October 14, 2025 • 42 mins
In episode 41 of The Adaptive Mindset, Brett Gallant interviews Dean Curtis, CEO of Ingage and former leader at Palm and Apple, as he shares insights from his decades in the tech industry and lessons learned during major innovation waves, including the rise of the iPhone in the enterprise.
Tune in for a conversation filled with strategies and stories that inspire secure and bold leadership in a digital age
TIMESTAMPS
[00:02:14] iPhone's push into business.
[00:06:15] Adaptive mindset and foresight.
[00:10:41] The importance of asking for help.
[00:12:45] Action vs. Knowledge
[00:18:25] Burn the ships mentality.
[00:20:48] The power of one more.
[00:23:44] Discipline as a positive choice.
[00:29:35] Involve users in tool adoption.
[00:33:15] AI in sales effectiveness.
[00:36:37] AI in sales processes.
[00:40:22] Mistakes in leadership lessons.
QUOTES
- "Sometimes we have to have that mindset to go up on that peak and look beyond what's coming or what we can't even see and have that openness to see it." -Brett Gallant
- "The past is behind us. This is our future. Win or lose, this is the direction we're going."- Dean Curtis
- "Discipline is a decision to get up and go, even when you don't feel like it." -Brett Gallant
SOCIAL MEDIA LINKS
Brett Gallant
Instagram: https://www.instagram.com/brett_gallant/
Facebook: https://www.facebook.com/brett.gallant.9
LinkedIn: https://www.linkedin.com/in/brett-gallant-97805726/
Dean Curtis
LinkedIn: https://www.linkedin.com/in/deanc23/
Instagram: https://www.instagram.com/deancurtis23/
WEBSITE
Adaptive Office Solutions: https://www.adaptiveoffice.ca/
Ingage: https://ingage.io/
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:02):
Welcome to the Adaptive Mindset. I'm Brett Gallant, cybersecurity thoughtleader and founder of Adaptive Office Solutions. Here, we
don't just talk tech, we unlock the strategies, stories, andmindset shifts you need to stay secure, lead boldly, and
thrive in a digital world. Let's get started. Welcomeback to the Adaptive Mindset. I'm really pleased to have with
(00:24):
me today, Dean Curtis. He's been on the front lines of threemassive technology adoption waves. Palm in
the early days of mobile, Apple during the iPhone's rise todominance in the enterprise, and now as CEO of Engage, where
he's helping sales teams bring interactive, measurable contentto a distracted world. Dean Curtis has
(00:46):
helped senior leadership roles at Apple, Palm, and Intellisync. Andsince 2019, he's been leading Engage as
CEO after serving as CRO and COO. Soin this conversation, we'll talk about what Dean has learned
about driving adoption, how to balance AI and authenticityin sales, and what it really takes to scale both revenue
(01:09):
and culture at the same time. Dean, welcome to the show.
Brett, thanks so much for having me on. I appreciate that. Awesome. Welcome.
Yeah, it's coming to your inbox. I promise you. There you go. It'ssuch a pleasure. I feel like I'm talking
to an OG of technology, Palm. Wewere just talking Green Room in the beginning. You mentioned
(01:38):
You know, it's funny, when I first got my first Palm, Ilearned how to use it by entering in all of my contacts to
learn, because you had to know like a little, an alphabet in order to enterdata in. There was no thumb keyboard, there was no
voice, you know, there's nothing. You had to learn, literally had to learn new language.
So we've come a long way, baby. There's a lot more toI've been through those waves, the Palm, the BlackBerry, and the
(02:04):
iPhone. I wantyou to take us back. What was it like being part of Apple during
Yeah. If you think back, so it was 2008. Atthe time, BlackBerry, as you mentioned, was dominant. There
was Palm, there was BlackBerry. Palm had very small market share. Theywere trying to unseat BlackBerry or at least compete with
(02:28):
BlackBerry. But BlackBerry owned business. TheiPhone comes out the year prior and everybody wants to use
it in business, but it doesn't have the right feature set to besecure, to be manageable. Like it's all these technical things
that actually prevent it from being adopted inbusiness. So I was brought over from Palm. Our
(02:49):
whole team basically left Palm and came over to Apple to leadthe charge in business. And our remit was very simple.
figure out what the needs are of the enterprise, bringthose requirements back and see how many Fortune
500 companies we could get to adopt as a corporate standard, the iPhone.
(03:10):
Yes, that's incredible. Andthat just shows you the power of mindset when
you make a decision and you had strong leadership andthen a great team. mindset to figure it out,
Well, I'll tell you, the mindset that had to shift was the mindset ofthe IT people at these big companies, because they
(03:35):
were in love with all of the things that BlackBerry had,because it was very robust. the encryption, the management, the
lockdown, the setup, the deployment, all of those things matter.
If you think about deploying thousands and thousands of devices toteams, the mindset of the IT was, I have job
security because I'm using BlackBerry. There's an oldsaying that said, I never got fired for buying IBM. Well, BlackBerry was
(04:01):
very, very similar in the tech world. We hadto come up with ways in order to make those
IT teams very comfortable with the security, the deployment,and the management of all of those devices on their network. Because
if you think about it, you're deploying deploying devices ata bank, you have to be very careful
(04:25):
of all the different things that are important from a security perspective. Sothe mindset shift was with IT. The owners, the
managers, they all wanted the devices because they were the shinytoy, but the mindset shift in IT was a massive mindset
Oh, and I was one of them. Back then, I remember workingin a construction fabrication company, and
(04:48):
we were in love with the Palm, and then we fell in love with the Blackberry, and then it tooka while for me to let it
Yeah. I remember my first interview at Apple. Iasked the, so I interviewed with the VP of iPhone and
I said, is it, do you really think you're going to be successfulwithout a keyboard? Cause back then that was the big debate. Can people type
(05:10):
on glass? Now no one thinks about typing on glass. Andhe's, he looks me dead in the face. He says, I think we're going to be okay. I
Isn't that interesting? And how often dowe really need to look at ourselves and really question
(05:33):
I mean, everyone believed that the iPhone, I mean, youcould go and do the research, but there are multiple CEOs of
competitive companies. Apple's not just gonna walkin and build a phone. This is what Ed Colligan from
Palm said. Michael Dell was veryanti the iPhone. Like, they're not gonna be able to do this. No one's gonna
(05:54):
type on a screen. Someone from Blackberry probably said that. And it'slike, yeah. You have to change your mindset. And
I think that's what made someone like Steve Jobs so aheadof his contemporaries was he could see
around corners like no one. And that's part of itbeing I mean, I love the title of your podcast being adaptive mindset.
(06:15):
being able to see around corners, being able to see the next trend, andit's not even predicting it. It's not like you're Nostradamus. It's really
understanding human nature, how people interact with things,user design, user experience. All those things
allowed him to see around the corner and say, no, it'll be fine. It'llIt's funny you say that, because you're making me think of
(06:41):
a presentation I seen aboutthree years ago in Nunavut. And it's very
much on my mind right now, because I'm about to go in Novemberto present. There was this beautiful woman
who got up and she talked about the story of the Innu people.
And she told the story about how in their culture, Theelders would go up on a mountain and
(07:08):
look from high to see another perspective,to see what was coming. And she related to that back
in their lives. Sometimes you have to go up high andlook and see beyond what is now and see what's coming at you.
So I always think of that moment and just what you said right now mademe think of that. Sometimes we have to have that mindset to go
(07:31):
up on that peak and look beyond what's coming orYeah, it's also, I think another good way to think about
that is disconnection. So we're soattached to these devices in our life. And one
of my things that I do to clear my head when I have big decisions tomake is I have this, I live in Northeast of
(07:55):
the United States and I live North of the city of Philadelphia. I'min this great path along the Delaware River, it's a canal path.
