E11: Mastering Strategic Planning with Eric Gilpin, CRO of G2

I'm very excited to introduce today's guest, Eric Gilpin, who is the CRO at G2. Eric has been in senior revenue leadership positions for going on 15 years. He's been a CRO for 6 to 8 of the last years, including a really exciting run at Upwork, 7 years there as Chief Sales Officer, and has now spent over a year at G2 as the CRO. So Eric, appreciate you joining me.

Yeah, no, Kyle, thank you for having me. Excited to be with you today.

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. But first, a word from our sponsors.

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Cool. So we are going to talk about driving alignment, strategy, and planning. We are in the throes of planning season and also teasing out the difference between a sales leader, a sales executive versus somebody who is a true revenue executive, somebody who has a seat at the, the most senior table and is driving company vision and company enterprise value. And so we'll tease a bunch of these topics out, but let me know, let the audience know what I missed in your background. Give them your 60-second intro.

Yeah, no, happy to. You know, so I got started in the, I would say like the tech world as like my first professional job and starting in sales at a desk. This was long before the assembly line of roles that you see in the sales motions today. I was what you would call maybe a full-stack go-to-market expert, but I got started in the rise of the internet in 2001 and was fortunate to be part of an organization that scaled globally and kind of grew within that organization, winning as a result of kind of that revenue machine. And as you mentioned, I was able to join Healthpark a little over 8.5 years ago, a tangential space to what I was doing, you know, kind of prior, but still in the kind of B2B marketplace kind of arena and had a huge mission, big problem statement. We were fortunate enough to take that company public in 2018 and almost 7 and a half years there. And then I just wrapped one year here at G2. And so it's been exciting kind of squiggles of success, but excited to be here.

Awesome. Awesome. And when, how big was Upwork when you started? What was the sort of range over those years?

Yeah, so we measured the business in, uh, what we call GSV or maybe GMV. And so total market, uh, kind of sales volume. And so when I joined, this was right after the marriage of Elance and oDesk that came together. So number 1 and 2, and we were doing about $1 billion in, uh, gross sales, uh, as a company. Um, when I left, you know, probably closer to $4.5 or $5 billion, uh, this year as a company, but The problem statement that I was working around was our enterprise segment. And so how do we make the magic of the workplace relevant to large companies? And starting there, it was, I would say it was more of like an entrepreneurship. You know, we had a scaled business, but not necessarily that customer persona or use case. And we scaled that business, frankly, from zero to almost $650 million in 7 years.

Wow, that's awesome. So lots of interesting alignment conversations that we'll have there to tease out. To sort of cue this whole thing up, I'm curious to hear your opinion on what's the difference between a sales leader. So there's lots of VPs of sales or CROs who just have that mandate versus like a real revenue executive. And this isn't about the title necessarily. I'm really talking about what is the differentiation between the person who is more siloed in their sales-oriented thinking versus like a real revenue executive that can drive enterprise value? How do you like to architect those two things?

Great question. I think it's a relevant topic regardless of your function, but it really shows up in go-to-market organizations. And so as I think about my first sales leadership role managing a team of representatives and At that phase of my career, I was just kind of in execution mode. I was running a play that, you know, was kind of tops down in the organization. And while there might have been some kind of creativity and flexibility of like how we navigated that, but I was, I was definitely in execution mode. I think as you move up into second line leadership, VP levels, potentially maybe running a function within the sales organization, the hat that you wear is more around strategy, but specifically like what is done. And helping identify like what are the tactics and strategies that you're going to pull through. I think as you move up into SVP, definitely CRO roles, the job to be done is more around who does what, and you become less attached to the how in some ways. I've struggled a lot, you know, with that. You're focused more on like the why we're doing certain things and like who's on first to pull these things through for the organization and for your customers. And you're less married to the what and how. And I think that's a real challenge as people move up of understanding that their job to be done. Hmm.

Interesting. And so just say more about figuring out who does what, like, like how do you learn that skill set? What are the things that you need to do differently at that level versus when you're more strategy and tactics oriented?

Yeah, I mean, I think the who does what is relevant in any leadership role, but I think it's magnified the higher you get in an organization. But I think there's two different sides of that story. You know, one is this idea of Patrick Lencioni calls it like your team one, and understanding that my team is not my direct reports. You know, my team are the fellow executives that are operating the organization. And so our CMO, our chief product officer, our chief people officer, CFO, CEO, and that is my team number one. And I'll park that one because I think that'll come back in a conversation in planning. And it's, but if you think about the who does what for my direct reports, it's really around this framework of, in my opinion, like how you hire and this idea of that you're searching for In addition to excellence and competence and being able to be both a while wide but a mile deep in the function or part of the, let's call it a customer journey that you need them to obviously perform and own, but also this idea of you're constantly hiring for the team, not just the role. And so I think a lot about range and I think a lot about inventory of this team that I get, you know, obviously the honor to lead. And as, you know, team members come and go, Am I constantly thinking about the inventory of the team? And so that could be creativity, that could be business acumen, that could be strong cross-functional collaboration, that could be strong analytic backgrounds. And so regardless if they're the best CS leader or if they're the best, you know, new business acquisition leader or the best RevOps leader, what are those attributes of the team that would raise the bar for everyone more so than just the function that they're leading? And that was also, I would say, a learning journey as, you know, building a number of different teams. And so I think about the function for the team more so than just the role.

Interesting. It's a similar analogy that I share often is when I'm building teams, I'm trying to build a basketball team. You can't have 5 centers, you can't have 5 point guards. You need a variety of skills that can flex into different places to have the right winning formula. And it's hard, especially I think earlier in my career, I really just wanted to replicate myself. Well, I'm awesome, so I'll just go hire a bunch of people like me and then everything's going to be great. And then you quickly realize that is not at all the formula for success. So I think this idea of team inventory is a really interesting one.

Totally.

And so we'll come back to team one and how to drive alignment across team one. But I want to pick at one more thing here. So it's less about the how. And so how do you guide people to the right how? This is the thing I think me personally, I also struggle with. I want to have an opinion on how to make sure those decisions are great. So how do you How have you tried to let go of the how and ensure that the how is still done at a world-class level by your team?

Yeah, great question. And it's, as you can imagine, something that comes up in planning cycles in a really big way. As you think about, we run the V2 MoM here at G2 and we debate a lot the metrics and I'm always curious, I'm like, is that really where we should be debating? But I'll give you an example. And so I think goal alignment and I would say the measures and metrics are really important. And if you can align on whatever needle you're trying to move, whatever conversion rate you're trying to improve, whatever outcome that you're trying to drive, you should be less married to how the team gets there. I mean, there's frameworks around ideas of discipline freedom or freedom and responsibility or how much surface area is available for, I would say, creativity and things. And I think those things should be embraced. I think where teams, especially revenue teams, if it's all paint by numbers and they're not necessarily a part of the how or solutioning that it comes through, it's less sticky and there's less ownership mentality of how we're trying to win on behalf of our customers. And so I think it starts with like, what are we actually trying to do and why are we doing that? And if we can have really strong alignment on the so what, who cares, what happens when we get there, I think it's a lot easier to kind of remove yourself from the actual strategies or tactics that need to be deployed as long as they're aligned with your core values and they're aligned to kind of customer value. I think it's really hard to do, but I feel like where I've seen high-performing teams, there's no question on the why or the what, and the how is less debated, I would say.

