Paul M. Caffrey (00:00.75)
I'm delighted to be joined by Rob Dumbledon, co -founder of 4 .4. Rob, how are you doing? Yeah, really good. And I'm excited for today's conversation because the technology that you are building, I think solves a big problem that we suffer from in the world of sales, particularly individual contributors. And that is being able to prepare for our meetings. What triggered you to decide to tackle this problem?
Rob (00:06.787)
I'm great, thanks Paul, how are you?
Rob (00:30.051)
So I think I sold a business back in 2022 2021 actually sorry and as part of going into the business that acquired us I got put into actually the product team because it was a good space for me to cut my teeth and get some experience into You know what it what it takes to develop compelling products within the b2b SAS space and it
Paul M. Caffrey (00:30.734)
So I think I started a business back in 2022.
Rob (01:00.387)
I learned about the jobs to be done framework. I don't know whether you know what that is, Paul, aware of that. That whole methodology, that whole framework is all about driving a better understanding of the customer and what the customer needs, but relating it contextually into their world. And I thought that was a fantastic way of looking at things, right? And we do that in sales somewhat, okay, because we talk about...
Paul M. Caffrey (01:04.814)
Yep.
Rob (01:27.555)
customers pain, but actually we've got to relate that pain to a day -to -day activity, a day -to -day task. And it got me thinking about kind of connecting those two worlds, right? And how product and sales need to come together within the B2B SaaS space and sell together, get a better understanding of the customer together, common language, right? And how that whole kind of movement can drive a far better...
comparison across different customers context so you can bring that knowledge, that research if you like, into the forefront when you are preparing to have a sales conversation or a prospecting conversation with somebody that's come in. Because everybody wants to know what the person before them's already done with you. Everybody wants to have that kind of credibility stamp of, you know, it's why G2 exists and all of these review sites, right? Because everyone wants to stamp of approval from...
other people have been there before. So bringing that into that context of a conversation when someone doesn't know necessarily the product they're selling, they don't know the world their customer operates in because there's too much to know unless you're very, very super specific. So that whole, bringing those worlds together to understand that customer context at the point of need was where I thought, well, there's a great opportunity here to serve information up really quickly at the point of need.
those little kind of activation points.
Paul M. Caffrey (02:56.942)
And.
I don't want to gloss over that point too much. And people may listen and think, well, that's ridiculous. You are selling something and you don't know what you're selling and you don't know the pains of the problem of the person that they're having problems and what that actually means. This can happen, particularly in SaaS sales, quite a lot. If you think about it, that you're typically selling to technology or to product people who have really, really deep expertise in what they're doing.
They're working in technology, so they also have that in their favor. And then you're in the position of you might join a company and they may have done millions in some cases, maybe they've even done billions and say whatever, whatever it is, if they're a large publicly called company, they've got some stupid numbers behind. So there's a tremendous amount of deals that have been done. But for you coming in as a new rep, you can only speak with people, which will be a few people on your team, maybe a few other teams.
You'll probably have some onboarding content to go through, which would be these polished case studies. And we never really get the opportunity to find out exactly what our customers are doing with the product or what customers of the business are doing that we haven't even sold to them yet. How do you recommend people use that info when they can find it?
Rob (04:19.939)
I don't necessarily think it's just the new folks coming in, by the way, or new reps coming in. I think we're all guilty of not keeping our ears to the ground with changing market needs. I mean, look how quickly markets move and needs and customer wants just rapid AI. All of a sudden everybody wants AI. I don't know why, but they want AI. It's great. So everyone keeping their kind of ear to the ground on...
Paul M. Caffrey (04:43.822)
Yeah.
Rob (04:49.219)
development. So I think it's both camps for sure that need to gather that information. But I do think that the kind of the... sorry you're gonna have to ask me the question again Paul because I've forgotten the context on that.
Paul M. Caffrey (05:04.526)
Well, what do you think people should do when they get that customer information or how people are using it? So how should sales folks actually use that info?
