Liam Mulcahy on this episode
Liam Mulcahy, go-to-market lead at Kleiner Perkins, brings deep sales leadership experience from MongoDB and early-stage startups to break down how B2B SaaS companies build sustainable, repeatable sales motions. Starting his career as an SDR while building a company on the side, Liam has lived through the evolution from founder-led sales to scaled sales organizations, giving him firsthand insight into the decisions that separate high-growth companies from those that plateau.
The core insight: most founders and early-stage sales leaders confuse activity-based processes with actual sales processes, leading to wasted time chasing unqualified deals and missing the leverage that repeatable systems create. Rather than hiring a sales leader first, Liam advises starting with strong individual contributors—revenue-generating product managers who can close deals without intensive management and simultaneously document how they win. This approach builds proof that salespeople can succeed at your company before asking a head of sales to bet their career on it.
The reframe lies in thinking about sales as a data and process machine, not just raw capacity. Even at the early stage, exit criteria, qualification frameworks, and simple documentation (a pre-call planner, recorded call transcripts, a handoff loom) create the scaffolding that scales. As companies grow, these foundations either compound positively—enabling smaller, more efficient teams powered by data—or metastasize into silos where marketing, sales, and customer success speak different languages and chase conflicting metrics.
The episode covers hiring sequencing, managing your obsolescence as a founder, the practice of "positive pessimism" in deal qualification, the underrated power of sales engineers, why over-automation and tool bloat waste rep time, and how data-driven territory assignment and scoring models let companies maintain yield as they scale.
What we cover in this episode
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1:18
First Sales Hire Sequencing Whether to hire sales reps, SDRs, or a head of sales first depends on ASP, founder sales experience, and ability to close deals solo.
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4:08
Head of Sales vs. VP of Sales Titles Title reflects career stage and scaling potential rather than immediate job scope; critical signal of whether candidate can grow with the company.
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14:51
Importance of Sales Process in Early Stage Sales stages with clear exit criteria and mutual action plans prevent reps from chasing every deal and wasting time on unqualified opportunities.
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25:26
Positive Pessimism in Sales Management Assume deals are unqualified until proven otherwise with data; constantly challenge why customers will buy and why they will buy from you.
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27:48
Polite Indifference and Qualification Push prospects to articulate why they don't solve the problem in-house; give them permission to leave the process at any stage.
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33:23
The Role and Pairing of Sales Engineers SEs unlock technical and business implications; the best SEs pair technical depth with AE ability to navigate organizational political and budget dynamics.
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43:17
Scaling Sales Teams and Process Breakdown Problems compound as teams grow; broken processes at five people become catastrophic at 15 or 50 without deliberate re-engineering.
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47:38
Data-Driven Territory and Account Scoring Replace capacity model with data model: combine firmographic data with proprietary signals to create a scoring system that directs rep activity where propensity is highest.
The lines worth sharing
I'd rather have two incredible salespeople than six C-minus salespeople. The output is going to be significantly different.
Liam Mulcahy · 2:20
Exit criteria and mutual action plans—a give-get—are incredibly overlooked. Most companies are so desperate to be paid that they just start serving the deal.
Liam Mulcahy · 20:15
If your ASP equals your time to close in days, you have product-market-sales fit. Conversely, if you're doing 36K deals in 70 days, something is severely broken.
Liam Mulcahy · 22:30
You have to give prospects permission to leave at any moment. They always need a second option. That's polite indifference.
Liam Mulcahy · 28:45
Common questions from this episode
Should an early-stage SaaS company hire an SDR, sales rep, or head of sales first?
Start with a strong sales rep who can close deals and document the process. SDRs only work if the founder can close deals themselves. Hire a head of sales only after proving salespeople succeed at your company—typically after you have 3-4 overperforming reps that a new leader can coach into A-player status.
What is the difference between a head of sales and VP of sales title?
The title reflects scaling potential and tenure, not immediate scope. A head of sales signals you're taking a bet on someone for 12 months but unsure if they'll scale with non-linear company growth. A VP of sales suggests they can lead through multiple scaling phases. Choose based on candidate pedigree and your confidence in their ability to reinvent as the company grows.
Why is sales process important for early-stage companies?
Sales process with exit criteria, mutual action plans, and qualification frameworks prevents reps from chasing every deal and wasting time. It lets founders delegate their sales vision to growing teams, ensures deals move only when prospects re-qualify themselves, and creates the scaffolding that scales as you hire more reps.
What is positive pessimism in sales management?
Assume deals are unqualified until proven otherwise with data. Constantly ask: Why would the prospect buy? Why pick you over competitors? Why now? Does this person have budget and authority? If you can't answer with data, not opinion, the deal probably isn't as qualified as you think.
How do you use data to improve sales territory and account assignment?
Combine firmographic data from platforms like Apollo or ZoomInfo with proprietary signals relevant to your business. Create a simple scoring model (1-5) to rank accounts by propensity to buy. Give reps an opinionated, data-driven hypothesis of where to spend time, replacing the old capacity model of just hiring more people to cover more ground.
Why do sales problems get worse as companies scale?
Broken processes don't self-correct; they compound. Adding more reps to bad systems creates silos, duplicate data entry, disconnected metrics, and reps doing grunt work instead of selling. Revenue ops, data teams, and clean tech stacks are investments that become critical, not optional, at scale.
SEO meta description
Liam Mulcahy from Kleiner Perkins on building repeatable sales motions: hire strong reps first, establish clear sales processes with exit criteria, use data to guide territory assignment, and avoid over-automation that wastes rep time.
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Read the full transcript · 58 KB · Liam Mulcahy
SPEAKER_00Welcome to RevOps Corner, where we talk about how B2B SaaS companies scale through revenue operations by interviewing amazing guests and sharing what we see in the trenches every day here at Union Square Consulting.
EDDIE REYNOLDSAll right, welcome to another episode of RevOps Corner. Today we're talking about building a repeatable sales motion with my guest, Liam Mulcahy.
