October 2, 2025 • 45 mins
This Week's Episode:
In this episode of Software Sales Simplified, hosts Kevin and Matt sit down with John Cavanagh, a seasoned sales professional, to explore the intricacies of software sales, the importance of mentorship, and the evolving landscape influenced by AI. John shares his career journey, highlighting the significance of internships (co-op programs), the value of understanding customer needs, and the qualities of effective sales leaders. The conversation delves into the necessity of empathy in sales, the role of training and role-playing, and the challenges posed by AI in the sales process. John emphasizes the importance of building trust and nurturing relationships in achieving long-term success in sales; success which John stresses requires a seller to remain curious to be effective.
About our Guest - John Cavanaugh:
John Cavanaugh 20 year software sales veteran, primarily in the online learning and HR Tech space. He works with customers to understand business challenges and form a collaborative approach to solve them. A multiple time President’s Club member, he started his career in pre-sales and sales operations before moving to enterprise sales 20 years ago. He currently serves as a Sr. Enterprise Account Executive at Attensi. Attensi is a bleeding edge provider of bespoke situational gaming simulations designed to be immersive, fun, and engaging. The outcomes are enabling behavior change at scale, increasing employee confidence, and measurable business impact.
Where to Learn More About John:
You can find John’s profile on LinkedIn: https://www.linkedin.com/in/johncavanaugh/
Chapters
00:00 Introduction to Software Sales Simplified
01:13 Inspirational Sales Leaders
02:39 John Kavanagh's Career Journey Begins
03:09 The Value of Co-op Programs
04:31 Understanding Their Benefits
05:04 First Co-op: Learning the Sales Landscape
07:08 Navigating Challenges in Early Roles
10:53 Transitioning to Sales
11:53 Culture Shock at Centra Software
14:19 Experiencing Virtual Learning
17:12 Learning from Different Personalities
19:15 Finding Your Unique Style
19:38 The Essence of Effective Selling
21:17 The Role of Leadership
24:05 Building Trust in Sales Relationships
27:33 Navigating the AI Landscape
32:18 The Importance of Customer Advocacy
33:10 Innovative Sales Training Techniques
38:40 Learning from Failures
39:45 Advice for Aspiring Sales Professionals
45:01 Bye for Now!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
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Send us your questions at - Sales@stratsalesllc.com
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:08):
Welcome to Software Sales Simplified Move to Success, your
weekly podcast for sales professionals who want to sell
better. Whether you're a seasoned
professional just starting out, make our podcast your go to
resource for the latest and greatest insights and trends in
the world of enterprise softwaresales.
My name is Kevin Donville, I have over 30 years experience in
(00:31):
software sales development implementation and I am joined
by my good friend and colleague Matt Long, who is also a veteran
of the industry. Matt, how are you doing today?
I'm doing fantastic today, Kevin.
Thank you. Well, it's great to see you and
a wonderful do I have you joining us all the way from the
wonderful world of Hawaii. We got a a guest on the show
(00:52):
today who's going to be sharing some of their perspective.
And before we end up talking with that person, I wanted to
ask you a quick question. Have you ever had a sales leader
that was really inspirational for you really knew how to get
the most out of you? And if you did, how much of what
you learned from that person carried over into your next job
and and when you eventually became a leader yourself?
(01:14):
Sure. Yeah.
I mean, I can think, I can thinkof a couple.
I've been fortunate to have pretty good sales leaders at
companies that have been at. And I think one of the qualities
that goes across all of them is that they really understood
every individual separately, as you know, in terms of what their
strengths were, what their weaknesses were, where they can
(01:35):
apply them, where they needed help.
And I think that's really critical because a lot of times
if you have a, a blanket approach to just training people
or managing people or, or pushing people, right, right.
It doesn't work the same for everyone.
People are motivated by different things.
So I think that's one of the biggest things they took out of
it is the motivation for for everyone is different.
(01:57):
And you really need to understand what that is to get
the most of them. And for sales, of course, that's
critical. So.
No, wholeheartedly agree and I've worked for you in the past.
You've been my boss. You were inspirational for the
career path that I took. So thank you very much for that.
And a lot of what I try to bringto the table reflects what you
taught me. And in order to kind of pass
(02:17):
that along, we're going to be talking with the gentleman who
not only is a top seller in his own right and has had the
opportunity had each so chosen to sit in the captain's chair,
as it were, but he also is a lotof experience with respect to
those training and passing on ofskills as well.
