E53: Sales Capacity Planning That Doesn't Suck (Jenny Dingus, SVP Global Sales @ Clio)

Jenny Dingess is SVP Global Sales at Clio, which recently raised $900 million at a $3 billion valuation.

When you're playing brand new in a space, you have to be prepared to have every single assumption busted.

She shares how she's pushing back against lazy thinking.

I had an executive just look at me and say, yeah, it's easy. People times quota, and that's going to give you growth. I was like, what? That's not how it works.

Jenny gets into the ups and downs of moving fast.

We're all excited, and then we realize the work we're going to have to do and the short amount of time we're doing it, and then we all get a little bit nauseous and then we figure it out.

And she shares what underpins effective communication.

More important than repeating it, people have to feel it. They can't just hear it. They have to really feel the impact of whatever it is you're trying to communicate to them.

We cover a lot of bases, have a lot of fun, and she shares all the goods.

I think what you're describing is the difference between good companies and great companies.

And the great companies are the companies that have well- Welcome to the Revenue Leadership Podcast. Today's guest is Jenny Dingess, who is the SVP of Global Sales at Clio. And for the uninitiated, Clio is the global leader in legal AI technology, and they raised a $900 million Series F, uh, a few quarters ago at a $3 billion valuation. And Jenny has led sales there since mid-2022 after a decade at RingCentral. from rep all the way through to senior sales leader. Uh, and today's show is gonna be a fun one because we are gonna talk about the death of linear capacity planning, a topic that I feel very strongly about. Uh, so I'm excited to dig, dig in. How should we think about, uh, capacity planning and rolling up to the number? Uh, Clio has also gone through a major acquisition recently, and so we're gonna talk about planning in the face of acquisitions, and I'd love to unpack a whole bunch of that. So, Excited for this one and thanks for joining.

Yeah, thank you for having me, Kyle Norton. It's great to be here.

Yeah, this is going to be fun. So I gave folks a little intro, but what else did I miss in terms of your career arc that people should know?

Well, I was at RingCentral for a little over a decade and, well, ironically, that could feel very linear. I had a super nonlinear path there, so I led everything from sales to cross-sell and expansion sales to retention. I was there during COVID so I, I gained a lot of experience across the lifecycle at RingCentral, and now here I am at Clio, moving from a horizontal product like RingCentral to a vertical product like Clio that just sells into legal organizations and law firms.

How different is that from a planning and strategy perspective? Was that a pretty tough change to make being in VSaaS after like a very, very horizontal product like RingCentral?

It's interesting. In some ways it makes it easier because you know your market and you can be maniacally focused on how you provide the most value to that market. But the counter is it's limited, right? Your TAM is your TAM. It's not like we've got explosive growth in, um, the, you know, practice of law and, you know, we don't have exponential, um, new volume of lawyers hitting the market every year. So, um, it's that balance. And for us at Clio, I think it's really important for us not only to look at the market that we have today, but to think about how we can create market opportunities by, um, helping to close the access to justice gap. So just— I, I realize that we're not talking about Clio here, but I think it's important to know that Almost three-quarters of legal matters in North America alone go unserviced. And so, anytime we can make lawyers more efficient, they can actually have more capacity to take on more caseload. And that's a really big opportunity that we have, not only to increase our market and our growth and all the things that we're looking to from, you know, a high-growth organization. Perspective, but also to do meaningful work in the area of law.

Yeah, that makes sense. Yeah, the verticals, I mean, I'm in the same world, vertical SaaS. And so the name of the game is after you get that market penetration, how do you continue to take wallet share and offer more value and really get deeper? And it's funny in our world, which means all of restaurant tech tends to converge on like a similar product portfolio, whether you're Toast coming online or DoorDash trying to go first party or, or us doing a bunch of different things. And I think we're seeing the same thing in legal tech now with the, the, you know, emerging AI players and you guys as the winning incumbent and some of the legacy tech, like the, the, the, uh, the battle is fierce for sure.

Yeah, it's fierce, but it's also so exciting because this market has been traditionally underinvested in. And the reason why why you're seeing investment all of a sudden pour into this particular industry is because it's ripe for disruption. And like the model of the billable hour just feels so legacy and, um, not customer-centric. And, um, all of this technology has the opportunity to change the way that lawyers not only run their law firms, but service their clients more effectively with more transparency and It's a pretty cool opportunity to be a part of.

Yeah. Yeah. It's interesting. You, you guys are getting a, a second tailwind because I mean, I know a bunch of early Clio folks and it was all about convincing people to use software, which is such a different pitch than why, why your software is better than, than the rest. And it seems like not all of the market, but a lot of the market has now gotten comfortable with technology and now there's this second big move within this market with AI, which is, I, I would imagine a tailwind for you guys because the, the openness to change is probably getting better or, or not.

Yes and no. We definitely have some very eager early adopters in our market that are bullish on AI, but you have to remember lawyers are trained to be skeptics.

Yeah, and son of a lawyer, so I'm very familiar with how— how—

daughter of a lawyer.

Yeah, yeah, yeah.

It's so like they're looking at all the reasons why it's unsafe, it's insecure, it's gonna, you know, get them disbarred. So there's a ton of risk associated with AI and, um, being a lawyer. And so part of our mission is to educate them, understand why our solutions are safe and secure, and really just make it more accessible. And we're trying to be a part of change management journey versus assuming that everybody's going to get on board and realizing it might actually take more time in this market than it might in other more technology-forward markets.

