Sales enablement reimagined — Where AI ends and humans begin

0:07Welcome to Mastering Sales Negotiations, the podcast for ambitious professionals who want to sharpen their skills, transform their conversations and deliver lasting commercial impact. In today's episode, we're joined by entrepreneur and sales leader, Mike Pritchett to explore one of the biggest questions in modern sales. Where does AI end and where most humans begin? We'll dive into how AI is shaping sales enablement by cutting out the grunt work, the critical human moments where trust, empathy and humour still win deals, and the evolving skill set sales professionals need to thrive. Mike brings real-world lessons on how to balance automation with authenticity.

0:51So let's get started.

1:00Okay, Mike, welcome to the show. Can you tell us a bit about your journey from making 100 cold calls a day in telesales to scaling Shootster to$20 million? Yeah, absolutely. So, look, it sounds like a long journey going from 100 cold calls a day through to scaling a business to$20 million ARR. But to be honest, it was just the exact same skill translated across and into my own business in time. So I've been an entrepreneur most of my life. Early days, I was straight out of school and into radio and into TV and producing. And I just loved that. And the way I got that job was literally just walking into knocking on doors of production companies and saying, I'll work for free for the first couple of weeks.

1:43And that got me those jobs. So I guess that level of just knocking on a door, picking up the phone, getting in there and trying was always in there and instilled in for me from early, early years. I was in telesales, as you said, and quite a funny story on that. I was in Australia, but we had an English sales manager and he had these P45 slips, I think you call them over here, that you get handed when you're no longer needed at the company. And my first day turning up to the sales job, He had three strings across the top of the desk and a P45 slip. And we're in Australia. I said, what is this P45 slip?

2:20And he said, well, it's quite simple. When that lands on your desk, you're fired. I was like, okay. And he goes, you've got three strings. You've got three warnings. It's pretty straightforward. I was like, great. What warrants cutting a string? And he goes, well, you make 100 calls a day. If you make 99 in one day, then I cut a string. Well, that's simple. I know my task. Sit down and get on with it. And I did. I was always over 100, normally 101, and one and then I'd run out the door. But it was always at least 100 calls a day. And that was great for me because it instilled that level of just do the work, do the work, do the work, and then you'll eventually get results.

2:56And it took me months and months to get results, but we got them and I knew I'd get fired if I didn't do the work, so we did it. Quite an incentive. And I'm not maybe as harsh as he was to us these days, but I definitely try and instill that into the team. And that's what built Shootster in the end was a company that I founded quite a few years later. I had a production company before that as well, but Shootster was a scalable video tech company that I built and sold. And we had 32 people in sales and marketing. And I was very clear with the team there as well. It was 50 calls a day by then and a little bit more nuanced in who you're calling, not just hitting the phone.

3:34But it was 50 calls a day where you're fired. It was quite simple. And we scaled the business really well. and we ended up with 72 % of the world's Fortune 500 company as clients. Wow. Brilliant. That's very impressive. Yeah, great. So in that experience then, when did you realize that sort of sales enablement was something that was really important? Was it important at that point to where you were going to get? Yeah, well, in my early days of sales, it was simply just make the calls and that's all I knew as a young SDR. I didn't even know the term SDR. I don't know if it existed back then. I'm 44 now, so this is 20-something years ago, 25 years ago.

4:14But then it was just do the grunt work. Now, of course, we have so many tools, possibly too many tools available to us to do all of these things and to enable salespeople to have the right information. As I built out my last business and as I'm building out BuzzTrail, we're realizing there are so many tools out there for the sales team to use. and it is important to just make sure you get the right information in front of the salesperson at the right time but I think it's all down to the efficiency that you can drive so that your sales people spend the most amount of time doing what they're supposed to be doing which is building human to human relationships.