Okay, so it's the what and the why. And So you mentioned a couple things that are above the how, and it's alignment on values, alignment around the customer. What else do you need to architect for your senior leaders to allow them to get to the right how?

Yeah, I think it does start with a why. And I'll give you an example with Upwork because I've been fortunate to be a part of a lot of mission driven organizations, but this one was, we did a really good job of like threading it all the way through all the communities we serve. And so if you thought about our vision as an organization, it was to build the world's largest work marketplace. And immediately you'd ask yourself, all right, well, so what? Who cares? But if you think about the why or the mission or why we exist, it was this idea of we want to create economic opportunity so people have better lives. And the motions that we run both for, we're a two-sided marketplace similar to G2, should be rooted in that. And if you think about Upwork, I mean, we were distributing jobs around the world, creating economic opportunity, but also helping companies scale agility and product innovation by having access to talent real time. And if you can have a real strong culture and DNA around why you exist, I think the what is like a little easier. And so the what becomes like, okay, exactly. Well, how do we show up for that? If you think about G2 today, like why we exist is to empower, you know, business professionals to reach their peak potential. You know, we do that by building the world's largest software marketplace rooted in trust and transparency, connecting buyers and sellers faster than ever before. And you have to spend a lot of time and it's painful, you know, getting alignment there. And then if you think about the— depending on your go-to-market, the customers you want to serve, why do you want to exist? I think the how of like the tactics associated with how you're going to grow the business and grow your teams, I think you get a lot more, I would say, involvement and participation, you know, from folks. And they feel like they're more of a part of it. It's happening through them versus to them in those scenarios. But I think a lot of companies don't spend enough time on the why they exist.

That makes a bunch of sense. So, so we'll come back to—

my guess is, is owner.com has a strong mission orientation based on the community that you want to serve. Yeah.

Yeah. Yeah. For us, it's about arming restaurant owners to take on their Goliaths. And it's this idea of empowering SMBs to be able to battle with the Dominos and Chipotles of the world and the Ubers and DoorDashes of the world. Like, they're under siege and we're trying to give them the tools to succeed. And we are absolutely deeply rooted in a very mission-driven approach. And then for me, it's all about trying to figure out how I can architect principles that can guide more specific decision-making. Because how does that— the question for me oftentimes is, How does that mission tie to a sales manager deciding on how do we architect our deal qualification criteria? Or how does it— how do we decide on the Salesforce project to prioritize? And so there's a level of, I think, abstraction there that I'm trying to fill in. Yeah, go ahead.

I was going to say why. And I think there's like, there's another layer in between that. So if you feel like you have like your mission and vision alignment as an organization, and I think specifically around go-to-market organizations, the next idea is this framework of like, who are we chasing? And I remember right when I joined G2, I asked this question to, you know, 6 people my first day, and you immediately go to these like competitors, and they'll remain nameless at this time. And And I was just kind of fascinated because in my mind, you don't chase your competition, you chase your customers. And it's like, who, what are the customers that we want to serve that are in support of that broader mission and vision? And I feel where a lot of organizations end up like shipping their org charts a little bit and potentially not meeting their potentials because marketing has a point of view on that, product has a point of view on that, your sales organization has a point of view on that. And if there's a ton of daylight between those beliefs, even when you get into thinking about like, how do you operationalize the qualification criteria that you need? That is a downstream decision that if you have upstream misalignment, it kind of doesn't matter because it might be very different. And so I feel like even after vision and mission, this idea of who are you chasing or who do you want to serve and why is a lot of the work that team 1 or the C-level team should be working on, because then it reduces lack of clarity down the organization because everything is in service of that strategy.

And when you first started at G2, I heard you talk about you narrowed your ICP. So maybe just share a little bit more about how you reframed the who we are chasing for G2.

Totally. And we have this very interesting pickle, if you will. And so we have a really interesting freemium model where any organization, regardless of size, can list their company on G2, start driving reviews and kind of building that customer voice. And as a result, we've got 160,000 products that are listed on G2. You know, our go-to-market organization, not tiny, but not huge. We've got, you know, a little over 200 sellers around the world. So we can't chase all of them. And we're in this, you know, kind of marketplace business where all categories aren't created equal. And so if you think about the 90 million buyers that look at G2, They're not all going to all 2,100 categories equally. So you've got, you know, categories like your CRM or sales and marketing down to back office software for veterinary hospitals. And so all revenue, as you know, is not equal. And so we did a ton of propensity modeling around the categories, around product signals, things that were really important to us, important to the customer, things that we could defend and prove. And that list started getting smaller. And as you continue to, you know, we're a big ecosystem player. We integrate with 53 other, you know, technology companies. And so that's a cut. You look at the category signals, that's a cut. Product adoption, that's a cut. You run your kind of GRR and NRR regression against your current customers, that's a cut. And then quickly you get to like a 19,000 number and then you start to, you know, look at where clusters are, like where we have competitors that are strong lookalikes and then You know, through that period of time, we got down to 3,000. Well, 3,000 customers is a manageable list, you know, to, to focus on in a year. And that's where we built our, you know, kind of account-based orchestration of like, all right, product, what are you doing on those 3,000? Marketing, what are you doing on those 3,000? You know, the revenue teams and then like, what role do you play in that buyer journey? The hardest part was getting to the 3,000. The execution, while challenging and we make mistakes daily, I would say that the hardest work was way upstream before we got to execution.

Yeah, the answers become a lot more clear when you've defined that group. Jordan Crawford, who's one of the smartest GTM AI thinkers, had a quote that has stuck with me. He's like, the list is the message. You know, when talking about building messaging, he's like, everything is downstream of the little micro list that you've built for this campaign. And so relevant to this, like once you get to 3,000, what they need is pretty obvious for like they've told product, the sales reps know what those people want. So that's fascinating.

Well, and I think a lot of organizations, especially G2, are also investing in, I would say, more product-led and like e-com motions. And so we can have a more capture motion on some of the long-tail things that we might not chase with humans, but they really trying to focus our human motions on higher-order problems that are going to have the best unit economics, both for the customer and for us.

Yeah. So I'm thinking about these layers. Like, I've been writing this document, which is basically like a— it's a go-to-market engine all the way from mission to playbooks. And so I'm like sketching out these layers and it sounds like you've got a good mental model here. So you've got Mission, vision, and vision alignment up at the very top. Who are we chasing seems like one of those foundational things. Like what else, what else is in there before tactics that you really focus on that first team alignment around?