Makes sense. Here's a familiar scene. A deal's in commit and the buyer says, can I talk to somebody like me? Next thing you know, sales reps are asking CSMs after hours. 5 people are in Slack trying to remember who helped last time. And that one customer who always says yes is getting burned out after 3 requests in a week. That's why this episode's brought to you by User Evidence, the platform that turns customer proof from chaos into a repeatable GTM system. With advocates, references, and real customer evidence all in one place, your team can share credible proof instantly and keep deals moving forward instead of stalling. Companies like Gong, Ramp, and Workato already use User Evidence to capture customer proof, build buyer confidence, and shorten sales cycles. See how at userevidence.com. That's userevidence.com. Okay, so let's crack into our topic du jour, which is one that I, uh, enjoy, and I've actually been looking for somebody to, to speak about on the pod, so I'm looking forward to it. And so in our prep, you were vocal that the people times quota model is broken. So the spreadsheet of like number of account executives times quota allocated equals our revenue growth for the year, which is the sort of traditional SaaS playbook that everybody's been running. So unpack that for folks. Like, why is the people times quota model broken in your mind?

Yeah, so I remember very vividly a moment at my last company where I had an executive just look at me and say, yeah, it's easy, people times quota, and that's going to give you growth. I was like, what? That's not how it works. You need pipeline, you need to have market opportunity, you need to have so many other inputs to make sure that your sales team can be successful. Look, we, we add headcount at Clio all the time. We're a super high growth organization and I certainly raise quotas, so I don't want my sales team to listen to this and think that I'm not, um, a proponent of raising quotas when it's the right time. Mm-hmm. But having a growth strategy that is focused on headcount alone and just like that brute force is not a sustainable way to drive hypergrowth. And rather, you have to have a more integrated planning process. You have to think about product, you have to think about what emerging markets you can go into, you have to think about all these other things. And then your sales headcount and your quota should be a byproduct of that strategic work versus, uh, making sales kind of the, the only thing that you're hinging your, your growth trajectory on.

Why do you think this? Because it seems obvious to me, like I, I have the same opinion that, that like it's, it's, it is, you need the right headcount to have the capacity to hit the number if you have the pipeline. But why do you think almost every growth spreadsheet for startups and scale-ups still is like rev— the revenue cell is equals Rep cell times quota cell. Like, why do we do this?

Because it's easy to input on a spreadsheet, maybe. Um, you know, I think, look, you have to understand a plan is a plan and you have to have all the different inputs of the plan to make sure that, you know, whatever you're chasing that following year is, is at least in reach. But I, unfortunately think that the functions that are at the center of the planning exercise are not the ones that are operating all of the time and, um, maybe don't even have the context of what it's like to be in a salesperson's shoes. And I think we just get caught in this trap because it's simple, but the reality is it's a lot more dynamic than that. And you've got to have a more multifaceted approach to the way you think about your plan. And it's not all on sales, it's on everybody to drive revenue growth.

Mm-hmm. Yeah, that is my assumption as well. It's just easy. Like it's, it's difficult to build a plan that is built from, okay, these are our channels and these, this is the probability of delivering this number of leads and this is the input and the kick. Okay, now we have these inputs and we need this. Capacity as an output, that's a very cumbersome and difficult and much murkier. It's uncomfortably murky, which is why if you're a finance person and, you know, you, you view the world through a spreadsheet, it's much easier to say like, all right, it's reps times quota. That's how we get to the number. So just hire the reps and, um, you know, I think it will suffocate the other functions in the process, right? Yeah. Yeah. And you know, most most people who have been around the block, you know, can, can take that financial model and then know what they need to do on the back of it. But I think this is one of the, the least kind things we do to first-time VPs of sales is we give them this plan and we, you know, their mindset is like, all right, I just gotta go hire the reps. And then you're, you know, two quarters in and you realize you're up against it. All right, let's get into Uh, what do you think the alternative is? Like, how should people approach planning in a way that gives them a much higher fidelity output and, uh, and roadmap to deliver the number?

Yes, I think you have to start by understanding your market and what you're going to be delivering to your market the following year. And so, um, in Clio's case, like I said, we're in a vertical market, uh, but we launched a ton of new products. This year. And, uh, you mentioned our acquisition. We just acquired a— or we're in the process, I'm sorry, of acquiring a company called VLAX, and that will close imminently. Um, but we are not only adding AI products, but we are going from traditionally being in the business of law, like how lawyers run their law firm, to also expanding our market to support the practice of law. So technology like AI-powered legal research. And that's a really profound shift in our business. And so we are really thinking through how we plan for next year, knowing that all of this is brand new. We've got a ton of assumptions we have to make about our ability to, um, penetrate these different markets. And, um, also like what, what our customer feedback's going to be. So For, for us, what we're doing right now is we're actually not planning for an entire fiscal year. We're planning for Q1. And I'm so proud of us as a team that we're making the decision just to plan for one quarter because it's gonna give us the opportunity to collect enough data where we can make an informed decision on the plan for the rest of FY26. By doing that, we're not, we're not over-hiring, we're not going to raise quotas to the point where they're unsustainable and unreachable. We're, we want to make sure that this really exciting moment that we're experiencing as a business is one that we're grounding the entire business in and we're not getting overly aggressive about what we think we can do. But we also know we're going to do a lot of great things.

Yeah. Yeah, that makes sense. Even the quota, the quota comment is interesting because nothing will take the life out of a business or the air out of a business than like quotas that nobody can hit. And so it's like, we've acquired this company, it's awesome. Your quota's up by 50%. And now I'm not excited about having new products because it feels like it's like, oh, like, nah, nah, it hasn't done anything versus an approach that I've consistently taken or tried to take when we're doing new things is like give somebody a number they can go beat and build a winning, like build winning momentum and then grow quotas on the back of it. It's an under— I feel like for us it's been an underrated contributor to like momentum and a culture of winning and honestly like employee retention and attraction. Cause you know, like people feel like they've got a number that they can—

Yeah. The worst thing you can do is have a moment where the company is celebrating and sales feels like they're not. Uh, it's like, like, talk about just completely like ruining the momentum of what should be a catalyst to your business. And we, um, are taking a more conservative approach, but, but quotas will go up. And here's the thing, when we raise quotas, we're going to be really transparent as to why. And we're going to explain to them the path to getting there. Like what, what are the, what's your path to quota and what are the effective sellers going to be doing to ensure that they can ladder their way into that number?