Rob (05:16.771)
Perfect, yeah. So sales folks should use research and analysis of existing customer needs, prospect needs, where they perhaps not won deals to first of all to qualify out so you don't have stuff in your pipeline that's not worth working on because you know you can't meet those needs. That's one of my biggest things is to make sure that pipelines are only populated with really strong sales accepted opportunities.
that have merit based on need and are qualified based on need. So from a prospecting perspective, it's definitely about looking at whether or not that prospect fits the need profile, not just the firmographic ICP fit profile, but the need profile. And obviously if you're collecting previously researched customer needs and bringing those into the mix, you can then begin to profile based on the firmographics.
You can begin to profile that prospect based on their needs fit and then qualify, unqualify. And then I think it's just making sure that you continue to develop those needs in terms of depth, really get to the bottom of how are those ranked? What's the priority order? And what do those different needs mean for different stakeholder groups when you get into multi -threading and developing opportunities forward? So.
activation points along the sales cycle for different stages, so whether it's a BDR all the way to BDM through to customer success and account development, it's having that intel analysis so that you can bring in additional information, tell a better story around how you've solved problems, solved pain, achieved impact for customers in the past and how that relates to the situation you're currently discussing.
with that lead in front of you.
Paul M. Caffrey (07:11.214)
OK, that is two things jump out there, Rob. One is it's keeping your sales process up to date. So I'm getting the feeling that by being able to dig into how customers are buying from you, that you may spot maybe trends, nuance, difference for maybe people, process of what's happening. Is that one thing that you think people should be looking out for?
Rob (07:37.915)
Absolutely patterns and trends in when certain needs are articulated by different buyers within your journey, all your stakeholders, your champions versus your exec buyers versus your potential gatekeepers, right? It's getting a in -depth understanding of the patterns that are occurring within your pipeline with different individuals across that process. So if you haven't heard
a particular need mentioned, for example, by an exec buyer. And that's your pattern so far. That should put off those warning signs of they haven't articulated the need correctly, in which case, you know, that's when you can start to intervene or really drive for qualification or requalification of that opportunity. Because you just haven't heard that information. I think it's those patterns and trends. We're all aiming for repeatability.
That's what sales processes are about, is how can we get repeatability in our motions. And what we're doing is taking it one step further to identify that repeatability in those needs. So it's a bit of a supply demand matching service of repeatability, I guess.
Paul M. Caffrey (08:52.046)
OK, so the manual way to do this is to look at all the deals that you won, whether it's your territory or your your segments or your your geography for a particular period, so maybe last quarter and go through all of the steps that happened in the sales process. All the people who got involved and identified that, we're seeing there's an uptick in people requesting a pilot.
because we're targeting maybe more tech teams now, CTOs, but we're also then seeing that that drags out the sales process and reduces close rates for these other deals over here. They close faster when they didn't do a pilot. So maybe we shouldn't be doing that. Although initially that probably feels like a really strong buying signal that they want to commit time and resource to playing with our product. I'm guessing that's the sort of insight that you're looking to try pull out of that.
Rob (09:49.219)
Yeah, exactly. And making it less binary. So I think sales methodologies are great at defining exit criteria for deal stages within the pipeline. And the right things to ask. And I'm not with no means am I saying don't use those. We actually as part of our methodology and how we programmed our LLM to apply those types of sales methodologies.
But this is taking it from the kind of less binary indicators to actually back to the customer of why is it compelling still for them to continue the conversation with us? And you've got to have that compelling need, that desire, that motivation the whole way through. And for us, it's those need signals that I think are paramount and being able to say, well, actually our successful kind of critical path deals.