So the old trade routes along the Delaware, AndI can walk for miles, for miles and miles. So there's a town that's
about seven miles from my town. And whenever I have a big decision,I put my phone away, I grab a notebook, I put my sneakers on
(08:17):
and I walk. And I leave in the morning and I walk up,I look at my notebook, I get back and I'm like, what am I going to do about this decision?
It's a total mindset shift of being away from devices, ofbeing out in nature, of like you said, changing your perspective.
It could be from a high hill, it could be from a riverbank, butYeah, I like to think of it as resets. You go for
(08:46):
a long walk and you're alone with your thoughts andeverything percolates and you just have that quiet
time and let your mind process. Idid that last year. I actually literally did climb a mountain. I snowshoed
up. And there was no way I was going to have cell receptionbecause there was none. I had three crazy,
(09:10):
great ideas and solved oneissue that was very much in my mind in that four and a half hours up that
mountain. It was incredible. That'sreally important that we do disconnect and
have that quiet time. That's so awesome. youwere part of that journey and now we're here on the other side. Now, you've
(09:38):
gone from technical leadership into revenue and then CEO roles. Whatmindset shifts did you have to have along the way, Dean, like
The first thing is I had to have the mindset thatI didn't know what I was doing. Accepting the fact
that as much as I have experience and it canapply to the new thing that I'm doing, reality was,
(10:03):
there's a lot that I didn't know. So the first is just accepting that,okay, I might need help. And I was never really good at
asking for help. I've always been a muscle through itkind of guy. And I talked to a lot of friends and they're like, I think that's They
could just because you're a guy like that's just what we do naturally isto try and solve problems ourself. And I think the biggest the
(10:25):
biggest shift for me was accepting that I didn't knowall the answers and having to go out and build a network of
people who do know the answers and our coaching program likea. there's a common practice of
trying to be in the room where you with people who have done thething you want to do, so that you can get around them, right.
(10:47):
So going and finding mentors who have donethe thing was the biggest change for me. And then not
only being there, but listening and actually doing the things that they recommended. ThatThat's the thing. So many people get comfortable when they go to the
event or be around the people, but you don't have the disciplineor the execution to actually do the follow through or make the
(11:11):
Yeah, a common phrase that I use with people inmy life is lessons will be repeated until they are learned. So
you may have to, because a lot of times we don't learnnew things. We just have to be reminded of the things that we've learned in the past that we've
never implemented or executed against. So it'sthe execution part that really matters. You can learn all you want, you can
(11:32):
read all the books, you can listen to all the podcasts, you can watch all the YouTube videos,Yeah, you've invested that time, but it's
sort of like the same analogy as what Iused to really live this example. I had a treadmill
(11:52):
down in my basement, and what itbecame was a glorified towel rack. But
I had it, I had the promise I was gonna get outand work out, but I just put the towel there with a promise. Yeah,
I invested in the treadmill. Ididn't execute it. It's like people who invest in a great coaching program, they
(12:15):
don't, sometimes they get comfortable, they don't executeand show up and execute on, on
I mean, there's, there's coaching calls that I'm on with hundreds of people. AndI often wonder how many people are taking notes and how many people are actually
good then. So let's say all, all the people took notes. Well, howmany people read them ever again? How many people then take action on
(12:38):
those and how many people then take action on the action to keep consistent afterit? It's just, being in the room is not enough.
It's great that you did that. It's great that you got off your butt and actuallywent into the room, but if you're not going to take action to implement
(12:59):
So we're both in Dan Martell's coaching programand he says something quite beautiful that I'll
be honest, I don't always live up to it, but I darnwell 95% of the time do it. It's what's caught, not taught.
And my notes sometimes don't even reflectwhat was being said, but it triggered an idea, so I write it down. Then
(13:23):
I go back and review it. And I go back to mynotebook from six months ago and re-read
it. I'm like, why did I write that down? But then, oh yeah, that's why. Yeah,no, totally. Trigger that, trigger it, you know? Yes. So
you've had these mindset shifts andwhat do you think, what's been the most challenging though from doing
(13:50):
There's a couple of big challenges. Going from a huge companywith prestigious name to a small company that
no one knows, there's a bit of a hit interms of reality. So when we were
at Apple trying to go into the Fortune 500, it didn't matter who we called.
Everybody wanted to talk to us. It wasn't a matter of if,it was a matter of when we were gonna get the meeting. Going to
(14:15):
a small company that no one knows about where you're trying to build a business fromscratch, you have to take a thousand reps
to try and get the one call. And I think that wasone of the hardest things is to not get
discouraged in those failures, becauseit was a lot of failures. We were trying to find product market fit for
(14:38):
a new product. We would go and we would tryto small business expo thinking, oh, it's going to be great because here's the reasons
why, didn't work. We went and met with a wholebunch of other companies, multiple verticals, didn't work.
Invested some resources because we had a really coolidea with this optometrist shop that we
(15:00):
thought would be a really interesting, didn't work. It's dealingwith failure in that massive overtime,
every time. Just to say, nope, nope, nope, and have that door shut.
It's being able to be resilient and that to say, okay, itwasn't a loss, it was a learning, totally fine. To
(15:20):
come back the next day and say, all right, who are we going to try next? Whenyou go from a big company where things are pretty much preset where
everyone wants to talk to you to that world, that was a big adjustment. Therewere some pretty dark days of feeling pretty terrible about yourself and
about what you're doing. But then there's sparks. Someonereally shows interest in what you're doing. In our case,
(15:43):
we found Product Market Fit through an inbound requeston our website. This is the whole reason we are in the business
and selling to the people we are today, because they opened ourOh, that's so awesome that you were receptive to that idea. And
it came probably at the right time, because sometimes you getknocked down and you get back up. But like, after a while, it's like, what
(16:07):
am I doing? Yeah, totally. So you totally hadthat mindset, that determination that you were going
all in and just kept plugging in. Mosttimes people quit. Yeah. And they're one.
one relationship or one call away from making ithappen. You had that inbound that you didn't even
(16:31):
That's right. It was our sale. I always give Charlie, our sales rep credit.
He said, he's like, Hey, we have a real opportunity here.
The company's new pro out of Boston. I always give them credit because it'swithout them. I don't think we'd even be in business today because they really helped
us get clarity on where we were going. And thatclarity plus belief, and then we were 100% committed.
(16:55):
100% of the time. 100% of the time, we were consistently going. Wewere like, all right, we're going to try this. Matter of fact, I
sold off a semi-profitable partof the business so we could focus on our new business. I essentially said,
if this is our path forward with the new product, which is why I cameto the company, I said, we have to shed the
(17:16):
old and we're gonna move forward with the new. So we sold theold product and old customers off to a partner. And
we said, we're all in on this new market. And that was a huge mindshift too of like, all right, the past is behind us.
This is our future. Win or lose, thisVery difficult. I'm capturing something right now with what you just said.
(17:40):
One of the commitments I made to somebody in the gym lastweek, I actually gave him a copy of Buy Back Your Time. And
he was saying, we were talking about books that have inspired us.
And we talked about thinking, grow rich. AndI told him I was making a promise to go
through that book again. I'm listening to it right now in Audible. Youmade me just think, I don't know if you ever read the book, but
(18:07):
there is a part in the book called Burn theShips. You burn the ships. The
boats were gone, you went all in. That takescourage and a mindset discipline to say, hey, I'm
Wow. Well, I mean, if you think about it, ifyou have 10 priorities, you have none. It's actually the opposite
(18:33):
of definition of priority if you say you have 10. Youhave to focus. I'm reading a really good book right
Just talked about that with my partner, my accountability partner.
