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Episode 18, Part 3 - Using AI in Sales to Enhance, Not Replace, with Alex Olley
31st July 2025 • The Growth Workshop Podcast • Southwestern Family of Podcasts
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In the final part of our interview with Reachdesk founder and CRO Alex Olley, we explore the role of AI in sales, emphasising its capacity to automate repetitive tasks while maintaining the human element in buyer interactions. Alex warns us against over-automation and AI champions, who aim to enhance, not replace, sales conversations. The episode closes with reflections on leadership, personal growth, and the long-term vision of giving back to the next generation of founders.

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Matt Best:

Hello. Welcome to the Growth Workshop Podcast with

Matt Best:

myself, Matt Best and Jonny Adams, and part three of our

Matt Best:

conversation with Alex Olley from Reachdesk, so founder, and

Matt Best:

now CRO at Reachdesk. And so Alex, we've talked a little bit

Matt Best:

about this offline, and I think it's really fascinating to dig

Matt Best:

into it in a little bit more detail, which is the part that

Matt Best:

AI has to play in a sales organization, and at SBR, we've

Matt Best:

had this debate a few times. We've had a couple of

Matt Best:

conversations on various different webinars, and there's

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sort of white papers that have come out of the team, and of

Matt Best:

course, those are all accessible via the website, but in that we

Matt Best:

talk about like, where AI fits in sales. And it's just

Matt Best:

fascinating, isn't it, to think of how much we're probably

Matt Best:

already relying on this. But is there a point where you go, you

Matt Best:

can go too far in the sales in a sort of sales team, and sales

Matt Best:

kind of operating, operating with them. What's your thought

Matt Best:

on that?

Alex Olley:

Yeah, I think you've probably guessed so far. I'm big

Alex Olley:

on, like the experience side of things, like a buyer standpoint,

Alex Olley:

and that's the bit I'm worried about. I'm worried that, like, I

Alex Olley:

took a look at an AI SDR, that essentially, like, spoke at me

Alex Olley:

and I would have a conversation. It was basically a means to,

Alex Olley:

like, qualify me. I didn't enjoy it, it, I wasn't very trusting

Alex Olley:

of the answer, because I think anyone could put any answer in

Alex Olley:

behind it. And the things that I don't think AI should even be

Alex Olley:

thinking about replacing is that the human interaction and

Alex Olley:

conversation. I'll give you examples of where I've seen it

Alex Olley:

work really well. We use, like, a power dialer. I've got lots of

Alex Olley:

we're very outbound heavy. We use a power dialer. And what

Alex Olley:

that does that AI should be automating the repeatable tasks

Alex Olley:

that essentially eroding productivity. You know, they're

Alex Olley:

then increasing effort so that that's bad, but at the same

Alex Olley:

time, it should be designed in a way that's going to elevate the

Alex Olley:

experience for the person, right, both the user and the

Alex Olley:

person. On the other end, I'm talking the concept of sales. So

Alex Olley:

we use this power data, right? What it does essentially dials

Alex Olley:

lots of numbers, right? It, when someone picks up, it gives the

Alex Olley:

information to the rep to say, these are the bullet points, but

Alex Olley:

the conversation should never it should never be a bot or

Alex Olley:

anything. It should be the human and the AI is dialing. That's

Alex Olley:

the repeatable task. It's doing the researching and surfacing

Alex Olley:

those insights, which takes a long time. It just allows the

Alex Olley:

person to have more, better conversations. And I haven't had

Alex Olley:

a single piece of feedback where it's like, this has been bad in

Alex Olley:

any way. So that's a good side of things. But I've also heard

Alex Olley:

of companies say, Well, we're going to now eliminate the human

Alex Olley:

and when the conversation is going to be with a bot. And I've

Alex Olley:

tested these things, I've actually been an advisor to

Alex Olley:

businesses that build these things, it's not playing out.

Alex Olley:

Well, it's not. And I've heard of like AI agents giving

Alex Olley:

ridiculous offers to people saying that you're going to get

Alex Olley:

50% off your credit card. It's like, no, no, that's not a

Alex Olley:

thing. Yeah, so it hallucinates and that's where I think we I

Alex Olley:

don't think we're even close to that right now. Maybe that will

Alex Olley:

change, but if you're, if you're doing it, where you're wrapping

Alex Olley:

it around those repeatable tasks that save them time, everyone

Alex Olley:

wins. That's where we should be. But I'm also seeing companies

Alex Olley:

just neglect the experience. And that's kind of my word of

Alex Olley:

caution to everyone, is think about the buyer. I say that a

Alex Olley:

lot, put yourself in the buyer's shoes, and ideally walk 1000

Alex Olley:

miles in them. Think about what they want. Do they want some of

Alex Olley:

these things to happen? Probably not. There are many use cases of

Alex Olley:

where it can work, but experience still needs to be at

Alex Olley:

the forefront of things. And as I said, we invest in AI tools,

Alex Olley:

but that's the first question, like, is this going to be a good

Alex Olley:

experience for good experience for the buyer? And if the answer

Alex Olley:

is no, don't even look into it.

