# PLG and Early Adopter Sales are Gone

How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

20Sales · Jun 7, 2023 · 51 min · 11,905 words
Speakers: Rich Liu, Harry Stebbings
Source: https://www.996.fm/episodes/20vc--ep-e2a9d127/

## Cold open

**Rich Liu** [0:00]:

That early adopter, that product-led LED sale does not work in a tight market. I'm not spending any money. Default is no. The only time that I'm going to spend something is if someone convinces me this thing is not what you think it is. It actually is going to solve the most important thing that you're afraid of right now.

**Harry Stebbings** [0:15]:

This is 20 Sales

## Intro

**Harry Stebbings** [0:17]:

with me, Stebbings. and 20 Sales is the monthly show where we sit down with the best sales leaders in the world to discuss how they build and scale world class sales teams. Today, I'm joined by Rich Liu, CRO at Everlaw, and a unicorn go to market exec, having scaled five multibillion dollar unicorns across two IPOs, a successful acquisition and numerous funding rounds from Meta to Navan and MuleSoft, this man has seen it all and stays an absolute masterclass.

## Sponsor read

**Harry Stebbings** [0:43]:

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## Conversation

**Harry Stebbings** [2:14]:

Rich, my man, I have heard so many great things. I've been so looking forward to this. Some of the references gave me things that we could talk about in the show, some we've just bonded about instead. But thank you so much for joining me today.

**Rich Liu** [2:27]:

Happy to be here, Harry. Thanks so much for having me.

**Harry Stebbings** [2:29]:

Not at all. The pleasure's mine. But I want to start with a little bit on you because you've worked in some of the most incredible orgs in the last kind of 10 years years of business building, really. And so I to start with how did you make your way into the world of tech and sales first?

**Rich Liu** [2:41]:

First of all, there's a lot of luck involved. I think it's a lot easier to see things going back than looking forward. But I started my career as an engineer, biomedical engineer. My parents are both engineers. We're immigrants. And so that idea of get a technical degree, get a technical background, and then you'll always have work to do was a little bit of what I grew up with. But after finishing, I realized, oh, wow, I watch the movies, I I see TV, and I really wanted to be some kind of a business executive. So I didn't really know what that meant. And I thought, okay, this was during the dot com bubble burst. So weren't a lot of jobs out there. And I was reading and doing my research and going it looks like a lot of these business leaders, these CEOs, they seem to have this like sales background. That's interesting. Maybe I should try that. And if I can't do it, if I suck at it, you know, I'll go back and take one of these engineering offers I walked away from. And so my first job was I was thinking the base salary was like $20,000. And so it was like, well if I can't make a good commission, I won't pay my rent anyway, so why don't we give this thing a shot for a year? That was really it, Right? I went into an investment company called Fisher Investments that was really transformational at the time, really trying to get people from all money management being distributed through your financial advisor brokerage house to, oh, we're to build this direct to consumer money management shop, what was junk mail, cold calling, and later internet advertising, search advertising to sell high net worth asset management into institutions. And so it sounded kooky, right?

**Harry Stebbings** [4:05]:

Dude, I've got this image in my head of the Wolf of Wall Street. You know, when they're like, garage, and they're, like, cold calling for penny stocks.

**Rich Liu** [4:12]:

Yeah. It was not quite Wolf of Wall Street. Right? It was perfectly legitimate. The company's now two, 300 billion in assets under management, like 5,000 employees. We were probably like 300 employees at the time, like really trying to get this like direct mail, direct thing to work. And I was an SDR. I was going out there cold calling wealthy people that we got to fill out junk mail reply cards for a little flashlight or a little booklet, call a 1-800 number. number, and that was really it. And then doing a bunch of outbounding to pull prospects to try to build this.

**Harry Stebbings** [4:43]:

Dude, that is funny. I to pick on a couple of areas of your career because as we said, incredible organizations And we're gonna do like a quick fire at the beginning to get to know each other. This is why I'm single, because I actually do this on dates too. So we're to start with Meta. What was your biggest lesson from your time with Meta, and how did it impact your operating mindset?

**Rich Liu** [5:03]:

Oh, gosh. One of the things I learned most about that company, and I know that sometimes it's derided, is move fast and break things. Like, the idea that you don't have to be perfect, but sometimes, especially in a fast changing market, speed is at a 10x premium. That was a lesson that was huge for me. Hey, everyone, just try to do the right thing, experiment, move fast, break things, and maybe a few of these will work, and then we'll start doing more of that. To me, that was mind blowing, but I think that really balanced out a lot of how I think about scaling now, which is there are times when you want really strive for, we gotta do things right, we got one cut at this thing, it's a glass ball, it's not a rubber ball, if we drop it, it's to shatter, to, okay, how many things are actually that, that, if we screw it up, if we fuck it up, we can't go back and try to fix it? It's actually fewer than we think, especially when scaling, because I I know I'm not the smartest person in the room. If I don't have the best answer with all the data that's gonna be right, why not have five more shots on goal instead of like, you know, waiting for that perfect shot? And I think that was actually a huge learning I had that even at a much larger scale than many startups, and I know that they don't often think like that now because it's a massive corporation. moving fast, trying a lot of things and really embracing that okay

**Harry Stebbings** [6:13]:

to fail mindset is huge. How do you create urgency in a sales cycle? In terms of moving fast, sales cycles are actually slowing now. How do you create urgency in a sales cycle?