It's really, really good because it's the idea that yourmind, your mindset going into something, when you say you're
(18:53):
in a 10x something, is you have to think of totally different pathwaysto solve the problem than if you're only going to go to 2x. It's
very similar to that same moment of saying, you know what, we're notdoing this anymore. We're going in this direction. If you're with me,
let's go. We did massive change. dozensof people in a company, we took it down to 17 in order to
(19:17):
be capitally efficient to move and grow. But itwas because Charlie said, I really think there's something here. We dug in,
we looked and we said, this is where it's gonna be. Now, fromone customer to hundreds to serving 10,000, tens of
thousands of presentations every single week because of that decision toYeah, there's a big takeaway for everybody listening right now. There's
(19:44):
somewhere that all of us can relate tothat and say, what do I need to revisit? What's
true right now? Maybe there's no need fora change, but maybe you need to dig
deep and look in places like Dean did, andI'll tie it back to what I said earlier about the constant failure. I
(20:09):
was no longer afraid to fail becauseI had failed so many times trying to find product market
fit in all these different places. If it didn't work, I knew itwas going to be okay because I knew there was going to be another thing that might come up. And
if it didn't, I was also okay with that tosay, look at what we did. Look at what we tried.
(20:30):
There was going to be something else down the road. There's always somethingelse down the road. This is just, the failure is
okay, right? Dan also says, you know, winners loseYeah. Yeah. You just keep going. You have to have that belief in that mindset
(20:52):
that it's going to happen. But so oftentimes we,unfortunately, sometimes we quit when we're just that, like I said, a
That's right. We on our on our SDR team,we asked them to make one more call at the end of the day when
they think they're done. Now,it doesn't really, does it make a material difference? Maybe
(21:18):
not, but it's that mentality of, I made my hundred orwhatever the number is for the day, I'm gonna make the next one more to
get one, because they think the power of one more, I got one morerep in. I might've been the one that made- I've read that book too.
And my let's book, the power of one more, right? That idea ofjust one, I'm gonna give it one more shot is, It's
(21:43):
so powerful. And it's a mindset thing. It's not a tactical,physical thing. It's a mindset thing that one more is actually something
And you're the person that keeps promises to yourself. So you say, hey, Istill have gas in the tank. What's one more call? What's
one more knock on the door? That's right. Weall have it in us. It's just, are we going to be committed to do it?
(22:09):
Totally. Like I did. one extrarep on one part of my routine this morning that I hate. I
did it. Like I did it. I don't likeI did one more. You know. You can't skip leg day. No
skipping leg day. I know, but you sometimes you want to. Whata total mentality, but that is, we're talking about mindset. People who love going
(22:33):
to the gym, but some people hate going to the gym no matter what, but they still do it. Andthen it's that one day, some people don't like whatever, right?
Whatever it is, legs is typically the one that no one likes. Everybody likes toskip leg day. You feel like marshmallows by the time you're done if
you, yeah, yeah. Yeah, but it's totally a mindset.
It's not, if you go into the gym only whenYeah, yeah, yeah. And
(22:58):
if you go into the gym like I do, I've been doing a pretty consistentroutine. My alarm clock goes off
at 4.45, I'm out the door by 5. Love it. Yeah,just getting it done. got
the podcast in or the audible. SometimesI watch something foolish and laugh mindlessly at
(23:20):
five in the morning. My wife's co-worker said, what is yourIf you relied on how you felt at 445, how
Oh, there wouldn'tbe, Not many. And
(23:44):
that's why there's a shirt I wear, Dean, it says disciplineis a decision. It's a decision to get
up and go, even when you don't feel like it.
Decision to make that extra call, even though you'reI think a lot of people have the perspective that
(24:05):
discipline is a negative thing, right? Because you discipline yourdog or you discipline your children. Discipline is
actually Latin for the same root of disciple. It'sbeing committed to. It's a very different mindset
around discipline than punishment, because a lot of people equate discipline topunishment, but it's the same. It's really about
(24:28):
having a level of commitment to a standard. And ISometimes four, because I get up early and I just say, yeah, let's
go, you know? Yeah. I lovewhat you just said. That was really powerful, what you just
related to the discipline. Somany people do look at it as a negative, but it's not.
(24:53):
Yeah. It gets you where you want to go. Yeah. Yeah.
When you put the reps in, you can go anywhere and just have tohave that belief. So Pivot
here for a moment. You've been atthe center of three major adoption stories, Palm,
(25:15):
which was incredible at the time, Apple, and now Engage. WhatYou said
it a little bit earlier, but- It's probably no different than anyone else, right?
Change is hard. Yeah. Think about your own life, anykind of change. You're gonna move, you're gonna go to a
(25:36):
different city, you're gonna start at a different gym, you're gonna starta new fitness program, you're gonna, heck, you're gonna start reading a
new book. There's momentum that has to be gained in order toget into that. It could be something as simple as reading
a book. Technology changes,I've seen from big companies to small companies, most
(25:57):
people don't really know how to deploy technology.
It is massively disruptive and where we play,our whole product is integrating into a
sales process. Well, if all of a sudden I messwith your sales process and you don't sell, That's
(26:19):
not good. There's highstakes. A lot of times when you do any technology deployment, there's high stakes.
There's all of a sudden, if I'm going to swap out all the laptops fromPCs to Macs, well, that could be a huge productivity hit. We
could lose two weeks of work because of some system that we didn't plan for.
I think as you look across technology adoption, there'sgreat research done on the technology adoption curve where
(26:44):
you have the early adopters, then you have the fatmiddle of everyone getting it, and then you have laggards that are adopting technology.
I think most people, you look at it, they're just afraid ofit. Because they're afraid of what they don't understand. And,
you know, I remember teaching, teachingsomeone how to use a spreadsheet, and they would always say, I don't want to break it.
(27:08):
Like, you're not going to break anything, there's an undo, whatever you do, youcan undo, right? So like, there's this, there's
this fragility, you know, you have to have almost theanti fragile model of saying, I know that this technology is
going to be really good for me. And we bought it becauseit provides these things of value. I mean, don't buy technology if
you don't know what the value drivers are, which say that Ishould hire. I always think about the hiring. What are you hiring the
(27:34):
technology to do, right? If you go back to your referenceearlier, buy back your time. You hire technology to
do a job that makes your life easier, typically.
Why would you buy a CRM? Well, you buy a CRM so youcan track your contacts and your contracts and
your deals and your leads, and you have a process for doing that. Well,if it doesn't deliver that value, you shouldn't buy it. Yeah.
(28:01):
And I think when people are, if you look at the adoption of technology, like yougo back to our work at Apple, we, it wasn't really going to
be possible for an enterprise until they could deployit, secure it, deploy it and manage it. Like that was the story. That's
what we had to make sure was true. And when we were able to provide thatvalue, it provided the value to the person deploying the
(28:26):
Yeah, there's a big takeaway there. Youhave to adapt to what the needs are for the customer and
I thinkeverybody listening has something in their house that they bought that they
look at today and they're like, why did I ever think that thatSo I have one. My wife wouldn't agree
(28:53):
with me, but I'm going to go somewhere just rightoff the ledge here. And I might regret
saying this. Of course, she doesn't listen. The ice machine. Iregret it. I hear that thing going off all the time, but she
loves it and the children love it. There you go. Whydid we buy that thing? but
(29:17):
there's countless real life examples though. Soif you were advising leaders listening right now on
The first step is to involve them in the process of deciding that thetool is something you should buy, right? This
(29:41):
happens all the time. We're at a conference, the leader's there, theysee our software. They're like, this is gonna be game-changing for our
people. I said, okay, well, do you have any of those people here? BecauseI want them to be as excited as you are about it. Or they
build this sales process and then they'venever involved the sales team in the process of building
(30:02):
the process or at least getting check-ins. It's the number one thing. I'lltell you a funny story back at Palm. We built a prototype for
the California Highway Patrol to do vehiclelicense lookups on a Palm. This is years ago. I
had this modem on it, but I could scan someone's driver's license andI could do a quick check to see if there was any, now
(30:26):
these systems are, of course, everywhere, but backin the day, this is like revolutionary. None of
this stuff existed. All the devices came backbroken. And we're like, this shouldn't happen.
