E23: A Guide to High Stakes Decisions with Ashley Grech, CRO of Xero

Today's guest is Ashley Grek, CRO at Xero. Ashley spent over a decade at JPMorgan before moving to Square, where she was the head of sales strategy and growth and then global head of sales for close to 4 years. And she grew sales contributed revenue by 10x in her run there. And a fun fact from me, Ashley gave a SaaStr talk 3 years ago that has become an important input to how I personally think about messaging and positioning. And I shamelessly stole this jobs to be done framework in terms of how I now talk about positioning. And it's actually a talk that I send quite frequently to founders and revenue leaders, like, 3 years later. So I've been following you since then, and I'm really excited for this conversation, Ashley.

Oh, thank you. I remember that talk, and I was embarrassed that it's not more complicated than just, like, what are the jobs to be done that your customers care about? So I'm touched that I, that made my day.

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. This episode of the Revenue Leadership Podcast is brought to you by Shore People. Shore People helps teams communicate smarter with science-backed personality insights that make every interaction more effective by By understanding how people work best, teams can collaborate better, make faster decisions, and drive real results. Get free access to SurePeople's Prism self-assessment at surepeople.com. That's surepeople.com. Now back to the show. Yeah, yeah, it was good. I remember it. So it's funny because I remember where I was walking as I was listening to it. And I have like an elaborate bookmarking scheme and like I put them into this playlist, the Spotify playlist of all the, of all the podcasts episodes I like, and positioning, something that I really find fascinating. So that was a good one. And especially people thinking about going upmarket, I'll link it in the show notes, but it's a solid one.

Love that.

So from my other research and listening, relistening to some of your podcasts, you can very quickly tell that you're a problem-solving machine. And what I really liked is that you can clearly tell that you're a first principles thinker. You're not reasoning by analogy. You're really solving problems from root cause. And you've gone through some interesting growth phases, both at Square and certainly at Xero. And so I want to unpack how you think about problem solving and solutioning and really help give people a framework to do this really well, because I think you're an awesome person to, to share some insight there. And so we'll get into decision-making frameworks and really unpack how you think about problem solving and then talk through some specific challenges, some like big, gnarly complex problems like going multichannel, multimarket, multiproduct to make things a little bit more concrete, which should be a lot of fun. So first question, why the heck do you like solving problems so much?

Oh, I love solving problems. Look, I know this describes all exec roles, to be honest, but I often think of it as like I solve problems for money. Like, I solve problems for a living. I know we all solve problems for a living, but I happen to also enjoy it. So, I often also joke, although it's totally true, that I don't get paid to say no. I get paid to say how to do something. And one time that came up with my kids, my oldest son asked me, he was trying to suss out like, 'Why me? Like, are there other people in the world that can do what I do?' I was like, 'There are lots of people that can do what I do.' And he's like, 'Well, then why you?' Like, 'Well, because I actually really enjoy solving problems, and I don't mind a bit of a mess.' So that's a different— that's a story for a different day. But I really enjoy the, like, process of coming to conclusions as much as I enjoy the successes of them. So I solve problems for a living and I get paid to say how. There you go.

I like that. I'm also going to shamelessly borrow, I get paid to say how. I love that as a heuristic. So I figured we could split the conversation on decision-making and problem-solving into sort of 3 pieces. Problem or opportunity identification, number 1, prioritization, number 2, and then solutioning. Like, once you understand the problem and the prioritization, how do you really define what the best course of action is. But first off, is that the right framework? Are there things I'm missing there? Would you change the order of operations, or how do you think about this sort of mental model more broadly?

No, I think that makes sense. Let's, let's jam.

Okay, cool. So let's talk about opportunity identification. So just we'll start generally. How do you come up with what you want to solve now? Versus later? How do you think about sourcing that information on what to go solve?

Well, I want to take a step back for a second, just talk about like why problem solving at all? Like why do I focus on it so much? And it's probably because you and I are nerding out about it. We talked about problem solving is a superpower, and I do think it's a bit of an unappreciated discipline, particularly in revenue. In that regulators have good instincts, but that is not quite enough. So, I think there's 3 things that keep me going when even on days where I'm like, this problem sucks, like, I really, I don't, this is not, this is not a fun one. On days that I feel that way, I remind myself first and foremost that, you know, it is impossible to have seen it all. And you simply can't rely on your firsthand experience forever. Like, that would have mean that we have seen everything and that we've seen every problem before, right? And so, I see it as like how to build confidence in scenarios when you just haven't seen it before. And I think we have to recognize that like you can't always hire a leader that's seen everything. You can't expect yourself to have seen everything either. The second is, you and I have talked about this before, I think it's kind of, it's unwise to run the same playbook. Even if the symptoms look similar from company to company, it's really easy, actually. It may look like you have the same problem, but until you get to the root of the issue, you can't be sure. And then if you run that playbook without the certainty of the root cause, you might not get the reaction or response you need. So that's a dangerous sort of assumption to go in on. And the third is if you can model it, like if you can demonstrate it, then you can teach it. And that is the key to not capping your own career or even what's possible for your team based on like what you know, right? You're basically allowing yourself to scale because you can teach it to others. And so giving others the framework that they need, like that's really, that uncapping is a superpower in and of itself. So that's important to me.

I love that. We're going to come back to how to teach others. That's an awesome one.

That sounds good. We talked about diagnostics. I've had the pleasure of, you know, joining a few different shops. And once you get there, you have the luxury of like a fresh set of eyes. And it's easy to sort of get thrown in and be like, okay, to be told, like, these are the things you should be focusing on at this time. But if you have the ability and time to do so, even if it's several months later, like, I really do recommend diving deep into the driver tree. And that's the diagnostic tool. Like, the driver tree is the artifact, the sales methodology that we talk about that gets the driver trees, like the 5 whys, right? Everyone knows like when you teach your rep to ask like why, and then why, and why again. It's the same thing with a driver tree, but a driver tree can often be like, it's the financial model. So it's like, why is this happening? Then why is this happening again? And so if you structure problem solving in both like a bottoms-up and a tops-down manner, not only does it make it easier to diagnose what's wrong, but you can also size where to fix it. So what do I mean by that, right? Think of it as building like a revenue waterfall. And you go, I'll give you an example. Example is the mid-market team is underperforming. And you're like, maybe the sales team says that there isn't product-market fit, customers aren't responding. Or the CEO concludes that this isn't the right And you're like, okay, it could be either one of those things. Like both of them could be true. But if you structure it such that you're working backwards and eventually you document it so that you can then, you know, bottoms up, tops down, that's a great diagnostic tool. It's also then the structure through which it's the same lens through which you could look at So, let's work backwards, right? Revenue is driven by quantity, quality, and velocity, right? That's, that's a, that's your most basic driver tree. So, you start documenting what's the time to value? What are the win rates by deal stages? What's the deal volume itself, both in totality and deals per rep? Like, what's the revenue size per deal? And then the deal source, inbound versus outbound, AE outbound versus BDR. So now you have a tree of inbound KPIs and outbound KPIs, and you can start to identify where it's weak. All right. And you'll start—

And then you're moving down the branches of, so you've got your velocity branch and you're asking why, why, why? Yes. Oh, interesting.