Normally follow this pen this trend and this pattern over time and therefore if this stakeholder has not talked about this need because they normally do at this stage of the Process or this pain or this impact or this buying job? Then we should probably drive to get that answer pretty quickly Or this isn't moving anywhere, and it's risky
Paul M. Caffrey (11:09.294)
And again, we've got the rudimentary signals that we see, like maybe if you're using Gong, you get the notification of this deal is in the sales stage for so long or we've were single threaded or there's only so many different. There's only so many different people who've been involved in this deal historically, and that will kind of tell you, OK, well, it's a higher or lower chance of closing. This is going a lot much further than that.
What I think is super interesting, if we think about the way the company sell, you know, typically there's an SMB motion. There's the mid market, which is normally a combination of SME sized deals and maybe some enterprise sized deals kind of squashed together. So you've got those, those nearly two deal tracks running and then enterprise being, you know, what is what it says in the tin. All very different. And the organizations tend to buy it because.
Rob (11:57.603)
Mmm.
Paul M. Caffrey (12:01.262)
They've got different needs and different outcomes and broadly speaking, marketing will be able to associate what that is with some sort of catch all terms and some catch all case studies. But the nuance is quite different. If I pivot onto the customer side, so what they're doing with the product and the outcome that they're actually achieving. What how number one, how do you find that information?
Rob (12:29.859)
Well, so it and yes, it it's related to the fact they've got in the palm of the hands your solution. They've started to use it in earnest. They're going to give you some feedback on the on the tech and how it's working. But also it's going to hopefully it's going to give them a bit of a primer in terms of what else is possible. I've used this stuff now. It's changed some things for me and it's it's it may have had an effect.
Referral impact or created maybe created pain elsewhere. I we can't guarantee that it hasn't Fixing one thing might break something else. I don't know and actually what we're looking for is not necessarily the Feedback on the solution the software the product itself because there's other tools that do that You know the gain sites and your usage and adoption tools what we're looking for is the hooking into those continued conversations with
customers that might happen with non -commercial people that might be exposed to little nuggets of information that again provide additional context on the account on what's going on, what people are seeing, what other jobs they're thinking of right now, so that you can start to then think about well what else could we do for this customer? What else have we left on the table potentially that we could meet with our solution?
And what else is out there potentially across all of our customer base that's common that we could address if we were to buy, build, configure, whatever it might be with an additional solution or recommend something else. Cause it's all about creating trust and impact with customers. And therefore there's other things that need to be met. So it's those little pockets, I guess, of additional things that are left unheard.
by a non -commercial person not being able to listen for... that's just been mentioned over there and because I can't be on every call as a commercial person I want to know that something's capturing it for me so I can see that moving forward.
Paul M. Caffrey (14:42.062)
OK, so you're looking at upsell, cross -sell opportunities, the more obvious stuff that maybe people are trained to look for. But then you're also leaning into product development. You know, there's consistent issues here and it's not getting to the CRO or it's not getting to the tech team or it's not getting to the C -suite. So you just don't know that if you added something that you may open up a new revenue stream or you may keep that customer longer or whatever that may be.
Rob (14:44.611)
you
Rob (15:10.819)
That's exactly it. And that's kind of full circle actually back to where we started on the common language element pulled around this of everybody's got to be communicating on the same wavelength. They've got to be talking about the same thing. It's got to be outcome driven. And within the jobs to be done, methodology and framework, the ODI outcome driven innovation piece is actually focused on
the outcomes the customer is looking for, the market, the wider market is looking for. And if you know those, then a really bright product team should come up with a solution to address them, not features that are requested. Right. Cause that's not helpful because then everyone's paying, you know, feature bingo. this is about identifying outcomes that then, cause you can sell outcomes. Features are difficult to sell. They really are.
because people with the purse strings want results, outcomes, ROI, they want impact, they want movement, they want change, not just a new button, a new witty thing that people might like. So I think bringing, couple connecting that together, you've got everything from better serving the customer's unmet needs to better qualifying the pipeline and identifying kind of, or bringing in great,
great stories that are relatable in context. Meanwhile, everything is being fed back to products so that everyone can work together to sell as one homogenous unit, which is what B2B SaaS businesses should be, not product build something over there, we'll try and sell it, or we're gonna ask for something over here, product will try and build it, but six months later, we don't want those quabbles. We want it all to be in harmony, and that's the end.
