Paul M. Caffrey (00:08.013)
Well, hello and welcome to the RevUpCharlie YouTube channel. And today I'm really excited because we've got a very special edition where we're going to be focusing specifically on sales. As I'm well known for saying, there are two words in revenue operations and revenue is probably the most important one because this is how we grow scalable businesses. And so today I'm absolutely thrilled to welcome Paul Caffrey to the channel.
Paul is a long time tenured tech salesperson and now provides coaching, advisory, speaking opportunities into tech companies. So Paul, welcome to the channel. Charlie, thanks so much for having me on. I'm delighted to be here and looking forward to the conversation. It's going to be an exciting one and a different lens for rev ops and revenue leader professionals to take a look at.
So maybe just a little bit of background to set the scene. I know that you spent a bit of your selling career at O2 before then spending a few years at Salesforce. Maybe share a little bit of that context and then a bit about what you do now. Yeah, certainly will. So at my career, I kicked off in science and I was going to change the world. Then there was a big shift in 2008 and research science was effectively across the board.
So I switched into sales, cut my teeth with Sun Microsystems, who were acquired by Oracle at the time. So it really was a great, great place to learn. And then from there, discovered cloud computing. Only 1 % of companies were using it around that period. So I thought, this is going to be pretty big. And I got the opportunity then to work selling Microsoft technologies, which was Microsoft Office 365. It was called BPOS all the way back then, the Business Productivity Online Suite.
Long story short, helped O2 Ireland sell a lot of cloud, then got the opportunity to do the same thing in O2 UK, where it was over a four year period. It helped take them from zero to a hundred thousand users. So it was really, really great period of high growth. And throughout that point, the sales was going really well. And this is probably the other side of things, which your audience maybe don't see, is for me, I was...
Paul M. Caffrey (02:29.998)
the sales rep who was training junior reps, I was out delivering projects. They also had responsibility to make sure the projects were scoped and delivered. Selfishly, that wasn't linked to commission because if projects didn't get delivered, you wouldn't get your commission for that. I reached a point around 2012, 2013 where I was four o 'clock in the morning heading to the airport on a red -eye flight in a rental car up to Manchester, doing a series of meetings and maybe in London the next day.
I remember being at 12 o 'clock sitting in a bar with the laptop out doing some quotes in the hotel, getting ready to go again early in the morning. And I reached a point going, I actually can't work any harder. I'm like, my time is maxed out. I've doing really, really well. How can I improve? And it was at that point where I was lucky enough to meet Todd Herman, who is an elite performance coach. And he would coach the likes of.
You know, the US Olympic team, Fortune 500 companies, you know, he's worked with Kobe Bryant and helped build the alter ego, a black mamba, which was a big thing for him being so successful. I was just very lucky that it was his first foray into online coaching. I got to be in one of the early cohorts. I just happened to know who he was. And then from there, then I realized, okay, if we want to kick on, if I'm an individual contributor, if I'm a salesperson, I want to get to that next level. Preparation is absolutely going to be key.
and being ruthless in preparation to make the most of the opportunities that I choose to work. And then also being brave enough to turn around and opt not to work on certain deals because the percentages of actually closing them are probably lower rather than just going after everything. So that went really, really well. As you mentioned, I went to spent a good few years then in Salesforce and around 2022 decided to step out and bring this, I suppose, this method that I've been working on out into the world.
So I released the work before the work, the hidden habits, elite sales professionals use to outperform the competition that details how elite performers habitualize preparation and shows you how you can actually deploy it, whether you're an SDR in an impromptu conversation, or if you're an enterprise, a working on closing that large deal. So these days I'm helping seed series a businesses build their GTM sales strategies. I'm.
Paul M. Caffrey (04:49.645)
coaching account executives. And there's so much there that we can get into, which probably your audience don't see because I get to hear the other side of the story of what's maybe missing from systems and what's missing from support. And the main thing for me now is keynote speaking. So I do a lot of that mainly in North America.