So then you start to see, you may see, for example, from this, from the driver tree that inbound deals are too small to hit targets on a per rep basis. I've seen that before. They're like, look, there's, it looks like on a number of deals basis, your team should be hitting their goals, but like the deals are too small and those are inbound. So that leads you to marketing, like that leads you to your solution. It's, it's pretty simplistic in that way. Or outbound leads aren't getting past discovery. And so, well, that leads you to listening to calls. Is it a value prop issue? Is it a skill or a targeting issue? Or you see that deal progression is high, but we still lose 20% of deals in implementation. So, that's like a, like, is there something about the product or the rep skill or the process through which we onboard customers? Like, all of these have a different solution. I recognize fully in talking about like a detailed driver tree, which in, in like finance terms is just like a regular waterfall, right? But I recognize that that is, you don't always have the time to build that, but that's a great way of like, it's a gift to the future in that once you have it set up that way, you can start to diagnose lots of problems in the same way.

It's really similar to the framework I teach my team that I pulled from Teresa Torres in the product world, which is the opportunity solution tree. And I looked up Driver Tree as you were talking, and it's just like a different— it's Opportunity Solution Tree is vertical and Driver Tree looks horizontal, but it's mapping to a similar thing. Like, what's that desired outcome? What are the key inputs? And then underneath, like, how many— what are the root causes? And then of the root causes, what are the potential solutions to each root cause? And then you end up with a map of things you can go tackle, which if you're doing it on paper, it's helpful, or even if it's just a mental heuristic, I've always found it clarifying for me to really think like, okay, and what else, and what else, and what else?

Yes. I like the driver tree because it often model— it like maps to the customer journey. Like there's an element visually and sort of logically as you follow it that starts at the beginning of a customer interaction with your company, and then goes all the way down to their, to the life cycle. And so, you're basically getting to, like, diagnose a life cycle and parts of it along the way. So, it's the same principle, and I actually really appreciate that there's, like, very clear sister problem sets, like, in coming from product.

Yeah, interesting. Is there one place where you direct people to learn about the driver tree? Like, when you're teaching your team about it, is there an external resource that we could link?

You know, there isn't. That partnership starts with your finance partners, honestly. It's like, and if you think about it, like, how could you do great annual planning unless you have a bottoms-up model? That's essentially what we're talking about, where you look at like deal volume, deal size, progression by deal stage, like win rates by deal stage, and then by rep. Inbound versus outbound, like that is how you have a really detailed and thoughtful annual plan. And so it starts with your finance partner. And I've been lucky enough to have a few really great rounds there where we've either had to build it or you've perfected over time.

Cool. And, and so how often do you visit this stage-by-stage analysis and sort of re-examine things from first principles? Like, is that a quarterly? Is that annually? Like, what's the cadence by which you're manufacturing opportunities?

That's a great question. I think in the early stages, you're like, you're trying to do full diagnostic. And so, probably at the very least, you're looking at it annually because then you're looking at opportunities every year of like, what do you need to improve each year? I'm chuckling because like right now I'm in it. Like I'm looking at everything. And so I'm like, is there a cadence? I just look at it all the time, every day. But I think in a steadier state and, you know, in the later outer years of Square, we're looking at it sort of quarterly and annually just so we can continue to diagnose. And you look at it quarterly because you're always standing up with experiments along the way. And so you're like, well, how is that performing? And like, how do you look at the like check engine dashboard, so to speak? And making sure you're diagnosing what's going well and what isn't along the way. But the short answer to your question of like, how often do you look at drivers is, is anything wrong? If anything is wrong, like if anything feels off, like revenue is slow, like any part of the check engine light lights up, like that's where you look at it again. And I think, Obviously the likes of Clary and other like revenue intelligence companies have really caught on to the fact that it is a bit of like an engine. It's a, it's a, like an airline cockpit, so to speak. And you're always checking all parts of it. And when you have visibility into it, then you can just make more intelligent decisions. So that gives me immense comfort. Now, I mean, you and I talked a little bit about the fact that like you can't always have all the information all the time.

Yeah. So you just have to be comfortable with that, but yeah, I mean, more and more these businesses are manufacturing lines, inputs go in the top and it's, it's opportunity or just like raw marketing spend. And then there's a series of stages, conversion rates along the way, and then you're consistently optimizing that, that manufacturing line and having the data to do it is, I think much of the time, like a challenge for many organizations. And, and so how do you make that programmatic? Is it, is it part of your QBR process and you've got your, uh, Biz Ops and Finance teams doing like a set analysis?

Or how do you keep this cadence on, on, uh, on calendar, on diagnostic, uh, diagnosing?

Yeah. And just like revisiting, is it, is it an alert system? Is this like a weekly summary that you're seeing and then that's going to tell you when you need to dive deeper? Like, what's the cadence of it?

That's a good question. Look, the, like, level 1 metrics, the metrics that matter the most to the company, those are often, like, the absolute outputs, the end of the line, so to speak. And those we look at monthly, right? Or quarterly, depending on your company size and the stability and velocity. And then the level 2 and 3, like those are the drivers and you can package them. Like I think you can probably imagine like what's the level 2. Level 2 is production by channel and then level 3 is activity levels by rep and like deal size by rep. And so you look at those in packages and they have different audiences. So for me as a CRO, like I will see all 3 of those. I'll see what we share with the full company and with my CEO on a monthly basis, but then I'll also look, drill all the way down. And like the sales leaders and sales manager accountability meetings, they're going at level 3. And then the regional leaders, regional sales leaders, they're operating like level 2, or if there's something wrong, then level 3.

Got it.

All right. And so everyone has a regular cadence, but everyone, we have different altitudes.

Makes sense. And is there anything that you're doing to get to true root cause? I find something I see is people either reason by analogy or they look at something and they make their first assumption on what's causing it. Oh, it's just we got to do more calls. But is there anything that you've been able to do to get to a first principles understanding of a problem?