**Rich Liu** [6:23]:

Yeah, I was just on a call with a number of other COOs, CRO business leaders thinking like, everybody's sales cycle slowing, everybody's seeing harder to get the deal, no budgets, fill in the blank. That early adopter, that product-led sale does not work in a tight market. And that's not a bad thing. It does weed out the people who are disciplined and actually build a story versus not. But in a market like this, a couple things need to happen. The default is, I'm talking to my CFO. I'm talking to my CEO, I'm not spending any money. Default is no. Don't even spend the time. Don't even open the door. The only time that I'm going to spend something is if someone convinces me, oh, this thing is not what you think it is. it actually is going to solve the most important thing that you're afraid of right now, efficiency, sales productivity, support utilization, whatever those things are for me as a business owner, unless you can speak to me in a very clear and concise way about why what you do solves that in a quantifiable way for the thing that I'm afraid of most right now, I'm getting nothing done. Now the flip side of that is if I get to the person who actually owns that budget and owns that decision and can speak to that with that quantifiable thing, then guess what? I can break through that. I can get my sale done even in a world where procurements the enemy, ops is the enemy. Everybody who's not an executive has heard, save money, save money, which means don't spend money on anything. We just had a large deal with a AMLA Am Law 100 100 firm that we closed, and right now, they're all looking to save money right now. It's tight times. And the sales rep and sales leaders got to the economic buyer and the cfo. And it wasn't just one. It was like a CFO, the managing partner of the firm. And been a customer. This was a large expand for years. And yet they they were not thinking about us as anything more than an awesome technology that applies AI and machine learning to help them do discovery better and shrink the haystack of evidence. But instead, that person heard, ooh, wait a second. If I'm able to do this more effectively, I'm turning a cost center into a profit center. Wow. I can retain my employees better. Wow. I can pitch for business better in a more differentiated way in a down market. That is a strategic business lever for me, not a capability that just helps me do something that I normally do.

**Harry Stebbings** [8:24]:

Before, we used to rock up, show you the product, and you go, oh, shiny. And now it's sell to our CFO, sell to procurement. Does that mean we need to change doc wise, team structure wise? Should we not invest in product or growth? Should we invest in enterprise sales?

**Rich Liu** [8:41]:

If I'm a founder, and that's the environment I'm in right now, and I advise and invest in a number of companies who are going through this exact same thing right now. right The sale is real different for sales automation or whatever the technology is just six or 12 months months ago. Right now, I need to figure out what is the problem my product solves and for whom. Getting back to that exact, okay, what is the problem I solve and for whom and how do I quantify that thing and how do I make sure that problem I solve is actually something that the CFO, the CEO, the COO actually cares about right now? Cutting costs, running an efficient business, sales productivity, margin. I need to be able to make sure I can map back my narrative of what my product does to that big thing. And unless I can do that, I'm not going to get in the room. How do I map that back right now? So I'm sitting with Jonathan Friedman at Demostack a couple weeks ago, and he's like, hey, we're we're trying to work on this thing. Great. Okay, you have a tool that helps people create demos, or you have a scratch pad that helps people shrink down the size of time spent. Right now, my CFO's going to be, that's just some other piece of stack that the sales team wants to buy to make their jobs a little easier. Don't do it. Use the tools you have already. Do it in GDocs. Whatever the case is, use your CRM. I just need to figure out how I can map that story back to what does that CFO care about? Operating more efficiently, sales productivity. If I actually invest in this thing, it's going to make my sales team that much more productive in a proven out way with these data points and with these sound bites.

**Harry Stebbings** [9:59]:

What else are you seeing with the CRO, COO discussions that you're having? Are you seeing a complete pullback in marketing? What other trends are you seeing in this new market? I'm fascinated.

**Rich Liu** [10:08]:

Yeah. I think right now, every founder, every board member, every CFO is being pushed to say, okay, in this shift from grow to shift to productive growth, what is the operating envelope that we can play in right now? I think we're looking right now, Sales leaders, COOs, CBOs, whatever the title is of the person that runs a go to market, is being asked to say, hey, how do you demonstrate that you are building an effective and productive go to market on a per rep basis, on a per seat basis? Whether it's my support org, my CS org, my AEs, my SDRs, my partner people, I'm trying to figure out how do I actually measure the effectiveness and productivity of that org? Bookings per head rep, source dollars per marketing spend. If I can start to normalize those investments to metrics that actually matter and I can start comparing to each other, then I can start making the trade offs of, wow, is my cost per booking or new booking customer or new booking dollar, is that actually better or worse with an SDR lead or a marketing inbound or an AE outbound if I say they're gonna spend a quarter of their time doing pipeline generation? That's the kind of effort that I think to just start having that conversation and actually making those trade offs even if you're a startup to a late stage private company to a public company, that version of that conversation needs to happen. And then we can decide for ourselves how do we make some decisions about where we to invest and don't want to invest in the spirit of what's going to drive efficient growth and productive growth.

**Harry Stebbings** [11:31]:

How are you finding renewals? I had Henry Schuck at ZoomInfo on the show and he said they're actually having to change that org structure because of the challenge of renewals being so much harder. And so they're actually placing a lot more people in data and data kind of enforcement, proving out that it's a really efficient tool to use within organizations before everyone just upsold anyway. How are you seeing renewals and what's the impact there?

**Rich Liu** [11:55]:

Yeah, so a couple things. Right now though, the default is the same thing that happens on the presale side is happening on the post sale side. Right? How am I rationalizing the use of this tool the tool to this degree? What am I actually getting out of it? Can we clean out a bunch of this SaaS proliferation across the company? That is coming across pre and post sale. and so the impact on renewals for the success org is we need to have a true business justification if we're going to expect that customer to stay with us. Think about it as the converse or the mirror image of what needs to happen on the sales side and why the sales and success side needs to be tightly intertwined. If a lot of these deals think about how we were doing deals like early days of TripActions, Navan, or early days of Everlaw. Awesome product. It's great. You sold to early days of MuleSoft. Right? Sold to a developer who's using it for a project. CFO, CIO doesn't care about that. Right? They to centralize on a tool. They don't see it's valuable. Like, they don't care who bought it and what lower level, mid level person bought it. So how do you do that in the post sale if a lot of your customer base didn't buy that way? That means, ooh, we got go figure out how to actually build that from the ground up, the bottom up. Oh, let's actually have a conversation about what is ROI? How do you measure it? What are the metrics that you think you should use, that we think you should use? And let's agree on what that looks like. Let's actually set the tone of what good looks like within that. Let's make sure your CFO or CIO or whoever is going to ultimately say yes or no is bought into that as well. And so we almost have to like redo the sale the right way with the value message, with the EB engagement than when when we hadn't done it in the front, which is tougher. Right? Are you using account manager to do it? you using CSM to do it? Are you using AE horsepower to do it? And then on the pure CS side, even if the profile of our CS rep is make them super successful, help support them, get them, launched and implemented, service the admin, the question is, oh, how do we arm that profile of person with enough commercial mindset and tooling and playbooking to say, oh, how do I help map the org? How do I help ask tactical questions to figure out what our adoption is or isn't? How do I get some preview into other parts of the org that can be using us or that can utilize different parts of the stack? Give them some of those plays that they can start to seed that and actually build it from the existing potentially tactical relationship out. So I think it's a two prong thing, but either way, without tying clearly to value, quantifiable value, and agreement of what that value is, that relationship's to be at risk.