Jonny Adams:

And your point, you said, talk to the buyer, because

Jonny Adams:

I think that's been missing in the marketplace a lot at the

Jonny Adams:

moment with AI. Is that? You say, think, but actually, let's

Jonny Adams:

ask our buyers in our ICP that we want to go to market with,

Jonny Adams:

and say, how do you want to buy with AI at the moment? And a lot

Jonny Adams:

of it's gonna be, I don't know what the future is, right, and

Jonny Adams:

that's gonna be, and that's gonna be the first response.

Jonny Adams:

That's absolutely fine, but what was the thing that you would

Jonny Adams:

like to experience? And I think that would also help. And brings

Jonny Adams:

me back to when I worked with another organization, it was in

Jonny Adams:

B to C, you referenced something about, a lot about customer

Jonny Adams:

experience today, and in SaaS, I can't see many CX directors

Jonny Adams:

within SAS, and I just wondered that's just sort of become a

Jonny Adams:

light bulb moment for me. Yes, CS, but CX customer experience

Jonny Adams:

directors that do the full suite. I don't see enough of

Jonny Adams:

those individuals, because when we were in B to C, we had to

Jonny Adams:

have a CX director because of obviously, the market is very

Jonny Adams:

led towards customer experience directors. But yeah, maybe

Jonny Adams:

there's something to learn from that as well.

Alex Olley:

We don't have a CS team. We have a CX team. We have

Alex Olley:

client experience reps. We have a head of CX. We so we do but

Alex Olley:

again, it's a proponent of what we do, right? We it's funny with

Alex Olley:

all this AI, boom, it's helping us massively as business that

Alex Olley:

more people are thinking, I want to create this physical

Alex Olley:

interactions, what I call these moments that matter, gifting

Alex Olley:

direct mail swag, these tangible things that people get their

Alex Olley:

hands on. It's actually like having this massive resurgence,

Alex Olley:

which obviously I'm incredibly happy about, but that's just one

Alex Olley:

example of something you can do to give a better experience for

Alex Olley:

a customer. I've actually got an AI agent in my inbox. Box that

Alex Olley:

filters out all the really bad outreach and marketing emails.

Alex Olley:

So I'd have to look at it. When something's good, it stands out

Alex Olley:

and actually pops into my inbox. And so we do this. We train our

Alex Olley:

customers out to this. I'll give you an example, one to one

Alex Olley:

outbound prospecting. We have this thing called the Amazon

Alex Olley:

Rainmaker, which essentially it researches you. It finds out

Alex Olley:

something like, you might like golf. You said you like golf. It

Alex Olley:

could say, like, notice this about you just had a promotion.

Alex Olley:

Yeah, great. Everyone does that. But I noticed specifically this

Alex Olley:

one thing that you said about a challenge you're trying to solve

Alex Olley:

around, like, low response rates, for example. Now notice

Alex Olley:

you, you're big into your golf. Here's a box of personalized

Alex Olley:

golf balls with your face on it. Let me know if the problem we're

Alex Olley:

trying to solve is of interest to you. So open question. If so,

Alex Olley:

like, let's talk. Hang on a second that it's like, well

Alex Olley:

researched. It's tied to a problem. There's an offer in

Alex Olley:

there that's not conditional upon me taking a meeting, and

Alex Olley:

it's a yes or no. It's quite binary. That's like, I think

Alex Olley:

that's a really good experience for someone. And so we're trying

Alex Olley:

to do more and more of that, and that's what's helping companies

Alex Olley:

break through the noise.

Matt Best:

Yeah, and it's, and it's again, using it, using the

Matt Best:

AI in that context, as a tool right to help shortcut the

Matt Best:

research, to shortcut finding the information, not to replace

Matt Best:

the human. I was talking to a friend just the other day,

Matt Best:

actually, and he's an expert in AI and in as a developer. And he

Matt Best:

was talking about, you know, the long term future being people

Matt Best:

wanting to buy non AI stuff, and people want to go back to that

Matt Best:

human you know, because if we keep just recycling the same

Matt Best:

thing, then there's no where's the innovation, where's the

Matt Best:

thinking coming from, and where's that sort of human

Matt Best:

connection that I think people will start to be able to

Matt Best:

recognize more clearly. I think right now, we're all just a bit

Matt Best:

blown away by how good it can be. And I've worked with Johnny

Matt Best:

you, and I work with with with clients all the time who are

Matt Best:

saying, Well, okay, but I hate, I hate the idea of an automated

Matt Best:

email. So we're not asking you to write an automated email.