We're joined today by an old colleague of mine, John
Kavanaugh. John, how are you doing today?
(02:39):
I'm doing well. I really appreciate the invite
and happy to talk about my career journey here.
And you know, this has been, this is great.
No, I really appreciate you coming on board.
We're going to be talking about that in a little bit about where
you are now. You know, I'm very familiar with
your, your work history and, andyour trajectory and success over
(02:59):
the years, but our audience probably is not.
So if you wouldn't mind, take a moment, take the floor and tell
everybody a little bit about yourself, where you been, how
you got there and the things youdo and how you do it.
Perfect, perfect. What a what a loaded question
so. I designed by design.
Yes, yes, yes. I guess that's why you have a
podcast here. So essentially when I was
(03:21):
looking at colleges, so we're going way back to 1718 years
old, I had, you know, I have, I got accepted into a few colleges
and I chose a college that had aCo-op program.
I think my theory was what's going to differentiate myself
(03:41):
versus all of these other folks that are going through college?
And I think I recognized early Iwasn't the brightest, I wasn't
the most suave. I need to do something to
differentiate myself and that was why I I chose a college with
a Co-op program and one that wasnot as rigid as like a
(04:02):
Northeastern which I did get into but and not a knock but
they are fairly rigid with theirCo-op.
I ended up going to Merrimack College, which was a smaller
Catholic school in Andover, MA, and they had some flexibility,
which I really liked because I just didn't know what I wanted
(04:22):
to do other than I wanted to go into business.
John, for for those of us that don't understand the term, what
is a Co-op college or program? Yeah, yeah, great question.
So a Co-op, a Co-op program essentially you take semesters
off as part of your college experience.
You take semesters off and you do a Co-op job.
(04:46):
And so you try, you can try out different industries, different
roles. It's a partnership between the
college and many institutions. Or organize business businesses.
And then when you graduate, you know you have some real life
work experience as well as a college degree.
OK. Yeah, fascinating.
So it's almost like a a plan forinternship in that's kind of
(05:09):
interwoven into the curriculum. Interesting.
It is. It is typically it's a five year
program. I had completed my freshman and
sophomore years. I knew at a younger age I wanted
to go into business. I was always fascinated.
I subscribed to Ink magazine in high school.
I was just always really enamored with business and how
(05:29):
transactions get done, innovation, all those things.
And I ended up going my first intern and my first Co-op was at
a company called Salience Associates.
So it's 2002 at this point. the.com bubble had burst.
What Salience did was offer turnkey sales teams.
(05:52):
Essentially they would outsourcethe a particular sector or the
entire sales teamtoa.com. So when I had got there, a lot
of their clients had gone belly up.
It was actually a really tough time my first day.
You know, I have zero business experience and the CEO was
(06:13):
outlining strategy and then lookto me and one other to
understand the value prop of this organization, how to
target, why we should be target targeting it, you know, and and
come up with the point of view. So it was pretty daunting until
I really started understanding why organizations would bring on
(06:34):
a a third party and partner withsalience associates.
What I learned was I did not like that model.
They were not selling. I mean, these were typically
multi, you know, $1,000,000 deals and it was a very tough
market, but it gave me some really important skills.
(06:57):
They taught me how to read 10 KSand read annual reports and find
which organizations we should goafter and where there might be a
good fit for an outsourced salesteam.
What were you looking for in thein the 10 KS?
Was it their strategy or gaps intheir in their business or what?
(07:17):
What kind of things would indicate to you that they were a
good candidate? You know, if they were entering
a new market or expanding into anew market or geographic region
that was, hey, this is a great fit for what we do.
We can hire from your competitors.
We, we probably have a lot of them in our database and then we
(07:38):
can, instead of you partnering with HR and let's say spending
six months to ramp up an entire sales team, we can do it in a
matter of weeks. The challenge was these were
very, very big ticket items and a lot of our client base we're
starting to, to churn. It really taught me how to look
(08:00):
for, you know, how to create a point of view and not just go in
with a widget. You really have to read, study,
get into the customer's mind andread articles.
That was my first Co-op. It ended up, and that was the
summer after my sophomore year. It was the culture there.
(08:20):
It was older, older demographic.Yeah, I remember my manager.
He just became a grandfather. And as someone who's 20, I had,
I could not find common ground with the gentleman.
He was super nice. But you know, it, it, it, it was
a suit and tie culture. And also like 9 to 5 where as
(08:43):
soon as 5:00 hit, people just lined up and went out the door.