**Harry Stebbings** [14:11]:

Speaking of kind of that tactical roadmap within orgs, I think kind of we've jumped a step here. But if we kind of go back into the question of sales playbook, who is the person to create the sales playbook? Is it the founder or is it the first head of sales or the first sales rep?

**Rich Liu** [14:25]:

If you're at that stage where you're still figuring out like that question of what is the problem my product solves and for whom, right? What industry, what use case, what profile a person, what region. If I'm still at that place where I feel like that's not a really repeatable motion and able to do at scale, if I'm a product founder, I gotta be close enough to help make sure that whatever is happening and whatever learnings we're getting is translating back so that that product led version of that product market or product customer fit is lights out and tight, at least at the tightest ICP before you scale it out. If you're trying to go bring in a head of sales to outsource that for you at that stage, that's pretty dangerous. Ariel at Navan was really involved with a lot of the earliest deals and knew the product, knew the people really well to the point where he got a really clear view of, ooh, this is our problem we solve for whom. This is how we'll talk about it. And then at that stage, let's say the CRO is coming in to actually help to scale that motion out. Now, you have an early stage salesperson, maybe it's an IC, maybe it's a team lead, maybe it's a player coach, you got to be really close to that person to make sure those learnings are coming back because that's what you need to happen. The learnings are going back to help shape that product product-led product customer fit. As you feel more confident that is there, then you can step further away from that and outsource it to someone who can tell that story to that ICP in the way that you would and then build a team around it that's to do that.

**Harry Stebbings** [15:45]:

Dude, if you don't know the problem, who you sell to and how you sell it to them, you shouldn't be doing this fucking company because you'll have zero luck fundraising, by the way, if you can't do that. You'll have zero ability to hire the right people if you can't do that because you've got no idea what you're looking for.

**Rich Liu** [15:59]:

What am I inspiring them about? What's the story? Right? And I met a lot of founders out there that they might have a big vision of the problem they want solve, and then it gets really murky after that. I don't to go work with that founder unless we've we've actually done a little bit of legwork to show there's some MVP of a go to market of a something that works there. And frankly, I've also worked with founders who you said you can't raise money in the previous funding environment. I've talked to and have friends who are founders that actually did raise money. And guess what? They had a murky version of that. Maybe they might have had some initial product market or product customer, some problem they were solving for some people, but maybe it wasn't big enough or maybe it wasn't meaningful enough. Maybe it wasn't going catch in any market. And guess what? They start scaling a team around it, and then six, twelve, twenty four months later, they're going, oh, we're not in the right business. We're not in the right thing. I can't go back now because I've already committed to this path. What do you do then? Give the money back to the investors? Fold up shop? Pivot?

**Harry Stebbings** [16:50]:

The question I have for you is okay, so we both agree that it should actually be the founder building out that playbook. then they kind of hire against it. Should they be hiring a sales rep to jack of all trades dog test it really just execute on that playbook, or should they hire a head of sales to build that team beneath them?

**Rich Liu** [17:06]:

Throw the title out the window for a moment. I think that first hire, when I'm looking to scale, I'm looking to scale me out as a founder. I'm trying to figure out how do I get someone who can continue to help me shape this message because it's not all done yet, right? I speak about it sometimes like it's binary. It's not. To help scale and continue to refine the go to market and can give me some scale so that I'm not doing all the sales, so that I have someone who's close enough to me that's given the feedback back so that we can iterate on that story, the ICP, on the product market fit, yet is helping me do more of those sales. To me, that could be a player coach. It could be a player who's stretching in a player coach. It could be someone who has that sort of creativity, but also can get out in front of the customers and help me continue to hone that message. The next role would be the person who can probably run that first line team and continue to help shape that narrative, but also manage a few people to do that. Right? And again, where you are in that spectrum of you're hiring that first player to help you or that first player coach to help you probably depends on how much conviction you have that what you have is ready for that, Right? Jumping ahead from that first player coach or person to go do it with me to the first person who's like more of a coach than a player and going to have a team of people doing it, I probably have to be comfortable putting those that amount of chips on the table. I don't gamble, but like I've been to Vegas. I'm gonna put five chips on the table instead of one. I to have enough conviction that I have enough to go build those five reps around that's going to give me the momentum to go learn it fast or deliver bookings against it.

**Harry Stebbings** [18:30]:

The transition away from founder led sales is I think the hardest thing in in startups in many ways.

**Rich Liu** [18:36]:

Oh my God. You do it too slow or you do it too fast?

**Harry Stebbings** [18:38]:

What are the biggest fuck ups that you see people make?

**Rich Liu** [18:40]:

The biggest fuck ups would be, one is staying too close. I speak sometimes with founders who have 10 sales reps reporting directly to them. Makes no sense. Five sales reps reporting directly makes no sense. It completely impedes. And then you also build this like sales model where like you are de facto head of sales or head of revenue and you're starting to play in territory that you might not be good at in terms of coaching and developing and holding accountability metrics, comp plans, that stuff. So I think that to me is a, hey, you maybe moved a little too slowly against it too quickly would be at a couple flavors. One is you hire someone who's like really large scale that has aspirations to be an early startup, thinks it's cool to be in an early startup. They don't really know what to do or they can't do it without hiring a bunch of other people to do it. That's a telltale sign of this person's too far or has been too far from it for too long and either isn't willing or able to go step back and get their hands dirty to the degree I need done. Build me a sales plan from scratch. I don't have an FPA team or CFO. I got Google Docs. Let's build a a straight up simple comp plan for your reps. Be able to play there and wants to play there and can readily play there.