Fantastic. Well, a very broad range of things that you're involved with there and supporting people in the community. So that's fantastic. Let's, I guess, you know, dive into a little bit about the world of an SDR and an AE. And I'm sure we'll pull on some some stories from the book and your podcast. When we think about an SDR, or indeed an AE and go right to that,
to use your phrase, the work before the work. So let's go before we've even getting in contact with a potential customer. What are some of the things that high performing SDRs can be doing just to sort of prepare in terms of understanding their territory, understanding the people that they're selling into? So there is a lot of obvious things that they need to do. And what I want to, I'm maybe not going to jump into that, but maybe some of the more, the less obvious things that
Once you hear them, you think, yeah, why aren't we just doing that all along? And that is the stuff which elite performers tend to do a lot better than everybody else. So the first piece is. They take a step back and they go, well, what am I actually looking to achieve and how am I going to achieve that? So, you know, if I'm an SDR and yeah, I need to probably, you know, book.
inbound meetings from the ops to come in or from BD or I'm doing the outbound side of things. But then it's a case of, well, why am I doing that? Do I want to get into sales? Am I looking at going into customer success? Is it something else? So then getting clear on what that longer term piece is and then working backwards. And I think this is something which is really, really fundamental because when we've got that, what we're going for in the long term, it really helps us then be motivated and to do the hard, boring work that we need to do in the short term.
Paul M. Caffrey (07:03.309)
So when you've got that piece figured out, and let's say typically, usual route is I want to become an AE. So great. If you want to become an AE, well, you're going to have to be hitting your number because numbers in that world is so, so important. So you want to be doing that when you're actually working as an SDR. So, I mean, a couple of really obvious things are, yeah, you need to know your ideal customer profile. We need to know the personas. We need to know the pain points. We need to know three, four, five case studies or anecdotes based on
different ways our conversation can go. And once we've done that, what really is table stakes research, then we have a look at, well, what's the territory that we're going to actually work on? What are we going to go after? And then it's making big bets and going after the bigger accounts or the ones that actually have those triggers or have actually shown higher potential for you to go after. Now, probably the key piece which a lot miss is,
There's really three lenses to it, right? You're looking at the person that you're reaching out to. So you've got to consider them and their world. So what are they looking to achieve? How are they going to achieve that? What other key stakeholders are maybe ancillary to that? So is there people in the C -suite that might be able to influence decisions? Is there maybe end users of the products that you are trying to sell that they're not going to buy, but they can certainly give you insight on what's happening in the organization.
And then there's selfishness, well, what do you want to achieve yourself? So when you're considering those, I suppose, those three lenses, then it's about getting into the position of crafting messaging. I don't know if you want to go deep into that or where you'd like to go next with this, Charlie. I think one thing that comes to mind is my wife and I used to run a babysitting platform.
So you could think Uber for babysitters, which was going quite well until a pandemic arrived. And then that was the end of that business. But a key part of that was interviewing and onboarding hundreds of sitters who tended to be 18, 19, 20 year old girls that were at university. And a part of that process was to jump on a call and have an interview. And coming from a sales background, I was totally blown away by
Paul M. Caffrey (09:22.997)
the utter reluctance of people of that generation to come on a call, even if it was to essentially apply for a job to be on the platform. They've just grown up in a world where you don't call your friends, it's messaging. And so I was just wondering in terms of that sort of preparation and yes, it's like learning about the product and the customer, but what do you see about sort of the soft skills or just communication skills of people coming into sales?
And I'm just not having this background of, you know, I don't pick up a phone normally for my friends and family. So they've got to pick that skill up. Yeah. The phone thing is super interesting because when we started out, I mean, like I remember when I started to two most important metrics apart from actually delivering leads was your talk time. And it was the number of calls that you did. Very, very simple. And I remember at lunchtime, some microsystems just went up on the wall. You got 100.
outbound sellers and their stats were there. Your leads, your talk time and the amount of calls that you made. And I mean, it worked, right? We tend to generate a lot of business. A couple of things that I think are super are really, really important is number one is having an opener. And it doesn't really matter what that opener is. That's really what I've come across. Some things like if you want to roll the dice.
Some of these things we've kind of, we see get a lot of traction on LinkedIn. That sort of opener tends not to work so well in UK, Ireland, Europe, maybe a little bit better in the US, but here, but at the end of the day, it doesn't really matter. It's just having a bit of confidence to go and know what that is going to be so that you can speak with someone online on, on, on that even keel. And then the other side of it is, is actually just turning it into a bit of a game and just having a bit of fun with it. And.
