Paul M. Caffrey (00:02.422)
And I'm delighted to be joined by Charlie Cowan, who is better known as RevOpsCharlie. Charlie, how are you doing?
Charlie Cowan (00:10.078)
I'm very good, thanks Paul, thanks very much for having me on the channel.
Paul M. Caffrey (00:14.442)
Yeah, I'm delighted that you're here. And maybe for people who aren't so familiar with your work and what you do, maybe give them a 10, 20 second lowdown.
Charlie Cowan (00:25.246)
Yeah, absolutely. So as you say, I work under the brand of Rev Ops Charlie, primarily helping series A, maybe series B founders with scaling up their go to market operations through Rev Ops advisory and consulting. But I come to the world of Rev Ops after a 20 year career of enterprise SaaS and consulting sales. So very much coming at the Rev Ops world with a focus on the word revenue in revenue operations.
Paul M. Caffrey (00:57.482)
I like that. And it is something that we can get a little bit, we can get sucked into the operations aspect of it because there's always a new software to check. There's always a new sales process to consider. How do you keep revenue at the core of what you do?
Charlie Cowan (01:18.29)
One of the things that I've learned as I've come into the world of revenue operations, and maybe if I step back a little bit just to explain a little bit of how I did come into that world of rev ops. During lockdown, like many people, I had a bit of extra time on my hands because I wasn't commuting. And so I used that time to write a book which was aimed at first time sellers.
At the time I was partnered up with a junior SDR who was just getting ready to go up for his first time AE promotional interviews. And so he was asking me some of the questions like, what's it like as an AE? What's the job involved? How do you take an opportunity further on from that initial qualification? And I felt at that point that there wasn't really great books to help you with the real foundational aspects.
There's lots of great sales books, Challenger, Spin, Gap Selling, but they all assume that you've got a bit of a basic grounding of selling. I pulled this book together called How to Sell Tech that was just about helping you with qualifying deals, with presenting to large groups of people, with building a forecast for the first time. That was a lovely exercise to do and it had the by-product of giving me some opportunities to get into some...
independent consulting and coaching and training for sales teams. But I was already having this sort of thought that actually the way that customers want to buy has changed very much over the last two or three years, especially post-pandemic where people aren't all sat in their office anymore. And just fixing sales, helping people to sell more, prospect more,
isn't actually solving the problem for the buyer who wants to do 70 or 80% of their buying process without any seller in front of them. So if you're gonna help companies to sell more, you actually need to spend a lot more time figuring out how to help their buyers buy more and buy better. And that led me to the world of revenue operations. So in February this year, I read a book that's eloquently called
Charlie Cowan (03:41.298)
revenue operations that came out last year. And it defines this methodology of aligning marketing, sales and customer success into a single team, a single aligned function. And it's all about helping your buyers to buy off you and for your go-to-market team to deliver more predictable revenue.
And I remember sort of reading this and then running off to my wife and going, Oh, I found it. I found the term that, you know, I can hang what it is that I want to help customers with. And that is revenue operations. And so for me, when I think about RevOps revenue operations and the work that I'm doing with clients, I've come to it from the sales background. My job is to help my clients sell more. And I do that by
aligning marketing sales and customer success. I'm not coming to it from the angle of how do I help my customers internal functions to operate better? That's kind of a byproduct of it, but the driving force is the revenue and selling more.
Paul M. Caffrey (04:54.074)
Okay. And putting the customer first, I guess it's always something that we've heard about in sales, but it's always very difficult to actually define what it actually is. I can see that you've went a ways towards that. But with predictable revenue, and you've rightly called out the change, people that want to talk to salespeople anymore when they're buying, or they want to talk less to salespeople than they did, feels like that's always trending down every time it's reported every few years.
What do you think has changed from the days of, let's say, predictable revenue and Aaron Ross and that Salesforce model with things to be around forever versus today? What should people keep from that? What should they drop?
Charlie Cowan (05:30.698)
Mm.
Charlie Cowan (05:35.531)
Mm.
Charlie Cowan (05:38.818)
So predictable revenue, I think, came out in 2004, and primarily out of Salesforce, and then gained a lot of traction in other SaaS businesses. I started selling in 1999, so predated it by five years. And on my first day of selling, I was given a phone. I was given a list of gold mine leads. Gold mine was the CRM of the day. And yeah. And.