EDDIE REYNOLDSLiam is go-to-market at Kleiner Perkins and started his career as an SDR while also building his own startup on the side and grew into sales leadership eventually at MongoDB before entering VC. Thank you so much for joining me today, Liam. Yeah, of course. Thanks for having me. So I'm excited to dive into this. Today we're going to talk about building a repeatable sales motion. We're going to talk about your first sales hires. We're going to talk about building the team as you're a more mature company. We're going to talk about building sales processes, about tracking metrics early, about how eventually all roads lead to outbound. And then we also, if we have time, we'll dive into over-automating the sales process with tools and systems. So again, thanks for joining me. I'm excited to dive into this with you. Same. So let's start off. And I want to try to balance early stage with more scale-up. And so let's start off with early stage. Who do you hire first in sales? You're working with a super early stage company. It's founder-led sales. The companies you work with at Kleiner Perkins, how do you advise them to approach their first sales hire? The companies that I work with inside of our portfolio are about 100% B2B.
LIAM MULCAHYSo it's pretty rare that I would ever work with a B2C company, just to set the table there. That's a different type of alchemy. Growth and go-to-market, I think, are very different. So let's just say that it's a series seed or maybe a series A company. The founder or founders have been able to take that to a couple hundred thousand, maybe a couple million of sales on their own. The fork in the road that a lot of them run into is, do I hire an SDR? Do I hire a sales leader? Or do I hire a sales rep? And all of those have different jobs to be done. So it's a bit dependent upon two things. One is, what's this founder's level of familiarity with working with salespeople? Could they manage an SDR? Have they ever worked with the head of sales? Have they ever worked with salespeople? Did they actually do the sales themselves? Or did they have a PLG motion or a lot of inbound based on product and good product market fit? And the sales are more transactional than them creating opportunities and going to close. And you can kind of roughly tie that to average sale price. So like if your average sale price is under 24K to start, you could probably go after maybe a seller or an SDR to start. So I do think there's something about lower ASPs and the sophistication of a sale, maybe with how many people are involved in a decision process or decision committee and the type of evals that they need to do. Where if you're just fielding demand or you need to create demand, you have a low ticket price and you have a pretty quick time to close under 30 days. To me, starting with a rep or an SDR is probably appropriate. They can typically handle those. And a full cycle rep should be able to do that fairly easily. You can recruit them out of a lot of other companies that have a similar selling motion and size. If the ticket price is over 24K, let's say it's like 36, 48, over 100. Starting with SDRs only works if the founders can actually inherit those opportunities and close them themselves from like a sales process and just sales know-how and then just their own bandwidth. Is this the most strategic thing they should be doing? If I had to stack rank all three in terms of the most common ways that I advise portfolio companies to do it, I'd love to start with sales reps.
SPEAKER_11With the most bang for the buck, they can cover basically the entire sales cycle, A to Z.
LIAM MULCAHYThey can field inbound, they can do outbound, and they're typically not going to cost you an arm and a leg, even though I would advocate if you can get a great seller, pay more for a great seller. Because I'd rather have like two incredible salespeople than six C-minus salespeople. The output is going to be significantly different and the quality is different. If you want to go with SDR because of either the transaction size or volume or the sophistication of the founders, I think that's fine. I usually recommend head of sales last. So it's pretty rare.
SPEAKER_13What is a head of sales to you, by the way? Yeah, a head of sales to me would be someone who is going to be judged by recruiting sales
LIAM MULCAHYreps and having those sales reps hit a number.
SPEAKER_16And why is that person not called a VP of sales?
EDDIE REYNOLDSTitle, like the title can be, the title can be a very fickle thing.
LIAM MULCAHYSo the difference between calling somebody a head of sales or a VP of sales isn't necessarily their pedigree or their background or their capabilities. It could be the stage of the company. It could be, are you taking a bet on them ahead of their career curve and you want to call them a head of sales because you're really confident they can probably do the job for 12 months, but unsure if they're going to scale with the company beyond that. Companies that work scale non-linearly, right? And the problem with a lot of people at companies is they scale in a linear fashion. To no fault of their own. It's just a very unique, rare individual that can scale and reinvent themselves to keep pace with the company that's growing non-linearly. So the title, you could be a VP of sales and a head of sales and basically be doing the exact same job at a startup. Sometimes the title is just how long we think you're going to be able to hold onto this rocket ship if it works. And a lot of head of sales can become VP of sales as a result, but it's less about anything tactical and it's more about like maybe their tenure in the industry and where they came from and how long we think they're going to be able to scale with the organization.
EDDIE REYNOLDSYeah. It does feel to me that if you give somebody the VP of sales title, for example, and then the company accelerates faster than they can keep up with it. And now you need to hire a much more experienced, seasoned VP of sales. Now you're in this tough position of, okay, I can't hire a VP of sales to manage a VP of sales. So do I need to demote this person? Do I need to fire them? Whereas a head of sales could report to a VP of sales and you may be setting yourself up for a smoother transition. At least that's my impression.
LIAM MULCAHYYeah, I agree. And I think that's why in the interview process, I'll only speak for myself. But if you have a good opportunity to join a company who has product market fit, that's growing fast in a durable, scalable, like efficient way from an economic standpoint, people that get over-rotated on the title is always just negative signal to me. Head of sales, VP of sales, like some of the best candidates I've ever recruited, the title like kind of rarely comes up. What they will do is they'll negotiate appropriately hard on things like compensation, expectations, equity packages, like that's all appropriate to me. But when I find people that are like, look, everything's aligned, perfect OTE, love this opportunity. But if it's not SVP of sales, I'm not going to join where, you know, we're off the mark
SPEAKER_25somewhere.