4:51Absolutely and what how do you feel about the tools that are the tools and the sort of processes that we've got at the moment in in that sort of sales enablement world do you feel that would you say a serious percentage of them are really giving the salespeople benefit or do you feel that some of them are just almost making more work for them you know making more work for people uh i have this uh i'm going to get in trouble saying this on this podcast and anyone listening is going to hate me for it but yeah i'm a salesperson myself so i'll say it salespeople and when i'm looking to hire salespeople you want to find people that are smart enough to be salespeople but dumb enough not to be something else

5:33oh you're so going to be in trouble wow

5:39I want the podcast to come on and say that anyway here we are uh so so as a as a sales person um you know I find there are other roles within the company whose job is to go out there and find the best tools for the sales people and they need to do those jobs. And everyone knows that hiring your best salesperson to be the sales manager is almost certainly going to end in failure. These sorts of things we know and we've seen them over and over again. I think with tools, my analogy was years ago and it still stands today is that when a salesperson goes into a field, they're in an open field and they're looking for gold.

6:16That's the goal. You're just supposed to dig the field and find the gold it's quite simple here you go start digging right there's a shovel dig and and essentially that's what we're getting a sales team to do is we go out there and say there's your empty field start digging um some people will just get their shovel and start digging most people when they get to a certain point go my my hands are sore i'm tired i'm over this i'm not finding gold this is frustrating me and the smart ones would go i wonder if there's a better way and they'll walk off and try and find a digger a tractor a metal detector something they'll go and do something the problem is half the time they go off and find an old digger that they can afford it's rusty it's off in the you know in the field somewhere they buy that digger they spend a bunch of money on it they fix it up they tinker with it for six months trying to get it to work they finally you know realize they need to buy a filter or this or that a new engine whatever it might be they bring the field the digger back into the field clunking ready to go they're all excited and the gold's being dug up by the guy who's just still there digging you know and so there's there's a level where you need to, you know, now you could argue the other side, which is, well, this guy's now going to come in with his digger and dig it.

7:22But you need to have different people in your team doing different things. And some people just need to put their head down, bum up and dig. And other people need to be, when you can get to that point to afford them, they need to be specialists in going and finding the digger. And I think with a lot of, it's a long, weird way to answer your question, but I'm Australian, so I do that. The long way of coming back around to your question is there are a lot of tools that are super, super helpful, but there's so much noise out there and there are so many things available to us that we can spend most of our time learning how to use a platform that takes us six months to become a specialist in when you could have just landed all the deals in the six months and got on with it.

8:07And I don't think most businesses these days have the runway to become specialists in 10 different software platforms when actually they just need to get some sales in the door and especially in the startup world make sure that their product is actually working and got product market fit rather than becoming specialists in hell you can do anything these days you can build your own product you can build your website you can do everything or you can get out there and have some human to human conversations sell the product and test and measure that it's actually something that the client wants. I think the fact that you mentioned this idea of human to human, clearly one set of tools, and it's not a thing, it's kind of multiple things now within sales enablement, within sales, particularly for those outbound callers from within contact centers or whatever it is.

9:00You've got an awful lot of that is now being powered by AI in one way or another. So where does AI add things to that process and where does it perhaps just, you know, you need to go away and tinker with it for a long time by which time you've lost the opportunity you were hoping to gain? You know, where do we stand on that kind of efficiency end of things with using artificial intelligence now? Yeah, absolutely. It's a great question. I think, you know, and it comes down to the agency question as well. So the agency question really sits in that same box of AI is how much can I give my job to someone else?

9:38And I spoke to an entrepreneur just this morning, actually, and she's a young entrepreneur and built her products. I'm really excited. She goes, Mike, I found this agency that can do all my sales. Can I just give it to them and they go do that at a commission basis and that'll be great? It's not the thing you want to give away and put in a box for somebody else. and it's also not the thing you want to give away to just assume that ai is going to do that job and and therefore you don't have to and you can sit back and enjoy it i'm afraid that utopia i believe doesn't exist i think you can use ai in so many great ways and the ways that you want to use it is to to make sure it's doing all the things that you're not needing to do right so if you're talking about crm updates if you're talking about bulk lead generation and finding your icp on linkedin And all of these things, you don't need to be sitting there searching LinkedIn going, okay, I want a Fortune 500 company.