Like if you're using them, the people inthe pilot were putting them under their tire, rolling
(30:47):
over them, bringing them back, crack the broken. becausethey weren't involved at all in the development of the software and the
user interface to make sure it was something that was actually gonnasolve a problem for them in the field. It was people in an office
that never went into the field designing software for people thatneed to use it in the face of real conditions. So
(31:08):
we were like, what's wrong with the hardware? It wasn't a hardware problemat all. It was a user experience problem because the people who
were going to be the end user were never involved in that process.
And that's the obvious first step, but a lot of times weforget about that, which we shouldn't be. Yeah,
(31:31):
Involve the people that are gonna be impacted by the changein the process of the change. It doesn't matter what you're doing. So
the technology, goals rolling out to your company, processchanges, rule change. I know a lot of companies have gone
from unlimited or from PTO to unlimitedvacation. but never include the people who are
(31:53):
impacted by that in the decision. So it's not just technology, it'sanything. Major decisions where you have change impacting someone, involve
them in the decision process. You can't give them, you know, approval,but at least have a say or have a
Have influence, they're involved. So, and Ibelieve everyone has a valuable perspective. So if
(32:15):
you bring it, you're only, bringing thebest out that will give you a better adoption and
overall experience for everyone. When yousaid that, it just made me think of
something that we had rolled out back in the similar time thatPalm was working for a construction fabrication company, and
(32:39):
we rolled out bioscanners for a construction site. Itdidn't go well. Part of the issue was we didn't involve the
end users. We didn't have thempart of the why. So let's talk about AI
for a moment. Everyone'stalking about AI and sales, but what's hype and what's real
(33:15):
I think, well, there's a lot oftechnology that will allow you to replace humans in the
sales process with AI process. So we'reactually looking at some of those things, call center software, phone
answering, appointment setting, those types of things. Ithink what AI can do is they can make your good sellers great and
(33:36):
your great sellers even better. The keythough, understanding the appropriate time when
it's going to be brought in. I'll giveyou an example. Someone sent me an email the other day, internally
at our company, and I asked them somequestions on it afterwards. had no idea
(33:58):
because they really didn't write the email. They usedAI to write the email. I think That's
one of the dangers of it is it can do so much thatyou forget to be the critical thinker in that process,
right? I think thephrase that I use is tool plus human is greater than human,
(34:21):
but you still need the human, right? Tools arenot greater than humans. You need tools plus humans to
be better than just a human by themselves, but it's like anything.
It's like any piece of software, any piece of hardware that you're using foryour business, for your personal life, if you're not in the middle
of it and you're not helping it to enhance, not replace, Ithink that's the big mistake. And I think a lot of people in sales are doing that. I
(34:45):
mean, I get cold emails all the time. Like this was totally AI written, generated,and it's lazy. To me, it's lazy. Use it to be
amazing rather than great. And then I thinkYeah, that's so true. A lot of times when I'm talking about AI,
I try to explain to people the way I use it. Iuse it as an extension of my brain, a thought partner. I
(35:10):
converse with it. In fact, this morning when I went for a hike, Iwas, I had my Bluetooth headphones on and I
was talking to it about strategy, Spartan partner,like just came up with so many, many
great thoughts and ideas, but it was, I wasin control. And I think that's the big lesson that people
(35:36):
But you have to be in control. That's right. I think the other thingthat it does for me, my own personal value of AI,
is that it solves the blank page problem for me. Iam really not good at the blank canvas. My
strength is taking something that exists and lookingat it, evaluating it, and making it better. That's
(35:57):
perfect for AI, because I can talk to, like you just said, I can talkto AI with my stream of conscious thoughts. It can get
me started, and then I can take that and mold itinto what I think is the right response, the right project,
the right goals, the right whatever it is. It can helpme distill and move forward much faster than I would on
(36:17):
my own. So very, very powerful, butYeah, the human needs to be driving the ship. So
what's like, engage, what's oneway you're using AI to move the needle forward
(36:37):
Yeah, so what we do in general iswe help sales teams build amazing content that helps
their sales process move and flow very, very seamlessly. Sotheir sales reps have confidence when they're selling. And we give the
tools to make sure everybody has the right content and then we can measurewhat people are doing with that content. So a lot of people have sent presentations
(36:59):
out to their sales team. They never know if they deliver them. They actually neverknow if they even use them. And they don't know if they maybe
change them and change the marketing message or the images or the waythe presentation is delivered. We give all those tools. Where
does AI help in that? It helps in, number one, idea creation.
That blank page problem, new customers coming to us, they're revampingtheir sales process, they want to embed it into our platform. We
(37:26):
help them using AI to brainstorm, outline,get the crux of the presentation because we
have thousands and thousands andthousands of reps of people using interactive content in the sales process
that we can learn from in order to create a great outline forany new customer. That's one. The second is
(37:47):
we're using it on the analytics side. So as we get data fromall of the different presentations that are being delivered, one of the things
we're working on now hasn't shipped is using AI tolook at that data to make good decisions based on how people
are using the content in the sales process. The other,what we don't wanna do is we don't just wanna wrap AI
(38:09):
around our thing and call us an AI platform. It'sa lazy approach. We wanna look at the data that
we have on our platform that helps train the AI so thatour customers today and our future customers can leverage all
the best practices of what people are doing and having success with. Sothat's our philosophy around is to build moats in our
(38:30):
business around the data that only we have tohelp our current and new customers get up and running as fast
as they can, get as much value as they can, and then solveproblems for them using the knowledge we've gained from all
So I wanna make sure that we point out, that wemake sure people know how to find you and find out more
(38:58):
Yeah, totally. I think the easiest way is Instagram. Ican send it to our website, engage.io with an I, so I-N-G-E.io,
like that's of course, head to the website. ButI think also Instagram has been becoming more and more of
a place that I like to talk with people first, because- Likewise,yeah. A website's kind of a headless thing. And for
(39:22):
some people, that's exactly how they want to learn, which is awesome. Youcan link over to, you know, PreCanDemo, you can get a demo. But
if you're, if you want to connect on Instagram and just message methe word Brett to let me know that that's how you found me, that would be amazing. I'm
So that'd be a great way to connect as well. Yeah, Dean has great content too,folks. So check him out. Dean, recently
(39:49):
I started pivoting more to just something fun atthe end of the show. And we had such a great time here today. I really
enjoyed our conversation. I want to endwith rapid fire questions. Oh, love it. Yeah,
so you tell me the first thing that comes to your mind when Iask these. What's
(40:10):
one book every leader should read? WhatTo Say by Phil M. Jones. Perfect.
What's one mistake you made in leadership that taught you theI slammed my hand on a desk in a meeting one time and I swear I'll never
do it again. What'sone leader you admire and why? Uh,
(40:34):
there's a man, one of my leaders at Apple, his name was John Brandon. SoJohn was the ultimate is a VP of senior vice
president of, of enterprise and worldwide sales. Andhe was, he was everything that you
thought he could be as a, as a leader and evenUh, in, in one sentence, what's the future of
(41:01):
The future of sales enablement is hyper-personalization byIf you weren't leading Engage, what would you be doing right
If money was not an issue and it just myHere's another one. biggest eat the
(41:34):
frog task you do in the mornings? Oh, I work out. Yeah.