Yeah, for sure. So coming back to like the alternative, you mentioned like an integrated planning approach. So as people think about 2026, we're, we're in it right now, uh, for almost everybody that I, that I speak with on calendar year. How should folks think about, about laddering up to the number? Because ultimately, like, we get a number given to us, or collectively we, we sort of say, all right, we're gonna 2x next year, and then sales at the revenue org has to go figure out, like, what's the path. Um, so how do you, how do you navigate that part of planning?

Yeah, so, um, as I mentioned, we launched a new pro— or a bunch of new products, and what we're first doing is we're building in assumptions around what we think— how we think these products are going to attach, not only for new logos that we bring on but for our growing base of existing customers. So that's the first thing. What do we think these products— what's the interest going to be from our market and how are they going to attach? Then there's a huge body of work around monetization strategy. I think monetization is one of those functions which I don't run, and I'm not a monetization expert, but fortunately have incredible marketing partners and an incredible monetization partner who is helping us think through like, how do we make sure that we can balance market penetration and capturing as much revenue as possible from the launch of these new products? And then also as part of monetization is, is opportunities to price increase, right? Like we might introduce a product at an introductory price, and then as soon as we get the traction we're looking for, uh, we'll evaluate whether or not that pricing model is the right place to be long-term. So we've gotta have monetization as a big part of this because you can't back into quotas until you understand what your possible ASP or ARPA is gonna be.

Mm-hmm.

In addition to monetization strategy, we work closely with marketing to talk about what the pipeline picture is going to look like next year. Because you can have as many sellers as you want, but if you don't fuel them with pipeline from not only inbound marketing, but from your BDR organization, from channel partners, etc., then you're going to have a bunch of salespeople sitting on their hands looking for another job, right? That's not where we want them to be. That's not how we're planning on investing in our sales talent. So. Uh, we spend a lot of time collaborating with marketing to ensure that we've got a full left-to-right plan across all of our segments that has a chance at supporting the headcount we have today. And then as soon as we realize that there's opportunity above and beyond what our BAU would be, that's when we start to layer on what are those incremental swings that we want to invest in that would then require additional headcount and sales and then the other functions as well.

Cool. So, so if I zoom out, instead of going quota times reps equal revenue output, you're saying, all right, start with all of the levers. Some of it is, some of it is more reps, more quota. Some of it is how do we move the ACV for net new reps. Some of it is expansion through either like seats or pricing or like other monetization levers. That's like basket 1 is all the levers, like what are all the things we can pull on. Then step 2 is pipeline, and then you're going like channel by channel. Are those the like 2 main revenue planning levers and revenue planning pillars, or is there anything else that somebody needs to think through there?

Um, I, there's probably a third bucket of what are, what are the emerging markets that we're going to be kind of introducing net new. Uh, and that might be segment. For example, we're launching an enterprise segment next year, or we actually just launched it. Um, and it's going to be kind of its own fully functioning department. Um, Or it might be a geography, right? So we recently launched in— we've got an EMEA team, we've launched in APAC, we've got a dedicated team for Canada. And so going more global is definitely a huge lever, but it's, it's how do you kind of layer on those additional growth, um, growth vectors that are not currently being realized in the plan today.

And at what point do you bake that into a plan. Because I think where a lot of companies go wrong is they have this, this like super speculative thing, new product, new market, whatever it is. They're like, oh, that'll be like a $10 million revenue line next year, $50 million. And then, you know, you, you have so little, uh, fidelity because it's, it's like something new that it's like, oh, it wasn't $50, it's, it's $15. And then all a sudden you're trying to clean up a, a $35 million gap in your plan. At, at what point, like how much do you allocate of your revenue target to that? At what confidence level? Like how do you, how do you think about it?

Our philosophy, well, we've done, we've done it wrong before, so, so we've definitely, you know, made assumptions that were way off on, on new product launches and stuff. But, uh, in general, I would say we've learned from those mistakes and we tend to have a more conservative approach. We bake bake them into the plan, but we bake them in conservatively, and then we consider them as upside to the plan and potential ways that we can de-risk other parts of the plan that start to surface throughout the, the year. Then once we have a year's worth of data and we can see how it performed and where we want to double down, that's when we'll start to get a bit more aggressive in terms of the, the targets and assumptions we build around some of those newer parts of the business.

Yeah. Will you replan halfway through the year and say, okay, these are— these bets are winning, these bets are You know, like not performing and, and we're, we're gonna reallocate or you ride it out.

It depends on the year. We've definitely done reforecast, but it's not something we're in the habit of doing. I would say we're, there's not a lot of appetite here at Clio for us to complain about our targets. I think everybody very much understands we're a part of a high-growth organization with aggressive goals, and you're here because you're an expert and we expect you to figure out how to get to, uh, these goals with us. But, but if we are way off, there's, there's the area to have that conversation and there's empathy to the sales team, um, when we need it. And I do feel very supported in any opportunities that we, we might need to look at it. But in general, it's, it's not something we are in the habit of doing very often.

Yeah, certainly not at your stage. In the hundreds of millions of ARR, it's a little different. We're a few stages behind as sort of late Series C and we'll replan almost every quarter at this point because there's certain things that are emerging winners and we say actually we want to put more energy and resources to it, but it's got to carry more of the number then. And so it's like pretty dynamic, but I'm sure that'll evolve as the rigor strengthens as we get bigger. So you mentioned you've got a bunch of these bets and you're planning conservatively and then there's upside. Is there a specific amount that you're trying to overallocate to? If you've got a few emerging things, do you scope and size it and say, you know, there's a probability here of X, so let's make sure that we think all of these bets cumulatively can give us, you know, 20%, 50% more coverage on the number?

