to know and I'm probably gonna push back and have my own opinion. And that's just my style. But you have to know I'm really open-minded and like, I want you to prove me wrong and like bring the data, bring a compelling argument. And that helps like frame somebody's comfort to disagree with me because it's hard, especially in these roles. Like you hire a new director and like all they want to do is impress you. And so you know, like disagreeing with somebody is not always the best way to address them unless you make it in, unless you share that context like you're talking about. Yeah, everybody should have a blueprint. I think that's a great takeaway.

I agree.

All right. I want to dig into like the finance relationship specifically. It is the most important, sometimes fraught. Any particular advice in engaging really well with your your CFO?

Embrace them. Um, and don't, you know, like, don't shy away from them. Bring them along. I often find where I've been successful is often by doing that which feels most unnatural, right? So it's like run towards the discomfort and just like embrace the discomfort. I try to bring finance along with me wherever I go. And, you know, typically, like, it's funny, like this person I was just doing a reference call for a minute ago had a very strong FP&A partner. And I, with his permission, I'm like, I'm gonna invite her to my lead, my leadership team meetings. I just want her there. Like, I just, I don't want there to ever be this perception that I'm trying to hide anything or I'm squirreling away or I'm, you know, doing some conspiracy. So I really do try to embrace finance as much as possible. I try to ask finance's opinion, see them as a partner, um, not as an adversary. And I really, what I strive for is to not have the relationship where I'm asking the CFO for stuff, right? Where it's like we are collaborating, we are trying to have a conversation together about what's the right investment strategy here as business partners. But that can be a difficult leap for, for folks. And that, by the way, is a two-way street because there's lots of different types of CFOs and not every CFO wants to have that relationship. I think some CFOs like to keep CRO at arm's length because You know, they, you know, so I'm kind of like, give me a hug. And they're like, oh, it's just handshake. So it's like, like, so I like the ones that will, that will embrace me back. But I do think, I mean, it's even like with FY26 planning right now with our, with our FP&A/CFO, you know, there's no, she knows every cell in the plan as deeply as I do because we've worked on it together and I've explained it and I've let her ask questions and I'm not defensive. I want her, I want her to be able to defend my plan to the CEO and board if I'm not there.

Mm-hmm.

Like, that's almost my subjective goal is like, the CFO understands what I'm doing so well that they could defend it and present it on my behalf confidently without reservation. That would be great.

Yeah. I, I think financial literacy helps a lot here too. If you want a great CFO relationship, you gotta go learn. The basics of how to run a spreadsheet and the ins and outs of how a software company runs. I'm oftentimes surprised when people reach out and they're like, oh, I want advice. My CFO's like pushing back on X, Y, and Z. And then I'll ask them a few questions. Like, I don't know what the LTV CAC is. Like, what do you mean you don't know the LTV CAC of like this channel? Like how can, like, what do you, On what ground are you presenting this thing? And so CROs definitely need the right amount of P&L acumen to be seen as trustworthy. I think, who said this to me the other day? Oh, well, one of our, we've got a woman who is like our head of writing internally.

Interesting.

And she was like, Trust is a combination between competence and caring, and I'd never heard it framed that way. And the caring is like, does the CFO know that you care about the financial health of the business? Are you just thinking about the sales and your comp plan? So the caring piece is number one, and the, but then the competence I think is oftentimes under discussed. Like, does the CFO see you as competent in a spreadsheet?

Right.

Can you unpack the cells and do the work back and, and provide specific feedback or explain the numbers behind the numbers?

I think I love that expression. I'm gonna write that down. But I also think the other thing that I've done, interestingly, not every CFO that I've worked for has cared about the same thing. So like, you know, at one company it was all about EBITDA. At the, at another company it was all about efficiency growth metrics and sales and marketing as a percent of revenue. And then I went to the next company and I was like, let's talk about sales and marketing as a percent of revenue. CFO didn't even know what it was, didn't care about it. It was all about ARR per employee. I'm like, okay, like, just, you know, so it's like, to your point, it's like, I wanna know what you care about and I'll optimize for that. I think it's also important with finance, like, they don't wanna feel like, you know, I, I, there was a conversation we had earlier this week where I can tell, like, our CFO, she's like, she doesn't wanna feel like she's the cookie jar holder, then she's deciding who gets cookies. It's like, it's like, you know, that's a terrible experience. So it's like, And, but I also feel like she doesn't feel, to your point about caring, that everyone is understanding or caring enough about what she needs to try to do to like manage stewardship.