It wasn't really for me. I was thinking about leaving and
they ended up going through a reduction in force and then
filing for bankruptcy not too long after that.
But, you know, it was my first kind of time seeing that type
of, you know, emotional impact that it had on people.
(09:05):
People that have been there for a number of years were let go
and you saw a kind of, oh, man, this, this is serious.
You know, people are crying in the hallway.
And you know, it's it's not a decision they took lightly.
I'm sure as business is business, if you don't have
customers, that many customers, you have to adapt.
(09:26):
And unfortunately, that meant reducing the company and then
eventually filing for for bankruptcy.
Yeah, I remember, you know, we're both Kevin and I started
in the.com, you know, in the late 90s, two thousand.
And then that's where I experienced my first round of
layoffs, right. I never experienced that before.
(09:46):
And so it's kind of started thatwhole process of like, wow, this
is a part of the business is that there's the upside and
there's a downside, right. And it does help you prepare a
little bit, but you never quite prepared, you know, when it
happens to you. Absolutely.
I mean it, it it just it it bring it brought some of the
human side of it of OK, it's I never saw a business grow
(10:09):
because it was my first job in in a in a corporate setting.
But you know, it also may realize, OK, there are some
serious like when a customer when you lose a customer, it's
not just, Oh, you know, that stinks.
I wish we could have done something different.
There's real impact to head count and PNL.
That's a great point. Also, it you can study business
(10:32):
all you want and you know, on paper it seems easy, but when I
was there, I think it certainly left an impression on me where I
was like, like sales is so important that if it doesn't
work out, all of these other folks, you know, are out of a
job and they have to figure out what they're going to do next.
(10:53):
So you were, you started out in that marketing world and then
you made that epiphany about howsales really feeds the machine,
right? It and it all starts with sales.
So was that when you decided when you came back in?
Because that's when I, when I first met up with you, that was
the role that you were, you weretaking on.
You were starting that journey in sales when you were making
(11:16):
that, was it a major challenge? Where did you take the sales
immediately? And if so, how did you manage to
fit into that mold so easily andso quickly?
Yeah, yeah. Great, Great question.
So my second Co-op job was at a company called Centra Software
and it could not be more opposite in a good way than
(11:38):
where I had come from. I remember my first day, I'm not
sure if you remember Joe Gordadaria, but he was walking
around in flip flops, a polo anda hemp rope necklace.
And he was the VP of professional services at Centro
when I started. And I was like with that, that's
(11:59):
AVP because I came from a place that was suit and tie.
I saw folks on, you know, scooters around the office.
We had cocktail Thursdays. And so the reason I went there,
I, I had gone back to my Co-op and said I need to do something
like, I just want to be in charge of something.
I felt like I was researching and then I was organizing filing
(12:23):
cabinets like it, it was not very I, I just did not enjoy the
work as much. I liked the research, but it
wasn't paying off. And so there was no, there was
limited satisfaction, right? If we won something, yes, I'm
sure that would be great. But I feel like I, I did all
this time, spent all this time teed it up and it, it never
(12:44):
really went anywhere. And, and again, it's no fault to
the folks on the business side. It was just a tough market
market. I ended up taking a job at
Centra Software. It actually paid $2.00 less an
hour. But they said your day will be
basically using this cutting edge virtual classroom software
(13:08):
and your role will be to interact with different sales
reps all over the world. And it also involves role plays.
You might be helping building out presentations and really
showing that this technology works.
I mean, 2002, that was the days of 56 K dial up and that was our
(13:30):
that was part of the value prop of Centra software was hey, we
download a lot of the content and the application prior to
launch so that it can operate ona 56 K dial up.
And I feel like a lot of those early meetings were just proving
that the technology works. And for me, I just thought
(13:51):
immediately, this is the future.I mean, using your computer to
see one another to share an application, you know, breakout
rooms when that came out, I was like, this is this is crazy.
It was such a pioneering technology.
And again, this is we were bigger than Webex back then.
(14:13):
You know, we were one of The Pioneers in that space targeted
towards learning and so. I think so Central was kind of a
communication type software thatyou could do with teams and
share, share documents and things like that.
Is that correct? Yeah, Yeah.