Paul M. Caffrey (17:01.87)
Gotcha. And you mentioned storytelling quite a number of times now. What do you think makes a good B2B story? What should people be sharing in that?
Rob (17:16.163)
Well, I've come across the marketing hero journey that I quite like as a story. Creating a hero out of the customer. It sounds a bit grander than it is, right? Heroics and heroes, you know. Making someone look good, right? And telling that story in terms of a journey. Where they started, what they considered. By the way, this is my sales tip.
we can bring in as well, is the storytelling aspect here, but making it compelling. So I think if you describe somebody's situation well and talk about their situation with knowledge, it's going to create empathy with your prospects and they're going to be like, this person really understands me, which is great because you've gone to those lengths to understand that individual, you've put them in that context. And then if you start to then talk about
some of the things that they've probably looked at already. That means that you're knowledgeable about the market, the wider market and where they've probably dabbled, but may have not had success. And then you frame there's something new that they could be looking at that will have impact, not what it is yet, but the pain itself, the impact it has. And then you move finally to what the new world would look like for them. And I think it's that kind of that journey and how you...
frame that story, not in a cheesy way, but in a nicely told, succinct, evidence -based, and that's the key, evidence -based way. And I think that's what people relate to. I really do. We all like stories. We all like being told stories. And it's far less binary, far more personable, and shows good EQ if you can empathize and go through that process. So that, for me, is storytelling within the sales context.
Paul M. Caffrey (19:12.782)
And something to drill down into on that is. It's very easy and somewhat lazy to just tell the story of the standard case study that's on your website that maybe is from a company from a different geography, maybe that persona doesn't quite meet the person that you're talking to across the table. Whereas if you actually do that bit of work, you don't have to name the company, but if you can find out that, yeah.
There is somebody who has the same role as you and they're operating in a similar, if not the same industry. And yet they're actually in this state or in this county or whatever. And then tell that story of where you took them from to where they want to go. And if there are similar pains there, people will resonate and they will see themselves as that person. I could, I could, you could make me the hero for here. I might go and achieve said thing and whatever that may be, whether it's promotions or something else off the back end.
Rob (19:48.291)
you
Rob (20:08.163)
Mmm.
Paul M. Caffrey (20:08.75)
I guess the other side of it is to be very careful of is it's very easy to put people off. If you tell them a story that's irrelevant, if you're talking to a founder and you're telling the story of, let's say, a Google or a Salesforce these days, it's going to miss the mark. You know, we helped Google do this. Well, that's great. They've got all those resources. I don't have that. So it's something to be really, really careful of. And sometimes if you don't have a good story, it's probably better off not to tell it.
Battered Intel are really bad one and disconnect.
Rob (20:39.491)
Yeah, it's a great point. It can be a, if you miss the mark, then a huge turn off. And that's why the kind of the context is so important. And let's not forget, you don't necessarily have to have the story from a successful customer. You've got insights from conversations that you've had throughout the pipeline. Just because you didn't close yet a customer, they might have chosen a different solution.
doesn't mean they're not going to come back in two years when they realize yours is better and they should have gone with you in the first place. They've probably still got the same pains that you can talk about and relate to and help other people relate to and relay and I think that's the they're the bits that sales teams often miss because we only really kind of tell the story from successful customers and those case studies and if there's no relevance there then it's hard to bring it back but don't forget you've got all of this rich...
Information everything you've learned in your experience in that sales process I did a post today actually on linkedin about the number of hours it takes to kind of close one customer in terms of conversations with Saos that you don't close to get to that customer and then sqls and it's it's about 70 hours, right minimum Per customer that you would you would go through. I'm going to say per customer not
that particular customer, but all of the other prospects that you went through and didn't manage to convert. And imagine what you've mined and gained from all of those conversations. Imagine the insights that you've got, but where does that go? It just gets left. That IP walks out the door as soon as that person does. And that's the challenge. I think it's how do you capture that and how do you bring that back to life? Let's call it that.