SPEAKER_24Yeah, I hear you there. And the reason that I'm kind of diving in on this is that I think founders a lot of times
EDDIE REYNOLDSare really struggling with who should my first hire be. And it's difficult for me to relate to this personally because I've spent my whole career in sales just like you. And so a lot of these things you're describing as a founder myself, I'm doing it myself. I'm making the cold calls. I'm closing the deals. And so as I think about we're hiring sales right now, and as I think about who we're hiring, what we need them for, I'm thinking about what is the activity that we need to do the most that I need to get off my plate? Because it's not that I have to hire somebody because I don't know how to do something. But what if I was in that situation? What if I was a technical founder? I've never sold before. I've somehow scratched together some customers via my network. And we're here and we've raised some capital. And now what? I don't know how to manage an SDR. I don't know how to teach an AE how to sell. I don't know how to design a sales process. I don't know what medic is or what it means or how to implement it. What do I do? What do I do then? Yeah, I think what you're describing is a lot of the work I end up doing in the portfolio
LIAM MULCAHYor the types of situations that I spend time with. So most companies, founders sell through concentric circles, right? Center of the circle is your network. And maybe the second ring is people that your investors can introduce you to, which I'd still consider network. And then that third ring starts to become inbound, maybe people that are easy outbound or folks from your previous jobs. And then it gets pretty cold further out. The reason why I like founders in those situations to hire salespeople or sales reps first, as opposed to a head of sales or an SDR, is one, with a salesperson, you don't need to teach them how to sell. So you do need to hire for someone that's going to be able to come in and you're not worried about their ability to sell software that looks like your software in some form or fashion that can handle the chaos of whatever company stage you're at. It doesn't have to be the exact same stage that you're at, right? But if they've handled a chaotic stage in a company that's hyperscaling or just scaling in a nonlinear way, you just need them to be comfortable. Like, how are they going to enable themselves when there is no enablement? So I think your first sales reps, to me, the pedigree you tend to look for is like a revenue generating product manager. Someone that's extremely comfortable talking to product people. They're very good with customers. They're probably a bit of a deal junkie and they just know how to go find deals when the opportunity arises. Managing them from a founder standpoint, like when you click back one level and now you're managing a sales rep, you're going to be measuring them on a lot of the similar inputs that you had yourself if you were doing founder-led sales. And I think it's important to focus on the inputs a little bit more than the outputs because outputs are obviously lagging, rear view mirror. So if you think about like how many people do we need to reach out to? Do we have a data-driven approach of where this salesperson is going to go spend their time? Like what is our ICP and what's one or two deviations away from it? Have I, the founder, done that work to give to them? And then how do we price? How do we package? How do we get a deal done, et cetera? Good sales reps at the early stage start to build those scaffoldings around the process as they're in it, right? Hey, I think this is a better way for us to send out MSAs. I'm just going to document it somewhere. And they'll keep doing that for each stage. And SDR is only going to take you a third of the way. No fault of their own, right? But that's just what you're hiring for. So as a founder, if you're trying to think about what are you going to get the most bang for your buck, an SDR can give you more leads, more conversations, but it's not going to help you close deals. And then a head of sales is completely different. If you think like what would really attract a world-class head of sales to leave where they are, which is probably a good growing company where they're gainfully employed and they're always passively looking to come to the most risky stage of company building. If I was looking for an opportunity like that, I'd at least want to see some existence proof that I could go hire another 10 salespeople and they'd be productive. So if I am talking to a founder who's done founder-led sales, even if they've gotten to a couple million and there's no salespeople there yet, and it's only SDRs, a lot of that risk burden is going to fall on me because there's no proof that salespeople have been productive here. I'd much rather walk into an opportunity and interview with a company that has even, I'll tell you one way that like product market fit manifests, like companies that have three to four salespeople who are probably C to B players, but are like way over their quotas.
SPEAKER_26So that's pretty appealing for a head of sales who can recruit a talent to go in and say like,
LIAM MULCAHYwow, this team is doing really well. I can help them become A players. And then if I take somebody from XYZ company that I know or that I worked at, who is an A player and put them in this organization, it's not really hard for me to be able to see how those characteristics and traits would make them successful. That's a much more attractive place to like interview from and for founders to recruit from than if there's no salespeople there.
EDDIE REYNOLDSYeah. I think that that makes a lot of sense because then you're just turning dials, right? You're saying, I need a sales rep that's going to make more calls. That's going to present a little bit better. And so we've got higher activity. We've got higher conversion rates. We've got, they know how to ask for bigger deals and offer less discounts. And so you just turn each of those dials and as they add up and they multiply on each other, you have a much larger number versus if, and I've made this mistake, if you're in a situation where the only person that can really close the deal is the founder and the sales process is so contingent upon the founder's personal knowledge. Yeah. When I started this company, we were more doing like Salesforce implementations. And so I'm like, I need to hire a sales rep who also can answer very technical questions about Salesforce. Good luck with that. And I'm not even talking like I was an AE at Salesforce. I'm not talking about that level. I'm talking about the questions that our SEs would get asked. I'm talking about the questions that the SEs would say, I don't know the answer to that. You have to ask the implementation partner. And now I'm doing all of this work myself and trying to hire a rep and say, okay, now I want you to do what I'm doing. I have 20 years of experience doing this now figured out in the next month. Like that's just completely unrealistic, right?
EDDIE REYNOLDSYeah. And I think it's the founder's first experience of what enablement is.
LIAM MULCAHYSo I'll ask founders to seed stage company, maybe. And they're like, hey, we need, we're at this crossroads. And let's say that we agree we're going to go hire a sales rep. I'll ask them like, what gives you the confidence that if any salesperson comes in here, they're going to be successful. What makes you think that anything that you've done is repeatable and not just the sheer brilliance of how good you are and how compelling your vision is around this product area or this problem set? So I think founders go from like sales rep and SDR, then they click back to maybe managing a seller and they become like founder slash super solutions engineer. And that lasts for a little while. You can do that to maybe five, six reps, maybe more depending upon the ticket size. And then they click back again to managing a manager, they hire a head of sales, right? And now they're further removed from the field, even though they should still be doing skip lines and talking to customers all the time. But now they're managing managers who control capacity in the team. So there is always this, like, you have to plan your obsolescence as a founder in these roles and go to market. And you're probably going to have to do the same thing with marketing and customer success to a degree. Otherwise, if you become the dependency that is going to break, it's not, if it's going to break, it's when. And when it breaks, it's going to be very painful. And you're never going to get out of the chaotic phase, right? Like the early parts of company building are doing a ton of unscalable things to earn the right to scale in a more like kind of methodical way. And you only do that by like trying to make sure you're putting little systems in place and enabling the other parts of your organization. And then you keep stepping back and having bigger impact on the team, as opposed to trying to do everybody's job and thinking that you're being very productive because you're very busy. But in actuality, you could just be getting in everybody's way and being like a single bottleneck that's causing this company to slow down.
EDDIE REYNOLDSYeah. And this is a perfect segue into sales process. And I've experienced this personally. I was the first AE at a startup. And when you think about like mapping out the sales process, that startup was built on top of Salesforce. So I was effectively selling Salesforce. And one of the big bottlenecks they had is this SE role you're talking about. But they had actually filled that because we had a whole implementations team of really smart people that would double as my SEs. So I had to do my own demos, but I didn't have to answer these really technical questions. I had somebody to help for that. So now the founder wasn't the only person able to do that. So now the bottleneck he was trying to solve for is I need somebody to make cold calls and run deal cycles. I don't need somebody to be an SE, which would have been impossible for me to do at that stage in my career. And same thing for us. Like we have a very similar issue. And so we've taken our VPs of delivery and turned them into SEs. And now that's worked really well. But you're only able to do that if you map out your sales process to understand what those bottlenecks are. And when we talk to companies that are early stage, let's call it sub 10 million, usually they don't have any or not very good documentation of what their sales process is. I'd be curious what you see.