I think it's never going to be perfect. So two things. One sort of quick anecdote is you said it's like a manufacturing line. It very much is. When I was CEO at Square, had encouraged me to study other industries when thinking about revenue. And I am forever appreciative of the fact that they encouraged me to to study manufacturing and like how to find the areas of most value, where the blockers are, and then prioritizing the blockers based on value or the size of the blockage, for example. And so, that's just one tidbit. You said manufacturing, I was like, huh, that's been very much a part of my Square journey. The CEO, this is not a new concept, but I really appreciated that the CIO for today at Xero, she has said, she has shared with us this thought of like gut, data, gut, right? Like you'll start with an inkling, and a lot of leaders might stop at the inkling because they have really good instincts. But like those, an inkling, for example, is like you'll start seeing things come up in There'll be signs and they're mostly qualitative, right? Topics come up in conversations with customers, a phenomenon is popping up in the market, or you're seeing a competitor be more successful or show up more frequently in your deals. But all of this tells you that you should look into it. And even in my case currently, there were things that I was hearing from teams and then interestingly, it popped up in an analyst call. And so like the same phenomenon came up in an analyst call and you're like, oh, now I should really look at this. Like this is not, this is more than just a coincidence. And so that's the gut element. Then you go deep on the data, then you get to go into the drivers and trends, and then you can use your best judgment to make a decision on what to do about it or to size it, for example. Like then you can prioritize it. But the The second order, which is the data portion, that'll tell you whether or not it's a permanent hearing, right? Or if this is something you should be really worried about. And then the third is you probably can get to about 70 or 80% of the answer. And there's probably not a perfect answer. So it's like, what's the best one? And that maybe goes to the third topic that you were talking about where you like how do you structure a solution? But yeah, that's like the third part is use your best judgment again and just determine what direction you want to take.

That makes a ton of sense. I love all of the Jeff Bezos stuff on the topic because he's, you know, thought so deeply about decision-making. Something I sent to my team today was, uh, was specifically on this topic. He said people think of Amazon as a very data— as very data-oriented. And I always tell them, look, if you can make the decision with data, make the decision with data. But a lot of the most important decisions simply cannot be made with data. And I think that's very much this, like, gut-data-gut, you know. You're, you're gonna have, uh, a certain fidelity of information to make a call, but at the end of the day You know, you're getting paid the big bucks to be able to synthesize and see patterns and use your intuition a lot of the time.

I forgot where I read it and it's a bit of an imperfect quote, but it was something like, you know, be data informed, not necessarily data driven. Like if you wait for all the information, I think you had said this, like the, so Jeff Bezos quote, like if you wait for 90%, it's probably too late. You're probably too slow. And I will admit, like, any regrets I've had have been waiting for too much information or not wanting to disrupt something for, like, or test from an experimentation purpose.

Yeah. Yeah. 100%. And so, are you doing anything? This is something I think a lot about, like, how do you think about tapping the wisdom of the crowd and sourcing information from sellers and frontline and managers? Sometimes I feel like like that is very ad hoc and I wish it could be more programmatic. Have you been able to do anything there to try to surface that stuff up to your level?

That's a really hard one because it's easy to chase a trend. And like if you chase anecdotes, for example, it can become a bit of a, becomes a bit of a self-fulfilling prophecy or a red herring. One qualitative way that I like to do this, and I know it's possible with a bunch of different platforms now, like Gong and And Clary, and many of them will do this, or they can, you can perform analytics on the total body of calls. You can talk about how, you know, you can pull how frequently certain words are mentioned, certain products are mentioned. You can start seeing, you know, when your rep talks about a specific product. This particularly helps when you're trying to go multi-product, like when we bring up this secondary product, does it improve or decline your win rate? Decrease your win rates. And like, that's really interesting because you're like, all right, these feel like natural, like these two products feel like really natural bedfellows. And then all of a sudden you're like, it's not, like something's not working. That is the greatest gift I think you could give your product team too, like both product and product marketing to say, we talked about this in 50% of our calls. And it is, you know, it's only increasing our win rates by X or it's only attaching at Y. You can, if you're lucky enough, you can do the same with your customer support calls. Right? So when I was at Recharge, it would be in the CRO role. I ran revenue, legal, enough sales, customer success, marketing. And when I was looking at support, we're looking at support tickets, you could really dive deeper into like, what are the most voluminous ticket types? And then determining like stack ranking from there. Like, is this a product problem? Or is this a, like, is it a UI issue? Is it a, like, is there a bug, for example?

Expectation setting, support capability. Absolutely.

And being able to pull that at scale from voice recording or from the ticket logs and like scraping it out of macros, all of that is possible today. And then at Recharge, we prioritized it by saying, what are the problems that are like hurting our customers? Meaning hurting revenue or annoying our customers? And then what are the problems that are simply annoying our teams? And if it hit both of them, we did those first. We went to solve those first because it was like your employee satisfaction and your customer satisfaction were impacted. So we fixed those first.

Makes sense. Yeah, we're trying to do a bunch of that with Momentum right now. I found the promise of call intelligence to be greater than the reality. Certainly, that was like my experience with Gong. And, but we're trying to now consolidate a bunch of stuff and aggregate data in a different way so that we can start to surface some of these trends because some of these data silos don't touch each other. Churn data and ticket data, support ticket data doesn't really overlap. With call intelligence data. So are you either cramming that all into Salesforce? Is it going all into Snowflake? And then how do you make sense of it?

Are you doing it yourself? Like, is your team doing it themselves?

Some of it we're doing ourselves. Some of it we're working with Momentum to try to figure out how we can pull that data at scale in terms of trends and impact. I think ultimately, Because it needs to marry with product data. Like, if you really— in SMB, because we, we are, we contract month to month, closing a deal is like important, but equally as important is like the quality of the setup, the, the customer, the product experience for that customer in the first 90 days. And so trying to bring together all of these different signals from, okay, like, was this the incorrect expectations which led to support tickets? Or is it a piece of product friction that's known? Is that roadmap? And trying to untangle it is a Herculean task, but we're endeavoring to do it.

But it is the, like, that's the Holy Grail, right? Because that information, like when you marry up through the customer interaction information with the product usage information, like all of that then, like that is useful for product. It's useful for go-to-market. It's useful for support. And honestly, that's a big— it's a deciding factor when I'm speaking to vendors on whether or not you can fully export the data. So like the official marketing playbook for 2025 starts at CMO Summit on April 17th. Join 150 of the world's top marketing executives in Atlanta for a one-day a 2-day event designed to redefine marketing's role in business growth. In a world of shrinking budgets, the CMOs who lead with strategy and innovation are the ones driving real results. This summit is where you'll gain the tools, insights, and connections to do just that. Hear from industry pioneers, engage in hands-on workshops, and surround yourself with marketing trailblazers who aren't just your peers. They're the minds who will inspire your next breakthrough. Visit joinpavilion.com/cmosummit to secure your spot today. Yeah, I—

oh man, this is like my number one biggest gripe. And the fact that Gong doesn't really write back to custom Salesforce fields, like I want specific things pulled out of calls because there's so much great unstructured data. That's why we are using Momentum because it can run across every single call. I can write custom prompts. Have that mapped to a specific custom field in Salesforce, and I can just yank out now structured data from unstructured call transcripts and give it some sort of shape in Salesforce. Now I have to get it into Snowflake because product data is going to be there and we have to figure out what to do with it. But we're slowly moving to this single source of truth where I will be able to just slap a language model on top of it. Because it has everything to pull from and get the answers that I want.