Yeah. And so if you have alignment around who you're chasing, the next question in my mind jumps out to like, well, how do we align our teams specific to the buyer journey? I think this is another example where revenue teams ship the org chart. Like our model versus their model all the time. And I think as buyer behavior continues to evolve, like you should be challenging your own status quo of whatever your assembly line looks like all the time. You know, and for us it was like, okay, what is the role of marketing and partnerships and where does that show up in those touchpoints? Full funnel. We run a— I call it hunter-hunter. It's not just land and expand, but, you know, we're constantly, you know, growing our customers. What is the role of implementation and professional services? Where does product success come in? And so as you can imagine, you have this, let's call it target account strategy across the top, map whatever your buyer journey is to you. And this is like design thinking workshops with everybody, including the customer, combining like terms of where all those funnels exist. And it might not look just like an amazing winning by design bow tie. That's a great starting point depending on your model. And then you start figuring out what it is for you and then say, okay, great. Well, how do I align our resources? I have a lot of passion around this topic of, and I was actually at an event in Boston and one day I heard, well, it's product-led growth. Well, then it was marketing-led growth. Well, then it was sales-led growth. And then it was like event-led growth and then eco-led growth. And I was like, team, like—

Community-led growth now.

I'm like, I mean, like our ego is getting in the way of winning for our customers. The only one that should get credit should be the customer. And so it's about working in orchestration in the most efficient way to help your customers win. And so if you can have like, you know, that surface area documented and alignment across product marketing revenue of what that funnel looks like, then you start understanding not the role, but the jobs to be done in each piece. And, you know, mapping like what are we going to do to help our customers get through that part of the journey? Some of it could be humans, some of it could be products, some of it could be AI. Some of it could be marketing nurturing, but really understanding that journey is incredibly important. And as you, as you think about the jobs to be done, once you have alignment there, then for me it's just, all right, well, what are the input metrics? You know, revenue happens. Like, what are the mile markers that we need to understand so that we can, you know, see around corners? You know, for example, you know, an average D2, like a new deal cycle is less than 90 days. We need to be able to, you know, have certainty, good or bad, 90 days in the future, because everything we do today pays us later. And so like, what are those input metrics that we're going to measure, you know, day over day, week over week, month over month, quarter over quarter to make sure that we don't necessarily get over— get ahead of our skis or go too slow on certain things. And doesn't mean that you wouldn't have outcome-based metrics, but if you get really good at managing the inputs, the outputs tend to take care of themselves.

Okay. And do you have a team vision document also written? Because there's always company mission values, company plan, and then oftentimes we dive down into like, and here's our strategy and the tactics for 2025. But do you have a layer in between that is about clearly stating the team vision that you want your senior people building towards? Is that something that you've roadmapped or Or are people like figuring it out, that stuff on their own?

Yeah, I, so, there's one that we do and then one that I haven't done that I'm really, unfortunately I haven't been able to prioritize, but I want to strive to do this year in planning. You know, I think we run the V2 MOM here at G2, and there's a company version of the V2 MOM and there's maybe 5, you know, methods that we're prioritizing. Every function takes that a level down and says, okay, great. What are the measures that you're going to do in support of that V2 model? Because there might be certain things that parts of the organization might not touch directly or feel like strong connection to like an overall method for the organization. And so they need to like bring it down, personalize it to exactly what they can do and what they can control. And so you'll see sub-V2 models by function.

Okay, so their, their document is in the V2 model. Format and it's, and it's a child of that company V2 Monparent.

Okay, totally. And we link them all together. You know, we use Confluence to have transparency measurements and kind of report back as an organization on it. You know, I think the one that, that I want to do in the revenue organization that I haven't been able to do, and I've been a recipient of this at another company and I just, I need to find a way to prioritize it. Is I think organizations that have really strong clarity around roles and responsibilities and decision-making frameworks are incredibly important. Like so many things get stuck because we actually don't know who the approver is or who the informed captain is. And I feel like even in revenue, if a strong DACI or RACI model with like clear roles and responsibilities of who's on first or who's single-threaded in these decisions, Cause you see it so many times when you do a V2 MOM review or a QBR internally, you just run into friction and you're like, why did friction exist? It was usually because of, you know, kind of this like circular conversation because no one, no one had the ability of understanding who's on first to actually advance it. And you didn't have clear escalation paths for like when things got stuck. But I feel like that is like the next unlock, at least for the revenue team here at G2. It's like, okay, let's take vision, mission, V2MOM, customers, input metrics, and then say, okay, great. Well, how are we going to play the game every day here? This idea of like, let's all ensue positive intent. Let's keep short toes, meaning we're going to step on each other, but like, let's have clarity and speed in which we can like accelerate the operating model. And I think that if you gunk that up and that's not super clear, it's like, it's just slow.

Okay. And so those are your team principles, the short toes thing. And I'm going to double-click on the principles thing. I just want to make sure. So the way I architect this, the way I've written this in my document, there's company mission, company values, company vision, team vision. We have a 3-year company vision, which we've documented. Now there's a 3, and there's a component of go-to-market there. Then there are the strategies, like what is our strategy for the next 20, 24 months to get there? And then I've got these principles, but I don't— principles and org design, but I don't have that model for like who, how do we define the DRI, who gets to make calls on what. I, we used to at Shopify talk a lot about is this like a level 1 or 2 decision? If it's 1, just go make it. If it's 2, like here's the escalation path. But That's a really interesting one that I need to tuck into my system.

Well, especially in the technology space, everything is cross-functional. Like, you can't do really anything in service of the customer without touching all those surface areas. And if you don't have like an operating model or decision-making kind of framework, whatever it is, it doesn't matter. It just— and it's not like lack of good intent by any means. It's just you just created your own kind of friction points and you don't see them. Like if I ran a little bit more on this idea, if you assume positive intent and you have short toes, like that is a good thing. And I would say that like as accountability is increased in an organization, like your job as a leader is to push accountability down. Like you're no longer responsible, you're responsive to the needs of the business. And so as accountability is pushed down, that should create pressure and pressure should create friction. And I would argue friction is where the magic is. And like, we have to find ways to get there as fast as possible because that's where we're like missing customer, like, uh, value points.

Hmm. I so deeply agree with this, this like friction is where the magic happens thing. We changed our comp plan recently to make the sales rep 100% only paid when the customer goes live. We're SMB, highly transactional, month-to-month contracts. So that cycle time is very short. And so the managers were like, oh, hey, we're getting some butting heads and there's some friction around this. And I was having this conversation with one of my long-term managers. I'm like, yeah, good. This is exactly what we want. The friction shows you what part of your system has weaknesses, and then you can address it. And then, oh, Good point. We didn't think about that. Let's buff it out. I'm going to steal this quote. Your job is to push responsibility down and pressure creating friction. I think that's like a really elegant way to think about it.

I stole it from someone, I'm sure. I don't really have any original ideas, Kyle. I just tend to steal and try to apply them where I can.

Yeah. I noticed from your bookshelf.