Every day. Yeah. Same. One piece of advice youJust be patient. Don't rush the
journey. Be patient. Good things are ahead. Yeah.
Finish this sentence. The best sales leaders in 2030 will?
(41:58):
Be adaptable. I love it. Howcan people connect with, I already asked, but hey,
remember folks, connect with Dean on Instagram, DMhim, Brett. And Dean, it's
been incredible getting to meet you today. And Ireally am glad we connected. I look forward to carrying on
(42:24):
Absolutely. Brett, I appreciate your time and your wisdom. Thanks soThanks for tuning in to The Adaptive Mindset. If you found value in
today's episode, don't forget to subscribe, leave areview, and share it with someone who's ready to thrive in the digital age.
Welcome to the Adaptive Mindset. I'm Brett Gallant, cybersecurity thoughtleader and founder of Adaptive Office Solutions. Here, we
don't just talk tech, we unlock the strategies, stories, andmindset shifts you need to stay secure, lead boldly, and
thrive in a digital world. Let's get started. Welcomeback to the Adaptive Mindset. I'm really pleased to have with
(00:24):
me today, Dean Curtis. He's been on the front lines of threemassive technology adoption waves. Palm in
the early days of mobile, Apple during the iPhone's rise todominance in the enterprise, and now as CEO of Engage, where
he's helping sales teams bring interactive, measurable contentto a distracted world. Dean Curtis has
(00:46):
helped senior leadership roles at Apple, Palm, and Intellisync. Andsince 2019, he's been leading Engage as
CEO after serving as CRO and COO. Soin this conversation, we'll talk about what Dean has learned
about driving adoption, how to balance AI and authenticityin sales, and what it really takes to scale both revenue
(01:09):
and culture at the same time. Dean, welcome to the show.
Brett, thanks so much for having me on. I appreciate that. Awesome. Welcome.
Yeah, it's coming to your inbox. I promise you. There you go. It'ssuch a pleasure. I feel like I'm talking
to an OG of technology, Palm. Wewere just talking Green Room in the beginning. You mentioned
(01:38):
You know, it's funny, when I first got my first Palm, Ilearned how to use it by entering in all of my contacts to
learn, because you had to know like a little, an alphabet in order to enterdata in. There was no thumb keyboard, there was no
voice, you know, there's nothing. You had to learn, literally had to learn new language.
So we've come a long way, baby. There's a lot more toI've been through those waves, the Palm, the BlackBerry, and the
(02:04):
iPhone. I wantyou to take us back. What was it like being part of Apple during
Yeah. If you think back, so it was 2008. Atthe time, BlackBerry, as you mentioned, was dominant. There
was Palm, there was BlackBerry. Palm had very small market share. Theywere trying to unseat BlackBerry or at least compete with
(02:28):
BlackBerry. But BlackBerry owned business. TheiPhone comes out the year prior and everybody wants to use
it in business, but it doesn't have the right feature set to besecure, to be manageable. Like it's all these technical things
that actually prevent it from being adopted inbusiness. So I was brought over from Palm. Our
(02:49):
whole team basically left Palm and came over to Apple to leadthe charge in business. And our remit was very simple.
figure out what the needs are of the enterprise, bringthose requirements back and see how many Fortune
500 companies we could get to adopt as a corporate standard, the iPhone.
(03:10):
Yes, that's incredible. Andthat just shows you the power of mindset when
you make a decision and you had strong leadership andthen a great team. mindset to figure it out,
Well, I'll tell you, the mindset that had to shift was the mindset ofthe IT people at these big companies, because they
(03:35):
were in love with all of the things that BlackBerry had,because it was very robust. the encryption, the management, the
lockdown, the setup, the deployment, all of those things matter.
If you think about deploying thousands and thousands of devices toteams, the mindset of the IT was, I have job
security because I'm using BlackBerry. There's an oldsaying that said, I never got fired for buying IBM. Well, BlackBerry was
(04:01):
very, very similar in the tech world. We hadto come up with ways in order to make those
IT teams very comfortable with the security, the deployment,and the management of all of those devices on their network. Because
if you think about it, you're deploying deploying devices ata bank, you have to be very careful
(04:25):
of all the different things that are important from a security perspective. Sothe mindset shift was with IT. The owners, the
managers, they all wanted the devices because they were the shinytoy, but the mindset shift in IT was a massive mindset
Oh, and I was one of them. Back then, I remember workingin a construction fabrication company, and
(04:48):
we were in love with the Palm, and then we fell in love with the Blackberry, and then it tooka while for me to let it
Yeah. I remember my first interview at Apple. Iasked the, so I interviewed with the VP of iPhone and
I said, is it, do you really think you're going to be successfulwithout a keyboard? Cause back then that was the big debate. Can people type
(05:10):
on glass? Now no one thinks about typing on glass. Andhe's, he looks me dead in the face. He says, I think we're going to be okay. I
Isn't that interesting? And how often dowe really need to look at ourselves and really question
(05:33):
I mean, everyone believed that the iPhone, I mean, youcould go and do the research, but there are multiple CEOs of
competitive companies. Apple's not just gonna walkin and build a phone. This is what Ed Colligan from
Palm said. Michael Dell was veryanti the iPhone. Like, they're not gonna be able to do this. No one's gonna
(05:54):
type on a screen. Someone from Blackberry probably said that. And it'slike, yeah. You have to change your mindset. And
I think that's what made someone like Steve Jobs so aheadof his contemporaries was he could see
around corners like no one. And that's part of itbeing I mean, I love the title of your podcast being adaptive mindset.
(06:15):
being able to see around corners, being able to see the next trend, andit's not even predicting it. It's not like you're Nostradamus. It's really
understanding human nature, how people interact with things,user design, user experience. All those things
allowed him to see around the corner and say, no, it'll be fine. It'llIt's funny you say that, because you're making me think of
(06:41):
a presentation I seen aboutthree years ago in Nunavut. And it's very
much on my mind right now, because I'm about to go in Novemberto present. There was this beautiful woman
who got up and she talked about the story of the Innu people.
And she told the story about how in their culture, Theelders would go up on a mountain and
(07:08):
look from high to see another perspective,to see what was coming. And she related to that back
in their lives. Sometimes you have to go up high andlook and see beyond what is now and see what's coming at you.
So I always think of that moment and just what you said right now mademe think of that. Sometimes we have to have that mindset to go
(07:31):
up on that peak and look beyond what's coming orYeah, it's also, I think another good way to think about
that is disconnection. So we're soattached to these devices in our life. And one
of my things that I do to clear my head when I have big decisions tomake is I have this, I live in Northeast of
(07:55):
the United States and I live North of the city of Philadelphia. I'min this great path along the Delaware River, it's a canal path.
So the old trade routes along the Delaware, AndI can walk for miles, for miles and miles. So there's a town that's
about seven miles from my town. And whenever I have a big decision,I put my phone away, I grab a notebook, I put my sneakers on
(08:17):
and I walk. And I leave in the morning and I walk up,I look at my notebook, I get back and I'm like, what am I going to do about this decision?
It's a total mindset shift of being away from devices, ofbeing out in nature, of like you said, changing your perspective.