Definitely. So I mentioned that with this acquisition we're in the process of making, we're going from not only servicing the business of law, but the practice of law, which in a lot of ways means that we're We're accessing a whole new share of wallet within law firms that we did not historically have access to. And one of the, the things we're debating a lot internally is what that demand's really gonna look like. Mm-hmm. And making sure that we're in a position to capture that demand, because the worst thing we can do is have a product launch like the one we just did and have all this interest flooding in and not have the manpower to catch it, right? That would be such a missed opportunity, right? And so definitely we levered into headcount planning in some of the segments where we were expecting more of that demand, knowing that we might be overshooting a little bit. However, we're growing enough in the other parts of our business that if we overhire in certain parts of the sales team, there are plenty of other places we can allocate resources. So we don't get into like the danger zone of talking about reductions. But yeah, definitely we're, we're making some big assumptions and ensuring that we've got the manpower to support it.

Yeah, that's the beauty of being in a high-growth organization. You do get so much more margin for error, like in our business, you know, emerging, emerging pipeline channels and the last 6 to 9 months, well, basically the whole of 2025, you know, we've, we've built new marketing channels and we've had to pivot, especially our BDR capacity from like cold outbound to this new thing to, you know, now we're like really trying, we're, we're hiring like 25 BDRs in 90 days and that's So, so that we have lots of capacity to catch what demand we think is gonna be generated. And if not, we have the, the backup plan is like, well, we really wanna pursue cold outbound in a, in a more significant way than we have historically. And so it's like, oh, like, you know, if we're wrong and we got a bunch of capacity, it's cool. Like, let's do, let's do outbound.

Yeah. I think as long as you know there's a place for those people long-term and you're transparent with them around what they're stepping into. Yeah, I, I think it's, it's healthy, and that's the exciting part of being a part of a high-growth organization. And if that's not for everybody, right, but, uh, most people want to— or most people that at least work at Clio really want that agile workplace. And I think exactly, it's exciting. It also creates career, um, career opportunities, right? Because you have the opportunity to dip your toe into a lot of different things when a company is growing this fast. Versus getting stuck in a role. I am curious why you're hiring all those people. I saw that on LinkedIn.

Yeah. Um, part of it is we hired a, like an incredible new CMO who, um, is just like, you know, 60 days in and the, the lead number is already flying. And he looks at, he looks at our opportunity landscape and is like extremely bullish. And he's, he doesn't come across as like an overly optimistic guy. Like he's like a very, uh, he was like a math UPenn math grad, like very iBanker, like, you know, pragmatist. But, you know, his assessment to me was very bullish. And I'm the same way as you. I was like, I am not going to get caught in a position where I don't have enough capacity to meet, to meet the AQL demand. That's like a cardinal sin of a sales leader. It's the worst thing in my mind, you know, like we always, so many of us spend so much time like wallowing in the dregs of not having enough demand. And so we wanna make sure that there is like ample capacity. Um, and you know, as, as the inbound number in some of these new channels has ramped, we've had to divert people out of outbound, out of like pure cold outbound. And we know that there's a big opportunity there. And so either Wyatt's gonna do what I think he's gonna do and we're gonna allocate some to outbound, but but a bunch of this will be in these emerging channels, or I'm going to take a much bigger swing at cold outbound. And it's a nice thing about being able to raise a bunch of money and playing for— we're playing to win the market, not to be like a successful little startup. We are playing to absolutely win. So we'll see.

We'll see how it goes. Yeah, I think that is important because You know, on the one hand you wanna protect your sales team and you wanna make sure everybody's successful, but when you're a sales leader or CRO, it is important to know what you're playing for. And Clio's also playing to win the market and yeah, we invest like we're playing to win the market.

Yeah.

Uh, and I, it sounds like y'all are too, so looking forward to comparing notes.

Yeah. Yeah. I, I've been talking about this a lot lately. I don't know if it, if on my pod or if this was elsewhere, but You know, I presented that GTM AI thing at Pavilion's event in DC, and my big caveat is like, you gotta know what game you're playing. And Owner and Clio and companies like us are playing a specific game. We're gonna raise a bunch of money, we are gonna friggin' send it, and playing like playing a go big or go home model. But that's what venture capital wants. Like they want power law outcomes. But that's certainly not everybody, and there's more ways to build a company now. With AI, certainly that can be more lean. You can, you know, raise one and done, you could bootstrap. But, um, this, this playbook is pretty specific. And, and you're— the advice I give to people is like, you need strategic congruence. Like, so many companies want to do what Oner does. And, and I, you know, like, I get asked to do all these things and people want, want advice, and, um, but they don't want to like they don't want to take the risk. Like, I was hiring senior enablement and RevOps people like really early, and it looked like our spend looked wonky. It's like, wait, you've got 10 account executives and like 4 people in RevOps? Like, that's crazy. But I was building the infrastructure so that when we get to 50, 100, 1,000 sales reps, like, we're not doing, uh, a complete rip and replace of Salesforce. We're not gonna build this like bloated thing with all this tech debt. We did it right the first time, but But you had to be comfortable playing that game. My CEO, my board, my CFO had to be aligned with it and it's worked, but that has to flow through every stack of your strategy. Your product strategy has to connect to your go-to-market strategy, which connects to your hiring profile and your, like, everything needs to be linked. And I find that people are sort of chickens with their head cut off. Like they want to do these things that owner does, but they want to be like bootstrapped and they want this hiring profile, but it makes no sense because, because of like these reasons. And so I think like one of the things I've been really pushing on with the founders I work with, or, or other, you know, CRO friends or, or mentees, it's like just like make sure there's connectivity because there's so many ideas out there. And I certainly fell into this trap early.

I think everybody does. And I think what you're describing is the difference between good companies and great companies. And the great companies are the companies that have a full left to right strategy that is aligned across the business. And, um, I know at Clio we have a lot of transparency around what we're marching towards. We do an all-company meeting with all, you know, 1,600+ employees every year. We, you know, are very transparent about what our OKRs are. And if you have that culture where you're really repeating what your goals are as a business over and over and over again, Um, not only can you make sure that people are, are marching in the same direction, but you can ensure that everyone knows that they know exactly what they signed up for. And I think it's important.