**Harry Stebbings** [19:40]:

Dude, with the reps, should we hire two at a time? Jason Lampkins, hire two at a time. You'll see who's good. Do we Do that or do we hire one at a

**Rich Liu** [19:48]:

I'm a big fan of two at a time. Right? Again, this is the engineer me coming out. The two at a time thing, right? So So much goodness comes out of it. First of all, if you don't have enough conviction in your business that you're hiring a rep to go hire two, get it to the point where you think you have enough for two versus one because ultimately you're splitting hairs if you're like, oh, I think I can support one rep, not two. Fundraise, get more conviction, the product, the story, whatever. But the two point is just so valuable because cohorting in terms of ramping, the supporting each other, the ramping, the competitive elements of it, it's really hard to know. is my product market fit fundamentally wrong? Is the way I'm telling the story fundamentally wrong? Is the PG messaging I'm using fundamentally wrong? Or is it the rep that sucks or the rep that can't figure it out? Having two helps to at least give you the minimum viable, separate the two and give you a little bit of signal about what's happening. Right? Now, again, if you hire two great reps, awesome. You have two bad reps, maybe you gotta press restart and do it again. But at least it helps to neutralize for now.

**Harry Stebbings** [20:42]:

Do you know what I see as a massive mistake? I see as a massive mistake people doing PLG and Enterprise at the same time. They're almost too nervous to do one and commit and burn the boats on PLG or just be a top down enterprise org. For me, I think that's a big mistake. When doing PLG and Enterprise, can you do both at the same time? And what are the thoughts here? I would

**Rich Liu** [21:02]:

say it's for operational definitional purposes, let's say enterprise meaning couple thousand, few $100,000 sales rep in a long protracted six to twelve month sales cycle. And PLG will call sort of pure sort of online self sell, self serve. And then there's probably something in the middle of it, which is like a velocity sales assist or inside or inside outside hybrid model. So again, I agree. it's really hard to do both well. Right? And it comes back to even how you design your product. So Facebook ads is inherently a self serve platform. Right? Built self serve first. you can use it self serve. you can now self onboard. And so the way that you built the people org around that naturally is, okay, let's make sure we can get everybody self serving and then using that as your funnel to figure out, oh, who are at the bigger spenders, who has higher potential spend, who's doing interesting things that we can then build back into the product? And then how can we use humans to augment the effectiveness those people are having to go extend them out? And that was what Facebook's mid market org did and had actually a lot of largest accounts in the earlier days. Zynga, Playdom, Living Social, right, Groupon, the performance advertisers, because they weren't out there selling Nike and Walmart and crushing that yet. They were helping the early advertisers find a lot of success doing that. That's a fundamentally different motion than let's go take someone to Super Bowl game, let's go build this great IO. let's go create this great creative pitch with the creative agencies to sell in. So that's just one example. But you build a product inherently differently and start to say like, ooh, we're going to do that well and have a really enterprise ready product is really hard. MuleSoft's on the other side of that. right? Heavy large enterprise integration APIs work inherently better for larger companies that have a bigger need than sort of small startups when you think about sort of enterprise corporate IT. For a company that has not built a product that is meant to solve for like anybody can come and use it like Zapier type of citizen integrator to say, oh, let's all of a sudden think with a different DNA, think with a different go to market motion, think with a different marketing motion. You're not doing multi touch attribution, lead gen marketing. You're doing consumer marketing. That's just such a different muscle from a product engineering, go to market marketing success standpoint that to do both well, you really have to have enough commitment and then DNA on the team and then resourcing to say, we're going to do it well enough to actually win in both. What I see too often is people say we're to do one and they don't really resource it. It's one thing to say you're gonna do it. It's another to actually do it effectively. And they don't truly understand, oftentimes because they don't even have the DNA or experience on the team who's built it to understand how different and hard it is. So I'm a huge believer of you gotta commit to at least one, and it's okay to evolve to the other, which is what going mainstream often means. But don't try to be too too early.

**Harry Stebbings** [23:38]:

Okay, so a quick one before we talk about hiring, which I can't wait for. Which one's easier to start in?

**Rich Liu** [23:43]:

It's a good question. The intellectual answer would be it depends on which space you're in and what your DNA is. If I'm building a security company doing enterprise security, I should probably start at the top of the market and then go down because that's where the inherent need is biggest. And if I'm building like an ads business, right, it's an online ads business publisher, like Facebook going bottoms up was absolutely right. So I would say a lot of it is depending on what space you're going after. If you're to ask me personally what I think is easier, personally, I think it's easier to start small and go up.

**Harry Stebbings** [24:12]:

I agree totally. I also think it's because it's the product and growth mindset that's inherent within a PLG led org it's product first. Yeah. It's so difficult to imbue that in an enterprise org. And she tacking on enterprise sales into a PLG motion, not as hard as one thinks. You get a Maggie heart of the world. She can do that very well.

**Rich Liu** [24:32]:

But just don't try to jump too far ahead of where the product is ready, where your success org is ready, where your services org is ready. That motion, if done right, I think can be super effective.

**Harry Stebbings** [24:41]:

We're to hire some people now. Okay? I ain't got no freaking idea how to hire them. I'm a young first time founder, and you're my advisor. So we're hiring our sales, first sales team members. How do I literally structure the hiring process? How many meetings? What do we do in the first, the second? Is there a third? Help me.

**Rich Liu** [24:59]:

I take a lot of my hiring philosophy from MuleSoft of all places. My wife was a longtime Googler who's was famous for doing the, you know, their executive committee as to approve every hire. The simple thing that I would say from my MuleSoft days, Greg Schott, if you're ever listening, thank you for the religion on this. People are the most it's an adage, it's over said. It's a cliche. People are the most important thing. Like, that was what that company did better than anything else is figuring out. not the product, not anything else, but hiring the best people and then figuring out how to utilize them. And how to do that is, number one, is what do you actually need to do in this job? Not just make calls or all that, but what are the like outcomes that you want this job to have? Help me figure out the narrative. Help me break into new customers in a evangelical sale versus a sort of a more tactical, we already know how we're gonna sell a sale. Is it a product sale or I need someone to go spice someone up and get them to believe in the world's round when everybody thinks it's flat. What are those things you actually need done? And then let's actually break that down into skills that support it. And then let's actually break down a process that helps us vet for those skills in an effective way. And interviews, by the way, if you think about it, they're actually a pretty ineffective way to understand if someone's to be good at something. Right? Whoever interviews well gets a job, but that doesn't mean they're a great engineer or they're a great CSM or they're great marketer. They interview really well. They're great in the room, and I'm terrible in the room, so that's why I say that. But what I need to do is design a process that vets for that. So say I decide, okay, for my enterprise AEs, I need really strong operational linear execution. I need strong coachability. I need great in the room skills. Let's actually vet for that, designing, number one, structured interview questions that vet for, Ooh, tell me how you had driven situation, action, result. Right? Tell me how you drove this type of interaction, what you did, what was the result, how did you do it? Having those structured questions that vet for those specific skills, and then knowing what a good answer looks like, what a bad answer looks like, and then making sure to ask that question at every time and ideally with the same interviewer so that you can get some calibration between candidates. That's really important. So if you build out a light structured interview process, say it's, I don't know, three interviewers, one for track record of achievement, one for this linear execution, coachability.