10:30And where would I find that person and I'll connect to them. And then, okay, that's taken care of. You can do it. People are doing it at bulk and at scale. I've got a company I work with, Haku Labs, and they're great. They can do that stuff. And they have a bunch of AI tools and a platform. You put it in, it auto generates everything. Fantastic. Go. That's the sort of stuff that I absolutely love. There are other companies that I work with that will take information from a meeting, a meeting like this, take it, put it all into your CRM, update it, and write the email for you, ready to go. Fantastic.

11:02Those things are great at increasing the efficiency of a salesperson. So when it comes to AI, and obviously, yes, I'll plug our tool, Buzztrail, as an AI video avatar that sits on your website, it can actually triage leads that are coming in. and it can do those demos, those sales demos as a human would and then do a warm handoff to a human. But that warm handoff to a human is key. I don't think we're at the point where, except the lower level deals, higher level enterprise sales, it's still trust. It's still people buying from people. So how do we get in front of the right people as quickly as possible?

11:42And I guess back to my early analogy, how do we find that gold as quickly as possible rather than just digging randomly in a field, you do need to send those salespeople out to dig. But where they're digging and how they're digging is what those tools can help you do. It's a really interesting analogy, that idea of digging in a field for gold. I don't know if you're aware, but the term canvassing comes from the 1849 gold rush, which is when you stretched a piece of canvas over a frame, poured silt into it from the river and pushed it through until you were left with the gold nuggets on top. That's the origin of that terminology.

12:20So when we're canvassing for sales, that's exactly what we're doing in the same way as politicians canvass for votes and all those things. It's the idea of finding the nuggets within a pile of mud, frankly. Yeah, you got that right there, didn't you? So that's the origin of the terminology. But I think one of the things, just to pull into it, I mean, we have a phrase that we use kind of repeatedly, which is fish where the fish are that's what you're talking about you're talking about that idea of well look have a focus rather than just scattergun approach of you know digging the entire field up but where where is ai augmenting the human and where where is the danger when it goes too far if you see what i mean is is is that something that you've you've you've seen the idea of, yeah, it can do these things for you, but immediately that you mentioned, and it can prepare the email for you, I go, yeah, and I know a number of salespeople who will then immediately hit send without reading it.

13:20And it's where's the barriers and how do you equip people with the kind of thought processes, the attitude to say, actually, I know what it can do. I also know where I need to get involved. How do you manage that balance? Oh, without a doubt. And I think the, you know, the conversation is always where's this going to end up, right? Where's it going to end up? If AI just keeps writing emails, if AI keeps sending LinkedIn posts, everything, well, we know where it ends up. We just put up more walls and more barriers and we speak to less people, right? And so that will empower more and more in-person events, more and more barbecues, more and more, you know, meetups and paddle competitions and these sorts of things, which I think is great because that's where we should all be getting back to post-COVID and all the rubbish that went on.

14:04So, you know, that's positive. The negative is, as you say, if somebody just goes hit send or more to the point, auto-sends 10 ,000 emails, you know, and we had a bit of a pre-chat about it, you said, great, now you get to annoy another 9 ,999 people. Exactly. Which I love because it's so true. You used to annoy 10 people a day, now you annoy 10 ,000 people a day. Yeah. Yeah. And that's not helpful, right? And we can all see through it. We can all see through it. Yes, AI is getting better and better and knows that it's writing. But if you're faking it and sending out just a load of rubbish, then that's what you're going to get back.

14:45Yeah. And I think the challenge now is how do we be more human because the AI is taking the other stuff. And personally, I look on LinkedIn and I just… Despair. It's not a great place anymore.

15:00Mike Pritchett:Yeah. It's just not a place I want to be. And I've written, and I lent into it for a little while there, and anyone that wants to go back and look at my LinkedIn and Instagram and everything else, I lent in for a little while, and we were like, okay, I'm going to do this. I'm going to post every day. I'm going to do this. It was great, but to be honest, despair is a word I got to because half the, maybe 90 % of the comments on there are just other people's bots commenting on it, trying to get their own reach from their own, you know. Yeah, yeah. And it's just nonsense, right? Now, the reality is it does work.