LIAM MULCAHYYeah, it's rare. Or their sales, they misconstrue their sales process for activities. And then a sales stage is titled an activity. You know, like demo is not, yeah, meeting or demo is not a sales stage. That's an activity within a sales stage, right? That could be an exit criteria or something you need to complete to move on to the next sales stage. But that's typically what I see. And again, it's no fault of their own, right? They've had no exposure to this. The majority of the time they become a founder, they've never had to get this in the weeds with salespeople or process. You'd hope that some of the early reps they bring on can show what they've done in the past. And maybe you keep 60 to 70% of it and then customize it for this company and what you're selling. But for the most part, it's pretty broken. But I've also seen the complete opposite too, where it's way, way too complex. They've like way over-engineered the sales process in the beginning and it's 12 stages. And to me, I think most companies under the sun, four to five sales stages with really clear exit criteria and holding true to strategically saying no when people do not meet that exit criteria is the key.
SPEAKER_34Yeah.
EDDIE REYNOLDSAnd so I wanted to ask you why you think sales process is important for an early stage company. And then I'll give you my answer.
LIAM MULCAHYYeah, look, it's again, I don't need it to be some sort of like a MedPIC, Terminator, TI-84 perfect process. I actually think that what we implement most often at the early stage is some kind of fever dream of MedPIC where you're taking certain parts of it, but it's not perfect or the classic version. It's really important because if you have a sales team, even if you have a sales rep and you're not taking a data-driven process-driven approach to how they spend their time and what they do when they're in an opportunity, you're going to wonder where all their time went at the end of the quarter. So I think you have to be opinionated about how they interact with customers, what qualified looks like, when you strategically say no, what fits our current product extremely well today. So even if we think we can sell to this person in nine months, we have to say no today and explain why and move on. And then when we're in deals, it's really just about increasing your percentages of winning, right? Like when we follow this process, it aligns to a really ideal customer journey of onboarding onto our product and it results in a good deal and them getting value very quickly after they've closed the deal and start to implement. So I think the sales process, another thing I see is like, it should not stop at closed one. I'm a big believer in like single threaded ownership where a sales leader should own the customer life cycle, right? They don't have to be an expert in all the parts of it, but they should be on the hook for implementations or doing good deals so that you don't have problems where reps are just out there closing anything with a pulse and then throwing a bunch of crap over the wall to a CS team. And they're like, what are we supposed to do with all of this? And there's a churn problem. And then the reps are like, well, that's not on me. That's on you. So I think you got to think about the ideal customer journey, map that out. And then think about what parts of your organization should own different parts of that ideal customer journey. And how are you going to measure if it's working or not? Some of that's going to fall right within the sales process. Some of it's going to fall all the way with top of funnel and marketing and demand gen and everything else. Some of it's going to fall with implementation teams and onboarding teams and the rest, but everybody should own a piece of it. And it should be a connective chain as opposed to separate silos. And then you have a quarter where the sales team is about to get fired, but the marketing team has party hats on. That should be impossible.
EDDIE REYNOLDSYeah, I very much agree with that. And the reason I think sales process is so important for sales teams, even in the early stage, is very much in line with what you said. But I think a lot about wasted time. I think about a sales process is reverse engineering all the steps we need to do to accomplish two things. Number one is to maximize our close rate and deal size. And number two is to avoid losing precious selling time, chasing the wrong deals. And what I see is by default, if you don't have sales process, especially if you have junior salespeople, then you just end up chasing every deal all the way to the end. You end up doing a demo, a proposal, negotiating price, maybe arguing over legal terms, et cetera, and then losing deals that were never, ever going to close in the first place. And then now you don't have time to prospect. You don't have time to build more pipeline. And so not only are you losing deals because you skipped steps that you should have taken that you might have won the deal, but you're also chasing deals you were never going to win in the first place and then not building pipeline to make up for that.
LIAM MULCAHYYeah, I agree. And look, if you're going to run experiments on different ways you can sell or who you're going to sell to or what the most effective way to sell is, you have to have some contours of that experiment. Typically, it's like, what's the most efficient way we can sell this product? But that is a two-way street. A lot of the teams where I go in and the sales process is either very long or very short or completely activity-based, meeting, demo, proposal. That's a one-way street sales process where it's only what we do for the prospect. So that's just servicing, right? And typically, a lot of those companies I would bet when they run into problems with deals or forecasting or just their growth rate in terms of ARR is they're getting dragged behind the boat with every deal. They're chasing customers. They're trying to get people to follow up. They're sending proposals out there. They're never hearing back. Their POCs keep getting extended. They can never forecast accurately. Their forecast variance is like 30-plus percent every given quarter, up or down. That's because they're not asking anything of the prospect, giving them homework or holding them accountable. So I think the other important thing, too, about sales process is just exit criteria. Like, you're in this stage, discovery. What do we need to do and what does the prospect owe us in order to move this opportunity one step forward to scope, let's say? But it is a mutual action plan. Like, we will do this if you do this. It's a give-get. You know, it's not the most complicated thing in the world, but it's incredibly overlooked in terms of sales process. I think most companies, they're so desperate at the early stage for anybody to want to buy their product and to pay them and to use it, especially if it's a known logo, that they just start serving the deal any way possible, which always ends up with you getting dragged by the deal and kind of pushing rope instead of controlling where that thing is going. Yeah, and you share a really good example of this.
EDDIE REYNOLDSFor me, it's the proposal. Every step in the sales process, if you think about it, like the first qualification call is usually 30 minutes, and then the first discovery call is sometimes an hour. And then you get into a demo, and now if you're doing a custom demo like I did at Salesforce, you're spending an hour or two prepping and customizing that demo and then delivering that demo and then following up thereafter. And so now maybe that's a four-hour activity all in. Then you get to proposal. You're building a customized proposal. You're putting together pricing, et cetera. That could be 10 hours of time. And it seems to me that it grows exponentially as the deal cycle gets later. And so that's why it's so important to help your reps realize, wait, are you ready to move into the proposal stage and commit, let's say, 10 hours to this prospect? Because you could spend that 10 hours prospecting instead if this deal actually has very little chance of closing.