**Harry Stebbings** [27:03]:

What happens in your coachability? track record, I get it. I go through MuleSoft, I go through Matter, I go through TripActions. What happens in coachability?

**Rich Liu** [27:11]:

Yeah. How do you actually vet for them? So again, I'll go to the other pieces, but track record by way, a lot of people screw that. Like, a lot of people leave a lot on the table for like, Hey, how'd you do? Oh, I was a top rep. I was this, that, that, And stop there. Everybody, any salesperson can tell you how they were the top. And then the questions that don't get asked are like, oh, what were the metrics that you were measured on? Okay, how did you do on that? Great. How many other reps were there in that that that cohort, in that region? I was the top of my region. I was the top 5%. Oh, I was the top of two reps. Cool. That doesn't tell me much. Right? I was the top one of 10 reps on new business sales, and the average attainment I did was one and the average attainment they did was 80. Oh, that's actually valuable. Asking those clarifying questions over what period, what was the metric, how were you measured, how many people were in that cohort, how well did the others do, so you can actually get a real sense of like, repeatability quarter after quarter after quarter year after year after year roll after roll after roll That's actually really important so that we don't stop at, hey, I was a top achiever. Cool. Done. That doesn't give you much. Any great salesperson can never be up past that. Coachability, EQ, those are like, hard to ask. How do you do that? Tell me about a situation where you were stuck in a deal. Why were you stuck? What happened? What'd you do next? What'd you do to get help? Well, what did how did you react Don't lead them. What'd you do to get help? Oh, help. I went to so and so. What'd you do in that situation? Did they engage their manager? Did they engage an sa? Did they go talk to partners outside to go figure out how to go crack that open? Okay, then what happened? Then what happened? Then what happened? And you can design these questions to start talking about, okay, what is it in a real life situation, in my role, what would I want them to do in that scenario to see if they're coached? You know, the classic one is, hey, What's you lost a deal. What happened? I'm looking for humanity. Oh, you know, all these other things happen. You know, it wasn't built right, and externalization, externalization, externalization, Or I really should have seen this. I didn't do that. I learned that I should have gotten to the EB earlier. Okay, how'd you not go to the EB earlier? Well, I thought I had a great champion that were to get the deal Oh, interesting. What did you do with that in your next deal? Did you do anything with that? Oh, that? was a one off. That was a one off, Harry. It was to happen. You can't prevent those from happening sometimes. And that's a very different response than, oh, I started to do things differently. I go work with my manager earlier to look at the deals and the deal reviews. I'm actually going to use these lines to go get to the EB earlier, and this is why. So you you can actually, without leading, see how they respond and when you ask them, then what? Tell me more, tell me more, You can get some more color around

**Harry Stebbings** [29:25]:

that. What are big red flags in what you just said? So one for me would be like, oh, it was Rich's fault, and you just have total denunciation of blame. When you look career track record, like track record and coachability, anything's where you're like, Harry, when they say that, be worried.

**Rich Liu** [29:39]:

Yeah, job changes, a lot of job changing, huge red flag for me. At some point, everybody's got a good reason. But if you say, do one or two year stints for like several in a row, that's a huge red flag. You know, performance, great sales reps know exactly how they did every year. Like can tell you, okay, in in this year, in 2007, I did this and I made this amount of money. I was number one on the sales I was number two on the sales board in Note three. John Holwick beat me. Damn him. He's an awesome dude. but, ah, I missed out because of X. Like, salespeople know their numbers. If they can't, like, quickly rattle and tell you those things or they start to hem and haw, that's an interesting signal when you start digging into track record. That's a really interesting For example. But again, the interview, structured interviews is only half the story and don't actually give you much. Having an exercise that really and you don't have to be a big company to do this. What is something that they would actually do that mimics what they would need to do in the role? Hey, here's a scenario. Make a cold call to me. Write a prospecting email. Run this meeting, but do a prep to say what we're talk about, like how you would set up a meeting, and then go run that meeting with me and how you pitch maybe our product, maybe it's your own product, and do that mock version of it super helpful and actually rate that. How did they show up in the room? How did they do at setting the tone for the meeting and running it? How they do at at doing discovery? How do they do at actually commercial teaching? How do do at closing for next steps? How do I make sure that I can quickly design that simple extras to see how they're doing at that? And it can be two parts, but it should be part of the process.

**Harry Stebbings** [31:02]:

I have to ask, do you do it on your company? And so you have the domain knowledge that you can judge and value them against? Or do you do it on their company where they're operating from a situation of safety and domain experience?

**Rich Liu** [31:13]:

Yeah. I've done both. Obviously, with your company, you can see if they can quickly do the research, assimilate all the information they get with how to pitch it, figure out the product, and pitch it back to you. If you do their product, you can demonstrate more about how they would run the meeting, how they would do the discovery, how they would practice these core sales skills. So it really depends on what you would want to get out of it more. And actually, I might do either one depending on do I have questions of if this person's either smart enough to do my sale or motivated enough to go do the research or is putting together the pieces or can actually help tell my story in a way that's better that I haven't thought about yet. If I have questions on core salesmanship or salespersonship, I might have them do theirs and and I can play into their role, or I might do a little bit of both. So we're gonna spend fifteen minutes on a meeting here, then we're gonna do like, a quick five minute. If you're prospecting and doing PG, how would you help PG me to take a meeting and go do you know, our product? But that exercise is super important. And then finally, like, references and back channels. I know sometimes people do the back channel thing is some you know, has mixed emotions out there. But I would say, like, if we know someone who we trust that as work with that person, it's obviously not gonna blow them up, that I trust in my network. I sure as hell want figure out some signal. References, you can easily give someone who's gonna sing my praises. Tell me if Harry's good or not. Hey, Harry's awesome. Cool. Thanks. Bye. What does Harry do well? What are the areas that you were coaching Harry in? What are the ways that others worked with him? You know, what are those things that actually get it out? And I set it up by saying, hey, I want make sure this person's set up for success here, that we're the right fit for them so that we don't put them in the wrong type of company. So the more direct you'll be with me, the more open you'll be with me, the more we can figure out that for this human who I know you love and like and trust, that's the best fit for them.