Yeah, I will. I would have the caveat that we
(14:34):
were a learning company. So Webex came at it with as
we're a meeting platform. We had an E meeting products,
but our core competency was e-learning and and virtual
classroom training, replicating the physical classroom on APC
(14:55):
with the webcam. And it really, you know, it's,
it's more of a niche, right, Because what you know, meetings,
everyone has meetings. When you get into e-learning and
training, it's a narrower focus.But that was really, you know,
our secret sauce, I think. You actually use your platform
to train the sales people, whichessentially was helping them
(15:15):
understand the value of it. But I imagine for you that was
great experience, right? Because you saw first hand how
this could move the needle, whatthe value was and the benefits
and all these things that you can articulate very well.
Absolutely. I mean we would and so
technically it was pre sales, right.
So I would be sitting in Lexington, MA and I would work
(15:38):
late. Sometimes we would have meetings
in California and then I would stay really late and help out
Australia. And for me, I'm like, I just met
with three Fortune 5. And you'd have kind of the
capabilities demos and then you'd have the role plays of
here's how you do executive leadership training on the
virtual classroom versus the, instead of flying all of your
(16:01):
leaders to one location and doing this.
And you know, we had ROI calculators and this was the
alternative was computer based training, send out ACD ROM.
I mean, it's not interactive. It's that didn't really catch
you on too well, as you can imagine.
And so, so you could have a capabilities demo where you're
just walking through functionality and then the
(16:22):
really good reps, which was probably the best part was just
getting exposed to all the different personalities.
You could have folks that were really smart, some that were
really funny, charismatic, others that were just into more
of the analytical side. And it just gave me some great
exposure of all of the differentpersonalities that were
(16:44):
successful or could be successful and how they kind of
get the customer to understand how this could fit in their
ecosystem. And that was really, you know,
just one of my, I loved going towork every day, let's put it
that way, because I was learning, I was seeing business
in real time. We're talking about real issues,
real business challenges that could be solved by this.
(17:05):
And you know, they were enterprise type deals for in a
corporate setting. Did you formulate an opinion at
that point as to which personality type or approach
worked best or and and did that change over time or was it just,
you know, you just got to see a lot of different approaches?
Great question. I think I tried to emulate
(17:28):
others for a period of time until I found my own voice.
I think that's, that's somethingthat, you know, it took me a
little while. You know, I, I won't mention his
name, but there was a British fellow and Kevin, you may
remember, and he he was hilarious.
He knows him. He knows him.
OK. Yes.
(17:49):
Name shall remain nameless to protect the innocent.
But yes, Hilarious. Wonderful chap.
Great biting. That's true.
Very true. Yeah.
So I knew and he would go in a room and he would swear and he
would have dirty stories and have everyone rolling.
I mean it was like a stand up special every time he presented
(18:13):
and people loved him and he was successful.
And then others, you know, were a little more serious, business
oriented, but there was a level of trust.
So I kind of saw both sides of, you know, OK, like you don't
have to fit into a corporate mold.
Be yourself. If you're funny, be funny if
(18:34):
you're more of an analytical person, just be that.
Whatever's you know, whatever you are and how you, your
approach to things, just be that.
And I think that was the lesson I, I learned was you don't have
to be XY or Z to be successful. It's all about human connection.
And the only way to do that is to be yourself.
So that I think was a unique kind of training experience
(18:58):
because every day I was, I was meeting with different folks and
executives, training leaders around the world.
And it was just a, an unbelievable training ground to
start out when I, when I, when Iwas there.
So you got, you had this wonderful kind of introduction
(19:20):
into the world. You got exposed to all kinds of
different styles and you found that there's not just one way,
right? There's multiple different paths
of someone can go down. Let's spin the clock forward.
You're now a veteran of selling in the marketplace is
particularly in your own space. How much of what you saw then is
true today with respect to what makes a good seller?
(19:44):
Is it that ability to understandwhat you're good at and to be
comfortable in your own skin? Or are there is there a little
bit more of a nuance around tactics and methodologies as
well? I would argue the first
statement that it is the most important, making those
connections, striving to understand what the customer
(20:05):
cares about. Methodologies are important, but
a good methodology without connection and trust and really
making those connections, it's going to fall flat.
And so that was that. That's something I think I don't
care where technology and AI goes.
We are still humans. And we need to connect with each
(20:26):
other as humans. And each of those personalities
or personas that I had mentionedearlier, they had that ability
to really connect, understand, put themselves in the customer's
shoes and have a level of empathy too, with maybe some of
the challenges they had, ask those second level questions and
then present how we can potentially solve that together.