Matt Best:

We're asking you to use or we're suggesting that you might use AI

Matt Best:

to shortcut some of the research to help build you out the body.

Matt Best:

It's not an, it's not, it's not a way of getting out, of lifting

Matt Best:

a single finger and just sort of the old Homer Simpson with with

Matt Best:

the bird, right? Just pressing the key over and over again, and

Matt Best:

something blows up....

Jonny Adams:

Another good analogy.

Matt Best:

You know, that's that I think is, is a really

Matt Best:

important thing for people to recognize, isn't it? And it's

Matt Best:

that sort of okay. I know. I know how to make this work for

Matt Best:

me and not see it as a sort of as a replacement, yeah, but it

Matt Best:

goes right back to what you said right at the beginning, Alex,

Matt Best:

which is that we're going to be really customer or client

Matt Best:

focused, do what it is that we need to do to that, and we're

Matt Best:

going to go at it with everything that we've got.

Alex Olley:

That's it, I think, more specifically in the term,

Alex Olley:

like AI and like, go to market predominantly sales, right? And

Alex Olley:

I think you just got a choice, like, do you want to invest in

Alex Olley:

the AI sales rep, or do you want to invest in the AI enabled

Alex Olley:

sales rep? And that's the obvious one for me. It's like,

Alex Olley:

it's one or the other. I'm yet to hear of a company that has

Alex Olley:

been successful at building something autonomous that can

Alex Olley:

replace what seller does. And it all comes back to the

Alex Olley:

conversation, right? Every word, every word of every conversation

Alex Olley:

a seller has with their prospective customer, their

Alex Olley:

existing customer, like those all matter and like, one

Alex Olley:

mistake, one hallucination, it's game over. And those could cost

Alex Olley:

people a lot of money. And we're just not there yet. We're just

Alex Olley:

not maybe we'll get there one day. I can't see it happening

Alex Olley:

anytime soon?

Jonny Adams:

Really, really curious. Alex, you referenced

Jonny Adams:

something really interesting earlier around founder, CEO at

Jonny Adams:

one point, and then vacating that position to then move into

Jonny Adams:

the CRO role. I mean, listening to you, I can see why you're so

Jonny Adams:

very good at being a CRO but a lot of people have the pride and

Jonny Adams:

maybe the ego that they want to be the CEO. So what was that

Jonny Adams:

reason? Was it business, or was it personal?

Alex Olley:

To be honest it was both. I never set out to be a

Alex Olley:

CEO. I you can probably tell I love go to market. I love that

Alex Olley:

aspect. I think of certain things I wasn't particularly

Alex Olley:

interested in. We spoke about my old CEO, Jay was one of our

Alex Olley:

founders, and we would spend a long time talking about, you

Alex Olley:

know, he was a CEO. Was like, Hey, I'm a sales guy at the end

Alex Olley:

of the day. And I wish I'd done that. I wish I'd got it to a

Alex Olley:

level that I was really proud of, because then perhaps after

Alex Olley:

that's the next logical step. I think a lot of it was from,

Alex Olley:

like, his his journey a little bit. But I remember, because I

Alex Olley:

love selling stuff. I think I earned my first tenant when I

Alex Olley:

was, like, seven, I was like, really happy about that, and

Alex Olley:

I've always been naturally good at it, and I never really had

Alex Olley:

that, like, massive motivation do it. But also, as a business,

Alex Olley:

we decided to get to the US fast. And I think I just had my

Alex Olley:

first kid. I think my wife would be too happy lifting us out of

Alex Olley:

the UK, having to go to the US, because that was essentially the

Alex Olley:

ultimatum. But I think we knew we're going to be a venture

Alex Olley:

backed company, and having a US CEO to like spearhead, that

Alex Olley:

would be really important. The ultimate thing just was, was

Alex Olley:

like, I would spend all my day thinking about, how can we

Alex Olley:

improve our outbound process, how can we improve our

Alex Olley:

discovery, how can we improve pricing and negotiation? I

Alex Olley:

wasn't thinking like, how can. We raise more money, and how can

Alex Olley:

we improve, like, investor relations, or I really want to

Alex Olley:

be doing all that, I would just obsess over this stuff I still

Alex Olley:

do. So it's that nerdy aspect of me that just wanted to, like,

Alex Olley:

really, get get down. It was one of the best decisions I made.