I love that. You, you talked about two things that are like very much on my mind right now. One of them is this annoying, like rewrite Salesforce and custom fields. And you can't fault Gong. I don't think anyone does it particularly well right now. And then the other element is being able to analyze the totality of the customer's interaction. That is That is going to be a game changer. All right. I'm going to follow up with you.

So it's like, all right, we are mid-flight on a bunch of this because we moved the support team out of their old tool. I think it was Intercom into Service Cloud so that all of the tickets are now in Salesforce so that it's, it's, you know, you could do the integration. It's just better to have them working natively in Salesforce. And now we're piping product data into a bunch of objects that we know are like really high fidelity on their, on their product experience to try to get a little bit more from. And then we're building it all in Metabase. So we're, we're a couple of months away, but we can talk more about that. Like, okay, so we've talked, we've gotten into how to find good problems. Now let's talk about prioritization. And, you know, a friend of mine, Dan Ross, always says this. Is like great companies always have more good ideas than they have bandwidth. And we were at Shopify together and for sure more great ideas than bandwidth. And so how do you think about what do you raise to the top of that prioritization stack and how do you get people rallied around the right things?

I mentioned before the very simplistic way that I was looking at sort of product problems and, and like customer support. So, in its most simplistic form, that was like, does it hurt the customer, hurt our revenue, and then does it hurt our employees? And if it does both, that would pop to the top of the list. That is a very simplistic view. I would say I, I think about 4 primary, 4 primary like conditions when I think about priority. Execution. None of these will be a surprise, but I try to make sure that we're adhering to all 4 of them. The easier ones are like resource constraints, right? Prioritizing issues that could be tackled effectively with the current team and budget. Like, that is, that's a thing. Like, let's just be honest. Like, it's not a bottomless pit of money. And also, frankly, sometimes you don't have the right team to tackle that problem. Time, right? That's real. The second is like, is it a blocker? I know that sounds sort of like obvious, but like, does one thing unlock many other things? And so, there, it might be a small thing, for example, like by size, but it does unlock or unleash other teams in a opportunity to be faster, more effective. So I do think of that as like there's a bit of a linchpin question there. Are any of these problems a linchpin problem? So relatively small fix but high impact. The third is a continuation of that. It's like impact versus effort, like focusing on problems with the biggest potential revenue impact or size within a reasonable effort level. And we do that a lot at Xero. We're like, what's the size of it? Like, should this rise to our like top 3 for fiscal year '25 or '26? And it has to be bigger than, like everything else is gonna be, have to be a side hustle. And so, like what's the biggest impact that makes the biggest difference for as many teams as possible in the company? Oh, and then what else?

Is it like a written process you go through? Are you scoping business impact to a dollar value or is it more of like a conversation model?

Yeah. We actually try to scope it to a dollar value.

Hmm, interesting.

Now, I mean, these are, lucky for us, like they're revenue problems.

Yeah.

Right? Like a product leader. These are quantified. Yeah, easily quantified. A product leader might have a a much more challenging time. And like the chief product officer and I, we talk about this a lot. We're like, how do we think about this other problem here where it's like, and we, that, you know, we talk about a feature and whether or not certain features should be built. Then we go back to the, the like customer support and the sales calls to see if we could build quantitative support for, like for her to make a business case on like which features should be prioritized and all that. Or not. But lucky for me, most of them are qualified.

Yeah. And then where do you think people go wrong in terms of prioritization? What are the biggest sort of failure modes there?

That's a great question. It sounds kind of obvious, but I think noise matters, and sometimes you can get thrown off by noise. So, like, something that customers are noisy about can sound like the biggest problem, but you're like, okay, I know this sounds really terrible. I don't mean it in this way, but it's like, there's a bit of, you know, noise about a specific feature type. On our stickiest product and like we don't see an impact on churn. And yet there is a blocker on, you know, in our onboarding flow and it's preventing us from bringing on new clients. And so as I think about like, you know, it's easy to get caught up in like the customers are telling us that this, this one feature is too slow or whatever, but it's our absolute stickiest product and they're, it's not changing behavior. That is customer noise or even employee noise. It's easy to let that lead. That's not always wrong. I think this sounds really bad when I say it like that. It's not the wrong instinct, but it might not be the first order of business, if you will.

It can easily bring you down the right, the wrong path. Kevin Dorsey likes to say, he's like, is it volume or volume? Is it just loud or is there a legitimate high volume of this thing happening that needs to be addressed? And yeah, the loud customer can definitely drown out the roadmap, especially in enterprise. I found this more selling and servicing an enterprise than I do in SMB. But like one really loud squeaky wheel that's always threatening to churn can take you off course pretty pretty readily.

Yes, absolutely.

Absolutely. And so how do you think about balancing like urgent versus important? I think one of the challenges that many folks have is just getting sucked into the stuff that is low-hanging fruit, easy to tackle, like, well, we'll give you the quick win versus like big strategic things. And how do you think about balancing those two?

Honestly, I go back to the 4 things that I talked about before. The 4th one that I sort of failed to finish off on was, does it align with our company's priorities? So we talked about resource constraints, blockers, like is there a linchpin and one that unlocks all others? A 3rd is sort of financial impact versus effort. Fourth is like, does it align with the company's goals? Because there's plenty of things that are important to me as a revenue leader that like are not the chief product officer's, that like wouldn't rise to her top 5 or 10. I don't need mine to be her top 3, that would be great, but like, is it close? And so, I think that's where you get into like this, you know, the mess of either too many things or not the right things. It's a tough one though. It's like urgent versus important. We're always trying to balance that, but trying to figure out like what is the greatest value? Does it align with, you know, does it align with our company's objectives for this year? And there will always be things that fall to cut.

Yeah. This is something that I personally struggle with and I think my team struggles with is because I love ideas and good ideas. And so it's really easy to see. It's like, oh, we should do this thing. That's great. This person can work on it. And then I step back and I look at all of the things that people are doing and it's like, oh, we got too much. Like, I tell myself this all the time, just like, focus, focus, focus. And yet we are unfocused. We're taking on too many things. I'm in this mode right now. I think it's a beginning of year thing where you want to take on the world after planning season.

But— Matthew?

I'm trying to think. Yeah.

I wonder if I'll ever outgrow that. Like, I always want to do all the things. I always want to do all the things. And so, sure, I'm trying to teach others to prioritize. But frankly, I'm also trying to teach myself to prioritize. It's hard.

Yeah.

I'm always good. And I just— then I just remind myself that it's OK. I'll just never be done. Like, we'll just paint the Golden Gate Bridge from end to end forever and ever. Well, just, that will just be something I tackle next year. Like this thing that I wanna work on now that I know is not the number one thing. A great example of it is we left a customer summit and we have one per, one big customer summit per region per year. And so we left the sort of North America customer summit and I said to my boss, I was like, it literally came up in every single customer meeting. And I was like, I really want I was like, okay, we have to build a playbook to create predictability, repeatability, and scalability for this one process for enterprise customers. And she's like, I know you heard it like 6 times a day for the past 3 days, but like, is that your number one right now? No, it's not. Like, it just isn't. Like, I know it. But so, I appreciate getting to work with people that will call me out on it. Call out my enthusiasm as a superpower, but sometimes needs to be kept in check.