It could be from a high hill, it could be from a riverbank, butYeah, I like to think of it as resets. You go for
(08:46):
a long walk and you're alone with your thoughts andeverything percolates and you just have that quiet
time and let your mind process. Idid that last year. I actually literally did climb a mountain. I snowshoed
up. And there was no way I was going to have cell receptionbecause there was none. I had three crazy,
(09:10):
great ideas and solved oneissue that was very much in my mind in that four and a half hours up that
mountain. It was incredible. That'sreally important that we do disconnect and
have that quiet time. That's so awesome. youwere part of that journey and now we're here on the other side. Now, you've
(09:38):
gone from technical leadership into revenue and then CEO roles. Whatmindset shifts did you have to have along the way, Dean, like
The first thing is I had to have the mindset thatI didn't know what I was doing. Accepting the fact
that as much as I have experience and it canapply to the new thing that I'm doing, reality was,
(10:03):
there's a lot that I didn't know. So the first is just accepting that,okay, I might need help. And I was never really good at
asking for help. I've always been a muscle through itkind of guy. And I talked to a lot of friends and they're like, I think that's They
could just because you're a guy like that's just what we do naturally isto try and solve problems ourself. And I think the biggest the
(10:25):
biggest shift for me was accepting that I didn't knowall the answers and having to go out and build a network of
people who do know the answers and our coaching program likea. there's a common practice of
trying to be in the room where you with people who have done thething you want to do, so that you can get around them, right.
(10:47):
So going and finding mentors who have donethe thing was the biggest change for me. And then not
only being there, but listening and actually doing the things that they recommended. ThatThat's the thing. So many people get comfortable when they go to the
event or be around the people, but you don't have the disciplineor the execution to actually do the follow through or make the
(11:11):
Yeah, a common phrase that I use with people inmy life is lessons will be repeated until they are learned. So
you may have to, because a lot of times we don't learnnew things. We just have to be reminded of the things that we've learned in the past that we've
never implemented or executed against. So it'sthe execution part that really matters. You can learn all you want, you can
(11:32):
read all the books, you can listen to all the podcasts, you can watch all the YouTube videos,Yeah, you've invested that time, but it's
sort of like the same analogy as what Iused to really live this example. I had a treadmill
(11:52):
down in my basement, and what itbecame was a glorified towel rack. But
I had it, I had the promise I was gonna get outand work out, but I just put the towel there with a promise. Yeah,
I invested in the treadmill. Ididn't execute it. It's like people who invest in a great coaching program, they
(12:15):
don't, sometimes they get comfortable, they don't executeand show up and execute on, on
I mean, there's, there's coaching calls that I'm on with hundreds of people. AndI often wonder how many people are taking notes and how many people are actually
good then. So let's say all, all the people took notes. Well, howmany people read them ever again? How many people then take action on
(12:38):
those and how many people then take action on the action to keep consistent afterit? It's just, being in the room is not enough.
It's great that you did that. It's great that you got off your butt and actuallywent into the room, but if you're not going to take action to implement
(12:59):
So we're both in Dan Martell's coaching programand he says something quite beautiful that I'll
be honest, I don't always live up to it, but I darnwell 95% of the time do it. It's what's caught, not taught.
And my notes sometimes don't even reflectwhat was being said, but it triggered an idea, so I write it down. Then
(13:23):
I go back and review it. And I go back to mynotebook from six months ago and re-read
it. I'm like, why did I write that down? But then, oh yeah, that's why. Yeah,no, totally. Trigger that, trigger it, you know? Yes. So
you've had these mindset shifts andwhat do you think, what's been the most challenging though from doing
(13:50):
There's a couple of big challenges. Going from a huge companywith prestigious name to a small company that
no one knows, there's a bit of a hit interms of reality. So when we were
at Apple trying to go into the Fortune 500, it didn't matter who we called.
Everybody wanted to talk to us. It wasn't a matter of if,it was a matter of when we were gonna get the meeting. Going to
(14:15):
a small company that no one knows about where you're trying to build a business fromscratch, you have to take a thousand reps
to try and get the one call. And I think that wasone of the hardest things is to not get
discouraged in those failures, becauseit was a lot of failures. We were trying to find product market fit for
(14:38):
a new product. We would go and we would tryto small business expo thinking, oh, it's going to be great because here's the reasons
why, didn't work. We went and met with a wholebunch of other companies, multiple verticals, didn't work.
Invested some resources because we had a really coolidea with this optometrist shop that we
(15:00):
thought would be a really interesting, didn't work. It's dealingwith failure in that massive overtime,
every time. Just to say, nope, nope, nope, and have that door shut.
It's being able to be resilient and that to say, okay, itwasn't a loss, it was a learning, totally fine. To
(15:20):
come back the next day and say, all right, who are we going to try next? Whenyou go from a big company where things are pretty much preset where
everyone wants to talk to you to that world, that was a big adjustment. Therewere some pretty dark days of feeling pretty terrible about yourself and
about what you're doing. But then there's sparks. Someonereally shows interest in what you're doing. In our case,
(15:43):
we found Product Market Fit through an inbound requeston our website. This is the whole reason we are in the business
and selling to the people we are today, because they opened ourOh, that's so awesome that you were receptive to that idea. And
it came probably at the right time, because sometimes you getknocked down and you get back up. But like, after a while, it's like, what
(16:07):
am I doing? Yeah, totally. So you totally hadthat mindset, that determination that you were going
all in and just kept plugging in. Mosttimes people quit. Yeah. And they're one.
one relationship or one call away from making ithappen. You had that inbound that you didn't even
(16:31):
That's right. It was our sale. I always give Charlie, our sales rep credit.
He said, he's like, Hey, we have a real opportunity here.
The company's new pro out of Boston. I always give them credit because it'swithout them. I don't think we'd even be in business today because they really helped
us get clarity on where we were going. And thatclarity plus belief, and then we were 100% committed.
(16:55):
100% of the time. 100% of the time, we were consistently going. Wewere like, all right, we're going to try this. Matter of fact, I
sold off a semi-profitable partof the business so we could focus on our new business. I essentially said,
if this is our path forward with the new product, which is why I cameto the company, I said, we have to shed the
(17:16):
old and we're gonna move forward with the new. So we sold theold product and old customers off to a partner. And
we said, we're all in on this new market. And that was a huge mindshift too of like, all right, the past is behind us.
This is our future. Win or lose, thisVery difficult. I'm capturing something right now with what you just said.
(17:40):
One of the commitments I made to somebody in the gym lastweek, I actually gave him a copy of Buy Back Your Time. And
he was saying, we were talking about books that have inspired us.
And we talked about thinking, grow rich. AndI told him I was making a promise to go
through that book again. I'm listening to it right now in Audible. Youmade me just think, I don't know if you ever read the book, but
(18:07):
there is a part in the book called Burn theShips. You burn the ships. The
boats were gone, you went all in. That takescourage and a mindset discipline to say, hey, I'm
Wow. Well, I mean, if you think about it, ifyou have 10 priorities, you have none. It's actually the opposite
(18:33):
of definition of priority if you say you have 10. Youhave to focus. I'm reading a really good book right
Just talked about that with my partner, my accountability partner.
It's really, really good because it's the idea that yourmind, your mindset going into something, when you say you're
(18:53):
in a 10x something, is you have to think of totally different pathwaysto solve the problem than if you're only going to go to 2x. It's
very similar to that same moment of saying, you know what, we're notdoing this anymore. We're going in this direction. If you're with me,
let's go. We did massive change. dozensof people in a company, we took it down to 17 in order to
(19:17):
be capitally efficient to move and grow. But itwas because Charlie said, I really think there's something here. We dug in,
we looked and we said, this is where it's gonna be. Now, fromone customer to hundreds to serving 10,000, tens of
thousands of presentations every single week because of that decision toYeah, there's a big takeaway for everybody listening right now. There's
(19:44):
somewhere that all of us can relate tothat and say, what do I need to revisit? What's
true right now? Maybe there's no need fora change, but maybe you need to dig
deep and look in places like Dean did, andI'll tie it back to what I said earlier about the constant failure. I
(20:09):
was no longer afraid to fail becauseI had failed so many times trying to find product market
fit in all these different places. If it didn't work, I knew itwas going to be okay because I knew there was going to be another thing that might come up. And
if it didn't, I was also okay with that tosay, look at what we did. Look at what we tried.