Yeah. Yeah.

Yeah. And be like, hey, if we hired everyone that everyone's asking for, we'd be out of business in 2, you know, it's ridiculous. Right. So, um, again, looking not, not as, and you also said something really interesting about your comp plan or whatever. Like even for me, I've had to see, I'll, I'll never forget this one experience, right? I had a, I had an issue. I had 3 sales. Leaders, and rather than dictate it, 'cause it impacted us all and them, I'm like, let's solve this together. One came out with, came out with me with a proposal that was clearly optimizing for that person's comp plan.

Mm-hmm.

The other one came at me with a proposal that was kind of neutral. And the other one came at me a proposal that actually hurt her a little bit, but was clearly the right answer for the business. And from that point on, I trusted her so much more because I'm like, oh, I trust you because you are caring about what I care about and you're not just caring about yourself. And it was like a very interesting aha moment about who you will see as a partner and a business partner and then trust based on how they answer your questions and engage with you. It's like super, super interesting. These like micro moments can make a big difference.

Yeah. And, and sort of the point you're nudging at is, is sort of my opinion that we give CROs these 50/50 comp plans and wonder why they're optimizing for the quarter.

Yeah.

You know, if half of your income, Mr. CFO or Mrs. Whatever, are, we're at risk, like, would you make the same decisions that you make today? Like, no, probably not. Cause you stare at that number and it's a lot of money. And so I've, this is like post my Shopify experience where I had zero variable compensation. I've really like pushed to not, not be overleveraged on variable and be tied to the same things as the rest of the executive team is tied to, which is like enterprise. Values.

Yeah.

How, how are we growing this company and, and, and the value of it? All right. I wanna switch to a slightly different topic and I'm gonna come back to this, like these individual relationships, but, um, a lot of people are currently in this place in 2026 planning where there's like a logjam where it's, you know, CMO has like a plan that doesn't match what CRO wants or the CPO's chasing different things than what what, uh, like the CFO wants and there's, there's like just disagreements, like significant disagreements that are really hard to get to. And so how do you think about working through like a logjam, especially in the context of like '26 planning?

So I'm in the middle of it now too, just like everybody else. And I think especially if you're trying to have a big year and do a lot of new things, it's really scary. And so I'm talking a lot around the framework of guardrail— excuse me, guardrails and then conditions for ignition. So it's like, this is the thing I wanna do. Here's the initial investment. Now it's really scary if you talk about annual investments. These can be very big numbers and it's like, it's, you know, especially if it's new, but, and you have to do that. You have to do that, uh, of course for planning, but the way that I'm approaching it right now is just really trying to give confidence that like, here's the, the, the green zone, right? Here's like where if this isn't working, we're comfortable, we're gonna monitor it. If it gets here, it's in the red zone. At a minimum, it requires a pivot and a pause and an adjustment. But at the same token, if it gets over on this side, this is the condition for ignition. We're gonna double down, we're gonna hit the, hit the gas. Because I also think, you know this very well, Have you ever built a plan that's where it's gone exactly according to that plan?

Like 5 days and you're messing with the model.