The reality is someone is going to tell you to stop calling me, go away. How do you get my number? You're going to get this negative stuff. So it's really embracing the fact that whether that call is a success and you get a lead or it is an absolute car crash, neither one of those really define you. It doesn't make you a better seller if you get the positive outcome. It doesn't make you a worse seller if you get the negative outcome. But then it's into the piece of
Paul M. Caffrey (11:42.541)
As you say, you're going into a conversation. When I'm working with AEs and STOs, I guess, you know, tell stuff like, you know, my manager, they might come and shadow me when I'm doing my cold calls, but they, you know, they don't tell me what to say. They don't tell me what to do. You know, we'll talk about it afterwards, but it doesn't help. And there's a lot of this, and particularly in later stage deals, I come across that so often. And the reality is that responsibility is on you. So.
What is a really good metric to look at, whether you are measured in your company or not. I don't think it should matter. You should be looking at doing 30 outbound calls per day. And that might sound like a lot, but when you consider the amount of conversations that you're going to get, it's going to be pretty minimal. If you have the data there, you can probably fly through that. And look, maybe you only get 15 calls made, but you get three or four conversations. And then it's the case of it's a cold call. You have interrupted somebody's day.
So even if they're super positive and like, that sounds really interesting. Yeah. Okay. And you have to realise that at some point they're going to remember, hang on a second, I'm doing something else here. I didn't even mean to speak with you and they're going to cut you off. So it's then knowing what your goal is. Well, how about I can get that, you know, meet and book in the diary where we both a little bit more time. But from that point, the only way to get better is to actually do it. And if you feel a little bit anxious, a little bit nervous, that's okay. That's perfectly normal.
That's just par for the course. And the really interesting thing is the higher you go in sales, you're always prospecting and you're always doing call calling. Sometimes it can come in different forms. I've worked with some enterprise sellers and they might just do six call calls per day, but they're really, really targeted. And I've been super impressed with this. I've seen men and women in their 50s and 60s still doing that hard work or
It's more lunches and it changes a little bit when you get up to that level. They still do it. I think that is one thing if, you know, if you're, if you feel a little bit nervous with that's okay. And then it's jumping into the value that you offer and you can get into that pretty quickly and it can have a perspective, a point of view. You know, I think that I'm, you know, I can see, I've seen this in your profile and I think that I can save you X, Y and Z by doing Y. I'm just getting them to talk, get them to be curious.
Paul M. Caffrey (14:07.821)
Yeah, some great advice in that. And it takes me back to when I started selling. And yes, we were in an office back then, because that's the way it was. But we would have two happy hours a day. So there's one, I think it was like 10 o 'clock, and then maybe one at 2 .30 to 3 .30. And that was when the entire team across the sales floor was cold calling. And for those happy hours, everyone would stand up. So it really got the energy going.
And then on each pod, we had tables, which was a pod. We'd actually bought some Leeds United football shirts. And so there was someone that was the Leeds sort of manager for that team. And so they'd wear the football shirt during these happy hours. And it just brought this whole idea of like, we're all in this together. Cold calling wasn't fun last year. It wasn't fun two years ago. It wasn't fun 20 years ago, because like you say, you're making an interruption. And so,
your natural sort of fight or flight, especially if it's your first role is, I don't want to do this. But if everyone's in it together, like you say, you can make it a little bit of a game, make it a bit of a challenge. Like, no one's out to get you. If you've interrupted someone, you caught them at the wrong time, you know, they'll tell you, you move on to the next one. But by doing it as a team, collaborative, I think that worked really, really well. Definitely more challenging these days with a lot of people working from home, because it's so much easier for that.
negative thoughts and the core reluctance to come in and I'll just do a bit more research or I'll just build this list a little bit more. But, you know, for today, that's a time blocking saying, right in your calendar, you know, 10 to 11 every morning or whatever it might be of just sticking to it and following a process. Yeah. And like the reality is we're coming towards the end of Q1 for a lot of, a lot of the tech companies that we'd be working with, for example, right. And there, I think this year you're going to see a push.
you know, from leadership for people to make more calls. So whether you want to do it or you don't, it's probably going to come forced at you at some point if you're in the SDO or all. So you might as well embrace it. And the other side of things are, you know, when you're at the, when you're working larger deals, there is going to come periods of time when you are going to be cold calling into different parts of the business to multi -threaded deal, for example, or so it is, it is a skill that is just so, so needed to have.