Yeah. It's funny, like all things, your greatest strengths, your greatest weaknesses.

100%. It's always two sides of the same coin. Always.

Yeah. And I think to get into roles like ours, you need just like a hyperactive sense of problem identification. Like my ability to see a thing is probably just greater than many, and I can't stop thinking about them. And it's what gets in my way, and it's what I think causes so many folks in these roles, like, angst and this feeling of, like, it's never done. You're never caught up. You're never there. But then I guess that comes with the territory.

Yeah.

Okay, so let's jump into solutioning. So you've identified a basket of things to tackle. You've got a rough idea of prioritization. So how do you think about getting to the right solution? And I'll give you a quote just to, like, cue this up. So I was listening to a podcast with an old colleague of mine, Farhan Thouar, who's the head of engineering at Shopify now, and it was on Lenny's podcast, and he said there are probably 10,000 right options for any problem, but, and everybody stops at the first right one. He's like, but you have to figure out of all of the right options, which is truly the best one. And that just resonated so much. So maybe I'll start with, what's your reaction to that first? And how do you think about avoiding stopping at the first right answer?

I, sometimes there is a right answer. Mm-hmm. Um, and I don't wanna be like all gray about it, but I'm just not a black and white thinker. Like, I just don't believe that for most problems, I just don't believe there's one right answer.

Yeah.

Sometimes there is, that, that's true. Like, but most of the time there's lots of ways to do things. Lots of ways to do it. And I think it's really lazy. That really irks me when people are like, this is the only way. I'm like, but you're not solving for this other thing. And so what I challenged myself to do actually, like before I, because I cannot help myself, I desperately want to solve a problem. Like I get so much satisfaction out of it. There's like anxiety that just dissipates when I like think I've found a solution. It's annoying to my family to no end. So, like, I recognize this about myself. So, even for me privately, like, before I enter a call, for example, I'll write down, like, what do I want the solution to actually solve for? And most of the time, it has to solve for a few things. And so, that's my principle of thinking around it. Like, this solution must solve for, like, let's just say a a custom, an ask that an enterprise customer is making of the business, and you're like, "This is one of our biggest customers. We have to do it. We just have to because they asked us to." And you're like, "Okay." You push back with the team. You're like, "Okay. What are the principles upon which we should judge this feature so that we never have to make the same decision really again?" And so, the principles, the solution is, Whatever the solution is, it must adhere to— let's just, let's try this on for size. Like, it has to be work that is applicable to other customers in some form or another, right? So, never just one thing for one customer and not replicable for others. So, it has to be replicable and relevant for other customers somewhere along the line. It has to rise above the level of a certain revenue impact. Let's just say, I'm just trying this one on for size. It cannot, you know, disrupt what your existing team, like, resourcing model, or at least not, like, you could set a threshold for that as well. And therein lies, like, there are going to be lots of options, but then you can score the solutions. Like, does this solution solve for? These 3 things. We did this recently at Xero, we were looking at comp plans, because I know, I can see in your face right now, every leader has views on comp plans, and that every person in every revenue team has a view on a comp plan. And it's like, it's both deeply emotional and it's also rooted in only our experiences personally. And so, we're going through this challenge now of like, What's the problem that we're trying to solve for? Like, what's the behavior we want to solve or what's the objective of the comp plan? We did our own diagnostic on where there was weakness and now we're in the solutioning phase. And if we go through the solutioning phase without principles on what we want it to solve for, we will wind up in the same, like, sort of back and forth. I'm like, well, I've seen this at Square or I've seen that at Shopify or whatever. Some of the principles that I can surface now are like, this comp plan has to be globally applicable, regardless of the maturity of the market. And so, people were getting all tied up on like, well, it should be different. I'm like, why don't you just make the quota different? Yeah.

Oh, don't get me started on this.

Right. The structure should be the same. The quota can be different. We'll set quotas however we set quotas, right? And they're like, oh, the accelerators have to be different. I'm like, do they? Like, let's talk about it, right? The second principle was, there are a few, but another principle was it has to be scalable for multi-product. I will not change it when we introduce new products. And it has to, and each country has different products. So, like, it has to be applicable for multiple countries and their own multiple products. And so, that's like an infrastructure question as well as a compliance structure question. Yeah. So, that, those are just some examples. And so, we, we take a principles approach to solutions as well.

That makes a lot of sense. I, I'm obsessive about principles and For everything we do, I try to distill things back to some set of organizing principles. I'm recreating our operating methodology right now, basically, like, how are meetings structured? What do you cover in meetings? How do we run one-on-ones? What's our weekly, monthly cadence of updates? And so rather than jump to, okay, here's what I want weekly, here's what I want monthly, I've spent hours and hours and hours documenting this operating methodology, which has organizing principles. It has to start with our company values, then it has to serve the customer, then the business, then the team, then the reps, then us as the managers. Okay, so now if I'm creating a new reporting cadence, is this about us or is this about the rep? And how does this serve the business? And I really want us to be async as a default. And so I feel like by organizing these principles, then I can give them to other people and they can go create. They now— my VP of marketing said this to me and I loved it. He's like, you're giving people the primary colors of this thing and now they can go paint with it but bring back something that that still works. So I'm very aligned on these principles.

I love how you— how they said that as well in that, look, we've all been through times in our career where you're just not seeing yourself scale anymore. You're like, oh, man, I am the bottleneck, the answer. And that's tough. Like, that's tough when you become a frontline manager, a manager of managers, you know, an enterprise leader, a functional leader. And so I've experienced that same sort of like push to principles over time, just because I feel like it does a few things. One is it is the blueprint or primary colors, as you said. It's a gift to them. And the other piece is I found that if you either co-create or you author the principles yourself, the answer that comes back is much closer to the percentage done. Like, if you give pure white space, you'll get an answer that is at best 50% of what you wanted. Yeah. Right? But if you give people the framework on how to think about an answer and the principles upon which, like, you want the answer to to be, you're much likely to get 89%. And so, that's brought me a lot of time savings, peace of mind, and also career growth, frankly.

Yeah. I'm pushing myself to do as much of this as I can. I view this as sort of my primary function in 2025 is just distilling all of the things that we do back to core principles that then people can take as sort of their building blocks and Lego pieces to to recreate the thing that they're trying to build, like the rules of engagement. We're rebuilding the rules of engagement on rotators and a bunch of stuff that is very gritty work. But if they understand, okay, optimize for the customer first in this thing, what's the experience of them getting bounced around from 3 reps? Okay, then your rotator is wrong. And I just find that we just went through this ROE process and I think documenting more clearly the principles made that come back in a much, much better place.

It also start— it helps with the rollout.

Yeah.