Yeah. We have a lot of the same ones. Yeah. Well, I mean, there's a lot of good inventory out there. I mean, if you can feed your mind, you know, good stuff every day, you get 1% better. I mean, who knows what happens? So, yeah. Yeah.

I noticed you had Working Backwards. I think I saw in your background in one of the pods that you did. And this, they, I think Amazon does a good job at that, you know, identify the DRI, the directly responsible individual, single thread them with ownership, like really keep it keep things tight, this is definitely something I'm going to do.

Well, and I would tell you, I got introduced to Working Backwards and actually Bill Carr, one of the authors of the book, did some work at my previous company. And I was like very intimidated and kind of like not interested in the 6-page memo kind of early on. I'm used to like slideware, give me some pictures, I can tell you a story and get out of there. And I would tell you that it is my preferred form of communication. And I probably spend more time, as much time writing as I do reading. It just like really makes you be thoughtful and it removes or increases clarity and kind of context. And there have been ideas that I had that when I started the first page of, you know, just trying to follow the template of the problem statement and like alternatives and how I think about it, that I ended up just not pursuing. And so it is like, it's one of those like slow down to speed ups, but I, it was definitely a turnaround story for me because I was like, no way, absolutely not. We're like not the revenue teams and we're not going to do this. We're going to go talk to customers. But at least for me in my role, especially cross-functionally when I'm trying to communicate with my peers, I actually really enjoy it. And actually now that, I mean, With ChatGPT and all the different AI-assisted writing things, like, totally, it's, it's, uh, it's almost like a cheat code in some ways.

Yeah, I think I'm probably 3 to 4 times more effective writing now with ChatGPT, just the research component, you know, like, oh, what was that? And a thing I do is for books that I've read, I'll go download the PDF and then upload it into ChatGPT so I can do a RAG search. Because I can't go back to my notes and find that one thing that I really want to tease out. But if I'm building training content and I want to reference it, I can take that PDF and I'll be like, tell it, like, there's a quote in here about X and Y, pull it out. Okay, now combine that idea with whatever. And yeah, it's incredible. And then I get to play the role of editor.

Totally. Have you done the notebook LM of it and just making a podcast to listen to?

No, not yet.

So you got to check it out. It's a Google product, but I've seen it. Yeah. We have a ton of customer use cases and case studies. We always have them coming out and I'm always trying to memorize 3 to 5 stories that I could just use to help our teams. And I'm like, all right, well, I'm going to check out this podcast thing. So I just loaded up our entire microsite of all of our case studies that we've made. And within like 4 or 5 minutes, I got a 14-minute podcast by 2 AI avatar voices, like had like amazing context. And it's actually, A lot of our rep training onboarding is now through this tool just to change up the medium a little bit, but another great AI hack.

That's fascinating. Yeah. And there's that Orwell quote, if you can't write well, you can't think well. And I think ideas are so amorphous until you can put them on a page and then structure it into a hierarchy of, okay, This is my top-level idea. These are the subcomponents. This is how they ladder together. There's too much here. The editing and pruning is so much of getting to clarity. And we're 100% no slides here. No planning can be done with slides because it's just so low bandwidth. It needs a voiceover. Yeah. Okay. So I want to come back to principles because we were talking about this layer between organizational design and organizational operating model, I think is a good way to put it. The racy-dacy ownership of things. But I'd love to double-click on principles that maybe is like a level higher in this chain. How have you architected the principles for your team? Is that a direct copy of company principles? Are there different things that your team operates by? And I'd love to hear about how you created them, and then we'll get into how you reinforce.

Yeah. And so I would say that they continue to evolve, at least for me, you know, in either new experiences or new companies or just like new just learnings along the way. And so I would say that even the 4 that I think about now, like they continue to evolve, but I always try to make sure they're not in conflict with like the company core values. And so, you know, if I think about G2 today, you know, it's an acronym, it's called PEAK, but it stands for performance, entrepreneurial spirit, authenticity, and kindness.

And those are the company ones.

Those are the company ones. And I would say those are, you know, your core values as an organization, but there also needs to be like some operating values. That I think that, you know, that can be nested underneath that, but it allows you to drive alignment and ownership across your team. And so they should be done in groups and how that shows up for the revenue organization. And so I think those exercises are really important. And so I have like my own personal leadership principles that I definitely convey, but there's this operating principles of like how the team's going to show up. And it's around like how we're going to be relentless and proving customer value. It's around like how are we going to be focused on growth every day and making sure that we're feeding your mind good stuff. It's around like how are we going to communicate with clarity and candor? The idea around the only difficult part of difficult conversations is not having them and how does that increase speed within the organization, but they're never in conflict. You know, with whatever the company values are, but it allows us to, I would say, put some more guardrails on our operating model of how we're trying to ladder back up to that why we exist. And those are always best done when you have all of your different functional leaders within the revenue org coming together to kind of co-author those. And those should evolve every year, just as the climate or the opportunity or maybe the headwind or the tailwind that you're facing, those should Culture is like, in my opinion, like a conversation of how things are done around here. And that should be ever evolving.

Okay. And so the relentless focus on growth, clarity in communication, and candor, those are— are those your personal leadership principles or are those your operating principles?

This would be like the G2 leadership team operating principles in the revenue org and this idea of like focusing on growth every day. And so How are we constantly learning as an organization and as individuals? I would say that the personal leadership rants, they weave in, but they're probably, I don't know if they're unique to me because I hear them repeated a lot. So they're hopefully they're sticky, but those are an evolving journey for sure.

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Okay. And so you said there, so you've got your G2 revenue leadership Principles, relentless growth, communication. Is there a fourth one?

This idea of, well, you said it, kind of growth, the focus on growth every day, but you covered it. Yes. Okay.

And then the short toes thing, where is that fit in?

I stole this from the CEO at Upwork. You know, it, it, and it kind of comes back to this friction thing. And so I've kind of ran with it, like getting from accountability or pressure to friction. But it's this idea of that you can be hard on the work, but not on the person. And I think sometimes people don't understand the difference. And if you, if you're rooted in this idea of assuming positive intent, and if that's just like rooted into the DNA, the ability to have short toes should be okay. Meaning that we're going to step on each other. Like, rubbing is racing. And if you start with this idea of assuming positive intent, it should be okay. If you really have, you know, as Kim Scott would say, radical candor, you know, short toes. And so I stole that, you know, from Hayden and have built upon that, this idea of like that accountability pressure to friction model should be celebrated. And how do we get there as fast as possible? And you can be hard on the work without having to be hard on the, on the person or team.

And say that one more time. Accountability to friction.

So accountability creates pressure. All right. Pressure creates friction. And we should get the friction as fast as possible around that idea, Kyle, that that's where the magic happens.