Paul M. Caffrey (16:35.053)
And it's just look, be playful, enjoy it. It's a bit of a game. It's a bit of fun. And the reality is there's two ways that you can do it as well, which is something that you can look at volume based. You can say, well, I'm only my 30 calls today. And if you're an S .T .O. you should be doing more than that. Let's call that out. But like, let's say if you're an AE, you've got closing responsibilities, you're kind of managing to. But then the other side of things are when you get really good and you kind of reach that elite level.
You then focus on the outcomes and you're, you know, you go, I'm going to keep going at this until I find the lead. Maybe that's three calls. Maybe that's a hundred calls. But the key thing is you want to be doing it every day. If you miss a day, okay. Don't miss two in a row. It's these little things that start to compound because a day can become a week, can become a month. And there's always a reason not to do it. But I mean, yeah, like it's, it's one of those, it's, I think it's, it's going to be table stakes again for us.
I think from the lens of revenue operations, leadership, or any leaders across sales, it's having that balance between the science of we've got this many reps making this many calls with this much connection rate and this many meetings booked, which is sort of a spreadsheet and to go right, we'll just put more people on the field to get to our numbers versus the art.
and the empathy and the understanding of what it actually takes to hear that brrrr brrrr brrrr brrrr brrrr brrrr brrrr
Is that doing ride alongs? Is it sitting alongside some of the SDRs and listening to their calls? Is it making some of your calls yourself? Is it going and meeting with customers to really understand their perspective and really understand what's landing and how you can add value to those customers? Because it's not just as simple as a spreadsheet and just putting people into battle. Yeah. And like,
Paul M. Caffrey (18:54.317)
Like if we call it out right, the spreadsheet, it's a bit lazy. It's a bit of a lazy way to plan and do things to say, well, if we do 50 calls, we get this. If we do 100, if you have that 10 reps, 20 reps, this, this, this is a book bearer of mine. And it's something that's always, I remember my first role when I was co -calling, I would tend to do 40 to 50 calls per day. And at the time, a hundred is what was, what was warranted, right? But the talk time,
It was two, two and a half hours when you're actually in conversation. So the talk time for me was always pretty high. The number of calls made was pretty low. And then by, you know, hitting those leads targets, I was doing that. And then there was another person and they would get called out as being great because this person has made 300 dials today. And we're talking about actually, you know, typing the numbers. There was no, you know, multi -dialer system at that point. But this drove me crazy because.
We would both be called out as being like, these two are really great performers, but I'm looking at this going, he is burning through six times the data that I am. That is so wasteful. We shouldn't be doing it. And the activity metrics are really, you know, that's one thing, but we want to be looking at, well, what is your conversion rate? So what is the conversion rate of calls to getting the leads booked? And that is something that is key because that means we're going to waste a lot less data.
In the sales end, when we get to sales end, people think hitting quota is success. And it is a mark of success. But if your win rate is 5%, you've probably spent an absolute force in generating all of that business to hit that quota. Whereas if you get your win rate up, this cost here can come down. So it's about understanding the conversion rates and going to that level. And that can be different per individual contributor. And it does take time and is more difficult to get to.
But that is where we want to be going to look at the efficiency and to look at the quality. And the key thing then is we're not pushing people to actually do more volume or we're not just throwing a load of data in. We're getting to your point of the art of it. We're developing skills. We're developing those soft skills so they can, you know, find questions. They can lean into curiosity. They can take conversation back on track to where we want to get to. And the same in deals.
Paul M. Caffrey (21:17.389)
So that is something I think if you're a revenue rev ops leader, you want to really be mindful of because again, that's another, it's harder to see, but it's another way where you will reduce the cost of your acquisition and of your business.
Yeah, absolutely. And I there's a massive shift that's been going on over the last couple of years from the seller having all of the information to now the buyer has all of the information because they can get it through their peers through private online networking groups. So they've got access to so much information that they used to have to come to the seller to try and get.