You know, this notion of like when you disagree with someone, always start with the thing you agree with. Like when you're going to roll out a new comp plan or when you're changing the rotator, You know, when you're changing the rules of engagement, there will inevitably be teams that just— individuals that disagree, always. But if you agree on the core principles on like, we are here for our clients, we're here for them, right? And mostly for them. And we're here to make your jobs easier as individuals. We are stewards of our company and we control costs and efficiency. Like no one's gonna, no one is gonna disagree with those things. And so it's like, they might, they might not like the answer, but they won't disagree with the principles. And so that's been, I mean, like, yes, it is an important problem-solving tool. Yes, it's an important solutioning tool, but like I found for myself as a revenue leader and having to roll out a number of different new initiatives and whatnot along the way, like it's a selling tool.

Yeah. That's one of my comms principles is always start with why. Because if you can explain the why for the customer, the business, the team, et cetera, then things downstream make sense. When I announced that we were setting up an office, I was super clear and very transparent with the rationale on why and what the business drivers were. And it seemed to resonate with people. And I got a bunch of messages saying like, hey, I just really appreciate you explaining it and like telling us what's going on and being like clear. Like, I didn't, hide the fact that part of it was about driving down cost. We've hired for SMB, an experienced SMB rep and paid at the top of market, but we're scaling from sort of 50 people in sales to 90 or plus this year. And if we can hire an earlier career rep, groom them up from scratch, then we can change the cost profile. And I said that openly to the team, and I think there was a level of appreciation. And, one of the principles in this operating methodology is just treat people like adults because I find people, leaders want to spin. They want to, "Oh, we're doing this thing and it's for these reasons," but the reasons are not quite— they're disingenuous and you think you're selling your team, but every single time you do that, you're chiseling away on trust. As opposed to saying, like, hey, I can be open with people that this is capitalism, this is a business. We are here to return capital to shareholders over time. Therefore, the cost profile of what we're doing needs to bend. And if you treat people that way, I find the response so much better.

I totally agree. Also, I can't speak for you, but I'm a terrible poker player. So if I am, if there's any inkling of me hiding something, it's written all over my face. You can feel it. People feel it. Even if they can't see it, they feel it.

Yeah, for sure. Okay. I wanted to come back to what you said right at the beginning of this topic on teaching it. So how do we teach this? How do you scale it to others? Because I think this is going back to your point about being a bottleneck. Something that folks really, really struggle with?

I first try to model it. So, like, we're gonna do it together a bunch of times, and then we'll write the principles together. That solves a couple of problems. It solves for agreement early on. It's like, no, we crafted these principles together. That sort of, you know, that solves for, that kills that bird. The second step along the way then is just asking them to give it a shot. Like, what do you think these principles should be? And then trying to create a little bit more independence for it. I'm lucky enough to work with a really smart and capable team, and there are lots of journeys that we as a team have not gone on yet. And so this principled way of thinking has helped immensely in just allowing more volume of work to get done because we can have more teams sort of operating independently at a time. So I know that's, it's not a very exciting answer, but it's really like I model it first and then I ask people to do it on their own. And it's the same thing for my children. I'm like, we'll do it together and then you can do it by yourself and then you can do it independently. Always.

Yeah. And then tons of feedback.

Yeah. Yeah.

Makes sense. Okay, so let's make this more tangible for folks and hop into, and so dealer's choice, we could talk about going multichannel, multiproduct, multimarket. What's a fun, complex topic to sort of unpack and talk through sort of the decision-making and rollout process?

I love, I mean, all of them are fun. Problems are fun. All of them are fun. I really like this notion of like, I see multi-channel and multi-region as actually kind of a similar challenge because you do have to assess like how much investment am I going to put into this same. Like, what does it look like? You know, I've seen it at, frankly, I saw it at JPMorgan when I was there. I'm thinking, should I put a new office in Istanbul or Milan? Or saw it again at Square, at Recharge, and now we're talking about having it at Xero. Like, where do we go next? And it's It's a lot of fun sort of macro, like there are a couple different very academic areas and then there's like active solutioning and problem solving. The academia is fun. It's like, what's the market opportunity? And like, that's just pure ivory tower stuff. It's like market research, right? What's the opportunity? What's the, you know, based on your ICP, like how do you cut the data so that you know what type of opportunity lies ahead and what you're sort of relevant addressable market is. But the most fun thing, I think, is creating like, what are the packets of investment? You can call it a bunch of different things, packets of investment, packets of change. One mistake I see is like, people go straight to, we should put people on the ground there. And you're like, I'm not sure that's the right option. It depends on the market, right? But like, is that really what you want to do? Or like, we want to explore a new channel. Like, let's go straight to hire a couple of reps dedicated to this new channel. Some fun examples or like thought exercises that I encountered along the way. Let's take Europe. For example, it was like the biggest opportunities in Europe are France, Germany, Spain, Italy, right? Like those are the biggest economies, um, or you know, the, the UK, but at the time we were already in the UK, but those would require a tremendous investment in order to, to really move the needle, like to create the awareness you want. To start driving inbound interest or even like successful outbound interest within a time horizon. And so, then you start looking at smaller economies and you're like, what— are these jobs to be done relatively similar? And can I get more traction in a smaller economy and self-fund for a larger one? So, in one instance, it was like, okay, It's a no-brainer. Actually, it wasn't a no-brainer at the time. It is a, it's a good idea to expand from the UK where you already have a presence into Ireland because you don't have to change your assets. You have some form, some halo of awareness. And once you start actually generating revenue in Ireland, which is a much faster ramp because you don't have any new assets to create, you can use the same, you can even use the same reps in the UK. For the time being, right? You improve your payback there and you have under 1 year payback, you can self-fund entrance into your next country. So you essentially, like, you're not entering Ireland, for example, because it's a huge market. You're entering because it's easy to make more money and then you can fund another region.

That makes sense, right?

To lessen the total, you know, financial impact of trying to enter Spain, for example.

Yeah. And your point about, you know, going straight to full boots on the ground in a market at Shopify, I can't remember the exact terms, but we identified, so there were 3 tiers of market expansion. There could be like exploration, there was something else, and then full development and exploration was part partner-led and done it out of another market. And then all the way on the full sort of market development was, okay, there's a regional hub, there's people in, in seat selling direct.

Yeah.

So the channel and market thing are very much interrelated, I think.