Okay. And so the, the short toes and assuming positive intent, are these your personal leadership principles? Or are these just like things that you talk about? Are these your team? I'm just trying to like fit them all into their—

Yeah. Well, and you're probably going to learn that like, this is the downside of reading a lot of books. You just steal from a lot of places. In fact, I get a lot of shit for, you know, people are like, you're just talking like one-liners. And I'm like, yeah, but there's so many of them. All of these are adaptations of just things that I've been able to get excited about and like strong conviction and belief in and then run with. But I'll give you my 4 leadership principles.

Yeah, I was just about to ask. Yeah.

Yeah. I mean, I think they're relevant, you know, potentially in any function, but like they really show up for me in the revenue org. And so the first one is this idea, you have to hire the best people possible, period. And like even also understanding that like bad hires will happen, but like sitting on them is not okay. And that would be like the first layer of defense for an organization. You promote what you permit. And I think having a lot of both rigor and conviction, and that includes the range versus just functional experience, but you gotta hire the best people possible, period, as a part of that. And hiring for, you know, the team, not necessarily just the role. This, the second one, Kyle, would be around this idea of you gotta provide absolute clarity of like where we're going and why. And that shows up in the company, you know, obviously mission and vision, but that also shows up in the jobs to be done of whatever function that you're leading. And there should be like absolute clarity on where we're going and why. And that is communicated daily, you know, through whatever medium that you have because I think Lack of clarity is probably one of the biggest withholds of company performance. And the bigger you get, the harder it is. And you have to constantly prioritize. Like, if you chase two rabbits, you won't catch either one of them. And so like, how do you order those things to be effective, not just efficient, but like absolute clarity of where we're going and what. The third one would be around this idea of like, you have to give everyone all the tools and resources to be successful. And what I mean by that, that's not just in bloating your rev tech stack even more. There are frameworks, they are operating principles, they're cadences, they're training and development, like all, there are a ton of things. And you have to have your ear to the ground constantly looking for like, where can we continue to invest in our teams? And so tools and resources isn't necessarily just about technology, but it's just like this idea of constantly developing and resourcing your team to be successful. And then the last one, and it's the hardest one for me personally, and something that I strive for and I get a lot of feedback on is, is number 4, Kyle, you got to stay out of their way. And so like, let me think about if you hire the best people possible, period, provide absolute clarity of where we're going and why, give them all the tools and resources they need to be successful. Then get out of their way. And I feel like that is where my journey continues of just trying to continue to push both accountability and empowerment down and making sure that I am not the bottleneck on it. Yeah.

And so there's a lot of conflicting discourse on this principle because And this goes back to some of the founder mode noise, but Toby Lukey has talked about this and I stole his sort of like micro coaching framework. It's like not micromanagement if you have more context, more understanding than anybody else, like you need to be involved in things. And this comes back to task relevant maturity from Andy Grove and high output management. How do you, what are you doing tactically to balance that? Like, how do you know where to get involved versus where to let people run? How are you doing that?

So for me, like, I think all of those methodology core beliefs or frameworks are relevant, but for me, it shows up in the stage of the organization. And I, If you think about, you shared your mission earlier of obviously helping small businesses win, like, you know, G2 is also a David and Goliath story. We have entrepreneurs all over our platform and they're using their customer voice to compete and win. And a lot of them are in their zero to 10 story or journey. I'd be the first to tell you that I would not be an effective leader at that probably stage of organization because I spend a lot more time in systems thinking. I would say reward and recognition systems, processes, and like things that scale as a result of a machine. And so, and if I think about that, like in my job to be done, I'm just trying to figure out how we can do the same thing and not just like in a, you know, predictable revenue model, but in a situation that will scale globally across tens of thousands of customers. And in order to do that, I can't, I can't have other than focusing on who does what and making sure that we have the right, I would say, capabilities, you know, kind of on the team. Like, I, I just don't think I would be effective if I had to not micromanage or microcoach, But I just, I think based on the stage of the company, the playbook may change, but that's one person's opinion. Yeah.

Okay. Interesting. And so I want to come back to this idea of team one alignment. And so I saw that you posted on LinkedIn, you were with your team one recently, and you made reference to Lencioni, who I love. What are you, what else are you doing? What else are you doing to drive team one alignment outside of what we've already covered? What are the other principles? I'm assuming that also strategic planning is one of them and we'll get into that, but what are the other big tools for you?

Yeah, I mean, I think it's in this like, you know, this, this like T approach in my mind of like, I need to be like super deep in the revenue organization kind of functional expertise, but if I want to build relationships, and I really want to connect with my peers, I need to know more and learn as much as I can about what they're doing. And even outside of the personal motivations and kind of communication styles, but like really how their organizations are also in service of the customer. And so thinking about their own assembly lines, thinking about their own kind of core functions and not a know-it-all by any means, but like, I feel like I can drive relevance and kind of connect the dots if I'm a student of kind of all of these things. And I try to reciprocate and not just provide a readout on revenue, but like details of why we are doing these certain things and like why it shows up and specifically where we need our HR team involved or like our finance team is super close to the customer. That's a huge— that's a major superpower for us because they, you know, they when you think about prioritization and planning, like it's not just the revenue team asking for things like, you know, we've got voices all around the place of like, what else could we do in service of our customers regardless of the function? And so I spend a lot of time just trying to like learn what's important to them so that I can be relevant in building those relationships. And I probably spend more than 50% of my time in that team kind of cross-functionally, which is challenging. And I probably, I would say a large portion of the other part of the time is just in front of the customer versus being in the like day-to-day operations of the business outside of like core things like forecasting and board meetings and, you know, planning sessions and things like that. But I tend to over-index there because I feel like if you don't get it right in that room, it just all falls apart down the organization.

So building relationships and sort of a deep empathy and understanding is the big principle, values and principles alignment, which we talked about, collaborative planning. Any other major team one alignment building things that you put in that list?

We invest a lot in conscious leadership here at G2, and there's a ton of different frameworks. Table Group and the Valencia teams have a great model here as well, but using using some sort of external both resource and coach to help facilitate connection. I've done it at both, both at Upwork as well as G2, and I really feel like that is such an asset to that organization to have both tools, a framework, and potentially external help facilitate a lot of that journey because it allows you to get strong connection and get to that friction stuff. It gives you a framework to get to friction so that when you get to planning, like, you know, these elephants in the room don't come out. Like, the elephants, you know, were taken care of earlier on.

Awesome. All right, let's jump to planning. This was super useful. These are great frameworks. So, Talk me through, let's start with annual planning. You're in the middle of it. We just presented last week to the board, so I'm deeply invested and imbued in this right now. So just walk through how you go about planning today, what that looks like for G2, and then we'll unpack some of the big lessons learned.