Paul M. Caffrey (22:28.238)
Yeah, absolutely. And for you now, we've a lot of founder sellers listening and they're in the position of starting the company, but then also carrying a sales target and everything that comes along with that. How are you going to go building pipeline for the business at the moment, Rob?
Rob (22:47.331)
Well, so loads of different avenues, but a lot of it in these early stages, first of all, is utilizing network. So people you know, people you've worked with, people who trust you, right, across the years and getting references and referrals and speaking to them and just sounding it out and asking for introductions and those kinds of things. Then there's the kind of the beating the streets.
doing the cold calls, you've got to do that. You know, you've got to get back in that driving seat. It's quite difficult for someone who probably hasn't done that for a while to get back into that world. And what I've found really helpful is actually listening to podcasts and watching kind of cold calls again online and just making, you know, just getting myself familiar with that again, that world. Obviously running various outbound motions in terms of.
contact via LinkedIn and outbound emails but adding value and trying to create blogs and interesting articles that have good referenceability and provide good context awareness and education you know it's a classic kind of demand generation cycle from an outbound and inbound perspective so yeah it's it's I actually quite like it I think I really like getting back into the seat because it
Paul M. Caffrey (24:06.286)
Yeah.
Rob (24:14.179)
Having good successful conversations is that buzz getting that buzz again of you've just managed to get through to somebody and you've kept on the phone for 10 minutes and you've had a great conversation you've really understood them as well and I think that's vital of just getting that understanding of who you're talking to and kind of what they're up to and what their what their needs are because you never know where that opportunity is going to go. So yeah, that's good.
Paul M. Caffrey (24:38.094)
Yeah, that's yeah, certainly good fun, hard, difficult, everything in between. The LinkedIn is an interesting place to be posting content. And I mean, one thing that I've seen work quite well is if you post something on a topic and you speak about giving value to somebody, sometimes that can be a soft way. And if you connect with someone, you kind of go, OK, this is a post I wrote that could be quite useful for you. So I think it's also been.
Rob (24:42.595)
dear, yeah.
Paul M. Caffrey (25:06.702)
being clever about when you're creating the content, OK, there's that one off hit where you might build an audience. But then how can you leverage and use that to bring a bit more familiarity to you? And you'll get a you know, you quickly understand which posts are popular and which ones are not. Are you just picking up the phone then and just blasting through a bunch of numbers? Rob, is that is that what's happening?
Rob (25:27.619)
Yeah, I mean pretty much, but actually, you know, thinking about doing the research first, right? And I know this is a lot about what you talk about, Paul, this is not something I'm certain, definitely not just saying this because we're having this conversation, but I am a huge advocate and I help other businesses to design their go -to markets on that whole research piece. Because what you're looking for, again, is just that little nugget, just that little
signal trigger that helps you understand them in a bit more detail and then you're going to ask them about that specific thing and you're going to keep putting the thread until it unwinds a bit more and they get more relaxed and so all you want is that that kind of one in and I sit there and I do research I look at what they've posted I look at whether what events they've attended and stuff like that and it and it takes it does take time it does take time let's not let's not move away from that.
So, you know, I know there are tools out there where you can just kind of just start blasting calls out. And whilst it's good just to call, just to get on the phone and just to start, you know, have a conversation as a founder and doing founder -led sales, you've really got to pick and choose who you call. You know, it's not spray and pray just so you can have a conversation. It's making sure that you are probably focusing more on your initial ICP.
doing an account -based approach so that you know who you want to target and who you want to talk to and be a little bit more measured about your approach, I think, at this stage.