15:29So there is a level that you've got to do that. And there is still something there. Will there be something there in two or three, five years' time? I don't think so. I think the whole thing is going to implode to a degree. Or we're going to go back to just saying, I just check it for this and I connect in with people and they're the only people I talk to. But I think we put up more and more guards. So when you're sending out content using automations and AI, I think it's the same as it always has been. and you should compartmentalize that. There's the stuff that's known as bulk content, and I'm fine to get bulk content.

16:02I'm fine if you want to send me bulk content, but don't pretend it's personalized with some bullshit attempt to add my name in there and your name and this, that, and the other because it's all done. That joke is over. I think now AI has to be helpful. It has to be useful, and it has to be something the customer wants. For example, in building our Buzztrail, we could have gone many, many directions, and one of them with AI voice is just, let's cold call the world, right? Now, I don't believe in cold calling the world with AI because all it's going to do is just annoy more people. But an AI avatar sales demo, which is an alternative from you either have to press book a demo and wait three days or maybe three weeks until you can meet with a rep and then you have to line up a calendar time and faff around or you get an instant demo, that's helpful, right?

16:48It's the same as anything that you're building for a customer. me you just want to make sure it's something that they want in their world um and same with the communication that comes in is this something that's actually useful yeah and i think sometimes you know when when you're interacting with your bank or insurance company or whoever it is you know you you've got the opportunity there to say you know contact us do you want to speak with the chatbot and there are times when yes frankly i do because if the alternative is listening to your hold music for 20 minutes then i'm going to speak to a chatbot please but actually a lot of the time those chatbots are a bit rubbish so i think i think there's a kind of quality threshold that you've got to get over with those things which i know you've been working on with buzz trail so that that idea of saying actually it's not good enough for it to be you know a bit dumb it's got to be really good one of the one of the stories that i i i trot out occasionally these people is there is um i live in the middle of the countryside and in the nearest village to me there is a very small indian takeaway and they do great curries it's run by two brothers they use a commonly available ordering app which you can log into and it remembers your order and i think i've got people that i spend significantly more money with a year who do not have that capability to remember who the hell i am and this is run by two guys in a small shop and yet you know they say do you want to order the same thing do you want to order another thing and i walk in and go oh i see you've changed your order this week robin how was you know is that is that why is that is it was the last one that you had okay so when i actually go in and pick the stuff up or when the delivery guy comes they ask me why my order's different so that they're getting more more information you know and this is just two guys working in the shop now you know if i'm doing the business to business environment why the heck can't it why can't the salesperson i speak to remember my order history or access my order history easily and if ai makes some of that stuff easier for people then i think that adds a benefit to both sides of the the equation but and even international you know i know from from my last business we had um the same client in in multiple regions or you You know, some Salesforce or Oracle or whatever would start in Singapore and then would have a sales opportunity in the US.

19:16And, well, they should definitely be giving examples of Salesforce Singapore. But did they know? Maybe that's buried somewhere in a CRM. They may not even know. So those sorts of triggers for AI to bring that up, I think, is absolutely key. Once again, with our avatar, you know, if you jump on the website and you're doing a demo, it says, well, actually, somebody else from your company has already done a demo and I can talk to the same points that they spoke about and they raised this and should we do that? So there's a lot of cool things that can be done that are better than humans, but there are a lot of things that at the end of the day are just really about, they should be about triaging that through, getting rid of the leads.

19:54Because salespeople tell me time and time again that 80 % of leads that are inbound are complete rubbish and they're a waste of time and they're talking to the wrong people and that just drains your energy. If you're sitting there for 45 minutes on a demo giving it your all, and then you find out at the end this person's got$2.50 as a budget, well, what did I waste my energy on? You want to curate all of that sort of stuff first, and then you're talking to the right ICP. So you've got this phrase then, just leading on a little bit from that, how do you get invited to the barbecue? So if you're going to get, if it's a salesperson, if you are going to get invited to the barbecue, how are you going to do that?

20:32What are the skills you need to be able to get that invite? Yeah, absolutely. So, yeah, I mentioned this one when we chatted the other day. For anyone listening to know how I know that. So the get to the barbecue phrase is really about a salesperson's job is to move from cold LinkedIn connect to being at their barbecue or their kid's birthday party as quickly as possible, right? You want to become friends. You want to have a relationship. You want to build that rapport. And every salesperson knows that. But most of the time, I think if you don't look at it in that linear path, you don't realize that you're actually going backwards quite often.