So now they're coming to salespeople much later and later. I say coming to that's either inbound or deciding to respond to the SDRs email or call, but they're making that connection much later. And when they do make that connection, they want a much higher level of business insight of advice and guidance. So anything that has come out through your sort of conversations, your coaching on how SDRs and indeed AEs can
level up their game and be able to provide a much higher level of business sort of acumen and insight that's beyond sort of low level product information. Yeah, absolutely. And the reality is, you know, we're going to see these reports that people want to speak with salespeople less and less. And, you know, seasoned executives, they probably don't really want to speak to SDRs to be put to an AE who maybe doesn't read the notes and, and go through all of that. So.
On that side of things, we have to be very mindful that we want to be given a premium experience. So there are, there's really two sides to that, right? So there is the, whether it's come inbound or it's, you know, we've gone outbound, it's business acumen, but taking it to another level. So I was chatting to Justin Michael yesterday, author of the Justin Michael Meta 2 .0 and sales to present. He does a lot of work in this field. And really what it's about is.
Paul M. Caffrey (23:26.701)
We have our perspective, we have our point of view. So we know that our product helps, does X and this outcome is Y for this company. But then it's taken a step back. If we're going to jump on a call and we're actually going to speak a little bit about the solution, what can we find out about that company of how that would actually impact that person or how that would actually impact the business unit itself? So you're really synthesizing that information and giving it a little bit more context.
So for an example, it could be, okay, you're looking to get this technology to improve how you hire. Okay, great. Well, if you could hire people, what does that mean? I'm seeing there's a lot of open jobs, so I'm guessing you want to probably get people in, you want to get them in a bit quicker, you want to get them ramped a bit faster, so then you can bring on more customers. The average customer stays with you maybe five, six years. So actually, this $50 ,000 solution,
could drive X amount of million of revenue for you if you got it right. So it's taken that piece to the next stage with them looking to validate that. So that's really at the, I suppose, at the very initial piece. So we're trying to really be seen as a bit of a peer here where I'm actually thinking about what your business is trying to do and what you're trying to get to. Most companies, their CEO or their leadership team have spoken and have
comments online that you can find that you can kind of use as a way to link back to. I suppose the other side then that we want to have a look at is if you're a little bit further on. So let's say you're doing the qualification or you're doing the discovery. OK. And the other person, they want to see a demo where they think they know what their they think they know what their problem is. They've self -diagnosed. What we want to be looking at is OK.
Unlooking what is the current situation? What is the problem? And what we want to then determine instead of going into, well, you've got this, you know, this problem, you need to increase your sales by 30%. And I saw the CRM and you know, CRM, I've proven that I can actually increase sales by 30 % and then jumping into the next stage or, you know, going through the demos or whatever else. It's taking a step back and it's going. What's the root cause of this? So what do you think is causing you to actually.
Paul M. Caffrey (25:46.701)
be 30 % to not be able to hit that 30 % growth that you're after. But what do you think is causing you not to be able to whatever your product does? And this is where we want to get the person to say, well, I think it's because our marketing is just, it's ineffective. We're not really able to take advantage of who's coming to our website. We have a lot of traffic, but we're not actually getting that to the sales team. So then you're into a really different conversation. So what's happening there? Okay, great. And.
Rather than going down the CRM route, you probably want to pivot and go down a marketing automation route because the reality is if you're selling something and it solves a problem so that they can have a problem, but if your solution isn't the way the solution that they think is causing the problem. So if you're not solving that root cause, they're not going to buy from you. They may go through your sales process, but you won't get the order for it. So that will be something I think is very, very key. And the way to think about it then is.
Okay, if we validated a root cause and that root cause is in line with, you know, something, a feature or a part of what our product can deliver, fantastic. We can work through that. Or if it's not, we can challenge that thinking and we can say, well, to our experience, people do it this way or they do it that way. And then you can have that conversation and realize if it makes sense or not. And at least at the early stage, then you can call out, well,
This is how we do things. This is what we think you need. You think it's something else. So, you know, what, what are we going to do here? Are we going to part ways or are we going to continue on? So roof cause is super, super important at that earlier stage. Yeah. And I think some companies are very poor at educating and enabling their teams on the world of their customers. So you talked a little bit about personas there.