LIAM MULCAHYYeah, I think there's little heuristics I like to use to get reps to think a little bit more strategically about how they spend their time because it's often not taught. I think I'm the beneficiary of having worked for great sales leaders who really held me accountable and performance managed how I spent my time and made me think differently about it. Most people aren't lucky enough to have that opportunity, right? So they just start completing all of these tasks and finding opportunities and not thinking about where their time goes. The one way you can do that is like, hey, if you have a 36K average sale price and you have an opportunity for that amount and you know that you have a four-step sales process and it takes roughly six meetings to close a deal from like discovery call to signed order form, then you can start to do some simple math there, right? It's like every meeting you have at this company should be worth $6,000. So all of a sudden, if you have a $36,000 opportunity and you're 15 meetings in, you're way in the red. Like you're completely bleeding time and this is no longer like an economically viable way to sell this deal. So I think just little things like that, you can click it up or down with your average sale price and how many meetings it takes. If it's a 500K deal, if it's a 10K deal, you can think through that, but just trying to be efficient and holding yourself accountable. And then also you could do little things like, does your average sale price equal the average time to close an opportunity? To me, that's always a unscientific view of product market fit or when a sales flywheel is going. So maybe product market sales fit, people are doing 50K deals in 50 days or less, 70K deals in 60 days, 100K deals in 80 days. That to me is a really good indicator that there's a good sales motion in place and it's an efficient sales team. Conversely, if you're doing 36K deals in 70 days, you have to stop the conveyor belt because something is severely broken and you are probably not selling and qualifying.
SPEAKER_16You are probably just servicing and chasing.
EDDIE REYNOLDSYep. And I was reminded of that lesson this morning, actually. The last deal we closed was a $300,000 deal that we closed, I think, in like two weeks. The last deal we lost was a deal we lost this morning. We've been chasing it for six months. I don't even know what the dollar figure would have been. It's been passed around a lot. It's been pretty complicated. And then we actually lost it because we walked away from the deal. But I think the terms and the issues were so difficult. And I looked back at this and I'm like, hold on a second. This is not even ICP. And we spent six months chasing it.
LIAM MULCAHYYeah. Why? It's hard. You really have to... Like, I think the mentality that I try to communicate to founders and heads of sales and reps is like positive pessimism, right? And it's a bit of a weird thing for founders. Again, if you're not familiar with being in sales cultures or most founders have never been in a QBR or an effectively run QBR, where you're kind of assumed to be wrong until proven with data that you're right, you know? Why do you think this company would ever buy from us? Why do you think they're going to buy our product? Why do you think they'd pick us over the competitors? Why are they going to do this? Why do they even need to do this this year or in the next two years, let alone doing it by the close dates you have in Salesforce? Why do you think this man or woman is a champion? Why do you think it's really performance management through positive pessimism? Because if you can't answer these questions and it's data from the customer and not just your opinion, that's not based in any data, then you probably have an incredibly qualified opportunity. And the company will welcome you with open arms to go throw all the resources at it to close it. So I also think reps have to be, and like heads of sales and founders managing reps or heads of sales, you can't get happy years. You can't, you know, if Netflix comes in and you're a series A company, you need to be highly skeptical that they are actually ever going to pay you for anything. Not because they never do that, but because they've got more resources than they know what to do with. Like, why would they be using and taking so much risk with us? And if you can have those tension filled, positive conversations with the prospect, then you're really going to start qualifying and running a good sales process as opposed to just hoping and chasing deals and then getting surprised when they don't close or they keep pushing quarter after quarter after quarter.
EDDIE REYNOLDSYeah. And this is one reason I like sales process and I like this being built out in the CRM so much because the mistake I made in losing this deal today that we spent six months chasing, I'm not blaming my team. I was the one chasing that deal. And it's because I wasn't looking at like the fields in Salesforce asking me these critical questions of like, is this ICP? You know, are they committed to making a decision here? You know, have we confirmed budget? Things like that. I'm super busy and I'm doing a million different things and I get an introduction to this founder and then I start chasing it. And then six months later, I realized like, why was I chasing this to begin with?
LIAM MULCAHYYeah. And I think you got to push, like push customers away. Like I heard a really amazing term that I've never forgotten where it's like polite indifference. If somebody comes inbound, you have to almost kind of not believe them and like take a bit of a polite indifference of like, Hey, look, I think I have a good understanding based on how your business works and what you're trying to achieve of how we could help and how we've done that with other companies in the past. What I'd love to get a better understanding is, is like, you're a big company. You have a lot of resources. I'm sure you could staff a team of nine people up on this problem and fix it in two weeks. Like, why wouldn't you just do that? I love that. You have to almost try to hit the pressure points in your deals and not necessarily try
SPEAKER_08to kill your deal, but try to reveal all of its weak spots so that you're doing more
LIAM MULCAHYtruth seeking behavior than hoping and like trying to only put the prospect in a box where their only path forward is to buy a software from you. They always have to have a second option of like leaving at any moment. And they need to constantly, almost every meeting, re-qualify themselves as to why this is worth both of your time going forward. Because their time is usually just as valuable as yours, right? So they should not want to waste their own time. Some people are happy to do that, unfortunately, but you always have to give them two options. Like, here's how we are going to move forward together on this. Here's our process. Here's what you've told me your process is. We'll figure out like a line in the middle or we can stop.
EDDIE REYNOLDSWell, and a lot of people just don't know how to buy. So it's not that they're doing it because they want to waste their time or yours or anything like that. They just, they haven't done this before. They haven't done it a lot of it and they're busy. And so they're just like, oh, I'm going to go look at the solution. And one of my favorite things to do is very similar is just try to convince them to kick the can down the road because in our sales process, like most companies, the biggest competitor is no decision. So why do we need to do this right now? Like, Liam, I don't understand. Why can't we just wait six months to do this? Why can't you just, you know, do something else? Like, why is this a priority? And if I'm early in the sales cycle and you can't convince me that this is important to you, it's not about the product. You have a problem you want to solve. Is this something you really want to solve right now? If it's not, I am not a good enough salesperson to convince you to change your mind about that. Yeah. And it's also, you raise a good point.