Yeah, that's exactly what I was thinking as well. In fact, I'm living it right now. We're looking at, at Xero on like how deep of an investment do we want to make in other countries? And there are 3 tiers of depth. And none of this is company specific, right? Like the 3 tiers of depth that you talked about was one is probably like, do we just test out like marketing-led demand generation, PLG, no boots on the ground, no language customization, nothing, right? Then tier 2 is, do you have you know, tier 1 plus a channel partner, right? And you probably stand up, let's say in tier 2, you stand up a very light product-led sales motion. If you just take the EU, for example, there are tons of call centers in Poland where they can, they have 15 languages right out of the box. Yeah. And they offer everything from sales, dev, all the way to support. So, it's like you contract with, with a company like that and they handle very light onboarding support. And then third is you put humans there and then you probably have some form of like tier 1, tier 2 investment, but you then have like active outbound sales force in market. And so, we're, you know, that is something I'm living right now. On just thinking about like, where should we, where should we apply tier 1, 2, or 3? And then the solution, back to the, back to an earlier part of our conversation, like, what's our financial constraint? Is this strategic to the business today? Does it unlock other countries? Like, does credibility in Portugal unlock Spain, for example, that's a purely academic question, but it's like, is there a linchpin answer there? And so any one of those countries on paper could be the one, but it's lazy thinking to be like, yep, this is the biggest economy. We should go after that one.

Yeah, that makes a ton of sense. When, what was the framework to figure out when to go into these new markets? I think you see so much failure here. Um, so how did you know at Square and Xero when it was time to go international at all and when it was time to take on a new region?

There's, there's a little bit of push and pull, right? Um, there's, there's always push and pull from, from different directions, right? Sometimes your investors are like, you gotta go. Like, um, there are plenty of investors of US companies that are like, if you can't prove yourself abroad, like You should just think your valuation's not going to change ever. So that's a, that's a push. A pull is you're seeing sort of regulatory changes in a market. That's super fun because like that's when the magic happens. Yeah. Like a regulatory change really changes like people's awareness of solutions. So, you know, we look at that that would be a pull. Another pull would just be, you know, proximity to other markets that do that, that are seeing regulations shift. The UK is a great example right now. The government is requiring digitization of tax information. That's like, now is the time. Now is the time where we should shift dollars away from even another one of our actual markets to put into the UK, right? So no question about the market dynamics factoring there. Market dynamics, consumer sentiment, competitor behavior, and then of course our global like resourcing constraints.

Right. I feel like a lot of companies try to do this too early. Like they don't have the maturity or even necessity to go do it. How do you know when is the right time? Like thinking about just we're, we're America only today and we want to do our first international market. Like generally, what is that point for you?

The way I thought about it at Square was, do I have— now it— but there's the added blessing or complexity that, you know, Square's publicly traded, so you have to meet a number. There's no hiding, right? There's not like you have an off quarter because you tried something new. There's just no such thing. And so there, if you think about it like on a maturity curve, like you have to have something that is mature, mature enough to be predictable and repeatable. And that one like gets to be the anchor, that country or that region or product or whatever it is, that team gets to be the anchor while you try something else. I would not recommend, and look, I recognize that this is coming from like a larger company view. I wouldn't recommend having a bunch of experiments running at the same time. So, I always feel better if there's like something stable that is the anchor team or, you know, product that you're selling, and then you start branching into others.

Right.

I saw that at Recharge too. Like, you have a core business that's doing really well and then you get to go sort of test it in another region or in another channel.

Makes sense. Has Xero been international for a long time? Or like, when was that? When did that happen?

It has been. Xero is a company that's founded out of a garage in New Zealand. And so, it is like, It is the number one player in the accounting and bookkeeping space in the Southern Hemisphere. It has a monster presence in the UK and has been in the US for the past decade as well. And so it's a, it's a very global footprint business. We have presence in Canada, the US, South Africa, the UK, Southern Hemisphere, and Asia and growing. And so it's a question that we ask ourselves all the time, like, you know, what, what do our customers care about? Where, where would our product be the most useful? That speaks to the regulatory tailwinds. You know, where we go, where we're needed, and we go where we think we can make a big impact.

That makes sense. And in terms of channel diversification, what's the right timing to think about adding additional go-to-market channels? What are the triggers? What's the model to think through? Like one, what, what's the right timing? And two, what's the next right channel to think to, to add?

Oh, that's a hard one. Um, the obvious one is when you're trying to diversify your revenue streams. And so it's like, all right, you have a stable one and now you're trying to sort of create a new one. So it's like win the present, win the future. So to speak. The other is a more customer-centric approach, really thinking about like meeting customers where they are. So meeting them in their decision-making process. A lot of companies will likely go independent first, like they're going straight to the customer first. But I don't know, a good example is knowing that a micro-business owner starts with just being able to take a payment. Right? Like I want to sell, I want to sell knit goods at my local farmer's market. Like I'm just going to, the first thing I'm going to focus on actually is just taking the payment. Then comes a bank account that is not my personal account, probably. Right? And then only later will I have employees. And so you start thinking like, all right, the ecosystem play there is If you are a payments business or if you're like banking, you start thinking about like, what are the most, what are the adjacent or ancillary jobs to be done around me? And that will tell, that will tell you what channel to go after.

Yeah, that makes sense. 'Cause I got to Xero through Stripe. I have Stripe set up for my Substack and for consulting stuff, and there's a, there's a product integration there. It's like, you can use, click here and set up Xero. And I was like, okay, cool. And that's how I set up my Xero.

That's interesting. That's exactly it. It's like the most important thing to you as a business owner, for example, it's like you just have to take payments. Like that's the dopamine hit of like, I made money today. That is like my livelihood. That's my number one priority. And then later the priority is like, how do I track it? How do I like start billing or billing my customers in different ways? How do I package it up to send it to my accountant? Like, those are not things you think about on day 1, but those are things you think about on like day 3, you know, it's weeks 3, months 3, right? And so the customer-centric approach will tell you sort of what does your channel need to change or can it diversify around? And then market dynamics matter a lot as well. I think one interesting thought experiment that I've seen over time is, do you have competitors that are very rigid in their, like, whether or not they want to accept other players on their ecosystem? And if they are, like, does that mean that you could be the anti of them? And so sometimes, well, you know, while I don't recommend over-orienting to what your competitors do or don't do. Like, you run your own game. But that does matter. That is factoring in from time to time. It's like, in this market, is your competitor very open or not? And that will tell you sort of which channels to pursue.

Makes a ton of sense. Any other last advice for people setting up a new channel? You know, they've been 100% direct and they're setting up, referral or reseller or anything else, any other key principles that you think are worth sharing?

We talked about failures before. There's definitely trip-ups on going a little bit too fast. And then unsurprisingly, I would say try to see it as an all-new business. Like give it the oxygen it needs to be a new business and to shed the like shed how you orient your thinking around everything you've done before in the past.

Say more about that. That's really interesting.

There are a lot of limiting beliefs based on like, oh, we tried that before and like, that's not how our customers buy. Like, okay, but is that really, like, is that true or is it, or is that just how you've always thought about our current channel? I'm trying to think of a good example here.