I think when people come in, and this is a rev ops challenge because enablement is one of the stools for the rev ops chair, a lot of enablement focuses on here's how our sales process works, the stages and gates and how you get your opportunity all the way through. And then here's how our product works. All you need to know about the platform and the features. There is very little about the customers themselves. At best,
Paul M. Caffrey (28:10.605)
you may skip over a slide that is the persona that we sell into. At best, there may be a slide on these are the top two or three industries that we sell into. But it's low level because the people that are doing that enablement are not healthcare specialists or CFO specialists themselves. So it's just something that's been gleaned. And this is where you see this separation between brand new reps.
and the tenured rep that's been here five years that is deep into healthcare and life sciences, absolutely knows the language of the customer, knows the people in that space and can have a pretty high success rate on their outbound because they're speaking that language. Are there any sort of, you know, ideas or anything that you've seen in the past where companies are doing a better job of raising the business acumen and the persona knowledge for
Yeah, there's two things that I've come across and reps can do this themselves as well. You can do this for your territory or your patch. It can work better if it's working across the whole business. But typically we don't know why someone has actually bought our service and we don't know what they're actually doing with it. And we tend not to know why somebody didn't buy from us. And it's like,
If you take someone, they didn't go ahead. Okay, they didn't buy from us. Well, all right. Well, what happens? You just picked an option in the CRM that's going to get you the least amount of hassle from management because you don't want to talk about a deal that you've lost. So you'll end up with, you know, went with competitor X and it's, you know, maybe it's probably not even true, right? Or it's, you know, funds weren't available or, you know, funding, whatever it is, but you pick that option that's not going to get interrogated too often.
And so if you, you know, if you're working on, if you've got a patch, whether it's deals that you have worked to the end and have not been successful, or you've inherited a patch and there's deals there that didn't happen, right? You can literally call up the decision maker and just call out, look, not looking to, you know, resell you, not looking to re -engage. I am looking to understand what was the, what was the reason, what was the thinking behind not.
Paul M. Caffrey (30:34.893)
going ahead because you spent a lot of time with us. You met us a number of occasions. You obviously felt that the problem you had, we could have solved, but then it didn't match up. So what was the reasoning behind that? And I know it sounds crazy, but you can literally just ask the question and then you will get told, well, this other person did this or something else that was missing or this wasn't actually addressed. We went with a competitor. We
You know, there was a stronger relationship there. So you knew you're always behind the eight ball, whatever that may be. But then the other side of things are, so you'll find out the reasons why you're losing. And even that language, as you mentioned, Charlie, you've got that then to actually bring into your next conversations, your next calls. But when you've won a deal or so this can be deals that you've won or this can be deals that are in the patch that you're managing or maybe just customers of the business, right? You know, there's probably a little bit of way that you need to navigate how you're contacting customers. But you should have some that you can reach out to.
And then it's looking at, right, well, yeah, we provide market and automation or, you know, we provide CRM, sir. It doesn't matter, right? Whatever your marketing says. That's one thing. What are you actually doing with this? So who's logging in, who's using it? What are they actually using it for? And what is that giving the business? And what you'll find then is typically like there's 60%.
are using it completely different because it solves this problem for that company. It solves something else for someone else. But you'll find that, you know, there's typically 10, 20, sometimes 30 % of stuff which is repeatable, which is happening again and again. And that then makes your outbound a lot more powerful because you're speaking to actual problems that people are solving with your products. And then you can go to those similar personas using their language. And that is something which if you're new and if you've got a new patch,
if it's a new FY for you or it's a new role, or even if it's something you've just never done before, the insight that will come from running that will be just, it will just really help you get a leg up. And if you could do that across the company, that's probably going to change your strategy. And for me, 25 odd years in sales, that's the bit that I love about the job. There are very few people in an organization that get to spend the majority of their time.
Paul M. Caffrey (32:58.029)
outside of their organization, speaking with other people, learning about other things. And some of the most enjoyable deals that I've closed have been in companies that I'd never heard of and industries that I didn't even know existed. And one, I'll just give you a little insight, was a company in Geneva that makes flavors and fragrances that they sell into CPG companies like a Unilever or P &G.
And as you start to walk around their factory and get to speak to them, they're like, do you know, we touch you 50 times a day, the smell of your shampoo, the smell of your toothpaste, the smell of a new car, the smell of your new pair of shoes. And I'm like, my goodness, my entire world around me has been manufactured and made to make me feel a different way. And I really loved learning about that business. And...