Paul M. Caffrey (06:01.41)
I remember you from cold mine. Yeah, it was.
Charlie Cowan (06:07.026)
I was a full sales cycle AE. You prospected into someone, you got them to take the first call, and then having done the first call, you do the second call, and the third call, and the fourth call, and you provided the demo, and then you issued them with a contract. You took them the whole way through. One of the advantages that I found of that was that as you go the whole way through a sales cycle, you learn a lot more, and in a lot more depth, about the customer's business, about the real problems they're facing.
and how your solution can uniquely solve those problems. And of course, the next day, you're prospecting again, and you bring all of that knowledge and intelligence back to the start of the process. I think one of the challenges with the SDR model, the predictable revenue model, is that you have this forced blockage whereby as an SDR or BDR or an MDR, you're only getting through that first or maybe that second call, and then you go back to the start.
you're able to provide less and less real insight to that customer on the first call. You can do your research, you can go on an enablement course, you can use a bit of chat GPT, but you haven't been in those meetings where you really are committed. And I think this is one of the things that buyers are frustrated about is that as that transition has happened,
buyers have had access to even more and more and more information. So the SDR is comparatively getting less insight than a full sale cycle AE was, and the buyer themselves has now got access to much more information through G2, through private Slack communities, through Pavilion or any of these networking events that they're going to. And so the problem now comes where in that first call, that first interaction, in many cases, the buyer knows more.
than the seller and they're frustrated. They're saying, look, I've filled in your form because I now want the pricing, I wanna see the product or I want information about integrations or the implementation process. And what they get is, I'm sorry, I don't have that information, but what I can do is book you in for a call with someone else. And that person might not even have the information. And so there's this frustration from buyers that, look, I could...
Charlie Cowan (08:29.978)
actually get a lot further on my own without you. And it's very much on sales or go to market teams right now to figure out how they can give the buyer a much better experience where they give them what they need when they need it.
Paul M. Caffrey (08:47.066)
Okay, so it is something which I've always found interesting is, you know, our, I guess our hottest, most engaged leads will contact us and potentially our most inexperienced people can be the first call. I know there's been some playbooks, you know, change that around a little bit. And what tips or tactics have worked for companies that you're working with or what have you seen to tackle this issue?
Charlie Cowan (09:00.407)
Mm.
Charlie Cowan (09:15.082)
I think there's a few things in that one is around defining whether you're going to have inbound leads going to the same team that are doing outbound. So there's a lot of discussion about MDRs and SDRs or combining them in a BDR. And also when someone is coming inbound, do they go straight to the account executive themselves? And a lot of the challenges here come around attribution and how teams are trying to justify their
existence. I did a little bit of research earlier in the summer of just looking at what is the total cost of an SDR and it was quite interesting when you start to look at the average salary of an SDR which you can get off a site like RepVue when you then look at all their benefits and the cost of providing them with their technology which you can get that kind of data from remote and other sites when you then look at their managers when you then look at their attrition
When you then look at the enablement of those people, actually the cost fully loaded of these SDRs is up north of 100,000, 150,000. When you then start looking at the number of ops that an SDR needs to create and the value of those ops, actually the numbers start to not stack up very quickly depending on the average deal size.
And really, if you're not doing average deal sizes that are over 15, 20, even 30K in annual revenue, then having this SDR in the front, it starts to become non-economical. And so that's a lot of the conversations that having with clients is, if someone's gonna call in, they've probably done that because...
they've touched one of your other channels. Maybe someone's recommended them in a private Slack community. Maybe they came to an event. Maybe they saw one of your paid ads. If they're then gonna speak to one of these expensive SDRs who's literally gonna head it on but with a very simple qualification call, get the attribution and pass it onto the AE, you've just wasted a lot of money. So...
Charlie Cowan (11:32.694)
This is another one of those reasons where revenue operations comes in by aligning marketing, sales and customer success and saying, what is it that we're trying to do here? Is our job to figure out how we can justify the expense of an SDR team or is our job to make sure that we close revenue? And if someone is calling in because they want pricing a demo, do we need to put this gate, this expensive gate in front of them?
Paul M. Caffrey (12:00.318)
Okay. And so I guess in that situation, when you look to take out your STRs, then that's typically the breeding ground for somebody to become a salesperson in your organization, and probably at a lower rate than you would have to get them externally. Are you, is it more now a case of get more experienced, more expensive sales professionals who are open to doing the full cycle?