**Harry Stebbings** [32:51]:

Someone once gave me the best advice on referencing. They said people will 99% of the time never tell you their real weakness. And so you say, hey, if I was hiring someone to work alongside or beneath Rich, what skills would they have? And they go, oh, that'd be super rigorous. that'd be very operationally focused, not need to be so creative, but that'd be very much kind of by the book and driven in numbers way operationally. And you're like, okay. you've just told me that Rich is not operational, but he's very creative. It's a really good one. Tell me, man, we need to give these guys an offer and girls an offer now. What's been some big lessons on comp packages for sales teams? How should I do it?

**Rich Liu** [33:30]:

I would say number one is sometimes I hear founders say, oh, that person's like getting an offer from so and so. They're competing with so and so. I gotta compete with this. And to get over anchored into throwing the kitchen sink and giving half the company to go get them. There are some good benchmarks out there for any role, AE, CSM, marketer, you know, partnerships person, ops person, strategy person. So trust that. Any all VCs, all the talent folks and recruiter will give you that. The bigger question is also trying to figure out, is the person actually at that level and with that experience that you are comfortable making that offer to them? I think a lot of the call it offer inflation out there that we had seen the last few years was like, okay, anybody can be a VP sales, CRO, CRO, at a series a, whatever company. The The whole titling thing got thrown out of whack because inflation is out there. Another thing is, okay. I do the job for a year. Does that make me a great COO? Because I got the title now at one place at a company that may or may not be similar, similar scale, similar problems to solve. That doesn't necessarily qualify me for the job. So I would be really clear around like, let's make sure what you need in the job is like based on I need to solve this end of the journey. Build a first sales org, go from first to second line leadership, take us from early adopter to mainstream as we were doing at Navan when I joined. These are the things I need done. Okay, great. What scope of person do I need for that, and what is the right titling for that, and what is the comp for that? Be really clear about that and then make sure that the person you are hiring actually fits that description. Titles aside, experience aside, and that's what you want use your interview process to go solve for. You know, we've had people who I've hired, hey. this is a, let's call it strategic sales director or RVP role. And that person might have that title at another company or a bigger title, and they're saying, no, I should be an SVP. Okay, Great. You can go with them on that. Or you could say, well, based on the work you're doing, based on the scope, as it translates to us, it's this role, this title. And it's okay to say, look, I recognize you can get that SVP, CRO, COO offer somewhere else. This is what this offer is. This is. why I believe it's meaningful. The vision that we're selling, the future that we're to create, the opportunities you'll have to grow and learn, opportunities to work with me, whatever those things are, to be really clear what they're getting there. But don't get caught into the like, I gotta do this title of this offer just because somewhere else. And if you do, do so knowingly. I'm trading off that I'm giving this higher title to someone, some person that I might need to up level later because now I can't bring someone on top because I've given this title, I've given this comp. I think that's really important to keep in mind. And sometimes it's easy to say, okay, just I need to do this to get someone, and there you go. And I'm a huge proponent of being intellectually honest and bringing the people around you, if you're a founder, to help you do that. Right? Your advisors who know go to market, your investors, the executive recruiters who, again, might have a bit of a conflict of interest in some ways.

**Harry Stebbings** [36:15]:

I to talk about some of the art of sales though, which is cool to kind of doing it well. And I'm to pepper you with questions. Number one, discounting. Do you do discounting? How do you advise founders on discounting?

**Rich Liu** [36:27]:

What is the model I'm trying to run? Right? Every approach has trade offs. It's a crowded race. It's a knife fight. We gotta capture share. I'm to do the lowest that I can possibly maintain from a margin standpoint to capture that share and do it efficiently, then raise the prices. Is it a, hey, we think we built, even in a crowded space, the best product. It's at a premium. I can clearly tell a story that is defensible and differentiated when I get into that room with the CFO and tell them why it should be worth more. Those are pretty different approaches. A lot of the founders I speak with will probably tell me, hey, We and Everlaw is the same way. We think we built the best product. We think we have the best team. We demonstrably get in the room and people say, yep, you guys are the best product. You built the best thing by far. Then it becomes a question of how much of a premium can I charge for it? Right? And that premium depends on how well I can tell the story, quantify the value, have proven results for delivery.

**Harry Stebbings** [37:15]:

Rich, let me ask you a very direct question. Yeah. Do you discount?

**Rich Liu** [37:19]:

Yes. Okay. If I'm running a PLG, don't waste your time getting into these cycles of discounting and not. But if I'm running like an enterprise sale, I like to hold a high list and then figure out how I need to discount to still protect the premium and get the deal done. I'm to discount aggressively if I need to break in a new space and market, but I need to know why I'm doing that and the trade off I'm in because now I'm eating CAC effectively. It's

**Harry Stebbings** [37:41]:

Deal reviews. How often do you do them? What makes a good deal review versus a bad one? How do you structure them?

**Rich Liu** [37:47]:

Yes, we do them. Bad deal review is everybody get in a room, let's go talk about the deal, see what happened. Great deal review. Let's actually go through and use a framework, any framework. MEDDPIC, you build your own. Right? Command of the message, pre negative consequences. What's the pain? What's the negative consequences? What are the outcomes you want? What are the after scenario and positive business outcomes? Use a framework, but be religious about actually using it so that you're not just getting in there, right, How's going on with the deal? And sometimes doing that for all the key deals that are not necessarily just going to close in a quarter, but that you need to go evolve from Whether it's 10 or 25% stage, to the 51, 90% stage, that's actually where the impact is driven. Like, when we're looking at the deals that are supposed to close this quarter, it's like, alright. you have a close plan. Do you have access to the EB? Have you quantified the metrics? Have you done the validation steps? It's actually that cohort of deals that's like, going, whatever you call it, that we've done the demo, there's something here. we haven't actually built it into like, a verbal commit yet. That's actually where the deal review is the most valuable. And I'm trying to grab those deals every quarter and make sure that either me or head of sales or head of Americas, whoever it is, is, actually doing that deal review with that set of deals every quarter. You get through them.