Paul M. Caffrey (27:07.214)
Yeah, it's a fine balance between the volume and the right person. So there is that piece. And I mean, it's interesting. Alex Hermosy would say, you know, do a hundred cold reach outs every single day and build things up. Absolutely makes sense in certain situations, certain businesses. Whereas Justin Michael, on the other hand, would say do 30. So there is there is nuance to it. So it depends on what you're selling, who you're selling to, so on and so forth. But the key thing and.
Rob (27:12.547)
Totally.
Rob (27:28.003)
Hmm.
Paul M. Caffrey (27:37.198)
everybody comes across this or shares this viewpoint is something that you need to do consistently and you probably need to do it every day if you can. And if you miss a day, don't miss two or maybe double up. Very difficult to do at the beginning and also difficult to maintain when the pipeline fills up and you've got a lot of meetings and times are good. So it's, it really is capturing, capturing the balance there. When,
Rob (27:46.083)
Yes.
Paul M. Caffrey (28:04.814)
What sort of sales process do you run? Are you to use a discovery demo, that sort of thing, or are you doing something different as a founder? I guess you probably have free rein to to run it whatever way you want.
Rob (28:22.371)
No, I'm actually pretty strict on this one. So I've got my own sales playbook, even though it's just me. And that's the preparation that I do. So I know what each of my stages entail. I know what the exit criteria is. And I'm pretty ruthless in discipline because I know at some point I'm going to have to scale what I'm doing. And I'm pretty disciplined in terms of moving things through that pipeline. So I actually have a kind of...
almost like a two stage selling process, a lead qualification process where I engage and connect with leads. I have those initial conversations with the initiator who could also be the champion and maybe even the exec buyer. And then it's a case of once I identify need and again, I use our tool to do this as well, which is great. Once I've identified those needs and that fit, I then assess that and say, right, well actually,
I think it's time to move this on to a self -accepted opportunity and then go into the rediscovery and deeper discovery with more demos and then the multi -thread approach. But what's nice about what we've created, which I think is super, super helpful, is the ease at which the technology can be trialed. Because that's a logical value step of see your information within our tool and it will bring it to life. And not every B2B SaaS.
salesperson has that luxury. Often it's quite, you know, demos from afar and lots of demos and configurations. And I'm not saying that's wrong. That's actually a really good approach. And often those have longer contract lengths and multi -year and things like that. But yeah, I think everyone, regardless of who they are and what position they're in,
in terms of the life cycle of their company, they've got to have discipline in that sales process so they can maintain that repeatability and ensure they do those tasks. So cadences and all that stuff, that's all set up.
Paul M. Caffrey (30:28.686)
It's refreshing to hear that because so often we come across founders and founders are selling. They use the network that you spoke about earlier on and they get meetings and even just the title is something a bit cool about meeting a founder. So they'll get the meetings, but then they tend to more often than not, not follow a process, get a meeting and be more concerned with getting another meeting instead of having that to follow. So the fact that you're doing that, I think is quite important for people to hear.
that you have to be ruthless and you have to have a process because let's face it, you'll probably have a few sales hires shortly. You'll probably have a team, maybe you'll end up with multiple teams. It's gonna have to be figured out at some point. So yeah, starting earlier makes a lot more sense. Rob, if people wanna find out more about you, more about the business, what can they do and where can they find you?
Rob (31:18.883)
Yeah, great question. So our website, we've tried to put everything on there. So people can go and look at resources and that's at 44 .ai. You can also find me on LinkedIn, Robert Umlton. I'm there, happy to have a chat. I'm pretty open for direct messages and discussions because I can't be a hypocrite. I'm trying to do the same.
So I always try as much as I can to respond but I'm sure you know this Paul, timing wise can often be an issue with those things but eventually I'll get back to people. So yeah I'm more than happy to have a chat with anyone who wants to talk.
Paul M. Caffrey (32:01.23)
Great, well Rob, thanks so much for coming on. It's been an absolute pleasure.
Rob (32:05.027)
Brilliant, thanks Paul.