Charlie Cowan (12:15.093)
Mm.
Paul M. Caffrey (12:27.491)
sales process and kind of taking a step back maybe to, I guess, the early 2000s.
Charlie Cowan (12:35.318)
I personally think so. I think it will depend on an individual company in terms of the products they're selling, whether they're selling to enterprise and SMBs, whether they have got such a large volume of opportunities in their pipeline that they need this extra team to funnel things down. So of course there's going to be nuances, but I really encourage companies to just not take the book.
predictable revenue or whichever book you're opening up and say, look, everyone else has an SDR team. This is the default. I encourage them to say, you've got to look at the economics of your actual go-to-market. If your AEs have not got a calendar that is absolutely blockbooked, then they should be doing the prospecting because they've got time on their hands. Clearly. If your average deal size is below 15,000, then you've got to look at the economics and go, does it even make sense for us to have?
this other person in there. And then when you also think, well, what is the career progression of an SDR or an SMBAE? Does that influence it? So I worked at an organization where we had some fantastic enterprise SDRs and in their role as enterprise SDRs, they got very familiar with the cadence of managing a large account of prospecting into these large enterprises.
And they almost got a bit blocked. Where do you go then? Well, their next role on their career path was to become an SMB AE, which they actually saw as a bit of a demotion because they've already been experienced learning the world of enterprise and partnering with the enterprise AEs. So they were kind of hoping they were gonna become enterprise AEs, but they didn't have the experience there. So that was another blocker for them. Whereas had they just started as SMB full-sale cycle AEs, then...
potentially there'd be a smoother path up to become an enterprise, that way.
Paul M. Caffrey (14:35.214)
Yeah, and I think the it's a very, it's a very different skill set. So they would probably struggle going into that role as well, right, with the speed and velocity that's expected in that part of the organization. OK. And so when I guess when we're thinking of, you know, prospecting and from an perspective and what tips or what advice would you give somebody who maybe, you know,
Charlie Cowan (14:43.099)
Mm.
Charlie Cowan (14:47.139)
Hmm.
Paul M. Caffrey (15:04.17)
has to build pipeline. Is there any plays that you've seen work quite well at the moment or there's always cool new tools, but is there any in particular that are maybe we're paying a bit of attention to? What do you recommend?
Charlie Cowan (15:19.738)
A couple of things and it goes back to good old fashioned prospecting. Even if you're in an organization where you've got too much pipeline, even if you're in an organization where you've got a fantastic SDR that is feeding you, as an AE, never lose that muscle for prospecting for your own opportunities. As I said a minute ago, you're the one that understands.
what objections coming up in the contracts. You're the one that understands exactly how customers are integrating this with their other solutions. There should be no one else in the organization that can prospect as well as you can into your territory. So definitely don't lose that muscle. One of the ways that I do that is to do time blocking. So whether that is Monday, Wednesday, and a Friday morning, have an hour and a half, have that blocked out for prospecting, just make sure.
that you don't get caught up in, well, I'm just too busy this month, I'm too busy that month, or I've done my dues, I've been in SDR and now I don't need to prospect. Make sure that you block that time in your calendar. Next one, don't be scared of the phone. So you can't see it, but in front of me, on my second screen, I've got two stickies. I'll send you a picture after this. One of them says, stop sending emails, and the other one says, pick up the phone.
Yeah, I'm 46 years old. I've been selling for 20 plus years. And I have to keep reminding myself that every single day because it is just so easy with all of the tools that we have and the automation to just go, oh, I'll just send them an email. I'll just send them this. I'll just send them that. And even from my very earliest days of selling, it's such an easy trap to fall into. Someone asks you a question, you start replying on email. Someone sends you a text, you start messaging back.
pick up the phone because that's how you get that synchronous conversation. You really get to hear their tone and you get an immediate answer. So for any kind of prospecting, I know people have been trained to create a sequence, create a cadence, let's just start building this thing out. But if you can just pick up the phone 8.30 in the morning before everyone else is doing it, you get someone and you'll probably be one of the only people that will call them that day.
Paul M. Caffrey (17:47.294)
Picking up the phone, yeah, agree with you. It's the fastest way to get the answer. We could go down that route. And for me, I would think every day, if you're gonna be sending out emails and working sequences, which a lot of people, it's mandated on them to do, right? I would mandate a number of calls yourself. And even just as little as 10. Can you do 10 outbound calls a day? Put together 30, 40 minutes.