21:11I hate seeing it when people have a LinkedIn connection and then they get an email address and they go back to sending messages on LinkedIn. No, no, LinkedIn's a step back. Emails are a step forward. WhatsApp's a step forward. Phone numbers are a step forward. In-person meetings are a step forward, like make the effort for Pete's sake. And then those steps forward are what you need. If somebody says to me, and it's a sales opportunity, look, we could catch up tomorrow on a quick call or the next day I'm in town and we could grab a coffee, I'm waiting a day and grabbing a coffee because that's a step closer to building a rapport and having that relationship that I'm going to get invited to the barbecue.

21:48One of our previous episodes, we spoke with a guy called Miles Richardson from an IT company called Zulka. And he's got this thing around, you know, are you on the WhatsApp group? Do you have a WhatsApp group with the key decision makers within the team or the key people who influence the decision? And similarly, do you have a past to head office? Can you actually walk into their organization unaccompanied and go and just chat to folk, you know, and have that conversation? That level of intimacy so that the organization, where the organization starts and the supplier starts is blurred. There is that kind of real, we're in this together, looking at the issues that you're facing from the same side of the desk.

22:32All of that kind of sounds like very trite management relationship building speak stuff. but actually there is a truth to it. It's why it becomes a cliche in a way, which is that idea of how do you get into it and how do you make time for that? So coming back to the kind of AI thing, which is kind of a key issue for this episode of the podcast, that link between, to what extent does AI help people do that, i.e. free up that time and space, and what skills do salespeople need if they're going to be able to both use and manage the technology bit of the relationship with the customer in such a way that it creates those opportunities for the real human contact that you want to move forward towards.

23:25And I have to say, we wholly endorse in terms of a way of building real value for the relationship with the client. How do you define what those skills are and how do you get salespeople with those skills or give them those skills? Yeah, absolutely. There's a lot of questions in that question and I will try and get to them all. And I also want to – I love those ones because I do it as well. Okay, I've got five different answers, but I'll get through them. But I also want to just quickly touch on the WhatsApp group I love that you mentioned from the other episode. That's fantastic. uh another thing we did was was a brains trust group uh which i think having a brains trust group um was so powerful key clients on a brains trust group felt like they were building the product with us so they were on our side of the table solving problems for us that's great um which was so great and i literally we left one of those meetings and and this client just you know put his arm around me he said mike i'm so excited about what we're building here and the fact that we're launching in the u.s and i'm sitting there going what do you mean we hang on that was my goal that was my goal he feels like he's part of our company yeah and and we actually ended up having a lot of clients come and work for us over time because they left their business to come join our business yeah because they felt like they were part of our team already and they had helped put things together and then all you need to do is bring a prospect to that and all of a sudden a prospect sitting there with the head of you know google or amazon or whatever going you know the head of marketing in those spaces and and video in our space um you know preaching to them about how they use it and that was a really empowering thing so anyone listening that does that that to me is that's the ultimate step to being at their barbecue but how do you use tech and ai to get to that that point um it is really just about in my mind the most powerful thing we can do is anything that you feel like you're spending time on that is not a um you know high value task just audit it and and i actually i work with a good friend of mine dan martell he's a business coach and he he has this book called um buy back your time and buy back your time is all about it's more for entrepreneurs than sales people but it's fine for anyone uh is all about doing a time audit of your week and actually literally half hour by half hour just putting down what did i spend time on was it high value did it bring in dollars just put a dollar sign next to it or it didn't was it was it painful for you and you you hated it or was it something that brought you joy you know and and And quite often you'll find the low dollar, high paying stuff, if you're a salesperson, is always going to be that admin rubbish.

26:02Like who wants to fill in a CRM? I've started working with a company called Joint Flows recently and I love their product. The idea that I can get on a video call, have a sales demo, and then it can take that information and go and fill my CRM and build other things for me around how that looks like in a sales pipeline. I never want to touch a CRM again. all I want to ever do is just look at the top end and go who are my top leads that I should call today and follow up and is AI there yet I can't hand on heart say any product does it absolutely perfectly but I think those sorts of products which you can find very easily by using AI funnily enough and searching for it and they will, that's the ones to focus on not the ones that are going out there and doing your job for you, you can't just put sales in a box and expect it to be done with AI.