Yeah. It's like literally we're selling washing machines now, whatever. It's like it never works out. So you, you have to have that slack in the system, but you have to, like, I, but part of it is part of my negotiation style is showing that I'm not going to be a cowboy about this, right? And that I'm gonna govern myself and my team and say, I will pull the plug on this if it gets to, you know, what? And I try to ask for that collaboration with the CEO, CFO, CPO. Like, can we all agree if it's this, we keep going? If it's this, I will stop and we will reevaluate things. But at the same time, what does it look like when we start to double down? That, that's a big part of it too. And then I think, you know, the other thing is to use like Challenger Sale methodology to get into like our practice. I try to, there is an element of like, what are you not gonna get if we don't do this? Right? Like, if we don't do this, what do we give up? What's the trade-off? Because I do think we as CROs don't have that conversation as well as we should. We're talking a lot about, I need this to do this. But you also need to say like, if this is not here, then this can't happen, or this is what's going to be at risk. And I think you know, kind of, I don't wanna say creating fear, I'm not trying to say this, I'm manipulating people, but just to kind of frame it, right? Like there's a reason. Yeah. Prisoning trade-offs. Yeah. There's a reason why we, we're trying to do the stuff we do. I do think sometimes we, we as CROs and sales and marketing can come across as like idea factories, right? And you have to be able to show, right, that you have a method to your madness to a certain extent. To a certain extent.

I think the trade-offs thing is very astute. Like, what do you get by not? And I oftentimes, the advice I give is like, you gotta be detached. You can't be like, I need this, I need this, I can't live without it. Because then everybody, like, people feel resistant, the reactance, it erupts. But if you're like, okay, like, if you don't wanna spend this, then that's okay. Here's how I'll do it and here's the outcome. It's like, oh, well that outcome's not enough revenue. Okay. And then you can problem solve. You can get back to collaboration, which you talk about, but being like less fixed on what you want, I think is a better way to get there because we do come across options. Yeah.

I mean, I do this with my kids all the time. It's like, there's no, there's no fourth option, which is do nothing. Right. It's like, that's what he'd try. It's like, there's like, there's three options and there's And, and maybe they're not all small, medium, and large. There's just different ways of approaching it that have different, different, um, implications. But I think it's very good advice what you're saying to not just be absolute. Like, no one likes to be faced with a negotiation where it's your way or the highway, or like, you know, you feel like you're, you're strong-arming people or you're like blackmailing people or whatever. Like, that's just not. It's not the right way. And by the way, it's not gonna be good for you because see previous comment, it's not gonna go exactly the way you say it's gonna go. It's just not. So you wanna acknowledge that upfront and be like, look, this might not work. Here's what I'm gonna do if it doesn't work. And here's how long we need to see if it's gonna work or not. You know, stuff like that.

Yeah. You, you mentioned previously change management is really like data-driven, like you emphasize driving change with data and being highly data-driven. Like how does that play a part here?

So let's see. I mean, I'll give you an example. Like I right now am working on a plan where for the sales team, we have this code called Contact in Future, CIF, which in, um, You know, they're not, the timing doesn't seem right. And I believe, however, that our sales team needs to get stronger at creating urgency in the sales process. This is something I'm, I'm make, I'm making this up. No one's ever had this problem. So I'm like saying to the team, the challenge is to the team, and this is gonna get into, now I get back into the multiplier, right? The challenge is the team, like, okay, I need to see CIF reduced by 15%. You can decide how you're going to do that, and you should decide how you're going to show me that you're making progress on it. Because until I see it reduced by 15%, it hasn't. And you're gonna tell me, no, it's happening. We're working at it. We're making progress. You need to show me how the progress is being made over time and what those milestones are so that I can, so I can see that. Because you're right. I don't expect it to just dramatically change. Overnight. But you've got to show me the milestones and the evidence to it. So I think like the evidence of the change, you have to have the evidence that the change is occurring outside of just the result of the change having occurred. But I really like to put that towards the team that needs to make the change. They will be far more likely to make the change if they own the plan of how they're going to make the change. And they are the ones that's suggesting like, hey, this is how I want you to to evaluate my success in making these changes. It's really hard. But the other thing is, I'll tell you from a sales perspective, like you can't hide anymore from this stuff with Gong and all these other tools. Like, hey, uh, I can see, I can run a report and I, or Highspot, I can see what content's being used. I can see what words are being said. I, you know, so some of it is, um, the data doesn't need, not need to be delivered to you. You can go serve yourself or your ops team can get it for you.

Yeah. So, so you're talking about this as change management through the team, and then are you also, like, do you have opinions on leveraging data in terms of like the executive decision making? Like, is there, is there an approach that you like there?