Look, if you only have to make two and you get a conversation, great. But it's these small things, they add up over time. I really like your point of blocking the time to actually do the prospecting because we're always busy. There's always something else that's more important or that's super urgent. And that's, you know, we prospect and go to the side. So, yeah, again, good to hear. Yeah, the basics are still super important. Now, I know that you've been working away on a new book. You've been teasing.
teasing people about it on LinkedIn, I would say, what can you tell us about that?
Charlie Cowan (18:47.486)
Yeah, it's called the Revenue Operations Playbook for founders. And the sort of brackets for founders is really important. This is about helping revenue leaders, founders, to understand how revenue operations can really help drive predictable, consistent, repeatable revenue growth as they scale up from series A, series B and beyond. And
The reason for writing it really came out of one of the sentences, paragraphs that I read in the original Revenue Operations book, where they interviewed a large number of senior executives at fairly large businesses. And I paraphrase it, but out of all of the executives that they spoke to, virtually none of them could explain what a revenue operations model was.
or how it would positively impact their business. And yet they all agreed that revenue operations was fundamentally important to their future success. So we all agree that it's really important, but we can't really describe what it is or how it's gonna be impactful. And so with the book, I'm helping founders to understand 22 different capabilities that their go-to-market organization needs to
develop in order to be successful. So it's split into two halves. So there's the external capabilities. And with that really helping founders to look at the experience that their prospects, that their customers and that their partners have as they travel through their own buying experience with your company. So, you know, how do we find out about
your organization? How do we find out about the challenge that you solve for us? How do we find out about the problems that you solve? We then look at the types of content that an organization provides to support their buyers. Are we just talking about our solution and why we're the greatest thing since sliced bread? Or are we helping buyers to understand
Charlie Cowan (21:05.654)
the problem, to diagnose the challenge, to understand the cost of it, to benchmark themselves against other solutions. And then we travel through their buying process. So the buying experience, going through the contracting, the onboarding, any upsell or cross-sell, and then onto renewal and hopefully no churn. So what is that like? And is it consistent in the experience and the content that they receive the whole way through?
So developing a great buying experience. And then the second half of the book is looking at the internal capabilities that an organization needs to develop in order to deliver those external capabilities. And so the internal capabilities... Sorry, go for it.
Paul M. Caffrey (21:47.208)
So this
Paul M. Caffrey (21:51.214)
I was going to say this was going to be my next question. And I think you're maybe going to address it. Everything that you've spoke about there, how do you get people to maybe take accountability when they maybe don't have a full-time rev ops person or when there's other functions that will need to be accountable, but how do you actually decide who's accountable for what and divvy that out?
Charlie Cowan (22:16.222)
I make the point at the start of the book to really reinforce it to the founder that they are responsible. They are the only person in the company that has got full responsibility across the entire go to market function, marketing, sales and customer success, and of course, into any product or finance functions as well. The moment you go down to your marketing director.
your VP of sales or sales director, or your customer success director, you're now into silos. And if you then hire any revenue operations person that reports into one of those, they are also gonna become siloed. So until you get to a very large, well, much larger size of organization, the founder is the one that's on the hook for this end-to-end revenue alignment.
Paul M. Caffrey (23:11.103)
Is that an equal? Because let's face it, most companies will have numerous founders. There'll be a few co-founders. So is that equally split or do you say, no, let the product or the technical founder just build the product and actually it's on you as whoever's on the revenue generating side, this is fully yours or is it joint responsibility?
Charlie Cowan (23:17.742)
Mm.
Charlie Cowan (23:33.114)
Yeah, I should clarify. I'm thinking about a founder CEO. So whoever's got that, you know, ultimate ownership of the, of the go to market function. One of the challenges that you see is that these founders can delegate go to market roles too soon. So take the example of the sales leadership. So at Seed, your founder led sales, you're involved in every single deal.