26:52I think any tool that gets rid of the admin, any tool that finds you the right leads, as you said, that fishing where the fish are, and any tool that triages the inbound so that you're left with quality leads that are high-value clients, they're the ones that I'd be chasing down personally. Yeah, and that's really interesting, that idea of saying it's freeing up the spaces. I was listening to a podcast with the founder of Anthropic just the other day, and he was talking about the challenges that AI ought to augment what people do, but there will always be organizations, there will be business leaders who think, actually, we can reduce headcount here, we can save costs by using AI.

27:43And he was saying, well, look, that works for entry-level jobs. If you're going to work in a law firm, most of what you're going to be doing is summarizing documents for somebody higher up the chain. AI can do that for you. You don't need to be there. So there'll be fewer entry-level white-collar jobs in that case. Salespeople don't have somebody who fills in the CRM for them at the moment. So it's not a straightforward replacement of a role. It's potentially giving you more capability to do other stuff if you've got that kind of sensible approach to the use of AI. I mean, I've also seen other organizations where they've got rid of all their sales training team because they're going to do it all with AI now, which is going to generate the content for them.

28:25And I just go, oh, great, you've turned sales training, which is one of the most exciting and interesting things that people do in their personal development activities, into something which looks and feels like doing the cybersecurity e-learning that you have to do once a year. You know, well done you. Good work. Yeah. You've just turned it into something everybody has. yeah exactly the one the one team building exercise that actually builds character and everything else around it is is gone and to support your your comment about the the job roles i don't know if you've seen recently but it's quite funny everyone in the creative world which has been a big part of my world for the last two decades uh is obviously freaking out going okay there goes all creative content marketing roles and etc etc anyway um open ai put a job that out 385 000 us dollars a year for a head of content development right and it's like okay well hang on you're hiring yeah but everyone else is saying that everyone's going to be fired because ai is going to do it that makes no sense but you're exactly right the the key people that know how to use ai in the right way will be able to do the job of 10 people that don't maybe 100 people that don't okay fine so can we reduce head count well definitely as a as a startup now in my space and and having built a scale up before i would have had half the employees and and a lot more of the profit by the time we got to that position would i have had less sales people no i would have just had more sales yeah yeah and and i think because i would have used more tools to put into those sales people to really supercharge each one i would have probably put higher targets on people over time, et cetera, et cetera.

30:12But I would have expected a lot more volume, inbound and outbound, based on the tools that are available. But at the same time, we're coming up against more noise. We're coming up against more friction. It's harder for salespeople these days. I think, you know, I used to be able to pick up the phone and have a conversation. Ironically, I still think you can pick up the phone and have a conversation. You just can't send an email and a LinkedIn and have the same results you did five years ago because there are thousands of spam emails and LinkedIn messages and people are ignoring them. Yeah. And, and also, you know, the, the, my AI is blocking your AI.

30:44So, you know, I mean, we've, we've got a, my partner and I've got a joke, which is that I keep getting calls, which are flagged up by my phone as likely nuisance. And, and my partner thinks that that's the name that I've put in my contacts for that, that illicit relationship that I'm having somewhere. Cause I keep going, oh yeah, it was likely, it was likely nuisance again. But you know that, but you know i just i just don't get spam calls because my phone is smart enough to say that's a spam call we know it is you know we've we've got a feedback maybe your ai and my ai could go to a barbecue exactly that's right they can go a barbecue and we could go to a different one that'd be fine but but yeah and and you know another slight digression but another story which is that we know that ai can beat any of the grandmasters at chess the chess world championships are still happening the prize money is phenomenal and who's providing the prize money the big ai companies and it companies because they still want to see real people play chess i don't want to see real people play chess i have to say i prefer to watch the paint on the wall opposite me dry but that's not the point somebody somewhere is investing in that because they see it is what tech is like and it's human to human, not bot to bot.