Yeah, I mean, I think, I don't know if there's any uniqueness to G2. And meaning that, like, you know, and we're evolving it even in this cycle as we've had a, you know, a lot of new leaders at the organization. So we have a new CFO, we have a new CRO, we have a new CMO as a part of this kind of planning cycle. And so as you can imagine, as you add new people to the team, that planning cycle will continue to evolve. And And, you know, we're obviously focused on, to your point earlier, around like what is that kind of long-range vision or plan for the organization? And then how are we backcasting or reverse engineering for what we want, you know, for the following year? And one of the things that we actually did this week, which I really appreciated, was even though we're in planning, we did a really thorough job and not really a postmortem, but evaluating like how are we currently doing on the plans? And, you know, I think a lot of organizations miss where it's like, all right, these are our OKRs for the year and now we're going to plan the new ones versus like really doing a strong postmortem or just reality therapy of like, well, what really worked and didn't work? And it doesn't mean that you shouldn't have the same plan the following year. Like there's probably some consistent themes that will always come through. But if your plan is completely changing every year, and I've seen this in organizations where, all right, these are the 5 things we're going to do the next year. Kyle, we're going to do these 5 things and actually we're going to do the next 5 things. Your customers are going to feel all of that. Your teams are going to feel all of that. And so trying to find a way to link the old to the new, but in the spirit of this long-range plan, I think is really important. And so we did a really big deep dive on how successful or unsuccessful we were in our current version and then making sure that we're bringing that learning or continuation into the, you know, kind of the next year planning cycle. It also starts a lot around this idea of like, who are we chasing? And so that we can prioritize resources across product, marketing, revenue, and service of those customers that we want to win or continue to serve. And so there's a lot of alignment up there. Like we spend a lot of time on like growth levers. And so, you know, we have this, you know, bigger horizon matrix of what we want to do. And but then zooming into next year, what are those going to be? And then you have got like your tops-down, bottoms-up assumptions that are in partnership with finance and revenue of like where you think, you know, closest to the pin could be. And then you look at like, you know, what are the financial goals of the organization? I think everyone's trying to increase durability and get to rule of 40 in a balanced way. And so, okay, well, let's figure out the containers, you know, kind of of those and like, what are the puts and takes, you know, that we need to look at? And it's more of a collaboration than a negotiation. I've been in the negotiation ones where everyone like comes in and like, this is all the things they could do and you'll fund any of them. And it's like the biggest waste of time and just like a morale killer for the organization. And so, but yeah, I would say, you know, this idea of like, we're keeping our mind on the Mercedes, but we need to get the Chevy out the door next year too. And, you know, thinking both long-term and short-term. But like having a really conscious effort of being reflective of like, well, how well did we do on the last one? And what is the continuation? Having the discipline to be like, well, that was a bad idea. We need to punt it. We need to stop doing that. The hardest one, and we haven't gotten there yet, but I would assume every organization is going to get there in their planning cycles. You got to get the trade-offs because you can't do everything. And so I think the next step before we do our You know, kind of next steps on the plan is like, all right, well, what's our stop-doing list at the same time? And those have always been the most challenging but rewarding conversations, I think, in planning.

Yeah, that makes a ton of sense. And so what's the starting point? So do you, when you're trying to come up with your big strategic themes for 2025, is that out of a 3-year plan that you've already architected? Is that from the CEO down, you know, really with the vision or what's the, what's the starting, the starting piece?

Yeah, I mean, I think it's somewhat nuanced by the organization and the stage of the organization. As you can imagine, you know, as Upwork, we were publicly traded, we had to be a little more short-term on certain things, you know, as a result, but it's still having a long-term vision. And, but I think it starts with, at least for us, it's like the jumping off point and, you know, understanding where are we going to end the year on a lot of these different, you know, growth levers that we had. And for us, you know, we run the kind of February or end of January to February calendar. And so we're in the middle of Q4. And while we have good telemetry, but we don't know exactly how it's going to end up, we're hopeful that we think know where that jumping off point is. And so there's some educated guessing based on our models of like where we're going to end. And that's kind of the jumping off point of like where we start, you know, kind of from planning. But then it does go back up to like, all right, who are we chasing? Like, where are the growth levers for next year and alignment around that? Then it's all right, prioritizing what teams are going to be invested in as a result. Some might get a lot, some might get zero, some might get less, you know, depending on, you know, whatever that strategy is. And then you break that up into your kind of measured methods and you break that up into inputs and outputs. And I mean, obviously there's some, you know, I would say governance around getting it approved and all those other things. But, and then it's, you know, month over month, week over week, quarter over quarter, learn, adapt. It's just like, how do we get the signal? You need to do more, do less, do something else.

Okay. What have been some of the biggest changes or learnings that you've made to annual planning specifically over the years? Where were the mistakes? What do you wish you had known? When you first started building large organizational annual plans?

I don't know if it was a mistake or a reality, meaning that like there's always going to be things you can't plan for. And I don't think that everyone's intentionally is like, do we have like an oh shit button in the plan? And I'll give you an example and one that I think Upwork navigated really well, but think about Upwork as a global provider of talent. And unfortunately, when the war in Ukraine started, which no one could forecast, we had a lot of talent on our platform that were working both in Ukraine, Russia, Belarus, and others. And based on sanctions and our own decisions, like, you know, we decided to do business differently in that region. But when you have tens of thousands of talent in that region and customers, and you have to make a material decision, you know, aligned with your values and like what you want to do. The whole like annual planning process in some ways kind of goes out the window. And I don't know, and we managed through that crisis and I think we're on the right side of all of those things. And one of my, you know, kind of proudest moments of being there. But the, I don't know if companies plan for that, meaning that like, do we have a, and I don't, it doesn't have to be like disaster recovery planning. I mean, obviously large organizations like you know, have a whole team for these things. But like a contingency plan, if it got a lot worse, what would we do? If it got a lot better, what would we do? And if it got, you know, sideways or we weren't making the progress that we wanted, what would we do? I think we set an annual plan. We're like, all right, let's go execute. But there's not a lot of agility baked in should things change. Like I think in conversations with other CROs like yourself, you know, maybe 6 months ago everyone was feeling some pain. I would say like 50% of the people I talk to are like, hey, things are actually improving. Like Q3 was better than we thought it would be. Q4 is building. And so like, how do we build some of that optimism in our plan? Yeah, yeah, yeah. And so my, I guess my, after my long rant there, Kyle, you can't have like a set it and forget it. There needs to be some flexibility and contingency planning on good, bad, or sideways. And I think that's where if you don't anticipate that, you're not ready to take advantage of it or get ahead of it.

Yeah. Yeah. We've done exactly this. We've built a financial model, which I'm pretty confident I can go beat. And there's an upside plan with some exciting product bets that we will only go tackle if we see ourselves with the same momentum coming out of Q1, Q2 that we have today. And if it is, then it's all gas because the venture market is heating up like crazy. We feel like we're in a really exciting direction, but we also don't want to build a plan that is the full send plan. We want to build a plan that leaves us some wiggle room for unforeseens going wrong and then some further unlocks if things keep going the way that they're going. And so that brings me to another question, which is how often do you go back to your annual plans? Like, what's the process to then actually make sure these things are happening quarter to quarter, month to month? Do you have a review cycle? Are these like, how do you operationalize it throughout the year?