and now you want to pass that on to someone else. And so you might think about hiring in a VP of sales or even worse, a chief revenue officer at that stage. Company's not ready for that yet. At this stage, you need a player manager, sales manager, sales director, someone that can get out in the field, selling alongside your first AEs, probably carrying a target themselves and go and figure out that
sales playbook. How do we sell? How do we acquire opportunities? How do we convert them? Because it's going to be different to how the founders did it because they've got all of this heritage. And so you need someone that is there in the weeds, not someone that is going to architect some big spreadsheet and commission plans and all of this. So when you're thinking about bringing in that sales director, player, manager,
They don't have the experience to architect this end-to-end go-to-market team. And it's very easy then for those silos to come in. So once again, the responsibility comes back to the CEO, the founder that's responsible for go-to-market, to still own revenue operations and tying these three teams together. As you hire in that sales director, you're also going to be having a marketing director probably coming in. You're also going to have...
customer success director or customer success managers coming in. And it's so easy for each of these three divisions to come in with their own perspectives, their own tools, their own ways of reporting, their own strategy. And if you as the founder above that are not on top of it, these silos creep in and then it's too late to recover or difficult to cut to recover.
Paul M. Caffrey (25:49.366)
And I guess something I'd seen in the founder world is we might hire in a marketing director or somebody with C-suite role and director next to it, but they're not at that level. They are a manager who is, again, it's a jump up in their career somewhat, but again, it's a smaller business, less responsibility. How do you ascertain what level or what caliber of person?
Charlie Cowan (26:03.618)
Hmm.
Paul M. Caffrey (26:18.742)
or to bring in? Is a marketing manager as a director an okay approach or should it be no, I want a pure marketing director who has that long-term vision? What sort of, what would you recommend people do?
Charlie Cowan (26:32.99)
It depends a lot on how fast the organization is scaling, but typically at series A, and these numbers vary substantially depending on what segment you're in and where we are in the economic cycle is not as great as it was a couple of years ago. But at series A, you might have 30 people in the entire company. And of that, maybe half of those are in go-to-market function.
So you've probably got a marketing manager or a marketing director that's also in a kind of player manager role, and then maybe one or two people underneath them. By the time you get to series B, you've gone from maybe 30 people in the company to maybe 100 people in the company. And out of those 100, maybe now 70 people are in a go-to-market type role. And of that, maybe there are 15 people in marketing. So there may now be five different teams. You may have some marketing managers.
And now is when you've probably got either a marketing director, maybe a VP of marketing, or you might to attract someone have called them a CMO, but it's probably a marketing director type person. And, you know, this goes the same across marketing, sales and customer success. It's about getting that balance right between stretching your internal hires so that you're really, you know, giving them an opportunity, but knowing when's the right time to bring someone else in that can take them.
take you to the next level. Now, if you've got a marketing manager, you can probably take them up to being a marketing director, but they're not going to be the person that's gonna take you from being a marketing director up to a CMO. Same thing with that sales director. Managing one team is very different to managing five teams. So is that sales director the right person to be your VP of sales? Once you've got a VP of sales, managing five teams is very different to opening up in different regions.
acquiring a new product or taking on the management of your marketing customers' success. So that VP of sales is unlikely to be the right SVP or definitely not your CRO. So it's bridging that gap of I want to stretch people but also knowing exactly we need to have the pipeline coming of these new people that can take us to the next level.
Paul M. Caffrey (28:49.818)
Okay, I like that. And that kind of brings us on to another question, which is something I've been looking to ask. And this question is from RevOpsCharlieGPT. So I was playing around with that beforehand. And basically, to summarize it, it's, you know, in startups, and in where you are, there's a lot of ambitious account executives, and they're looking to advance their career. So it's two pronged.
What advice would you give account executives looking to get promoted faster? And then what advice would you give founders for nurturing and helping younger talent flourish in their organizations?
Charlie Cowan (29:31.886)
I think for anyone that is trying to think about where their career is going, it's to do stuff that is outside of your core role. So that might be taking some consideration either of what your manager is doing or two levels up what they're doing and getting a bit of a view into their world. Can you support in terms of helping to develop a pipeline plan? Are there?
cross-functional groups that are looking at launching a new product or building the demand gen strategy Anything that can help you get some exposure to something that is outside of your core role is going to help you when it comes to You know future promotions one thing that has definitely helped me through my career is Just to never ever lose sight of the customers
business and what they're trying to do. The more you can, as an AE, understand what's going on in a specific industry, in a specific country, in a specific role, that is sort of gold dust information that will help you navigate into selling into new territories, it can help you get into new roles, or it can help you get promoted.