(20:48):
Yeah, fantastic. I make I, I really think you
just put together a recipe book in that little, that little
description there about how folks are going to be able to be
successful. Because Matt and I are very big
on being able to understand if you can figure out what is the
problem that's keeping the customer up at night, that's
preventing them from being successful and keeping them from
(21:10):
their objective and then presentto that person.
Here's the path to to remedying that you gone and taken this
from being a conversation about selling something and all about
partnering towards success and solution and relief going
forward. How let's flip that around a
(21:32):
little bit. So now we understand Kate, what
what makes it good for a seller?What kind of leaders are the
best at being able to bring thatout of people?
Do you think with respect to of sales teams, because we've
worked for a lot of different kinds of personalities over the
years? Yeah, yeah.
And you know, I've been super fortunate in almost every role
(21:55):
to have a really good leader that to really.
And what I look for is someone Ican learn from, whether it's
skills, approach, how do I get better in in my job?
What don't I know? And I think a part of that is
checking the ego at the door. It's something that probably
took me a little while to do. A level of hubris, especially if
(22:17):
you've had success of I know what I'm doing and I've done
this before. Just, you know, for folks just
starting out, just try to take that out of it and just learn.
Always be a student and if thereis something you can learn from
a leader, embrace it. Don't look at it as a threat or
get defensive. Embrace criticism.
(22:39):
Certainly, you know, that that'ssomething that I think it takes
some years and some thicker skinto realize like, hey, they're
doing this to to help me insteadof, you know, as long as they do
it in the correct way. And, and that's really what I
look for someone who's a, you know, being a great sales leader
in all of the attributes that I mentioned across all of these
different leaders that I've worked for, all of them, one had
(23:01):
trusted me. They were not micromanaging, you
know, they were, they were therewas a level of trust.
There was a level of coaching and hey, maybe you should think
of, you know, building this particular skill at, you know,
(23:23):
in your job, so kind of challenging you to get better.
That's something I think that asI look at and some of them, you
know, would teach me a, a skill,something I, you know, I, I can
learn. So I'm actually learning too.
I'm not just, they're not just saying, you know, you need to
brush up on how to leverage AI in your sales process, right?
(23:43):
They're saying, hey, here's how I do it.
Here's what some of the innovators in this space are
doing. You know, why why don't we sit
down for a little bit and I'll show you some practical examples
of how this can help as you're, as you're doing your job.
That is the number one thing is just, you know, having your back
and being a really collaborativecoach.
(24:05):
Yeah. Getting back to that trust
though, because that's a common theme, you know, in any
relationship, right? I'm curious, do you think that
you earned that trust, This is why he gave it to you or that
leader was just a general genuinely trustworthy person or
how did that come about? And if you, if you did earn it,
what was it about you or your approach that that warranted
that? Great, great question.
(24:27):
I think trust is earned, right? It's it's tough on day one to
say, you know, let me let me do my thing.
You know, it, it comes with it'sa gradual process to really
build that trust. And some leaders I've worked
with, you know, adjacent for a while.
So when they became my particular leader, there was
already that level of trust. It could because we were
(24:49):
colleagues and then they were, you know, potentially promoted
or just org, org shifts and theywere above me.
And, you know, it's almost like leading from the front where,
you know, hey, here's how to here's my approach, here's how
we do it together. So yeah, definitely, you know,
positive influence with all the leaders I've worked.
(25:10):
With yeah, definitely. I know there are a lot of
different kinds of management styles.
There's those that delegate and there's those, as you say, lead
from the front. I know which style I prefer.
I much prefer someone sitting next to me in the trenches,
someone I can learn from, observe and pick up those skills
passively and actively from. But not everybody, you know, has
(25:30):
that particular makeup in their in their repertoire.
But nonetheless, I follow what you're saying.
If I can paraphrase and tell me if I'm getting this right, a
good sales leader is as much coach and teacher as they are
executor of the sales strategy out in the field as well.
And they invite that trust. Is that a fair representation of
(25:53):
what you're saying? Makes up the, in your mind, an
ideal sales leader? Kevin, you that is the succinct
answer that I was hoping to give, but I rambled on.
But yes, that that exactly is what we're you know, to to
really paraphrase down to 2 words coach and close, you know,
coach me on being better help meclose business.
(26:16):
That that is the the two word answer to even make your your
answer even more succinct. Totally believe that.