(20:30):
There was going to be something else down the road. There's always somethingelse down the road. This is just, the failure is
okay, right? Dan also says, you know, winners loseYeah. Yeah. You just keep going. You have to have that belief in that mindset
(20:52):
that it's going to happen. But so oftentimes we,unfortunately, sometimes we quit when we're just that, like I said, a
That's right. We on our on our SDR team,we asked them to make one more call at the end of the day when
they think they're done. Now,it doesn't really, does it make a material difference? Maybe
(21:18):
not, but it's that mentality of, I made my hundred orwhatever the number is for the day, I'm gonna make the next one more to
get one, because they think the power of one more, I got one morerep in. I might've been the one that made- I've read that book too.
And my let's book, the power of one more, right? That idea ofjust one, I'm gonna give it one more shot is, It's
(21:43):
so powerful. And it's a mindset thing. It's not a tactical,physical thing. It's a mindset thing that one more is actually something
And you're the person that keeps promises to yourself. So you say, hey, Istill have gas in the tank. What's one more call? What's
one more knock on the door? That's right. Weall have it in us. It's just, are we going to be committed to do it?
(22:09):
Totally. Like I did. one extrarep on one part of my routine this morning that I hate. I
did it. Like I did it. I don't likeI did one more. You know. You can't skip leg day. No
skipping leg day. I know, but you sometimes you want to. Whata total mentality, but that is, we're talking about mindset. People who love going
(22:33):
to the gym, but some people hate going to the gym no matter what, but they still do it. Andthen it's that one day, some people don't like whatever, right?
Whatever it is, legs is typically the one that no one likes. Everybody likes toskip leg day. You feel like marshmallows by the time you're done if
you, yeah, yeah. Yeah, but it's totally a mindset.
It's not, if you go into the gym only whenYeah, yeah, yeah. And
(22:58):
if you go into the gym like I do, I've been doing a pretty consistentroutine. My alarm clock goes off
at 4.45, I'm out the door by 5. Love it. Yeah,just getting it done. got
the podcast in or the audible. SometimesI watch something foolish and laugh mindlessly at
(23:20):
five in the morning. My wife's co-worker said, what is yourIf you relied on how you felt at 445, how
Oh, there wouldn'tbe, Not many. And
(23:44):
that's why there's a shirt I wear, Dean, it says disciplineis a decision. It's a decision to get
up and go, even when you don't feel like it.
Decision to make that extra call, even though you'reI think a lot of people have the perspective that
(24:05):
discipline is a negative thing, right? Because you discipline yourdog or you discipline your children. Discipline is
actually Latin for the same root of disciple. It'sbeing committed to. It's a very different mindset
around discipline than punishment, because a lot of people equate discipline topunishment, but it's the same. It's really about
(24:28):
having a level of commitment to a standard. And ISometimes four, because I get up early and I just say, yeah, let's
go, you know? Yeah. I lovewhat you just said. That was really powerful, what you just
related to the discipline. Somany people do look at it as a negative, but it's not.
(24:53):
Yeah. It gets you where you want to go. Yeah. Yeah.
When you put the reps in, you can go anywhere and just have tohave that belief. So Pivot
here for a moment. You've been atthe center of three major adoption stories, Palm,
(25:15):
which was incredible at the time, Apple, and now Engage. WhatYou said
it a little bit earlier, but- It's probably no different than anyone else, right?
Change is hard. Yeah. Think about your own life, anykind of change. You're gonna move, you're gonna go to a
(25:36):
different city, you're gonna start at a different gym, you're gonna starta new fitness program, you're gonna, heck, you're gonna start reading a
new book. There's momentum that has to be gained in order toget into that. It could be something as simple as reading
a book. Technology changes,I've seen from big companies to small companies, most
(25:57):
people don't really know how to deploy technology.
It is massively disruptive and where we play,our whole product is integrating into a
sales process. Well, if all of a sudden I messwith your sales process and you don't sell, That's
(26:19):
not good. There's highstakes. A lot of times when you do any technology deployment, there's high stakes.
There's all of a sudden, if I'm going to swap out all the laptops fromPCs to Macs, well, that could be a huge productivity hit. We
could lose two weeks of work because of some system that we didn't plan for.
I think as you look across technology adoption, there'sgreat research done on the technology adoption curve where
(26:44):
you have the early adopters, then you have the fatmiddle of everyone getting it, and then you have laggards that are adopting technology.
I think most people, you look at it, they're just afraid ofit. Because they're afraid of what they don't understand. And,
you know, I remember teaching, teachingsomeone how to use a spreadsheet, and they would always say, I don't want to break it.
(27:08):
Like, you're not going to break anything, there's an undo, whatever you do, youcan undo, right? So like, there's this, there's
this fragility, you know, you have to have almost theanti fragile model of saying, I know that this technology is
going to be really good for me. And we bought it becauseit provides these things of value. I mean, don't buy technology if
you don't know what the value drivers are, which say that Ishould hire. I always think about the hiring. What are you hiring the
(27:34):
technology to do, right? If you go back to your referenceearlier, buy back your time. You hire technology to
do a job that makes your life easier, typically.
Why would you buy a CRM? Well, you buy a CRM so youcan track your contacts and your contracts and
your deals and your leads, and you have a process for doing that. Well,if it doesn't deliver that value, you shouldn't buy it. Yeah.
(28:01):
And I think when people are, if you look at the adoption of technology, like yougo back to our work at Apple, we, it wasn't really going to
be possible for an enterprise until they could deployit, secure it, deploy it and manage it. Like that was the story. That's
what we had to make sure was true. And when we were able to provide thatvalue, it provided the value to the person deploying the
(28:26):
Yeah, there's a big takeaway there. Youhave to adapt to what the needs are for the customer and
I thinkeverybody listening has something in their house that they bought that they
look at today and they're like, why did I ever think that thatSo I have one. My wife wouldn't agree
(28:53):
with me, but I'm going to go somewhere just rightoff the ledge here. And I might regret
saying this. Of course, she doesn't listen. The ice machine. Iregret it. I hear that thing going off all the time, but she
loves it and the children love it. There you go. Whydid we buy that thing? but
(29:17):
there's countless real life examples though. Soif you were advising leaders listening right now on
The first step is to involve them in the process of deciding that thetool is something you should buy, right? This
(29:41):
happens all the time. We're at a conference, the leader's there, theysee our software. They're like, this is gonna be game-changing for our
people. I said, okay, well, do you have any of those people here? BecauseI want them to be as excited as you are about it. Or they
build this sales process and then they'venever involved the sales team in the process of building
(30:02):
the process or at least getting check-ins. It's the number one thing. I'lltell you a funny story back at Palm. We built a prototype for
the California Highway Patrol to do vehiclelicense lookups on a Palm. This is years ago. I
had this modem on it, but I could scan someone's driver's license andI could do a quick check to see if there was any, now
(30:26):
these systems are, of course, everywhere, but backin the day, this is like revolutionary. None of
this stuff existed. All the devices came backbroken. And we're like, this shouldn't happen.
Like if you're using them, the people inthe pilot were putting them under their tire, rolling
(30:47):
over them, bringing them back, crack the broken. becausethey weren't involved at all in the development of the software and the
user interface to make sure it was something that was actually gonnasolve a problem for them in the field. It was people in an office
that never went into the field designing software for people thatneed to use it in the face of real conditions. So
(31:08):
we were like, what's wrong with the hardware? It wasn't a hardware problemat all. It was a user experience problem because the people who
were going to be the end user were never involved in that process.