Like, what do you mean by that? Like changing like the executive relationships or?

No, you know, like making good decisions or convincing people. So like product is another like area that I think can be really squishy, you know, like sales wants X, product wants to do Y. And sometimes it's because they serve products to serving the user. Sales wants to serve the decision maker and, and like we're just optimizing for different things. But I'm wondering if you've, you've, uh, in sort of being data driven, you've found success. In the past, like driving consensus through the data?

I mean, it's an interesting question because like the, the answer to me is, is like, unfortunately, like not super interesting. It's kind of obvious, but I'll give you an example of something like where the team will come to me, like sales, it's many, many times at many, many companies, sales has come to me and said like, this, the UI, you know, is, is too complex or it's not user-friendly or things like that. That's really not actionable. Right? I will push back and just say, or, you know, we're not enabled. How many times do you get, I don't, we're, the team does not feel enabled. Like, that's why we can't sell this because we're not enabled. And it's like, okay, the, the onus is actually back on you to give me what are the 3 to 5 things that need to happen, deliverables that are measurable and actionable, that if those 3 to 5 things happen, you would thus feel enabled. And I just did this right now. I'm having a situation where I'm getting feedback about some stuff with customer experience and there's a lot of frustration about it. But when I go and talk to folks that work on this, the data that I'm shown is you might have some squeaky wheels, but on the, you know, the 80, the 80/20, the 20 is the 20, there's issues with the 20, but the 80 is fine. I, I kind of do put the onus back on the, on the, the complainer, if you will. Like you have to prove this, right? Don't bring your feelings to a, to a data fight. So, I don't know if that's a very good answer, Kyle, but it is just like you have to prove your thesis. The onus is on you. And I, I also think when you give feedback or you're asking for something, you have to be prepared to defend it and you have to be able to say with clear articulation what it is that you want. I don't feel enabled. It's pretty hard for me to react to that.

Yeah, I like that. Okay, I wanna move to our quickfire so I can get you outta here on time. What do you think separates a good CRO from a truly great one?

What separates a good CRO from a great one? I think a great CRO really cares about the customer.

Mm-hmm.

And a good CRO really only cares about sales efficiency. Um, and that's a really Pollyanna answer, but A great CRO cares just as much about CSAT as they do about your win rate, you know?

Yeah. It's, it's actually similar to an answer I give. The great ones can think holistically about enterprise value and, and because you see it all the time, this is probably like one of the biggest self-owns you see in sales is you just like care about only your one thing, your own number and comp plan and everything falls apart if that's the case.

Totally.

What's, what's the most common advice you give to like new VPs of sales or first-time CROs? They were, you know, uh, an awesome lieutenant somewhere else, but now it's their own mantle.

My best advice here comes from Sherry Redstone, of all people. I was at this talk. Oh, I know, right? I was at this, you know, the information, the, the, the publication information. They have this thing called WTF, like Women in Tech, Finance, and Media. I was at this thing and she spoke and She talked about the value, tremendous value of horizontal growth versus vertical growth and how, like, if you're ambitious and you wanna grow, she's like, too many people are really focused on climbing up, but really the great people, the people that grow the most really focus on going wide. And so I think we, as you grow vertically, you have to be very cognizant of growing horizontally as well, because the higher up you get, the more valuable and important it is for you to have a broader perspective on, on the business and not just your thing. This is what you and I have said a couple times today. Like, if you only care about your thing, you start to lose credibility.

Mm-hmm. I, I like that framing. One of my favorite books is Range by David Epstein, where he talks about the value of having skills and knowledge from many domains and putting them together. And so I, I think that's really good. What's the hardest lesson you've had to learn in your career?

That not everyone is gonna like you and not everyone's gonna to believe what you believe. And, and that's fine. Um, that's just part of this. And then, you know, like, and a lot of times it's really painful because it's like one of the worst feelings ever is when, you know, people are frustrated with you or they don't like you or whatever. And it's like, because they don't know something that you can't tell them, you know, stuff like that really sucks. And, um, and that's just, that's just part of it. Um, I, I would also say the hardest lesson I've had to learn, this is where I, this is the part of the podcast where I compare myself to Beyoncé. So bear with me.