I think anything that helps you to understand more about the world that your customers are in and the problems they're facing always pays back in dividends.
Paul M. Caffrey (31:07.31)
Cool, some sound advice there. Might run through a few questions, a little bit of a quick fire mode. So we're gonna change things up a bit. What is your number one prospecting tip and something that you haven't mentioned already?
Charlie Cowan (31:14.534)
Mmm.
Charlie Cowan (31:22.866)
Number one prospecting tip for me above picking up the phone is just to think about how you can deliver some kind of present to that customer. And I don't mean a physical present like a gift, but like what have you got that they haven't got in terms of insight or information that they'd be like, thank you. Is that a diagnostic tool?
benchmark, is it some insight that you've gleaned from a competitor's financial report? If you can position yourself as someone that is providing 10 presents to 10 different companies, it completely changes your perspective from cold calling that you're not asking them for something, but you're providing them with something.
Paul M. Caffrey (32:18.19)
like it, give them something they're not expecting. Excellent.
Charlie Cowan (32:21.642)
Yeah, and if you can't think of what that is, then that's the problem. If you haven't got anything to give them that's of use or a value, then that's where you need to spend a little bit of time before you get into a calling block to figure out what those things are.
Paul M. Caffrey (32:38.942)
Yeah, and information, insight, there's a lot. It doesn't necessarily need to come from someone else in your business. This is something that you can go out and figure out as well. I think that's something to be mindful of. Okay.
Charlie Cowan (32:47.704)
Mm.
Charlie Cowan (32:52.498)
There's some good statistics from a company called Corporate Visions, who do a lot of enterprise sales training. And I think the stat is 77%. But 70% of buyers will choose the seller that was the first one to provide them with some unique insight about the problem that you solve. So if you're ambulance chasing with intent data and finding out that all these companies in market is too late.
Really, you want to be figuring out how you can go to people that are not aware there's a problem and share that kind of unique insight with them about what's going on in their industry. And if you can do that, then prospecting becomes a whole lot easier.
Paul M. Caffrey (33:34.398)
Yeah, totally agree. And actually, that even works out great in your sales process. And I think your corporate visions are all about, what are the unconsidered needs? Because the buyer is putting you into that box with all of the other products. What they not considered maybe missed that you can solve that's outside of that your competitors can't solve. It's not an easy thing to do, but yeah, definitely something to go check out. And their content is great. So, yeah, absolutely check out corporate.
Charlie Cowan (33:45.059)
Mm.
Charlie Cowan (33:51.317)
Mm.
Charlie Cowan (33:58.364)
Yeah.
I just could say that this goes back to the, you know, the initial book that I wrote, How to Sell Tech. The first chapter in that is all about developing empathy for your buyer, for your customer. And for me, it's just one of the most important skills for any seller to have. And in this day of AI and automation and sequences, like what is the future?
Paul M. Caffrey (34:02.414)
Scott.
Charlie Cowan (34:28.85)
of a salesperson in an AI world. For us to be humans, we've got to be able to take something human to that person. Otherwise the machine can do it. And so spending that time on really researching your customers in industry, but not just then researching, but doing critical thinking about if you worked for that company, if you were in their industry, what would you do?
how would you solve their problems? And if the answer to that question is, well, I'd buy our product, well, bingo, let's get on the phone and start explaining to them the challenges they're facing. But if it's not buying your solution, then you need to go back to the drawing board and maybe you're not selling into the right type of customers or to reframe. But it's that thinking time that is gonna make being a human salesperson so important. So again, with your time blocking, you're gonna be time blocking for
prospecting time, time block for some thinking time. There shouldn't be a stigma to you just saying to your manager, I'm spending an hour thinking. Well, what are you thinking about? Well, I'm thinking about my customer's industry. I'm thinking about my customer's business and I'm putting myself in their shoes and thinking if I was in their shoes, what would I be doing? Because if you can spend an hour doing that, the kind of conversation you're gonna have with the buyer when you get them on the phone is gonna be completely different to.
Can I talk to you about my product?
Paul M. Caffrey (35:59.818)
Yeah, I think in time it's super. I mean, it is something which, look, we know the top founders do it, right? Top founders will have time in their diary to do the same. So, you know, why not you, if you want to be a top performer? So I really, really like that. What is your number one sales tip?