Just through that excitement and passion, you end up building a relationship with people. And yes, you're going to end up rolling out Google, which is what we were doing there. But you do that with the understanding of what that business does and why people work there. And for me, that's so enjoyable. And so for anyone that's getting going in sales, for anyone in rev ops that's trying to understand how do we sell more, it's that curiosity for what is it that your customers are trying to do.
What are the challenges that they're facing? And if you were in their situation, what would you do? And if what you would do is buy your product, then, you know, go for it, you know, position of why that's the right thing. But also, if it's not what you would do, if you're in that situation, then that's a great example of where you qualify out and move on where you where you can be a best fit. But, you know, so many sellers will say, I'm curious, because it's what they've written in their script.
Be curious. Don't actually just say it, but actually do. And it's it's what I've so much enjoyed about the career over the past 20 or so years. Yeah. And I'm with the curiosity thing that people are going, OK, well, how am I curious? I'll ask a question, right? So if you ask a question and you get the answer back and then you go, you know, what makes you say that? Can we unpack that a little bit more? Then you get the next answer. And even then just repeating the last three words that they say gets them to open up. So if you're if you're
Paul M. Caffrey (35:20.781)
curious about something, you want to be going three or four levels deep on that, because that's when you'll find the real answers. And if you get a pause along the way, and it might start to feel a bit uncomfortable, because you feel, no, do I need to fill the space here? Don't fill the space. Let them actually come back with an answer, because that means you're asking questions that are making them think that perhaps others haven't done, and you're going to get the real answers. So that goes across the board, whether you're trying to open up an opportunity or whether you're
you know, right at the end, you're trying to get something closed and you're being curious. You know, for example, OK, if OK, well, we've got agreement in place and I'm going to send over the document and you'll be able to get it returned by say Thursday and then Thursday, Friday. Yeah, no problem. Yeah, we'll get it sorted. And then is it OK? Thursday, Friday. What's going to potentially cause the delay to Friday? And then you're just
you're finding out what's going on. You're just going three levels deep. And again, like, so as to your point, yeah, if you if you want to be curious, be curious to have a little framework behind it. Coming to the end of our session, there's a lot of conversation at the moment about the future of the SDR model. SDR model.
For many people might think, well, this is the way it's always been, but it's only really gained prominence since the mid 2000s as Salesforce drove a lot of that. I started as a full sales cycle AE, and there's a lot of discussion now linked to what we've talked about here. Buyers are coming in more educated, more motivated, and so do we need this sort of two tier? If I'm...
I'm VP of RevOps and I'm thinking about how I'm going to plan and structure our sales team over the coming years. What's your perspective on the future of the SDR role and does it evolve in terms of when we use it and why? So my view on the SDR role is it is no longer just somewhere where you just take a graduate, you park them there for 18 months to learn the business and then put them into a sales role.
Paul M. Caffrey (37:38.221)
Cause it used to be a cheap way to get salespeople in the door and get them acclimatized and out you go. I think now what it comes down to is, I think there's still a place for the SDR model. But what you want to be looking at is it being a little bit more competitive and then figuring out, well, you know, who are the top five or 10 % who actually have a chance to get into my, into my sales team. And then.
the others, well, what, where are they going to go? Are they actually a much better fit for customer success? And I really come down to being very, very clear in, you know, with the SDRs of potential career paths. And equally, it's a case of if it doesn't make sense for them to be with you in the long term, you know, having those conversations and knowing, so everybody has transparency on that. Now, what that means for the SDR is you need to know where you want to go towards. You want to know what you're trying to achieve.
And it really means you're looking to operate at a higher level. Ultimately, ideally we want, you know, sales A's to have their pipeline completely full and to be working the best, you know, to be, to be working deals where they don't have to prospect. The reality, I think this will stay the reality for a very long time is the best pipeline that you're, you're going to find is the pipeline that you're going to find and source yourself because you're going to build up a network. You're going to build up contacts.
So I think if you want to be in President's Club and always doing well, you're going to have that balance of doing prospecting yourself, running those dinner events, running those whatever, whatever that more high touch piece is, asking existing customers for referrals, using your network to get introduced to other people on top of inbound that comes your way.