Love this. We're clipping this one.

I got this feedback once that like about the value of developing a persona and, you know, and this is when I first got more senior and I was just getting into some tough conversations and it was like, you know, just the feedback gets harder and harder the more senior you get. No one really says great job anymore after a certain point. And it was just hard. And, um, hard not to take it personally. And I read this thing about Beyoncé. Someone was like, Beyoncé, you always say you're so shy, but then you're on stage and you're Beyoncé. And she's like, that's not Beyoncé. That is Sasha Fierce, she said. And she's like, it's a totally— it's like when she reads things about herself, she's not reading about herself. She's reading about this other persona. And that has been a very impactful tool that I've used. And people have given me dolls that— because I say this to everyone. My friend Wanda gave me this little bobblehead that says Sasha Fierce on it, because I think it does resonate with people, but it's like develop a persona that's the professional version of you that is not, that's not you. That helps you be a little bit tougher, I think.

So Todd Herman is the guy who wrote the book called The Alter Ego Effect. And he, he built the Black Mamba alter ego with Kobe and the whole, that whole program. So he's coming on the podcast in a couple of weeks. And so I just read his book because he's coming on. And it's this exact thing. He talks about Sasha Fierce and Beyoncé in the—

that's so funny—

in the book. I don't know if he worked with her directly, but he's worked with like all these crazy guys like Roger Federer, Ronaldo, and like, it's the amazing who's who. And it's all about trying to give yourself, like, picking an alter ego and who you need to be and being able to, to cross the plane and put that person, put that persona on and The totems and, and it's a very real thing. And, and yeah, it's certainly something that like I'm thinking a bunch about now. Like, I would know what, what alter ego do I wanna bring to bear in the play in, in the right places. So do you have, have you given yourself an alter ego? Have you named it yet?

Oh, it's just Sasha Fierce. I just copy Beyoncé. So, because I feel like I'm in the same arena as her. So my car is named Sasha Fierce. Like I've really embraced the the ethos about it.

I love it. You'll, you'll, you'll enjoy this book then.

I will.

Um, all right. Last question. What's the best thing you've read in the last 12 months?

Oh, I saw that question. I mean, I don't know that I have anything businessy that's like the best thing that I've read in the last 12 months. All right.

No, no, it's about, it's anything.

It's anything. Okay. So I'm reading this book right now called Bad City. That's all of, it's like a written by a journalist about this crazy story with the LA Times and USC and corruption and. It's like, it's super, super, super fascinating to me. So I highly recommend, highly recommend that book. I also love— you're new to the Bay Area. Another book I read recently is called Season of the Witch, and it's about the history of San Francisco. And, um, it's so interesting because you can read about what would ha— what happened in, in the Bay Area in San Francisco in the 1960s and be forgiven for not thinking it is today. It's like boom, bust, drugs, recovery, boom, bust, drugs, recovery. It's like, it's wild. And there was stuff I learned about San Francisco. Like, did you know that San Francisco in the '50s was like a super conservative Catholic city? Like you just, it's like, you would never think that, like, it's, it's, I totally, I cannot recommend it enough.

Okay. I'm going to read this book. I love stuff like this. And just like learning, my wife teases me. She's like, you love tidbits, like little fun facts and tidbits.

Cliff Clavin. You like to be kind of the Cliff Clavin, like useless fact. Fun facts guy. Oh, he's got something to say. That's great. You'll learn a lot of that, um, from that book.

And yeah, she'll think I'm insufferable for having all sorts of San Francisco fun facts that I'll, yeah, be pulling out, uh, here and there.

I love it.

Well, uh, this was awesome. I, I was excited to see your intake and some of these topics cuz this has been bubbling for me, like wanting to, to get into this, uh, arena and talking about executive relationship management. It's something that I, you know, like there's not a lot of conversation about, but is one of the single most important things that I think we can do to, to be great at our jobs. So appreciate you going in and the vulnerability. And this was, this was for me.

Totally awesome. Thank you.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link 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.