Charlie Cowan (36:19.25)
Number one sales tip. I mean, it's what we just covered there. And I was trying to think of something else. So it wasn't just that, but it is absolutely that. If I was in your shoes and I worked for your company, what would I do? And I use that phrase with customers. If I was in your shoes, I wouldn't be doing our product. I wouldn't phrase it like that, but you know.
I'd be thinking about that, or have you thought about that? You've already got a product that does something like this, or you could just reconfigure what you've already got to do that. And what I've found is that if you direct the customer in the right direction, they'll end up becoming a customer of yours. Maybe not today, it might be for something later on, but they'll understand exactly what it is that you do and that you're someone that they can trust. So by focusing on solving their problem first,
then you end up with people buying stuff from you. If you go in with the 100% objective, like I have to sell this person something regardless of their situation, you'll end up coming away with a lot less.
Paul M. Caffrey (37:30.582)
Yeah, really, really like that. And I guess, wrapping up, what book would you recommend people read if they want to be more successful in sales in 2024?
Charlie Cowan (37:45.114)
I'm going to recommend two. If you're an enterprise seller, then I'm a big fan of Jamal Reimer's Mega Deal Secrets. Jamal tells a wonderful story about his first Mega Deal. I think it's north of a $50 million deal. But he brings to life the characters in that story and specifically how he leveraged some of the senior executives in his organization.
to get right in at the top. And he uses the analogy of a mountain. So many sellers think that the way you get to a mega deal is to start at the bottom of the mountain, do a very small land deal, get in with some of the individual contributors and the low level managers, and then use that as credibility to get one level further up and one level further up as they climb the mountain. And the reality is...
that a lot of salespeople get trapped in the bottom of the mountain, or it takes so long, it just takes 10 years to claw your way up. And he uses the example of actually being taken in on a helicopter by your senior execs right in at the top of the mountain, that actually if you wanna take down a mega deal, it's about getting in at the top and building a real strategic proposition for the senior leaders.
and have that trickle down. So that's a fantastic book for enterprise sellers. And then the book that I'd recommend for anyone that is a founder of a seed or series A business is this one, come out fairly recently, the go-to-market handbook for B2B SaaS leaders, which is by three very experienced SaaS leaders. And that's got 10 lovely little workbooks in it.
It's all about defining the right ideal customer profile and the value proposition for those ideal customers. And the reason why I recommend that is in a lot of the work that I do with clients, the problem is we've missed our targets. The problem is deals are slipping. The problem is customers just pushing things. And actually when you dig into it,
Charlie Cowan (40:07.638)
The reason those deals are pushing is because there's not enough pipeline. And so people are keeping things in longer than they should. And why is there not enough, not enough quality pipeline? Well, it's because our value proposition isn't landing with customers. And why is our value proposition not landing? Well, it's because we don't really have a great ideal customer profile. We've not really figured out who we solve the problem for. And the workbooks in that book are fantastic. It really
They use this phrase uncomfortably narrow, getting uncomfortably narrow on who is it that we solve a problem for and how can we create a great value proposition around that.
Paul M. Caffrey (40:50.274)
Fantastic. I really look forward to checking out those two books. Even, yeah, Jamali, so he's doing a hundred million dollar playbook for a client at the moment, which is incredible considering where the economy is at, that there is still business at that scale happening. And uncomfortably narrow. I've definitely witnessed those conversations where people, they just don't want to go down probably that level far further that they need to actually scale the business to go back up.
Charlie Cowan (41:11.007)
Mm.
Paul M. Caffrey (41:18.034)
So yeah, really looking forward to giving them a read. Charlie, really enjoyed chatting with you. How can people find you if they want to learn a little bit more?
Charlie Cowan (41:18.97)
Mm.
Charlie Cowan (41:30.298)
For all of my content, the best central place is revopscharlie.com. So that's just revopscharlie.com, all one word. And on that, you'll find access to lots of free templates, calculators, diagnostic tools. I've got a revops maturity assessment, so you can assess yourself against those 22 capabilities in the book. Or follow me on LinkedIn, just under Charlie Cowan. And I post there daily.
with valuable tips for Series A founders and revenue leaders.
Paul M. Caffrey (42:04.942)
Great, well look, go check it out. Lots of valuable tips there, lots of help when you wanna improve your sales. Charlie, thanks so much for coming on and look forward to the next time we speak.
Charlie Cowan (42:14.818)
pleasure. Thanks Paul.
