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July 30, 2025 • 14 mins

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 (00:00):
Hello. Welcome to the Growth Workshop Podcast with

(00:02):
myself, Matt Best and JonnyAdams, and part three of our
conversation with Alex Olleyfrom Reachdesk, so founder, and
now CRO at Reachdesk. And soAlex, we've talked a little bit
about this offline, and I thinkit's really fascinating to dig
into it in a little bit moredetail, which is the part that
AI has to play in a salesorganization, and at SBR, we've

(00:24):
had this debate a few times.We've had a couple of
conversations on variousdifferent webinars, and there's
sort of white papers that havecome out of the team, and of
course, those are all accessiblevia the website, but in that we
talk about like, where AI fitsin sales. And it's just
fascinating, isn't it, to thinkof how much we're probably
already relying on this. But isthere a point where you go, you

(00:45):
can go too far in the sales in asort of sales team, and sales
kind of operating, operatingwith them. What's your thought
on that?

Alex Olley (00:52):
Yeah, I think you've probably guessed so far. I'm big
on, like the experience side ofthings, like a buyer standpoint,
and that's the bit I'm worriedabout. I'm worried that, like, I
took a look at an AI SDR, thatessentially, like, spoke at me
and I would have a conversation.It was basically a means to,
like, qualify me. I didn't enjoyit, it, I wasn't very trusting

(01:16):
of the answer, because I thinkanyone could put any answer in
behind it. And the things that Idon't think AI should even be
thinking about replacing is thatthe human interaction and
conversation. I'll give youexamples of where I've seen it
work really well. We use, like,a power dialer. I've got lots of
we're very outbound heavy. Weuse a power dialer. And what
that does that AI should beautomating the repeatable tasks

(01:37):
that essentially erodingproductivity. You know, they're
then increasing effort so thatthat's bad, but at the same
time, it should be designed in away that's going to elevate the
experience for the person,right, both the user and the
person. On the other end, I'mtalking the concept of sales. So
we use this power data, right?What it does essentially dials
lots of numbers, right? It, whensomeone picks up, it gives the

(01:59):
information to the rep to say,these are the bullet points, but
the conversation should never itshould never be a bot or
anything. It should be the humanand the AI is dialing. That's
the repeatable task. It's doingthe researching and surfacing
those insights, which takes along time. It just allows the
person to have more, betterconversations. And I haven't had
a single piece of feedback whereit's like, this has been bad in

(02:21):
any way. So that's a good sideof things. But I've also heard
of companies say, Well, we'regoing to now eliminate the human
and when the conversation isgoing to be with a bot. And I've
tested these things, I'veactually been an advisor to
businesses that build thesethings, it's not playing out.
Well, it's not. And I've heardof like AI agents giving
ridiculous offers to peoplesaying that you're going to get

(02:41):
50% off your credit card. It'slike, no, no, that's not a
thing. Yeah, so it hallucinatesand that's where I think we I
don't think we're even close tothat right now. Maybe that will
change, but if you're, if you'redoing it, where you're wrapping
it around those repeatable tasksthat save them time, everyone
wins. That's where we should be.But I'm also seeing companies
just neglect the experience. Andthat's kind of my word of

(03:02):
caution to everyone, is thinkabout the buyer. I say that a
lot, put yourself in the buyer'sshoes, and ideally walk 1000
miles in them. Think about whatthey want. Do they want some of
these things to happen? Probablynot. There are many use cases of
where it can work, butexperience still needs to be at
the forefront of things. And asI said, we invest in AI tools,
but that's the first question,like, is this going to be a good
experience for good experiencefor the buyer? And if the answer

(03:24):
is no, don't even look into it.

Jonny Adams (03:26):
And your point, you said, talk to the buyer, because
I think that's been missing inthe marketplace a lot at the
moment with AI. Is that? Yousay, think, but actually, let's
ask our buyers in our ICP thatwe want to go to market with,
and say, how do you want to buywith AI at the moment? And a lot
of it's gonna be, I don't knowwhat the future is, right, and
that's gonna be, and that'sgonna be the first response.
That's absolutely fine, but whatwas the thing that you would

(03:47):
like to experience? And I thinkthat would also help. And brings
me back to when I worked withanother organization, it was in
B to C, you referenced somethingabout, a lot about customer
experience today, and in SaaS, Ican't see many CX directors
within SAS, and I just wonderedthat's just sort of become a
light bulb moment for me. Yes,CS, but CX customer experience

(04:08):
directors that do the fullsuite. I don't see enough of
those individuals, because whenwe were in B to C, we had to
have a CX director because ofobviously, the market is very
led towards customer experiencedirectors. But yeah, maybe
there's something to learn fromthat as well.