Yeah. Yeah. In hiring, it's, that's, it's a great example. It's like, are you fully transparent in your hiring process of like what this is like? Because if you're a Clio or an owner, things change fast. Like it's like we acquired a company. Your job is totally different now today than it was, you know, 9 months ago. And you're like, oh, but I was hitting my quota, I was making, making money, I don't want to have to like learn a new thing. It's like, well, that's not the, that's not the offer here. Like, the offer was high growth, lots of career opportunity, high change. And, and we, we hire and screen for it like very deeply so that we can find people who have that like, uh, appetite for pace and change and have shown, shown the resilience. And you got to start people who look great on paper, but like, you know, just don't have that. Don't have that because they become a stick in the mud and they slow everything down and, and you can't have it cuz speed is the name of the game.

Speed and execution. Yeah. The last thing you, like what I screen for when I'm hiring is ideas people. Like, I love your ideas, but how good are you at actually executing your ideas? Cuz if you can't execute, you're just gonna be in the way and you're gonna depend on everybody else to execute. So That's, that's huge for me for sure.

One thing, so I'm interested to hear how you deal with this. So something that we're doing in our planning process is actually going like channel by channel is more on the marketing growth side, but we're going channel by channel and assigning like probability, like confidence intervals to things. So it's like, okay, our core channel is like meta video. We like rip and we can basically, we basically know like we can spend more money and like more leads come out of it, but then there's all these other channels that that could be really high upside, but we don't have the confidence. And so we're spending, you know, Q4 and some of Q3, like understanding, all right, these are our channels. And if we gain confidence in these channels and there's a bigger, like, spend wallet that we can lean into, then we can have higher confidence. So we can, we'll have like more pipeline for next year. How are you guys thinking about this, like, confidence interval probability calculation of these things?

I wish my CMO was on the call to help answer that question. We've got a very sophisticated, um, marketing machine here at Clio, and we use—

or even in sales, like, as you think, because like you were giving examples of like, we don't know what the, the, we don't know what the demand is going to be for that new product. You don't know like the monetization. How do you think through just the uncertainty, maybe is the different way to ask it?

Obviously we have a very data-driven approach to it, and when I say data-driven, I'm not talking about once a month we pop into the reports and see how things are going. We're looking at it right now minute by minute because we launched this like a week and a half ago, right? And, and then we're making real-time changes. So, um, you know, we might say, hey, we want to have a dedicated group of people to take these types of leads, and we're going to play around with that. But if that's not working, we're going to change quickly. And if it's working, we're going to double down on it and we're going to pull more people into that motion. So we meet after a product launch like this, we meet multiple times a week to review the data.

Wow.

And, and that doesn't only inform how we allocate resources to certain marketing channels or, or pipeline channels. It also helps us determine what our enablement strategies are gonna be and where do we need to lean into hotspots within the team around a competitive landscape that is brand new to them. And I think that. Having an aligned set of KPIs that you are like literally hitting the refresh button every 10 minutes.

This is me. You're describing me in, yeah.

Yeah. Like, you know, you have a problem in Salesforce. It's like you can't refresh. It's been under a minute. Um, so, but that, but that's how fast this business is moving. And then to react as fast as the, uh, trends that you're seeing is, is the key there. And so. Agility is probably the best way to describe.

I think that's a great, I think that's a great way to frame it. And then that agility and that time horizon or the feedback loop time horizon can grow as you're gaining confidence.

Exactly. Yeah. With time you're gonna have more confidence naturally cuz you're gonna have more data, you're gonna have, uh, more anecdotal information from customers and that, that conviction's gonna go up. But when you're playing brand new in a space, you have to be prepared to have every single assumption busted by something you weren't expecting for, and, and then know how to act when those trends surface.

Yeah. Yeah, that makes sense. Uh, it's your comment around you can't refresh more than once a minute is, is hilariously on point for me.

We are recording this on the last day of the month too, Kyle. So the fact that you and I have been talking for this long and I haven't refreshed my dashboard is Really?

You said that and I had to hit the button cuz we're like half a percent.

Well, I have to—

Yeah. Yeah. We're half a percent off of our crazy stretch goal, which, uh, which we're gonna deliver. So amazing.

Congrats.

Yeah. Yeah. Don't, don't jinx it. We go, I'll, I'll, we'll refresh at the end and we can, uh, uh, see if we're congratulating each other. So I wanna, I wanna dive more into, um, this acquisition. And I, I think you can, uh, apply a lot of these learnings to any like majorly disruptive event, launching your own new product, or, or if you're an early-stage company, maybe like a big pivot, uh, because I have a feeling a lot of these are going to be, uh, broadly applicable. So let's just start high. So the acquisition, you, you decide you're going to do this thing, and where does GTM start? Like where, where, how did you start unpacking this thing? What was the, what was the process like to plan? And then we'll, we'll run it all the way down to like frontline enablement.

Yeah. So I think to be totally vulnerable, we decide we're gonna do it, we're all excited, and then we realize the work we're gonna have to do in the short amount of time we're doing it. And then we all get a little bit nauseous, uh, and then we figure it out. So the way that we organized this, it was a huge project. Um, just to ground everybody who's listening on the timelines here, I think we made the decision, um, kind of mid-summer to acquire this company, and we had the aggressive goal of launching an integrated product to the market in October.

Wow. So think about it, because your event, right?