Yeah. So as I mentioned a couple of times with the V2 model, we've got 5 I would say overarching, you know, kind of methods throughout the organization. And so there's a lot of different cadences and some of them are cross-functional. We elect, you know, stealing from both Netflix and Amazon, this idea of like a single-threaded informed captain, you know, for all these V2 models. They have a cross-functional team, you know, that's obviously working together on these things.

Each method has a, as a single-threaded owner.

Correct. Correct.

Nice.

And usually you could say that that, you know, is like they have the most surface area of that problem, but sometimes not. You know, sometimes it's another leader of the organization that is stepping up, you know, to better help, you know, kind of, I would say, cross-functionally align around it. And they have a number of different cadences, you know, as a part of that. I think we do a decent job of communication, both on a monthly, quarterly basis of like how all of our both measures and metrics are adding up. You know, we had our all hands actually today here in Chicago. And one of the parts of that every month is we kind of go through the V2 model performance and we try to pick out some stories of things that are going well, things that are not going well, and what are we doing on it. And then we do, I would say, more probably more like a QBR format, you would think, but every month the cross-functional team that is assigned to, you know, to that method will come in and do a deeper dive with the senior leadership team, all the folks that are on their team. And it's not scorecarding or report cards like those are like set in advance. This is more around the risks, dependencies. Where are we stuck? Where do we need to move? What did we learn? What do we want to do differently? And I would say those have gotten more collaborative in nature versus a readout. You can just— you could send the readout.

Yeah, yeah. Write it and read it.

Discussion-based. That's right. And then as a senior leadership team, as I mentioned, I don't know if we were on recording or not, but we do these sync weeks. So we get together like a month and the V2MOM review is a big part of that. We have a couple of offsites a year. V2MOM is a big part of that. And it's, if you believe in this idea of like what gets talked about gets done or like what gets measured gets managed, like we try to vote with our our wallet, our time wallets in that way.

Right. Yeah. You were talking about Sync Week before we recorded, so maybe just give some more— unpack that a little bit. Like, what does Sync Week do? What do you build around it? Would love to share more with the audience there.

Yeah. So if you think about G2 today, we've got, you know, close to 600 employees globally, and we have some hubs in places like Chicago, London, Bangalore, but we also have a distributed team. Around the world and we maximize our hybrid environment. There are some teams that are, I would say, more co-located in hubs, but we have this distributed model as well. And as a leadership team, we decided we were going to get together for 3 days every month to spend time together. And we realized that in addition to the, I would say, distributed cadences that we had or virtual cadences, like it really allowed us to like move the needle quickly. And be a lot more collaborative. And so we said, or at least in revenue, we said, hey, why don't we do that in the revenue organization as well? And so one week of every month, we invite everybody that's local to Chicago. We don't have everyone fly in for it, but a lot of our team members in revenue are pretty close to Chicago. And so we have them come in and we try to Tuesday, Wednesday, Thursday. And so we try to do all of the one-to-many experiences that same week. And so we'll have our all-hands. We're doing a ton of, I would say, sales process stage and like med fit qualification work right now with our sales team. And so we try to stage all of those experiences, you know, kind of live. We have a customer event, you know, here. We'll have 30 customers that are doing kind of a product adoption session this afternoon. We've got partners that have flown in and the leadership team's taking them to dinner this evening. And so we try to like jam it all in. To create some energy and excitement and maximize— it will be distributed, but one week a month we're going to be as collaborative as possible. And we're a couple of months in and we're excited about the results so far.

Nice. And so that's your revenue leadership team all the way down to ICs. Every— most, most people come into Chicago for those couple of days.

For the ones that are local, we're not asking folks to fly unless their team is, you know, has a meaningful reason for them to come in and do that, and they'll use their, you know, T&E budgets to pull that through. We're not against it by any means, but we're just trying to maximize both. I think with all the noise with return to office and all these things, like we're just trying to be very transparent up front of like, we're just going to try and do both. We're going to maximize, you know, this distributed model, but then we're also going to recognize and celebrate these, you know, in-together or together experiences when we can.

Yeah, we're going through the same thing right now. I'm in our new San Francisco office. We've been 100% remote the entire company's history and we're thinking through what are the ways to take all of the benefits of being remote. Like, I think we are as a company staying remote in our foundation and then layering on enough in-person connectivity to go faster in a bunch of ways. And so that means a commitment to writing and documentation, a commitment to the remote digital experience being just as good as the in-person experience. Not over-orienting to having people in person that don't need that level of collaboration. It's a tricky needle to thread for sure, but clearly people need to come together. I'm here for a product offsite this week and it's just magic, like secret hackathon projects and the energy. There is some place for it.

I put it in this. My dad used to always say, Eric, you can't walk and chew gum. Like he would pick on me with this. Like, you got to be able to walk and chew gum. And there are so many and opportunities, I think, in business, but everyone's like polarized in their ors. Well, it's either this or it's that. And I'm like, yeah, but there's so much magic in the and. And I think the distributed work is like, great, like, let's maximize both. You know, as a part of that, you don't have to be all in on one side, but be flexible. Be agile and kind of celebrate the opportunities in both versus I think similar to most things, people are dug in on one side versus maybe thinking about, no, it's an and play. Yeah.

For sort of bizarre moral reasons, it seems like people have taken a, there's a religious fervor to in-person versus remote. And clearly there's lots of benefits to either, and different working models make sense in company stage. Yeah, the fastest way that I pass judgment on somebody when I see their writing on LinkedIn is just binary thinking and absolute conviction in things because there's just so much nuance in the world.

We get that question a lot of like, well, what are you doing with the sales team? And I'm like, well, it kind of doesn't matter. You need to do what's best for you. And all of these other things are just data inputs that you can use, but like, it's a nuanced answer and it depends on your company, your culture, your go-to-market, all those things. And like, I don't think that's something you just want to copycat. You need to be intentional in how you think about it.

Yeah, makes a ton of sense. All right, last question before we move to our lightning round. So you've got these cadences sort of monthly and quarterly to review the plan, to track progress. At what point do you make change? Like, what is the point where you say this plan is no longer connected to the reality of the market today, or just like it was the wrong idea? And how do you refactor on the go?

So I think this is the I think the real opportunity for organizations, and like G2, we're trying to navigate through it as well, because if, as I mentioned before, if you're really aligned on the measures and like, I'll give you an example, like, you know, one of the things we're trying to do is increase customer ROI to obviously reduce churn in the business. Like a lot of organizations are thinking through this. The team should feel empowered. As long as it's in that container of our core values, as well as it's, you know, things that are two-way doors versus a one-way door, they should be empowered to like be very agile and test and learn as fast as possible. There are going to be some core bets that they're going to make, you know, that takes more instrumentation and alignment. But like, we don't want to get in the way of them trying to figure out how to move that metric for themselves. And so in some ways it should constantly be evolving based on what that signal is. And different teams are going to get different signals as a part of that. And so I would say that the expectation is, is that you should be entrepreneurial, which is one of our core values, and how you're attacking that problem all the time. And we'll celebrate that even if it's a failed plot. I would say the bigger swings that are, say, more systems thinking about how we're doing, you know, different things as an organization, especially if they're aligned across product, marketing, and revenue. I would say quarterly is probably our current cadence of that because we've got enough runway to understand signal that if we want to continue and stay the course or if we want to pivot or if we want to double down in certain areas. But our hope would be is that the teams that are responsible for the how are constantly trying new things. And that's one of the reasons I love being in go-to-market. Yeah, we have tools and processes and obviously we partner with product and marketing, but We can be so creative in how we both communicate, how we like structure certain things, the cases we want to run with our customers, the messaging. And so we should be, we should be changing it up all the time.