And that's the obvious first step, but a lot of times weforget about that, which we shouldn't be. Yeah,
(31:31):
Involve the people that are gonna be impacted by the changein the process of the change. It doesn't matter what you're doing. So
the technology, goals rolling out to your company, processchanges, rule change. I know a lot of companies have gone
from unlimited or from PTO to unlimitedvacation. but never include the people who are
(31:53):
impacted by that in the decision. So it's not just technology, it'sanything. Major decisions where you have change impacting someone, involve
them in the decision process. You can't give them, you know, approval,but at least have a say or have a
Have influence, they're involved. So, and Ibelieve everyone has a valuable perspective. So if
(32:15):
you bring it, you're only, bringing thebest out that will give you a better adoption and
overall experience for everyone. When yousaid that, it just made me think of
something that we had rolled out back in the similar time thatPalm was working for a construction fabrication company, and
(32:39):
we rolled out bioscanners for a construction site. Itdidn't go well. Part of the issue was we didn't involve the
end users. We didn't have thempart of the why. So let's talk about AI
for a moment. Everyone'stalking about AI and sales, but what's hype and what's real
(33:15):
I think, well, there's a lot oftechnology that will allow you to replace humans in the
sales process with AI process. So we'reactually looking at some of those things, call center software, phone
answering, appointment setting, those types of things. Ithink what AI can do is they can make your good sellers great and
(33:36):
your great sellers even better. The keythough, understanding the appropriate time when
it's going to be brought in. I'll giveyou an example. Someone sent me an email the other day, internally
at our company, and I asked them somequestions on it afterwards. had no idea
(33:58):
because they really didn't write the email. They usedAI to write the email. I think That's
one of the dangers of it is it can do so much thatyou forget to be the critical thinker in that process,
right? I think thephrase that I use is tool plus human is greater than human,
(34:21):
but you still need the human, right? Tools arenot greater than humans. You need tools plus humans to
be better than just a human by themselves, but it's like anything.
It's like any piece of software, any piece of hardware that you're using foryour business, for your personal life, if you're not in the middle
of it and you're not helping it to enhance, not replace, Ithink that's the big mistake. And I think a lot of people in sales are doing that. I
(34:45):
mean, I get cold emails all the time. Like this was totally AI written, generated,and it's lazy. To me, it's lazy. Use it to be
amazing rather than great. And then I thinkYeah, that's so true. A lot of times when I'm talking about AI,
I try to explain to people the way I use it. Iuse it as an extension of my brain, a thought partner. I
(35:10):
converse with it. In fact, this morning when I went for a hike, Iwas, I had my Bluetooth headphones on and I
was talking to it about strategy, Spartan partner,like just came up with so many, many
great thoughts and ideas, but it was, I wasin control. And I think that's the big lesson that people
(35:36):
But you have to be in control. That's right. I think the other thingthat it does for me, my own personal value of AI,
is that it solves the blank page problem for me. Iam really not good at the blank canvas. My
strength is taking something that exists and lookingat it, evaluating it, and making it better. That's
(35:57):
perfect for AI, because I can talk to, like you just said, I can talkto AI with my stream of conscious thoughts. It can get
me started, and then I can take that and mold itinto what I think is the right response, the right project,
the right goals, the right whatever it is. It can helpme distill and move forward much faster than I would on
(36:17):
my own. So very, very powerful, butYeah, the human needs to be driving the ship. So
what's like, engage, what's oneway you're using AI to move the needle forward
(36:37):
Yeah, so what we do in general iswe help sales teams build amazing content that helps
their sales process move and flow very, very seamlessly. Sotheir sales reps have confidence when they're selling. And we give the
tools to make sure everybody has the right content and then we can measurewhat people are doing with that content. So a lot of people have sent presentations
(36:59):
out to their sales team. They never know if they deliver them. They actually neverknow if they even use them. And they don't know if they maybe
change them and change the marketing message or the images or the waythe presentation is delivered. We give all those tools. Where
does AI help in that? It helps in, number one, idea creation.
That blank page problem, new customers coming to us, they're revampingtheir sales process, they want to embed it into our platform. We
(37:26):
help them using AI to brainstorm, outline,get the crux of the presentation because we
have thousands and thousands andthousands of reps of people using interactive content in the sales process
that we can learn from in order to create a great outline forany new customer. That's one. The second is
(37:47):
we're using it on the analytics side. So as we get data fromall of the different presentations that are being delivered, one of the things
we're working on now hasn't shipped is using AI tolook at that data to make good decisions based on how people
are using the content in the sales process. The other,what we don't wanna do is we don't just wanna wrap AI
(38:09):
around our thing and call us an AI platform. It'sa lazy approach. We wanna look at the data that
we have on our platform that helps train the AI so thatour customers today and our future customers can leverage all
the best practices of what people are doing and having success with. Sothat's our philosophy around is to build moats in our
(38:30):
business around the data that only we have tohelp our current and new customers get up and running as fast
as they can, get as much value as they can, and then solveproblems for them using the knowledge we've gained from all
So I wanna make sure that we point out, that wemake sure people know how to find you and find out more
(38:58):
Yeah, totally. I think the easiest way is Instagram. Ican send it to our website, engage.io with an I, so I-N-G-E.io,
like that's of course, head to the website. ButI think also Instagram has been becoming more and more of
a place that I like to talk with people first, because- Likewise,yeah. A website's kind of a headless thing. And for
(39:22):
some people, that's exactly how they want to learn, which is awesome. Youcan link over to, you know, PreCanDemo, you can get a demo. But
if you're, if you want to connect on Instagram and just message methe word Brett to let me know that that's how you found me, that would be amazing. I'm
So that'd be a great way to connect as well. Yeah, Dean has great content too,folks. So check him out. Dean, recently
(39:49):
I started pivoting more to just something fun atthe end of the show. And we had such a great time here today. I really
enjoyed our conversation. I want to endwith rapid fire questions. Oh, love it. Yeah,
so you tell me the first thing that comes to your mind when Iask these. What's
(40:10):
one book every leader should read? WhatTo Say by Phil M. Jones. Perfect.
What's one mistake you made in leadership that taught you theI slammed my hand on a desk in a meeting one time and I swear I'll never
do it again. What'sone leader you admire and why? Uh,
(40:34):
there's a man, one of my leaders at Apple, his name was John Brandon. SoJohn was the ultimate is a VP of senior vice
president of, of enterprise and worldwide sales. Andhe was, he was everything that you
thought he could be as a, as a leader and evenUh, in, in one sentence, what's the future of
(41:01):
The future of sales enablement is hyper-personalization byIf you weren't leading Engage, what would you be doing right
If money was not an issue and it just myHere's another one. biggest eat the
(41:34):
frog task you do in the mornings? Oh, I work out. Yeah.
Every day. Yeah. Same. One piece of advice youJust be patient. Don't rush the
journey. Be patient. Good things are ahead. Yeah.
Finish this sentence. The best sales leaders in 2030 will?
(41:58):
Be adaptable. I love it. Howcan people connect with, I already asked, but hey,
remember folks, connect with Dean on Instagram, DMhim, Brett. And Dean, it's
been incredible getting to meet you today. And Ireally am glad we connected. I look forward to carrying on
(42:24):
Absolutely. Brett, I appreciate your time and your wisdom. Thanks soThanks for tuning in to The Adaptive Mindset. If you found value in
today's episode, don't forget to subscribe, leave areview, and share it with someone who's ready to thrive in the digital age.
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