Yeah, because we have our big user conference, and that's an opportunity for us to get in front of the market and create some buzz. And so You know, we're talking literally like 3 months to build a product, integrate all the systems, enable the sales team on a thing that's not even built yet. I mean, it really, every single part of this process was wrought with uncertainty. And one of the values that we have at Clio is called Draw the Owl, which the first time I'd ever heard that was at Clio, which is basically you have, you know, half of an owl. How does the team work together to complete the rest of that picture without having any information? And so that is really foundational here. And everything about this project was about drawing the owl. So the way that we organized was we had dedicated leaders for specific streams. So like go-to-market readiness, what is our SMB strategy? What is our enterprise strategy? What's our monetization strategy? And every single one of those leaders was empowered with a team of people to help them not only design and build the strategy in a very accelerated way, but actually deliver on that strategy. And so depending on, on what our function was, I was leading one of the streams and, and still I'm obviously deeply a part of it is, you know, we determine what our headcount plan's gonna be, um, what our messaging's gonna be. What our pricing is going to be, every single facet of it. But it was organized in these really clear streams. And then we had touchpoints throughout the week where we had—

How many were there? Like order of magnitude?

Yeah. So there were probably, there are 5 key streams. People was one of them that was less, you know, GTM-focused, but more, you know, there's a lot of people components to an integration this big. But we were to spend, you know, 70% of our time on this work. So, this was not like an extracurricular activity. You talk about big bets. This was something where we said, hey, we're kind of pausing everything that we thought were our priorities this year, and we are going to put all of our weight behind this integration to make sure we're successful. So, a lot of, a lot of time and resources in a very condensed amount of time.

And that's the same as the dedicated resources under those people. It's like, hey, your, your day job's paused. You're like, this is, this is what matters.

Yeah, exactly.

Very cool. And so for each of these work streams, did they have like similar amounts of people? Was it like 2 people dedicated to the project? 10? Like how, how many?

I mean, some of these work streams would have like 30, 40 people on them, but, uh, okay. Yeah. So, we really had, because there's not, there wasn't enough time for like 2 people to go learn a bunch of new skills, right? And we needed everybody to have the context in real time to help us make decisions and then implement those decisions. So, we would pull the entire group along for the ride and then we would have kind of a core set of leadership that would make sure that everybody within that stream was rowing in the right direction.

And, um, were those all Clio people or did you, could you, were you allowed to bring in the, uh, we were allowed to bring in the folks from the company we're acquiring.

Um, but we had very, very strict rules about boundaries we were not allowed to cross. And we had, it was funny, we have, we work with Bain on this project and so we'd have consultants in all of our meetings. Kind of guiding us and making sure that we would never cross a boundary that would put the deal at risk.

Right.

Um, so there was a, a lot of stuff around data sharing and, um, you know, people information that we had to be really careful about because this was just too important of a deal to risk.

Makes a lot of sense.

Yeah.

Um, all right. So you start the process by putting together these work streams. You're, you said you were meeting on it. Like constantly meeting on it, like multiple times a week. How do you think about change management? So like, let, let's talk about the change management from the company and then I wanna unpack like sales readiness, 'cause that's, that would've been a beast.

Yeah. So I think Clio is one of the best companies I will ever work with that really thinks about what our messaging is and making sure that there's continuity in our messaging. To the market, to our investors, to the company, and then how that cascades down to individual departments within a company. Uh, we still do an all-hands every single week. And yeah, so, and there's a whole team of people that support our all-hands, and in that all-hands, like, we're constantly reinforcing what we're working on as a business. So we spent a lot of time educating the company on the decision to acquire this, what the vision of this was, and then making sure that as soon as we had updates around what the product would look like and the value it would bring and what customer feedback would look like, that we were giving that to them in real time so that every single person at our company was along for the ride. Uh, and it wasn't just like we dropped this thing on them the day before it launched. Uh, is we needed to build that context so that We were all ready to talk about it when it launched.

Makes, makes a lot of sense. And this is another one of these things that it feels obvious, but then no, like very few companies do it with the right, with the right amount of diligence. And this is like, is this just a Jack-on-down thing? Like it's one of the—

it's very Jack-driven. He, he is so good at First of all, having a really crisp point of view around where we're going. I think, um, you talk about clarity and strategy. At Clio, we have a CEO that is so passionate about the work that we're doing and also very focused on the type of work we're doing. Uh, he's not— we're trying to do a lot here, but it's a, it's a comprehensive integrated strategy. It's not a chaotic scattered strategy. And Jack is really good about articulating his vision, working with our internal comms team, our PR team, and making sure that that vision is translated into a comms plan that cascades in all directions.

Yeah. So what are the principles that you've picked up from what good comms look like? Consistency and repetition is, I'm guessing, one of them. It sounds like.

Yeah. Somebody used to say 5 times, 5 different ways. Um, so just, yeah, constantly repeating what it is. But I think more important than repeating it, people have to feel it, right? They can't just hear it. They have to really feel the impact of whatever it is you're trying to communicate to them. And you have to give folks that aha moment where they connect the practical application of whatever you're— it is you're trying to do with the vision. And if you can't bridge that for folks, then you're leaving this area of exposure where they're gonna be allowed to make their own interpretation. And that's when things get dangerous. That's where strategies get risky, because if everybody's interpreting the strategy differently, then you're gonna have people moving in different directions. But if everybody sees, you know, the way that a product is applied in an actual customer's environment and the reaction that they have and, you know, the impact it's going to have on their, their business, that's when you can say, oh, okay, this is— I get it now. And now I can not only translate that into my work, but I can translate that in customer calls and the way that I communicate et cetera.

So you gave one example. What, can you give some other examples of like how to make, what was your language there? More importantly than hearing it, they have to feel it. So what are some other ways that you, you like close that interpretation gap?