**Harry Stebbings** [38:54]:

Rich, how often do you do deal reviews? Weekly at least. Weekly at least. Got you. Who comes to the deal review?

**Rich Liu** [39:01]:

The rep, the frontline manager, and an executive, the VP sales, the SVP sales, me, someone should be there.

**Harry Stebbings** [39:07]:

What are the most common reasons that you don't get deals over the line?

**Rich Liu** [39:11]:

I think there's a few places that comes up. Number one is you never had true buy in to start with. You didn't do the deal the right way, yet you're trying to prosecute and just go through the sales stages. I'll send out contracts. Boss, I got 10 contracts out. Alright. Are any of them to sign? By when? By what? Actually trying to do the contracting and the like, operational sale without actually getting over the hump with your champion, with your economic buyer, with a business case that matters. That's a huge issue, particularly right now in a changing market. A second one is not getting to the economic buyer and actually selling to them. Right now, oh, I got the EV in back behind the scenes. That's not a true champion. You don't have a deal. Those are probably the things that are hurting deals the most right now in this current environment, in this changing

**Harry Stebbings** [39:53]:

What are the biggest red flags in the first month of a new sales rep joining?

**Rich Liu** [39:59]:

They don't do PG, number one. They don't generate their own pipeline. They won't make the calls. They won't actually get out there and get their hands dirty.

**Harry Stebbings** [40:05]:

So PG is pipeline generation? Correct.

**Rich Liu** [40:08]:

If they are not doing if they're not doing it early in their tenure, that's a sign. If you've set up an expectation that they should be doing it, to me, that's a big one.

**Harry Stebbings** [40:16]:

And how do you tell Ratchy look in Pipedrive and see? Do you look in their calendars and see their email?

**Rich Liu** [40:21]:

Yeah. There's as tactical as activity, but if we could set up basic Salesforce reporting on how many ops they're generating, good rule of thumb is like an AE in my book should be generating at least a new op a week by themselves without SDRs, without marketing helping them in an enterprise software sale, outbound sale. Are you at least doing one off a week? If you're not, okay, are you doing activity? How are you doing it? Do you actually know how to do it? That's the hardest part of selling. If they don't have either the appetite or the skill to do that, you better get it fast because you're not gonna work here. And granted, we should be vetting for that in our hiring process going back to what we just talked about. That's number one. Number two is when they just don't seem to grok the product. If I don't if I can't grok the like, talk track, how to talk about it, how to use the product, how to share it, yes, we talked about not going straight to a product led sale, a driven sale, but if they're not showing that at a pretty fundamental level and quickly grappling onto those sound bites, talk tracks, that's usually a big red flag for me. So between those two, those are pretty early, because those are the precursors to can you actually get pipe? Can you actually build late stage pipe? Can you actually do deals? It doesn't matter how good they were in the room because they might not ever get there.

**Harry Stebbings** [41:20]:

What are the biggest fuck ups you've made as a sales leader, Rich?

**Rich Liu** [41:24]:

This is one where probably good advice for founders and for sales leaders and heads of sales are just getting really aligned on expectation of what's possible, what's So number one is I talk to a lot of early stage go to market leaders and early stage founders who will tell me the flip side of this same question, which is like, what's possible? I was talking to a founder and he had just turned out a head of sales. And he's like, I wanna push them hard. I wanna make sure that, you know, we're striving and we're, you know, this is like a 10x type of year. We should be growing five x this year. I believe the product is so good that it should be doing that. His sales leader didn't have that belief. His sales leader is like, hey, I this think like a 2x x year, 1 and a half x year, 50% growth year. Here's why. And there was that gap between what each side thought was possible. And instead of solving that and figuring out a target, the CEO sets founder sets a target that's like crazy high. Sales leader like, I don't have the confidence to push back or bring this to a head or leave and takes that. And we'll bend over backwards, to try to make it happen, see what happens. And then even if you get to 90% of that crazy stretch target, man, it feels like, oh, we burn run ourselves ragging. We still didn't hit it. You know, maybe the board's like, ah, how come you didn't hit this target? And meanwhile, growing four 4x on a 5x target might have been freaking amazing, taking all the weird expectations out of it. I've certainly fallen into that camp. That's one of the biggest things that I've done as a sales leader. So I think it's just so important to get no daylight between what we think is possible, what the appropriate amount of stretch is so that we set the expectations around the right way. We motivate the team the right way. They have the right feelings of winning. We set the board expectations and company expectations the right way. And most importantly, in this environment, we're investing the right way. Because the worst thing is I invest for a 2x x growth year and I grow one and a half and I took the cost to grow 2x x and it grew.

**Harry Stebbings** [43:02]:

What would you advise sales leaders in terms of accurate forecasting in 2023?

**Rich Liu** [43:08]:

Now is the time more than ever to go inspect what is real and what is not because things that might have been a deal that you could feel 50%, 75, 90% confident in a year ago might not close at all this year or might get delayed this year. So like the difference between deals pushing, deals not closing at all, or deals coming in way smaller is do I have direct access to an EB? Do I have a real business case or am I selling it off of a cool, this is a nice product we'd love to have? If I'm doing that kind of inspection for true business case, direct access to EB, do I have a close plan in front of them or an evaluation plan that we've talked about? By this date, we will do this. By this date, we will do that. You are looking for these three things to go make a decision. These are who the people are who are going to make the decision by this date, and this is what we will show them. If we don't have that, even if it was a good deal last year, it's probably not to close this year and it's definitely not gonna close on time. So that level of inspection of your mid stage pipe and what are the things in your sale you need to have a deal right now and take a fresh look at it, that is what I think everyone should be doing in your entire sort of mid stage pipe and building into your early qualification deal process or sales process if you don't have it. Those are the things I'm seeing like, in different sales, different industries, different velocities. It could be different things. But that's the thing that's gonna keep us from getting surprised around, hey, I had this pipe and I had this thought I had this great pipe coverage. It turned out it was like fake pipe and just slipped out.

**Harry Stebbings** [44:27]:

I can talk to you all day, my friend, but I to move into a quick firearm. So we're to start with what sales tactic have not changed over the last five years?