LIAM MULCAHYEven if somebody is like, no, this is really, this is making my job horrific. And this, this is the bane of my existence right now. Thinking about where they sit in the org chart or their tenure at a company, you have to think about the blast radius of that pain. Sometimes it's really searing with that individual and nobody else cares. Even their manager might be like, Hey, that's why we hired Eddie. You know, I know that it kind of sucks, but that's his job. So you really need to also figure out the blast radius of that pain. Like how far does it spread? Ideally, the best problems that you can find have a blast radius that goes from like a single person on a team to like a board deck. And you can thread the needle from those two through the concentric circles of like management and champions and EVs that you would involve. So just testing them on like, who cares about this? Is it just you, your team, your entire side of the organization, the company, the board, the market, your customers, like, give me the size and shape here. If they don't know, then that's fine. You can still have a good conversation. Even if you don't hear what you want to hear, you're not going to bet the deal on them, or at least you shouldn't. You should try to go find somebody else in the organization above or on the side to figure out their POV. But then past behavior is also the best predicator. So a lot of deals, I'll go into portfolio companies and we'll do a deal review and I'll look at some of the opportunities and I'll ask them to show me their champion or who they're betting this deal on. And I'll just say like, hey, does this company they work with, have they ever bought from startups before? They're like, oh, that's a good question. I didn't ask that. Or like, what was the last piece of software this person bought and what role did they play in that? And how meaningful was that software? Oh, you know, I didn't ask about that. And I think it's because reps just get stuck into the weeds and they're really hoping that them or they bring their SE on the call. They're just going to say like the perfect technical thing and the prospect's eyes are
SPEAKER_16going to like roll into the back of their head and they're just going to start asking for the order form to sign it. I've been trying to figure out how to do that for like 20 years and I've yet to figure it
LIAM MULCAHYout. It doesn't, it never happens, right? It's really important to be able to go into those weeds and kind of dolphin up and down at different altitudes, but you have to have like a business problem you're solving with a technical solution.
EDDIE REYNOLDSOr the mistake I've made, it's not that I'm going to say something so smart. It's that someone else is. I've got this person on my team, my manager, my SE, one of my SVPs of RevOps. They're so incredibly smart. And I genuinely feel that way. And I think that it's true and I'm going to bring them in and they're going to just like drop this mind blowing wisdom on my prospect. And they're just going to ask, where's the order form? And I've tried to do this a thousand times and I don't think it's ever once worked.
LIAM MULCAHYYeah. It's a death knell of a lot of salespeople, right? Like, oh, we were technically selected or we have a technical champion. And it's like, usually that person, maybe they have influence, maybe they have authority, but they rarely have both. And you need both to be a champion and not a coach, right? If we're in the med pick side of the universe. But I think you have to, that's the best pairing of an SE and a salesperson is one can really unlock things from a technical level. That's why SEs are so unbelievably valuable.
SPEAKER_39But then you also have to understand like, what is the business organizational implication
LIAM MULCAHYof not doing what we just talked about? Well, this brings us back to me that you have to do it.
EDDIE REYNOLDSAnd this brings us back to sales process. So my experience at Salesforce is like SEs are really expensive. A lot of the SEs I worked with would make more money than 80% of the sales reps and they were a scarce resource. We had to really fight for them. And in order to fight for them, we would have to literally go into Salesforce and fill out the fields on the opportunity, answering similar questions, the ones that you're asking right now. And the SE would say, I'm not even going to talk to you about this deal until you fill out Salesforce and I can read through it. And then I will ask you pointed questions about the deal. What I'm not going to do is let you just book an hour on my calendar, which is already full and just dive into a meeting that might be a complete waste of time because you haven't prepared properly for it. And so that forced this mechanism for us to ask really hard questions, especially when we were bringing in an SE to fight for it and say, no, this deal is buttoned up. I've got the right people in the room. We've asked the right questions. This is what they need to see. This is the agenda for the meeting, et cetera, et cetera. And anyway, I wanted to bring this back to sales process. We're geeking out a lot on sales and I'm really enjoying it. But when we're talking to an early stage company, why should they care about all of this? Because at the end of the day, they just want to close that next deal. The founder's like, I've got these wraps. We're making calls. We got a meeting tomorrow. I just want to close this deal. How can I justify taking a step back and sitting down and like documenting process and spending all this time talking about this when we're like, we've got a number to hit this month, Liam.
LIAM MULCAHYYeah. And it's also awkward too, if you're having that conversation and there's like five of you in the WeWork somewhere, you know, and your SE is like slacking you when you're three feet away, like, Hey, justify why I should spend my time on this. And you turn around and you're like, dude, what? So I think the reason the process is so important, we've said it before. One aspect of like, it's going to determine how your reps spend their time and what is qualified and what is not. But it's really the first way that founders and heads of sales can delegate their vision of the field to a team that's going to continue to expand. So if you, it's only going to get more chaotic as companies grow, as you get more customers and as you hire more reps. So if it's already super broken when it's five people or four, it's going to be excruciating when it's 10 or 15 or 20 or 50.
SPEAKER_39And just because you add more people, it does not mean that the process somehow magically
LIAM MULCAHYcleans itself up. It usually gets worse. Yeah. It usually gets way worse, right? So what I would advocate for is don't let perfect get in the way of good, but have an opinionated process in terms of sales stages, exit criteria, qualification docs, a simple Google doc for a pre-call planner can take care of a lot of what you just outlined where it's like, here's the person LinkedIn. Here's why I think they're a champion. Here's the company, maybe a button, like a bullet or two about what the company does and the opportunity. Here's the notes from my previous call or a link to a loom recording of me walking through it or copying and pasting a gong transcript or linking out to an opportunity in Salesforce and already having all that stuff filled out or going into HubSpot. I almost care a little bit less about what tools people choose. It's more, is this stuff documented? Is there a way for people to get up to speed on opportunities very quickly, async, so that you're not wasting time trying to catch people up? If founders are flying all over the country and meeting with investors and trying to recruit and building product and trying to close deals, and you need to pull them into a deal that could be worth half a million bucks, and it's the first time they're talking to somebody, how can you get them up to speed if they want to do it at three in the morning when they're
EDDIE REYNOLDSon a red eye?
LIAM MULCAHYAnd you can't talk to them, you know?