Yeah, so def, at least from the sales perspective, we have really sophisticated demo environments. And so, you know, we, we enable the team, we'll get them on, you know, courses, et cetera. But really where we find the true learning happens is when they can put their hands on the product and that they can actually play around with it and they can put their, um, themselves in the seat of a lawyer in our case and ask a legal question to, um, our new AI research product and see the output and really kind of give them the opportunity to play and give them that sandbox environment. That's definitely one. I think talking to customers is probably one of the most powerful. So, uh, when we were at our Clio Cloud conference a couple weeks ago and we launched this product and we had everybody, you know, flooding our, um, demo area to see it, you think about that, we just launched the product. Actually, I think we, we hadn't even launched it yet. We were launching it a week later and the sales team had like just gotten access to it. So they're trying to figure out how do we even talk about this? How do we demo it? Yeah. And so our, our go-to was actually, hey, if you had a question to ask this thing, what would you ask? And so, rather than sales kind of pushing some sales pitch that we told them to push, we let the customer guide the demo and we were able to discover like, these are the things that they care about. And that actually might be different than what we had assumed they would care about. And we can use those stories to kind of fuel the, the reinforcement of our enablement programming across the team. So customers demoing it, that kind of tactile approach to feeling it is like, when I say feel it, I really mean feel it versus just telling somebody a story that isn't backed by any depth.

Yeah, that makes sense. So, uh, in terms of comms and clarity, consistency is one. More important than hearing it is feeling it. Anything else that is noteworthy on how to do great communication and, and create like unity?

Um, so for my organization, I've got a, you know, several hundred person sales organization. I make sure that I pull leadership along, or I try as best as possible when I can to pull sales leadership along ahead of the broader team so that they have time to contextualize and internalize big change management events so that they can help support it as opposed to having that deer in headlights moment and not experiencing it with everybody else. Yeah, we don't want them experiencing it with everybody else. And sometimes we are moving so fast where we, we don't have that, that time to sequence the communication that way, but I do think that whenever you have the space to give them a preview, make sure they understand it, then they become one of your biggest assets in a change management and communications plan versus a liability.

Yeah, I cannot support this enough. This is like one of our big learnings from the last couple of quarters is getting the leaders enabled, comfortable so that they can have the conversations because ultimately, you know, some, in some of the previous environments or previous iterations, it's been like, look, if you have questions, come talk to me. Like, I want to engage and get your feedback. And people are never as comfortable coming to the CRO as they are to their manager. And so the manager has to really competently be able to handle that situation, understand the nuances. And so we write FAQs for big changes and make sure that they've gone through the, the learning Yeah, I think it's like one of the biggest ones.

Yeah. And actually you just said something that is worth mentioning here. So depending on what the injection is and how big of a change it is for your team, making sure that they're supported with the right resources to, you know, give them the information they need in real time. So one of the things that we did is we tried our best to come up with like every single FAQ that we could possibly think of. And then we ingested that into a gem. And now anytime someone's on a call, like, they can just go to that gem and say, hey, how does it— this work at another company? Or what's the person just, um, like a Gemini gem? Yeah, yeah, yeah. Um, and so, and it's, it's restricted, right? It's just drawing context from this FAQ doc, but it's just that dynamic way of Hey, I just got this objection. How should I respond to it? And you know, when we had to spin up enablement programming as fast as we did, that was a super handy AI application that, um, not only was available at launch, but something that we're ingesting questions from our Slack channels every single day and continuing to fuel this doc and, and the, the Gemini gem. So that's another way to help people feel safe in the time of change. Because if they don't feel safe and you've let them feel insecure, that's another danger zone.

Yeah. AI is a really interesting addition to this whole thing because, you know, people can get answers that come from the right thing and, and you can be more cognizant of controlling the right information, you know, so it's not misinterpreted.

Exactly.

That's a cool use case. All right. So switching gears from comms, I'd love to hear about like frontline enablement. So what did it look like to teach somebody? Because this, I don't even know if you've mentioned it, but this was like a big acquisition. This is a, it was like big in terms of product.

A billion dollars.

Yeah. I didn't know if you were allowed to say, okay.

Yeah.

That stuff like, and big in dollar value. And so it's not, not like a little tuck-in thing. So how did you think about getting the frontline teams ready to sell this thing and integrate it with your positioning, like all that sales readiness?

Yeah, so like I mentioned before, we were building product pretty much up until the last minute, right? And then all the systems to go along with supporting sales, actually being able to transact. So enablement was one of the most challenging parts of this whole story because not only were we having to kind of tell them, hey, this is what this will look like once it's finished, but we had to make sure that they were ready to sell it on day one. And we took the approach of kind of taking a step back and making sure, again, they understand the big picture, why this is so powerful, and then doing a lot of industry training on how lawyers use legal research, how, how important it is for them to have an AI tool that would allow them to compare contracts really quickly and do redlines. All these things that like they just weren't used to talking about, making sure that they understood the terminology and the difference between how litigators and transactional lawyers would use this type of technology. We're so used to talking in practice areas at Clio. So are you a family lawyer? Are you a criminal defense attorney? Are you in personal injury? But now there's this whole other aspect of. how they bill and how they do research. And if they do research that the team had to learn. So we did a lot of that context building so that by the time the product became available for them to start playing around with, they understood the broader messaging and positioning and could get into more of the application-based enablement. I think the biggest learning though is enablement does not stop when you launch. In fact, that's just phase one. That's kind of the, the pre-enablement period. And now that we're actually selling it, um, that ongoing enablement programming is so important because every single day we're learning something new that we weren't prepared for, and we have to make sure that the team feels empowered to respond.

And so how do you— how have you created that feedback loop so information goes quickly from field to enablement field?

So we have centralized Slack channels where we've encouraged folks to ask their questions with no judgment. I, I know when you've got, you know, several hundred people in a Slack channel, it can be really scary to post your question, but we really want to hear those questions because what we'll do then is at the end of a week, we'll say, okay, these are the, the biggest themes we saw from the team this week. Um, these are the questions we really need to make sure that we're answering for them. These are the, the assets we need to build for them to be successful. And that's not just me and enablement, that's our product marketing team. That's the product team being super involved. That's the team from Vilex, the company that we're acquiring. So everybody's really leaning in to make sure that the team is getting the answers in real time, but then we're able to extract those themes and then pump them back into our newsletter for the week, into our manager meetings in the box that we create for them. To practice into the Gemini Gem that I described earlier. So, yeah.