Alex Olley:

And I'm like, really lucky to work with a CEO at the moment

Alex Olley:

who's just like, I mean, the gap between me and him, it's scary

Alex Olley:

in terms of, like, he's exited five businesses, being able to

Alex Olley:

learn from someone like him. That's one of my big things, is

Alex Olley:

I wanted to have someone I could learn from because perhaps that

Alex Olley:

will happen one day, not not here, I don't think, but I want

Alex Olley:

to keep going as a CRO but it was that revenue leadership that

Alex Olley:

I just obsessed over. And you know, when you sort of found

Alex Olley:

that, that sweet spot that you think, I think, I think,

Alex Olley:

shouldn't say this, but I think I'm quite good at it. I love it,

Alex Olley:

and that's what I live and breathe, and breathe, and

Alex Olley:

that's, that's what gets me up in the day. And the the thing

Alex Olley:

that really resonated with me was, I think it was, I think it

Alex Olley:

was J maybe someone else. He said, happy people are

Alex Olley:

successful, not the other way around. And that, that said it

Alex Olley:

all. I think I remember that that's always stayed with me

Alex Olley:

today, and I thought I'm really happy doing what I want to do.

Alex Olley:

This is what I love doing, and perhaps that's what's gonna be

Alex Olley:

thing that's gonna make things successful. If I'm trying to be

Alex Olley:

successful at something I may not be happy. So what's the point?

Jonny Adams:

Unbelievable. And you know, we don't regularly ask

Jonny Adams:

this question, but just the last thing, you know, you seem like

Jonny Adams:

say one to watch, but you're not just one to watch. You support

Jonny Adams:

so many other founders and other businesses in the marketplace,

Jonny Adams:

and you give a lot. You talk about that, and your principle

Jonny Adams:

is about the give to get that, the art of reciprocity, but

Jonny Adams:

yourself in terms of that, like, in 10 years time, because you

Jonny Adams:

give a lot back to the market, like, where do you see yourself

Jonny Adams:

in 10 years time?

Alex Olley:

I'm not sure if I'm allowed to say this or not, but

Alex Olley:

I think hopefully we've always built this company to sell it.

Alex Olley:

We want. We we put it in a position where this company can

Alex Olley:

last forever, right? But we do want to hopefully be part of a

Alex Olley:

great acquisition, perhaps. But I think 10 years from now, I

Alex Olley:

would love to have exited a business, but ultimately, I see

Alex Olley:

a world where I just spend all my time doing what Fergus and

Alex Olley:

Jay did with me, which was just like helping putting a mirror

Alex Olley:

up, and I get so much out of it. For some reason, I get a lot out

Alex Olley:

of just essentially, it having been really hard for me and

Alex Olley:

having had a lot of help, and knowing what that does,

Alex Olley:

sometimes, I sit down with other founders. I was speaking to one

Alex Olley:

yesterday, just raised that seed round. He's so happy, but he's

Alex Olley:

also just like, I just think this is going to really hurt.

Alex Olley:

What have I done? Like, quite negative conversation. I was

Alex Olley:

like, Dude, you should just take a step back and say, I'm really

Alex Olley:

fortunate to be in this position. And he called me this

Alex Olley:

morning, said those words, like, just motivated me in a different

Alex Olley:

a different way. Those are the same words that were said to me.

Alex Olley:

And so I'd love to be in a position where I can continue to

Alex Olley:

do that. And I'm not saying I've done anything great, but I think

Alex Olley:

that there is a lot to say for having someone who can, like,

Alex Olley:

put a mirror up, who can break things down with you, and who

Alex Olley:

can help you execute on them, and I get a lot of satisfaction.

Jonny Adams:

I love it. Yeah, yeah. Resonate with that. It's brilliant.

Matt Best:

Wonderful. Look Alex. Thank you so much for for

Matt Best:

joining us on the Growth Workshop. Some really great

Matt Best:

insights. And calling them tips would be, would be undermining

Matt Best:

their value, I think, like some real depth in in some of the

Matt Best:

advice that you've given, and I know our audience can really

Matt Best:

appreciate that, so we thank you very much.

Alex Olley:

Awesome, look guys, thank you for having me. This

Alex Olley:

has been a real treat, pleasures all mine.

Jonny Adams:

Brilliant. Cheers, Alex, thank you.

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