EDDIE REYNOLDSAnd to your point about the SEs, when I was at Salesforce, I sat five feet away from my SEs. And when I was the first AE in a startup, I also sat five feet away from my SEs. But in both instances, they were busy. The SEs at Salesforce supported like 40 different reps. My SEs at the startup, they're our implementation team. So they're in back-to-back calls with clients actually implementing our software. And so if I just pull them into all these meetings, I can't always get in front of them. They might sit next to me, but they're busy. And so to make best use of company resources, it would have been better if I had things buttoned up at that startup. And that's why we did have things buttoned up at Salesforce.
LIAM MULCAHYYeah, then I think having like a data machine that powers your go-to-market team is really important because you can think about it throughout the entire lifecycle of a customer journey and then what each part of your go-to-market team owns. So in the beginning, whether it's top of funnel, demand gen, or product marketing, like are you using something like retention.com to reverse engineer who's visiting your website or Clearbit? Are you uploading that to something like Clay so that the data is fully enriched by the time those leads go to your reps or that your reps are looking at people that are on a self-service journey and you can understand who are they, what company are they from, what parts of their site that you visit. And then if they do want to engage with a company, those companies are already automatically uploaded into Salesforce. Like if reps are manually, I got off a call this morning with the startup, reps are manually uploading each account into Salesforce as it comes along. That is a complete waste of time. It is an unbelievable waste of time. And then when they're on the call with somebody and they're qualifying, are you proactively giving them information about what this person's done on the site and what their company does? Because it's also not that difficult to do anymore. How are they taking notes? Are they recording the calls? Are those transcripts then going back to your CRM? Or are they like, again, the same company from this morning, reps are trying to spend two to three hours just moving notes around, moving notes into certain fields, contorting them into Salesforce objects, making sure that they get to the SEs because they use separate
SPEAKER_12Google Docs for that stuff.
LIAM MULCAHYAnd then there's also shared Slack channels for opportunities. So now they have to copy and paste it over there. Like that's all grunt work that reps don't need to be doing. And then when you go to hand off an opportunity, even if it's closed, what is the CS team going to inherit or the implementation team? Typically it's this horrific thing. That's like this Frankenstein ball that's rolling towards them that they get hit with once a customer buys. Instead of just having it like the easiest way to do handoffs, for example, or from like a more of like a process driven machine approach is just have your sales rep record like a two minute loom explaining who the people are, what the company does, the opportunity to champion the pain, next steps, things to look out for, opportunities to highlight. Like it takes 120 seconds. They can put it on one slide. They could have Salesforce up in the background. They could have LinkedIn or the deck they use is a go, no go deck. Like, and then you just link to the loom and the Salesforce opportunity somewhere. Like it doesn't have to be this crazy, overly engineered, sophisticated thing. But when you look at a lot of the bloat in the systems of even series A companies, simple Zapier integrations can make reps lives easier so they can spend time with actual prospects and prospecting instead of like it's 7 PM. They had a full day of meetings. Their SEs had a full day of meetings. Now both of them need to work until 10 PM just to update Salesforce.
Yep.
EDDIE REYNOLDSI mean, we have a similar workflow where the second that I close a deal, an email automatically goes off to our delivery team, automatically goes off to accounting to create the first invoice. We have, we use Quip to keep all of our notes. So they automatically go in, look at all the Quip notes, book an internal call. I could do a loom, but there's usually a lot of context that I want to share and answer questions because we do like pretty big deals with our customers. And then we book the kickoff call and then I joined the kickoff call if I can, but it's all automated, right? So now like the second I close, I don't have any work left to do other than join the calls that I'm being invited to or answer questions. If somebody reads through the Quip and says like, I don't understand this. I love the loom video idea. Maybe I'll, maybe I'll, I'll use that. But the point is that.
SPEAKER_35Yeah, it's simple.
LIAM MULCAHYLike it doesn't have to be like incredibly like the most sophisticated, you know, $500 million ARR implementation of a sales machine and like a sales tech stack. But there are some critical components of like, one, how does context get shared amongst deal teams? And if you're recording your calls, it's like 50% of the battle.
SPEAKER_01Oh yeah. And then what do you do with those call transcripts, you know? Auto record. So it's just like on top of that, Hey, just go look at the recording from the last, last
EDDIE REYNOLDSmeeting. And we're implementing an AI tool probably in the next few days that summarizes all the calls and it puts the notes all into like some concise summary. And then you can also listen to the recording. So it makes it even easier than like watching a zoom recording, for example.
LIAM MULCAHYYeah. And you talked about enablement before, right? Like some of the most enlightening conversations I have with founders or heads of sales or solutions engineers in our portfolio are like not completely extemporaneous, but they happen in meetings where we may be talking about an opportunity or a roadmap item. And then we have like an incredible way that somebody explains something that we wish we recorded. So what I've started to do is say like, Hey, why don't we just record more of these meetings and you could do it on whatever you can record audio notes on your phone. You could do it on zoom. You could do it on gong or anything else. And then you could just take that transcript, put it into a enterprise version of chat GPT and then say like, Hey, make this a training document on X process. It's not going to be perfect. It's not going to be like the most beautiful thing a sales enablement team has ever built, but it's something. And especially when you hear about new hires, their first 30 days where they're not completely inundated, people are really willing to consume as much as they can. And most of the time it's gong calls. And I really do believe that's because it's portable. Like if I'm on a run or if I'm dropping my kids off somewhere, I can't read a document. And that's also why I like loom videos. Like I could be commuting into the city on the train and listen to a handoff loom. No problem. But like, I'm not going to do that. And you can listen to it on 2X. Yeah, 2X and I can go back to it. Or I can like, you know, it's, you just want to try to make your communications for deal
SPEAKER_34teams and anything you think could be an enablement material, very portable.
LIAM MULCAHYAnd audio to me is typically the best way to do that. And because we're on Zoom so often, like why not just start recording stuff and be okay with sharing video on things like loom, zoom, gong, or anything else.
SPEAKER_84Yeah, I love this.