So tell me more about those specific tactics. So there's a newsletter, and that's every week to sales?

Every week to sales. Yeah, and we have like kind of cute branding for it and everything, and so that's kind of where the most important themes of the week are surfaced, and we build enablement there. We enable our teams, our managers with this thing we call meeting in a box where the enablement team packages up slides for them that not only has information but also exercises that they can do with their team. So like role play type scenarios and questions like discovery questions that you can play around with to ask with your prospects. And then actually something that I didn't mention is, and I know you and I actually talked about this several months ago, is we ended up having a POC with Hyperbound going on at the time of all this. Right. And for them it was like right place, right time. We decided to bring them in for not only sales, but part of our CS organization. And the team is practicing with the personas we build in the Hyperbound bot. So they're not necessarily having to do this for the very first time with a, you know, expensive lead that comes in. But they, we have these custom bots that we've built and the team is loving it. They really are appreciating the opportunity to kind of fall on their face and like get that initial talk track out of their mouth with a bot that's going to, you know, just give them some basic feedback versus, a customer that they might lose a sale on.

Yeah, yeah. I'm a huge advocate of AI role play and AI coaching. We, we use Avara because I'm a control freak and I can do like, I can have way more specificity, I found, in Avara. But same sort of thing, like we now, when new BDRs go through training, like instead of doing, you know, maybe 2 hours of role play with their manager, which was the typical standard, I think, for many companies, it's like 20 hours of like these hyper-targeted, just open the call, just work on your, you know, hypothesis of need, just work on your offer value. And it's like repetition after repetition. You can build, you can, you can build so much more skill that way versus like trying to practice everything on a live call when with a customer, when your cortisol's through the roof as a new man, a new rep doing a new thing.

Exactly. I totally agree. We demoed several vendors and some of these bots are better than others. I'm sure you've seen some bad ones, but I really am impressed with how realistic these scenarios feel. And also the way that it can deliver managers insights about how they can get more targeted with their coaching. Um, and, and these, these bots aren't hard to build. You can build them rather quickly. So if there's a new persona that pops up or a new situation you really want the team to double down on, you can do that and get it into their hands pretty quickly, which is awesome.

Yeah. We've got like 40 to 50 sims now. Wow. Anytime. Yeah, that, that's another reason I, I really like the Avara experience is because I can load in docs, it'll interview you. There's the AI sales sim and then there's the also the like builder AI. And so you can just sort of talk to it and then spin up, hey, you know, we're releasing new pricing and this is how we want people to talk about it. I've uploaded the, you know, pricing document and the, you know, the spreadsheet, yada, yada, yada, and it'll spin them up. So every time we make any change or anytime we want to focus on a specific coaching area, we like spin up the accompanying sims and, and That's like our, one of our core, that's one of our core training experiences now. Okay, so let's move to quickfire so we can get outta here on time. What do you think separates a good CRO from an exceptional one in your mind?

I think humility is a really important quality, especially right now with everything changing so much. I think we have to stay curious and humble and make sure that we are creating the space To learn not only from like market trends, but from our people and from our customers and understanding that you don't have all the answers. And that's actually, if you, if you are open to being humble and curious, you create so much space for these new discontinuous insights to flow in and, and help change the trajectory of your business.

Yeah. Well said. What's the most common advice you give to new leaders, like first-time VPs or first-time CROs? Well, if you give them one piece of advice, what is it?

It would be irrespective of what somebody's title is, their experience, their tenure, don't assume they have all the answers. And leaders are looking for the experts in the field to help them form an opinion. And so if you happen to be in the room for a conversation, you're there for a reason, and make sure that you're contributing in a meaningful way.

What's the hardest lesson you've had to learn in your career?

Oh, um, what is the hardest lesson I've had to learn? Let's see, probably that you can't say yes to everything. And as someone who is, you know, I'm I'm super motivated. I, you know, I'm a mom. I'm balancing everything, it feels like, all the time. Uh, if you say yes to everything, you're gonna do nothing well. And learning how to prune effectively to make sure you're spending your time on the highest impact things, both personally and professionally, by the way, uh, is such a skill that especially new leaders, I don't, I think that's something that they have to learn over time because it's hard to say no to someone. Um, but it's actually a really big asset if you know how and when to do it.

Yeah, for sure. I, I maybe haven't learned this lesson all that well myself.

I'm still working on it every day. Yeah.

Yeah. Yeah. Um, what's the best thing you've read in the last 12 months?

I read for fun a lot, so, and right now I'm on a bit of a Kristin Hannah kick, so like historical fiction, like The Nightingale and The Women. I love it. But, but my favorite business book— I, it's been longer than 12 months— my favorite business book I've ever read is The Happiness Advantage by Shawn Achor. Um, and his thesis is that happiness feels success and not the other way around. And there's something about the way he articulates that in his book that just really stuck with me and probably is one of the most foundational components to my leadership style. So, Happiness Advantage, pick it up.

I love that. Yeah, I had Dr. Michael Gervais on my, on the podcast a couple months ago, and he's one of my favorite authors. I've been like listening to his podcast for a decade, and one of the things that he shared that I hadn't really seen from him is he's like, I've never met a high performance person who's not fundamentally optimistic. And, and, uh, I was like, I love that because it's so true. Like you, you can't really achieve real greatness unless you have like some sense of optimism that it's possible. And I, I think happiness is the same, you know?

Yeah. And, and also like we only get to live once, right? So why not enjoy what you're doing even on the hard days? Yeah. Try, try and find the good stuff, right?

Yeah. Yeah, exactly. Well, Jenny, this was awesome. I got a ton from this conversation. I'm really excited to go acquire my first company because I feel better prepared to do that than ever. So appreciate you coming on and this was a blast.

Thank you for having me. This was so fun. Talk to you soon.

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.