Alex Olley (04:22):
We don't have a CS team. We have a CX team. We have
client experience reps. We havea head of CX. We so we do but
again, it's a proponent of whatwe do, right? We it's funny with
all this AI, boom, it's helpingus massively as business that
more people are thinking, I wantto create this physical
interactions, what I call thesemoments that matter, gifting

(04:44):
direct mail swag, these tangiblethings that people get their
hands on. It's actually likehaving this massive resurgence,
which obviously I'm incrediblyhappy about, but that's just one
example of something you can doto give a better experience for
a customer. I've actually got anAI agent in my inbox. Box that
filters out all the really badoutreach and marketing emails.
So I'd have to look at it. Whensomething's good, it stands out

(05:06):
and actually pops into my inbox.And so we do this. We train our
customers out to this. I'll giveyou an example, one to one
outbound prospecting. We havethis thing called the Amazon
Rainmaker, which essentially itresearches you. It finds out
something like, you might likegolf. You said you like golf. It
could say, like, notice thisabout you just had a promotion.
Yeah, great. Everyone does that.But I noticed specifically this

(05:27):
one thing that you said about achallenge you're trying to solve
around, like, low responserates, for example. Now notice
you, you're big into your golf.Here's a box of personalized
golf balls with your face on it.Let me know if the problem we're
trying to solve is of interestto you. So open question. If so,
like, let's talk. Hang on asecond that it's like, well
researched. It's tied to aproblem. There's an offer in
there that's not conditionalupon me taking a meeting, and

(05:49):
it's a yes or no. It's quitebinary. That's like, I think
that's a really good experiencefor someone. And so we're trying
to do more and more of that, andthat's what's helping companies
break through the noise.

Matt Best (05:59):
Yeah, and it's, and it's again, using it, using the
AI in that context, as a toolright to help shortcut the
research, to shortcut findingthe information, not to replace
the human. I was talking to afriend just the other day,
actually, and he's an expert inAI and in as a developer. And he
was talking about, you know, thelong term future being people

(06:23):
wanting to buy non AI stuff, andpeople want to go back to that
human you know, because if wekeep just recycling the same
thing, then there's no where'sthe innovation, where's the
thinking coming from, andwhere's that sort of human
connection that I think peoplewill start to be able to
recognize more clearly. I thinkright now, we're all just a bit
blown away by how good it canbe. And I've worked with Johnny

(06:46):
you, and I work with with withclients all the time who are
saying, Well, okay, but I hate,I hate the idea of an automated
email. So we're not asking youto write an automated email.
We're asking you to use or we'resuggesting that you might use AI
to shortcut some of the researchto help build you out the body.
It's not an, it's not, it's nota way of getting out, of lifting
a single finger and just sort ofthe old Homer Simpson with with

(07:08):
the bird, right? Just pressingthe key over and over again, and
something blows up....

Jonny Adams (07:12):
Another good analogy.

Matt Best (07:15):
You know, that's that I think is, is a really
important thing for people torecognize, isn't it? And it's
that sort of okay. I know. Iknow how to make this work for
me and not see it as a sort ofas a replacement, yeah, but it
goes right back to what you saidright at the beginning, Alex,
which is that we're going to bereally customer or client
focused, do what it is that weneed to do to that, and we're

(07:37):
going to go at it witheverything that we've got.

Alex Olley (07:39):
That's it, I think, more specifically in the term,
like AI and like, go to marketpredominantly sales, right? And
I think you just got a choice,like, do you want to invest in
the AI sales rep, or do you wantto invest in the AI enabled
sales rep? And that's theobvious one for me. It's like,
it's one or the other. I'm yetto hear of a company that has
been successful at buildingsomething autonomous that can

(08:00):
replace what seller does. And itall comes back to the
conversation, right? Every word,every word of every conversation
a seller has with theirprospective customer, their
existing customer, like thoseall matter and like, one
mistake, one hallucination, it'sgame over. And those could cost
people a lot of money. And we'rejust not there yet. We're just
not maybe we'll get there oneday. I can't see it happening

(08:20):
anytime soon?

Jonny Adams (08:21):
Really, really curious. Alex, you referenced
something really interestingearlier around founder, CEO at
one point, and then vacatingthat position to then move into
the CRO role. I mean, listeningto you, I can see why you're so
very good at being a CRO but alot of people have the pride and
maybe the ego that they want tobe the CEO. So what was that

(08:44):
reason? Was it business, or wasit personal?