EDDIE REYNOLDSSo this whole conversation, I was trying to figure out how do I bring this back to scale ups, right? You and I both work with companies that are well beyond like the startup founder led sales first sales team stage. For sure. And, you know, we get into companies that are doing 20, 30, $50 million in revenue. And I'd be curious what you see. But what I see is a lot of times these problems we're talking about, they exacerbate, right? Instead of having three reps, we now have five or 10 reps in S&B. And then we've got five reps in enterprise. And then now we've got multiple products and then we've got all these different marketing channels that are completely disconnected and the team grows and becomes more disparate and more siloed. And now like we not only have Salesforce, but we've got Marketo and they're not connected and marketing has their report and sales has their report. So to your point that you brought up earlier about you think like as we grow, we'll solve these problems. I see the opposite happen. I feel like you can build the perfect sales engine at a million dollars in revenue. And if you just set it and forget it, when you get to 10 million, it's going to be really broken.
LIAM MULCAHYYeah, it's horrible. They metastasize, right? Like things can compound negatively as well as positively. And a lot of these problems just compound in the wrong way. It's like if you have a bad crack in a foundation of a home and then you make it 10 times as big, it's like not going to get better. You know, if you add more people onto a broken process, it typically gets worse, which is why I think you've seen an appropriate trend of rev ops people getting hired more early in companies journeys, data teams getting hired more early in companies journeys, and some of the best sales teams on the planet really being powered by data, data enrichment, and like a very clean, effective sales tech stack. Because it does one of, it does two things. And maybe this is like a stupid analogy, but this is what I thought of this week, randomly on a run. Like if you, most startups are going after a certain ICP, even scale-ups, right? 50 million, 100 million, doesn't matter. You probably have like maybe one to three variations of an ICP for your product or your SKUs. It's kind of like going after a certain fish in the ocean. The problem is the ocean is a very large place. So is anybody that you can sell to. And if you don't tell those boats or your team where to go, how do you have any idea they're spending their time appropriately? So typically what you would do if you were like fishing is you can understand where those fish are, migratory patterns, and get a map of where they tend to be at any part of the year, at any point of the earth, and then sail towards it, right? And then use the right bait to go catch the fish. Otherwise, what you try to do is, I guess you would just get as many boats as possible and cover the widest area possible to go find them. That to me is like the way that sales has been done in software for the last 20 years. It's a capacity model that use humans as these like observability tools in the market where they're like bloodhounds that get a sniff of something. They're like, Hey, this is our ICP. We're going to hire a hundred salespeople that are MedPick robots, and they're just going to scour the earth for people that look like this. And then when they get someone on the line, we're super confident we can close them because they've been trained in MedPick. I think the more modern version of where sales is going is really thinking about infinite capacity. How small can you keep a sales team and how much data can you use to power that sales team of where they spend their time and then how they spend their time in deals and how far can you push capacity? Typically scale-ups, if you're doing like 30, 40, 50 million ARR, your teams are going to be giving you a yield on their OTE of like 3X, right? 4X, 5 if it's really working. You know, you're paying somebody 200K and they're closing a million bucks. It's pretty efficient. It's usually a little bit worse than that, kind of oscillates between three and four. I think you can actually do, like you can have better yield with smaller teams if they're powered by data. And I think a lot of the assumptions we make in the market, like only 70% of reps are going to hit. That number probably is even worse if you look at historical averages now. And like close rates are only going to fall between certain areas and average time to close and average time to ramp is what it is. I just don't believe in any of that because I think people are not using data and sales tax, sales tech tax in a very intelligent way for reps to spend their time where there's the highest propensity to buy. And when they find that, close it extremely effectively and efficiently.
EDDIE REYNOLDSWe're really big proponents of this. I mean, I had Jeremy Donovan on the podcast and I think the one I did with him releases this Friday, if I remember correctly. And he was talking about in his past job, sales reps had 2,000 accounts. We're talking S and B here. And so then now your sales rep is your rev ops analyst. Okay. I've got 2,000 accounts. I can maybe cover a hundred or 200 of them. Which ones do I call? You are now asking your sales rep to be a data analyst. That is not their job. And to the analogy you shared earlier, I think about this through the lens of if you give a rep a million dollar quota, that means their quota is $500 an hour. So now let's say it takes them 10 hours to analyze their territory doing data. I'm not talking about like account by account research, which I think is really valuable for salespeople. Okay. You have now taken something that you could pay somebody in rev ops to do. Your sales rep's not nearly as good at it or as fast at it. And you're paying $500 an hour for them to do a pretty shitty job of it.
LIAM MULCAHYYeah. And it's also like, to me, the old way of selling is you have a rep 2000 accounts, or maybe they own a couple of states or a couple of letters in a couple of states. If you're starting to really scale up, the old answer would be like, well, how do I, which ones do I go after a sales leader would just say all of them, you know, like as many, like as many as you can handle for 15 hours today and then come back tomorrow and do it all over again. To me, I think what a company and what a founder and what a rev ops team and what a CRO or a VP of sales owes a sales team is a data-driven opinionated view and a hypothesis per territory of how they should go spend their time.
SPEAKER_92And it doesn't have to be again, like, I think sometimes when people hear this, they're like,
LIAM MULCAHYlook, man, I can't, I can't drop 500 K on like a sales ops person or org and make this really sophisticated. All I'm talking about is combining firmographic data of what companies that you want to sell to look like. That's typically available in anything like Apollo or zoom info or clay, you name it. And then maybe a couple of proprietary metrics that could be publicly available. It could be like number of certain titles on a team. It could be something like we have a company in the portfolio named permit flow. So maybe it's like permitting volumes that they're trying to go after. And if that's not readily available in a database, there are also a lot of very willing people that you can outsource that to on Fiverr or different platforms where you tell them exactly what you're looking for, Hey, I want a database of all companies in the United States that have this attribute, or I want them stack ranked by these attributes and you pay them five grand. They are happy to do it. And they usually do an exceptional job. And then you dig that into a simple scoring model, right? One through five, five is like, go meet with this person in person as soon as possible. Perfect lead. One is avoid at all costs. Not good. Right. And then you're really trying to be more data driven about two through four and where reps should spend their time.
EDDIE REYNOLDSI love it. I could keep going, but we're at time and I want to make sure that you can get to your next meeting. Liam, thank you so much for joining me.
EDDIE REYNOLDSHow can people find out about you? They want to hear more.
LIAM MULCAHYI'm the only Liam at Kleiner Perkins. So it's pretty easy. And you can look me up on LinkedIn. You can reach out to me on LinkedIn as well. I have a Twitter. I don't really use it. So I think LinkedIn is probably your best bet.
SPEAKER_01Awesome. Thank you so much for joining me today.
LIAM MULCAHYYeah, for sure.