Nice. Awesome. Okay, quickfire round and then we'll wrap it up. What do you think separates a truly exceptional, great, best-in-class CRO from just like run-of-the-mill?

The ones that I learned the most from have this like commitment to constantly stretching themselves and learning. I remember, you know, the conversation that we had, you know, maybe a month and a half ago when we were talking about this podcast. There were a number of takeaways I had in that call, and I can see just in my interactions with you and how you show up in LinkedIn and like some of the voices and things that you obviously, you know, had on this podcast. Like you have this like deep commitment to constantly stretching yourself and like taking in application of new things. And you don't think of your— you're probably constantly expanding your network and constantly looking for like, how do I like feed my mind good stuff and like soak up new things that you can steal and apply. And very, just as much external as you are probably internally focused. And that might seem like a chore or like a, how do I get started?

Or—

I love it.

I have a blast doing it.

Yeah. Or, hey, am I really going to be the most effective? And I'm like, yeah, but if you're not constantly taking like outside-in thinking, like you're not growing as an organization either. Like, and so I feel like the people that I learned the most from and where I've had the biggest ahas is like, you got to get out. Everyone's going through the same thing. It might be a little nuanced and different, but like, we're all more alike than different. And I feel like the best leaders have a commitment to like growing their, not just network, but experiences and learning just as much outside of the walls as they do inside their corporate walls.

Yeah. And I've learned so much from other facets of the world, like learning from product leaders and engineering folks and learning a ton about marketing, like, you know, that. I think, I don't know if you referenced the book directly, but David Epstein's Range. Yeah, it's, it's, there's so much truth there.

Well, it's another one of those, it's another one of those and stories. Like you can do 10,000 hours like the Tiger Woods approach, or you can be Roger Federer. Like both can, both can be true.

Yeah. Toby Luque from Shopify used to say being T-shaped. So what is the deep part of your T? What do you have those 10,000, 20,000, 50,000 hours at? And then how do you develop breadth? I think is a big piece of it. What is the most common advice you find yourself giving to your leaders or mentees, people you're taking into your team? What do you find yourself going back to the most?

I spend a lot of time, and this is like an Amazon steal, but I spend a lot of time on like, what are your own input metrics regardless of your role? Understanding that our biggest competitor is time. And like, you know, choosing to do one thing means we're explicitly, hopefully choosing not to do something else. And if you don't understand like what that mile marker of signal is, like you end up like getting off track and you go through these course corrections that are, that are that are challenging and they're hard. And so regardless of your role, like what are the input metrics? Everything's a funnel, I think, in business. And so like what are the input metrics to just like give you confidence or conviction that you're on or off track? And getting it wrong is okay, meaning like these losses in altitude are going to happen. It's all about how you react and what you learn, you know, kind of forward from that. But I spent a lot of time on that in the revenue org, like Probably too much. But it's, as you can imagine, like, especially with a seller or team, I'm like, all right, let's pull up the inbound metrics because I can actually go back 67 days ago and tell you like when you got off track. In fact, one of our top sellers, you know, she's hit 100% of her plan in October for the year and you can see it. It's just starting to fall off and I'm like, don't do it. Like, don't do it. Like, you're, you're in, you're in accelerator dollars and you're going to hate it come February. Like, you got to fill that funnel.

So yeah, yeah, that is such a good one. What's the hardest lesson you've had to learn in your career?

There's a bunch. And it's probably around that you may have heard me say earlier, like the only thing difficult about difficult conversations is not having them. And I would say all of the big things that I've learned from or like failures along the way, I talk a lot about these ideas like losses in altitude. You saw them coming. If you had to do them over again, you would have done it all faster. And, uh, oh yeah, and that's hard. Even like the really hard decisions, um, you probably would have made faster. Um, yeah, but it's, it's not procrastination, it's, it's not like lack of self-awareness. Um, I think we're just human and, uh, hard things are hard.

Mhm, for sure. Last question. I'm particularly excited to ask you this one. What's the best thing you've read in the last 12 months?

Oh man. I finished it last weekend. So I'm a big Seth Godin fan. And so if you go back to—

I saw you post this.

Or All Marketers Are Liars, Linchpin, whatever. But he actually wrote this book called Small Is the New Big, but that's another good one. But this last one he wrote is called This Is Strategy, and it's like 293 appetizers, meaning like all these little good nuggets on a menu that it's just like rapid ideation in my mind. And like, I just, it was one of those like 250 pages done in 2 hours, didn't stop and probably came up with like 10 good ideas. And it was just rapid fire, like ideas. And it was excellent. Now I actually thought it was great for planning based on like where we're at, like in the stage of the year. It was great. He's fantastic at those.

He's good. The Dip is in our owner book bar. It's one that we recommend a ton. I like Seth Godin. I haven't read nearly as many as you have, but yeah, he's definitely a man. Is he just like a different thinker? You read those books, you're like, I just wish I could have this level of creativity and insight.

Well, and it's like his simplicity is so elegant. You know, another one to your point on cross-functional partnership, I'm also reading Marty Cagan's new one, Transformed. As we continue to strengthen—

I'm a big Cagan guy though.

Yeah, like Empowered was really good and our teams have done some sessions with them, but as I'm trying to like strengthen my relationship and understanding with our product partners, but I'm excited.

Awesome.

Learn a little bit more about why they why they hate dates. But I need to learn if I want to, you know, obviously build partnerships.

So, yeah. Awesome. Eric, this was great. I learned a ton. I think people are going to learn an immense amount from this recording. I have a bunch of quotes that I'm going to forget to credit you for, so I apologize in advance, but—

Well, you can't credit me for them because I stole them from someone else.

Yeah, there you go.

Yeah. Yeah.

Where can people find you? Where people want to hear more from you, what's the best place to get more?

Yeah, I would say I'm most active on LinkedIn and so, you know, pretty responsive on direct messages there. And, you know, if you're in the SaaS community, I'm probably coming your way anyway because you're a G2 customer or prospect. And so thank you in advance for the time. And it was great to connect with you and how we're helping, you know, owner.com as well. So.

This is awesome. Uh, appreciate it. And, uh, thanks again for coming on. Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe, and you can find a link in the show notes. And be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.