**Rich Liu** [44:35]:

I would say I'm a huge fan of force management and that the value framework, you know, whether it's force management, whether it's like challenger selling, that idea of needing to attach, do enough pain based discovery to figure out what are the most important problems or worries or fears or existential threats that company is facing, that the CEO is facing, that the economic buyer in your org is facing, like, doing that level of pain based discovery has not changed. And actually getting to that true, I don't know, sandwich called like, level three pain of, like, what is the true business pain and figuring out how to map what you do, your service, your platform, really back directly to that in a quantifiable way, that has not changed.

**Harry Stebbings** [45:13]:

What sales tactic has died of death?

**Rich Liu** [45:15]:

I would say for me right now, having that perfectly crafted email, hey, I did a great YUI now, it's two paragraphs, I've done a lot of research, or I've done the cheap thing where it's like, hey, you went to Yale, you the captain of the volleyball team, what do think about Yale volleyball this year, Rich? Like, those types of like, pure write the perfect email and you get a response, like, that's not going to work right now. I would say like, multi touch. And if you're an sdra d r a e, like, multi touch. I don't get a lot of calls. I won't take a lot of calls, but I will say like, send me the text, leave the call, send me the text, hit me on the voicemail, send me the video. figure out how to get through to someone. I think needing to actually be creative and multi I'm always shocked at how many reps don't do the quick video or don't do the LinkedIn or don't do the Twitter or don't do the G chat.

**Harry Stebbings** [46:00]:

What is the biggest mistake founders make when hiring sales team?

**Rich Liu** [46:04]:

The biggest mistake I think is hiring ahead of what you actually have conviction to do. You think You are ready to scale and you're not ready to drive efficient out. The second is just hiring a leader that is is not really well suited to what you need done in terms of what you need to accomplish in the next twelve to eighteen months, not twenty to thirty six, and not moving quickly enough to go make changes if it's not working.

**Harry Stebbings** [46:23]:

What one piece of advice would you give to a sales leader starting a new role today?

**Rich Liu** [46:28]:

Be quick in identifying and driving alignment with the CEO or founder or your boss. What are the most important things we can get done this quarter? And what are the one or two metrics that I need to show you to show that we're doing this right?

**Harry Stebbings** [46:41]:

What would you most like to change about the world of sales?

**Rich Liu** [46:44]:

Oh gosh, more people get into it instead of feeling like when I got into sales, I was a gangly engineering student from Yale and and I had this understanding that it was for like slick, well spoken white guys that could tell the story the right way. And I had that chip on my shoulder. I would say that I would love to see more people consider it as a career coming out of any major with any background because it's an amazing career. I've learned a ton. I've met some really cool people doing it. And the reason I'm still doing it is because I keep learning and I keep figuring out ways to do it differently. And in an environment where maybe AI is gonna take our jobs, ability to go connect with people in a real way, the ability to go show value, the ability to go do deep discovery, I think that's at a

**Harry Stebbings** [47:23]:

premium. And sometimes slick, well spoken white guys aren't very good at slick. I I was listening oh, I feel judged.

**Rich Liu** [47:31]:

No. sorry, sorry, Sorry. didn't mean some of my best friends are are that I don't

**Harry Stebbings** [47:36]:

know why my ego is sufficiently inflated anyway. I will be fine. But I do wanna finish on my favorite actually. Other than Everlaw, what one company sales strategy have you been most impressed by recently?

**Rich Liu** [47:48]:

It was a while back, but I think one of the plays that I think really helped me even during the pandemic. So we bought People dot ai during the pandemic at TripActions and Bond. And it was initially to go get like contact capture so we can build our database to go track activity and go go better do marketing to those folks. And they did this thing where they did the like, hey, we know you don't to buy this expensive analytics offering. we think it can give you some insights. And I'm like, no, I got a great analytics team. CKCU is the best on the planet. You know, Roll size like, amazing. Like, we got our own stack. We're good. And they were like, well, we'll give it to you for free for six months. Just try it out. Like, we'll help you implement it and stand it up. And if it's anything other than amazing, like, you don't have to pay for it. But they built it in the contract. So was like premium in an enterprise software sale. They built a freemium thing into the contract. They worked with us to stand it up and make it successful, and sure enough, we signed the check to do the broader platform buy after that was done despite a lot of skepticism on my part that it was valuable. Now that's not to say that's the only way to do it, but in a world where we're trying to drive more bundle size and basket within our customers right now to keep them sticky in an environment that is going to be more friction around buying and keeping pieces of hardware software, thinking creatively around how to actually build that expansion, that cross sell into your sale upfront. I think that was a great example of that. And you had a travel company to buy more software during a pandemic when the revenue went down to zero, I

**Harry Stebbings** [49:07]:

think is a pretty cool Dude, I love this. Thank you so much for putting up. It's Friday afternoon, so I've been more casual than I normally am in my straight, you know, lined English box. But I love this. It's been so much fun. You've been fantastic. So thank you so much for joining me man.

**Rich Liu** [49:21]:

Oh my gosh, Harry. Much enjoyed on my side. Always a pleasure and I hope you have a wonderful weekend.

**Harry Stebbings** [49:28]:

Well, I mean, that was a free flowing discussion. Rich really put up with the wayward schedule there. If you wanna see more from us, of course, you can on YouTube by searching for 20 20VC and I always love to see you there. But before we leave you today,

## Sponsor read

**Harry Stebbings** [49:38]:

you might remember in our amazing episode with Maggie Hot, she mentioned a tool she could not live without called Pocus. What is Pocus? Well, Pocus is a revenue data platform that makes it easy for go to market teams to analyze, visualize, and action data about their prospects and customers without needing engineers. Pocus helps companies like Miro, Webflow, Loom, and Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment so reps can take action quickly. Pocus gives you a 360 degree view into product usage, empowering you to act on insights and fill your funnel efficiently. Sales teams save ten plus hours per week digging through data to surface millions in new revenue opportunities. Learn more about why top PLG businesses trust Pocus as their revenue data platform by visiting pocus.com/demo. And SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new SalesLoft, and so can you. It's the new way to sell. Find out more at salesloft.com. As always, I so appreciate all your support and stay tuned for an amazing episode this coming Friday.