I think the maturity of a business like you— this, this rings very true to me because I've— we've gone through this ourselves. We've tried to set up a partner channel like 2 years ago. We didn't have the market presence or brand equity to get a ton of traction. And then, you know, we basically like stopped doing that. And then maybe 7 or 8 months later hired a new very senior person to like give it another attempt, but do it at a very different scale and make like a more significant investment. Now it's a very material part of our business, but our presence in the market and people and just the brand equity is completely different today than it was 2 years ago. When we tried to do it. And it helps, you know, we hired a leader from the space who's very credible and knows everybody in the space. But I think like the timing can matter. Just because something didn't work one time doesn't mean it can never work later.

Yeah, that's a really big one. One thing popped to mind where at one point we were considering at a prior stint, we were considering whether or not to use resellers. And there was this notion internally of like, well, our product is too complex. Like, and also like the margins don't make sense at resellers. Like, do you give away what will be as much as half of your margins to a reseller? Like, that'll just never work. And, you know, lo and behold, you see a ton of, a couple of competitors run that play. And it's like something is working over there and that there's clearly a principle difference. There's like a belief difference that they must have that we don't see. Right? Like, it's impossible for them to think that they're just like, they're not doing it underwater. There must be something economically that's making it work. Right? So what has to be true in order for us to consider it? We sell What would have to be true is either we give a much smaller percentage share of the cut or that we sell multi-product. And so the average ticket is a lot higher, for example. And so I do think that like limiting beliefs can be, you know, most often the blocker or even just ways that we think about the business today are often blockers to trying a new channel. And the like reseller one is a good example because the margins are thinner. And you do have to simplify your offering if you're going through a reseller. That is real. Like, it's, you have to create either simplicity of the product itself or like the offering, the package that you're putting in someone else's hands. And so, you know, I try to challenge myself and others to think about like what has to be true in order for us to do that. So, if my boss said tomorrow, build me a reseller program in a year. I don't get to say no, I have to say how. Yeah, so off I go.

Yeah, that makes a ton of sense. Well, this— that's great. Okay, let's move to quickfire because I want to get us, uh, wrapped up on time. Um, what separates a good CRO from a truly great one in your mind?

Oh, I don't know, Kyle, I'm learning from other CROs all the time. And I wish we all knew the answer to like, what's a truly great CRO? So I'm only going to be able to orient from my own perspective today. I would think that a great CRO is a truly enterprise leader, one that can think about problems beyond revenue. and knows how to solve their peers' problems in legal, in product, in finance, as well as their own. I have to assume that that is it, right? It's like, that's the, that's the difference on someone who's going to drive a number. And that is, that's, that's immense value, right? That's what we're hired, we're all hired to do, but also then can they be a partner of changing the business as well?

Mm-hmm. Enterprise value. Yeah. What's the most common advice you find yourself giving to your leaders or mentees?

A few tidbits come up consistently. One of them is the old Abraham Lincoln quote of like, "Whatever you are, be a good one." I think so often we focus on like, what's next? And I get into the next thing and like the fastest way to be great and to be given the next job or project or what— or opportunity is to be great at what I'm doing today. And so like owning, own the shitty phone calls that you have to make, like whatever it is, like just own it today. And I have been so grateful because like there are lots of really uncomfortable things that I've learned how to do over time. Because I've been in the job at the time. The other is just a reminder of like, you know, your comfort zone was once an unknown frontier. Like, that constant discomfort is the greatest gift you can give yourself. And so I have learned to love it. And I try to encourage other people to like really live in that like frontier of their comfort. That means putting themselves in projects that they, that make them uncomfortable, in situations that make them uncomfortable because they will learn. And I think the greatest gift back to me is I had one of my directs say, this past year has been so uncomfortable in the best way. I was kind of touched. I was like, oh, I'm so happy. Yeah, that really made my year.

That's awesome. Uh, what's the hardest lesson you've had to learn?

There are lots of hard lessons. I don't know about hardest. Um, I try not to sort of over-orient on any one or another. Like, you know, they'll dwell or stick with me. A couple of lessons that I've learned the hard way is because I'm naturally a very curious person, I can hold the grief for people and I've been sort of slow to judgment. And that has been like, I was, there are times where I wish I had sort of made a call earlier.

That's a good one.

Like, I, for example, if I get a negative reaction out of someone, I'm quick to say like, I can understand where they're coming from. They're not like, even though I don't like their reaction, like their perspective is not wrong. But if you, if you're more permissive of that, like you'll sort of allow people, you hold the gray for them and with them for a long time, it can have negative impacts on team. So, those are, that is a regret of mine. It's like, I do see it as a superpower that I can hold the gray. I don't mind that things are messy. I can be in a mess and not pass judgment on it. But the flip side of that is sometimes you have to or you should.

Yeah. Last question. What's the best thing you've read in the last 12 months?

What's the best thing I've read? Last one, please hold. There's so much good stuff. What's the best thing you've read in the last 12 months?

Probably The Power of Moments by the Hughes Brothers. It's so clarifying from both a customer experience and an employee experience perspective. And especially in a remote environment, like, how do you think— how do you make things feel special? How do you elevate moments to a place where they have, like, real significance? Because, you know, the crazy thing about remote is, like, the best day of your career, you're just, like, sitting in front of your little screen. The worst day of your career, just, like, sitting in the same chair in front of your screen. So how do you— how do you manufacture moments that have, like, a lasting impact on people? And the Heath brothers have some really great frameworks for it. And so we've been trying to build more recognition into our environment and more of these special milestones.

I love that. I'm going to pick that up for sure.

It's so good.

I read a lot, actually. I read quite a bit. And so I'll just give you two that I found were really fun. I love basketball, so I reread Eleven Rings by Phil Jackson.

I've never read it.

I just love him. And I think what I love, one of the things I admire most about him is that, you know, you could say, well, he's, he was given the gift of really talented players, both on the Bulls and then later on the Lakers, but he really did have to get them to play together. And he was in the business of bringing out the best in them, and then also bringing out the best in their partnership. And then also finding ways to create talent that will bring out the best in others. And so the Scottie Pippens of the world and getting Shaq and Kobe to play together. So I just, I love that. And the other, now working for a New Zealand-based company, there's a book called Legacy by James Kern. And he writes about the principles of the All Blacks, which is the winningest team. Sports history of all time. The All Blacks are, I think they have won like 50 out of 53 international titles. They're just one of the most amazing teams and just this warrior spirit coming out of beautiful New Zealand. So both from a cultural standpoint and from like a business education standpoint, I really love to tap into that. So both are very good.

What was the name of the All Blacks book?

Legacy by James.

Legacy. Very cool. Well, that's awesome. I have a raft of notes here, and I feel like I learned a whole ton of stuff myself. So this has been awesome. Where should people find you, and how can they be useful to you?

You can find me on LinkedIn. I love to meet new people. Like I said, I'm always learning. Leaders are learners, and I just, I listen to your podcast, I listen to plenty of others. And so, if anyone has a great podcast recommendation or has a great story to tell or problem solve, please connect on LinkedIn.

Awesome. Well, Ashley, this was amazing. Really appreciate you coming on, and we'll have to do it again.

Thank you, Kyle Norton. Great to see you.

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.