I think it's always going to be that mix. So I think the SDR piece is going to become a lot more competitive. It's probably going to become a little bit smaller and the standards are going to have to raise. I mean, it's interesting to get your view on this. I mean, some people are saying that this should be like a really junior SMB full closing role for SDRs instead of just appointment setting. Again, it's down to what you sell. That's how I started.
Paul M. Caffrey (39:51.149)
And one of the benefits that I had from that was because you go the whole way through the sales cycle, you're able to bring that business insight back to the start. So it wasn't just about getting someone on the phone and making that meeting, because you actually then were taking them through, you might be meeting them in person, you're helping with the contract, you're helping them to get live. And all of that insight that you learn later on, you bring back to the start.
And I think it's a real challenge for people that don't have that experience because they just don't know what they might be asking. So I think this is a balance. I think certainly in larger scale opportunities where AEs time is fully maxed out, there's lots going on, then it can be a great, great benefit, but definitely a fluid time. And I definitely recommend to any clients I'm speaking with,
Don't just take the blueprint of this is what everyone else does. Therefore we have SDRs and we have AEs. You need to work through the economics of it based on your ACV and when that's going to make sense. But also, like you say, what's the career path of these SDRs and does it make sense that actually they're just coming in as full cycle SMB AEs to start with before moving up into enterprise?
Like should you be hiring them if you actually see there is no career progression path? You know, you just know that's not going to be there. So are you taking them away from better opportunities? I mean, the two things I'd say like from, you know, with my kind of RevOps hat on, should I say, is yeah, we want to have those activities. So we want to know, right, the amount of calls, the amount of accounts, the amount of individuals that you're expecting your SDR to reach out to. Yep, activities for AEs as well.
but really focused on what is the conversion rate when I get an SDR speaking or communicating with a decision maker to an appointment set. And then what is the win rate of my of my AE. And I want to be looking at, well, what do I need to do to get those two numbers up? Because it's not necessarily about volume of activity. It's about improving their skills. So what what what skill gaps have they got?
Paul M. Caffrey (42:06.925)
And probably a great way to think about this is if you want to improve, let's say, the skills of your AE, you know, there's, there's sometimes tends to be a push towards, well, let's look at negotiation. Let's look at closing. Let's look at all that. But when you go a step back, if you go a step back to the demos and actually delivering a top 1 % elite demo, or even a step back before that is in running an elite discovery that hits the root cause. When you're fixing something, which is back towards the top of the funnel. And if you can get that right.
That then improves the end results massively, which I'm sure most people listening will understand that from building out these models. So if you're looking at where to start, start at the earlier point in the journey. Paul, this has been a fantastic conversation. I'm sure that for everyone from a rev ops background, it's a real insight that B2B sales is not a computer game. You can't win it with a spreadsheet. At some point,
As I always say, at some point, a human has to speak to another human and making that first conversation, that first outreach and then building that relationship is the art of B2B sales where the operational side is the science of it. So I think we've added some great insight to the discussion. So with that, Paul, what's the best way of people getting in touch with you and finding out about your book and your podcast and everything that you help people with?
Yeah, absolutely. So website is paulcaffrey .com. So you'll find out about my speaking there. Book is the work before the work. It's available Amazon, anywhere you can get books. Basically, you'll come across a really, really good place to start and then reach out to me on LinkedIn. So Paul Caffrey mentioned the show. It'd be great to hear that you are following Charlie. And then from there,
And yeah, I'm speaking to SKOs and bringing the, you know, that strategic outcome based stuff, put a mix of tactical tips that people can take away and use. And I've also I'm looking at providing, well, I do provide master classes now. So if there's an area of your sales cycle that you want to improve, let's say it's discovery or getting your demos, you know, getting them to be actually connecting with your prospects and getting them to.
Paul M. Caffrey (44:31.213)
want to go onto the next stage as opposed to zoning out and tapping on their phone. They're something I'm delivering, they're delivered virtually and they're very, very powerful. So if you want to give people a real boost for Q2 and get them going, that is also something. Everything is on paulgcaffrey .com. Charlie, big fan of what you're doing. Thank you so much for having me on and it's been a blast. A pleasure. We'll make all those links in the show notes and thanks Paul. We'll chat again soon. Absolutely.