Alex Olley (08:47):
To be honest it was both. I never set out to be a
CEO. I you can probably tell Ilove go to market. I love that
aspect. I think of certainthings I wasn't particularly
interested in. We spoke about myold CEO, Jay was one of our
founders, and we would spend along time talking about, you
know, he was a CEO. Was like,Hey, I'm a sales guy at the end
of the day. And I wish I'd donethat. I wish I'd got it to a

(09:07):
level that I was really proudof, because then perhaps after
that's the next logical step. Ithink a lot of it was from,
like, his his journey a littlebit. But I remember, because I
love selling stuff. I think Iearned my first tenant when I
was, like, seven, I was like,really happy about that, and
I've always been naturally goodat it, and I never really had
that, like, massive motivationdo it. But also, as a business,

(09:28):
we decided to get to the USfast. And I think I just had my
first kid. I think my wife wouldbe too happy lifting us out of
the UK, having to go to the US,because that was essentially the
ultimatum. But I think we knewwe're going to be a venture
backed company, and having a USCEO to like spearhead, that
would be really important. Theultimate thing just was, was
like, I would spend all my daythinking about, how can we

(09:49):
improve our outbound process,how can we improve our
discovery, how can we improvepricing and negotiation? I
wasn't thinking like, how can.We raise more money, and how can
we improve, like, investorrelations, or I really want to
be doing all that, I would justobsess over this stuff I still
do. So it's that nerdy aspect ofme that just wanted to, like,
really, get get down. It was oneof the best decisions I made.

(10:09):
And I'm like, really lucky towork with a CEO at the moment
who's just like, I mean, the gapbetween me and him, it's scary
in terms of, like, he's exitedfive businesses, being able to
learn from someone like him.That's one of my big things, is
I wanted to have someone I couldlearn from because perhaps that
will happen one day, not nothere, I don't think, but I want
to keep going as a CRO but itwas that revenue leadership that

(10:30):
I just obsessed over. And youknow, when you sort of found
that, that sweet spot that youthink, I think, I think,
shouldn't say this, but I thinkI'm quite good at it. I love it,
and that's what I live andbreathe, and breathe, and
that's, that's what gets me upin the day. And the the thing
that really resonated with mewas, I think it was, I think it
was J maybe someone else. Hesaid, happy people are
successful, not the other wayaround. And that, that said it

(10:53):
all. I think I remember thatthat's always stayed with me
today, and I thought I'm reallyhappy doing what I want to do.
This is what I love doing, andperhaps that's what's gonna be
thing that's gonna make thingssuccessful. If I'm trying to be
successful at something I maynot be happy. So what's the point?

Jonny Adams (11:08):
Unbelievable. And you know, we don't regularly ask
this question, but just the lastthing, you know, you seem like
say one to watch, but you're notjust one to watch. You support
so many other founders and otherbusinesses in the marketplace,
and you give a lot. You talkabout that, and your principle
is about the give to get that,the art of reciprocity, but
yourself in terms of that, like,in 10 years time, because you

(11:28):
give a lot back to the market,like, where do you see yourself
in 10 years time?

Alex Olley (11:32):
I'm not sure if I'm allowed to say this or not, but
I think hopefully we've alwaysbuilt this company to sell it.
We want. We we put it in aposition where this company can
last forever, right? But we dowant to hopefully be part of a
great acquisition, perhaps. ButI think 10 years from now, I
would love to have exited abusiness, but ultimately, I see

(11:52):
a world where I just spend allmy time doing what Fergus and
Jay did with me, which was justlike helping putting a mirror
up, and I get so much out of it.For some reason, I get a lot out
of just essentially, it havingbeen really hard for me and
having had a lot of help, andknowing what that does,
sometimes, I sit down with otherfounders. I was speaking to one

(12:13):
yesterday, just raised that seedround. He's so happy, but he's
also just like, I just thinkthis is going to really hurt.
What have I done? Like, quitenegative conversation. I was
like, Dude, you should just takea step back and say, I'm really
fortunate to be in thisposition. And he called me this
morning, said those words, like,just motivated me in a different
a different way. Those are thesame words that were said to me.
And so I'd love to be in aposition where I can continue to

(12:35):
do that. And I'm not saying I'vedone anything great, but I think
that there is a lot to say forhaving someone who can, like,
put a mirror up, who can breakthings down with you, and who
can help you execute on them,and I get a lot of satisfaction.

Jonny Adams (12:47):
I love it. Yeah, yeah. Resonate with that. It's brilliant.

Matt Best (12:51):
Wonderful. Look Alex. Thank you so much for for
joining us on the GrowthWorkshop. Some really great
insights. And calling them tipswould be, would be undermining
their value, I think, like somereal depth in in some of the
advice that you've given, and Iknow our audience can really
appreciate that, so we thank youvery much.

Alex Olley (13:09):
Awesome, look guys, thank you for having me. This
has been a real treat, pleasuresall mine.

Jonny Adams (13:13):
Brilliant. Cheers, Alex, thank you.
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