That's what I look for, especially as, you know, I may
want more if I'm just starting out, but as someone who's been
doing this for a period of time,you know, coaching and closing
that, that's what I look for in leadership.
Yeah, someone who sat on both sides of that equation, both
(26:39):
being and by the way, that the whole ability to develop and
build people and and and make them better sellers is largely
what drove drew me into sales leadership and what was my
motivation. So I I understand that
perspective. It's interesting though, in
today's day and age, we've got asituation where those abilities
(27:01):
to have that kind of exchange asboth the individual contributor
and the manager can sometimes becompromised, right, because of
just the demands of the job and doing less with more.
In your industry in particular, I mean, you guys focus and
specialize. The tool you're working with now
is all about training, all aboutskills development, right?
(27:21):
There's a lot of pressure in themarketplace now to do less with
more, and AI seems to be complicating things,
particularly in your space. How are you seeing that, both
with respect to what you're trying to sell and also with
respect to your ability to get what you need from your sales
(27:43):
leaders? Now that's a pretty broad
question, but you know, I'm curious.
You know, AI is in every industry.
It's a big buzzword. I think people have a hard time
deciphering how AI can help themin particular, because every
vendor, you know, everyone is just AIAIAII think that as I
(28:11):
look, there's there's a couple things that are happening that I
see. One, the pace of innovation is
skyrocketing. I mean, you know, in our, I'm at
a company named called the Tennessee where we can have, and
it came out maybe a little over a year ago, virtual AI
conversations with a, with an avatar, right?
(28:34):
And it's using a Gentek AI to look at all of these multiple
areas of trying to replicate an authentic human conversation.
So from that, from that standpoint, it's making the pace
of innovation shorten. I mean, it's, it's, it's amazing
just how advance has been. I, I've been at the organization
(28:56):
for six months and I mean it's revolutionizing everything.
We're incorporating it in other e-learning products and really,
you know, just on sitting on that bleeding edge of what is
possible within corporate learning.
I think on the other side of howit's been a challenge from a
customer standpoint, there's so much automation and AI, it
(29:21):
allows reps to cast a wider net,make it more relevant.
And just the sheer amount of messaging, whether it's through
LinkedIn, e-mail, it's, I think it makes it a bit tough for a
potential customer to sift through.
What is everyone saying, AI? How do I sift through all of
(29:42):
these, all this different messaging that I'm getting?
And I, you know, my point of view is just the level of
outreach, you know, to executives is just exponentially
higher than it was maybe 10 years ago.
Do you think that even with it'sfunny that you're mentioning
this and it actually coincides with some things we've heard
from some of our most recent guests on here.
(30:04):
It's like we're getting more, but it's actually in many cases
less actionable because of the fact that there's this this
deluge. And even though AI purports to
being able to help you sift through it, if AI is creating
it, are you, are you coming out with a net neutral at the end of
the day? So how do you how do sellers
(30:24):
like you then engage with your prospects and help them make
sense of just the sheer noise toto really get to here's my
problem and here's what I need, how I need to solve it.
Yeah. And we've had these discussions
internally too, because some of the traditional ways of selling
calls, emails, LinkedIn, it's tough to breakthrough,
(30:47):
especially to a certain industries that are really tight
knit. So one of the things that we're
doing is really just being of the industry.
So we're looking at where we've had success, how do we turn
customers into advocates and share their story?
Because that is, and it's going back to basics, right?
(31:08):
This hasn't changed. If I'm buying a Ford F-150 or
I'm thinking about buying a FordF-150, I might call my two
friends that have Ford F1 fifties to see what their
thoughts are. It's the same type of, you know,
basic human connection that we're that we're trying to
leverage, right? Is how do we get into those
networks, become a, you know, become of the industry?
(31:30):
We're not just selling, but we're trying to give something,
whether it's knowledge or insight, Hey, here's how you
know, so and so who's very similar to you is approaching
this potential problem. And now we're adding value.
And we're not just, you know, trying to sell.
You're right. We're, we're, we're adding value
along the way, hopefully. And when they are ready to buy,
(31:54):
we'll be, we'll be top of mind. And if they call colleagues,
hey, I'm having this challenge. Hopefully their colleague, if
we're doing the, if we're doing things the right way, will say,
hey, you got to call this this organization.
I've had two friends or two folks in the industry that I'm
connected with that have had really good results by
(32:17):
partnering with said organization.
Yeah, I, I go ahead, go ahead. I'm.
Sorry, so you're. The software that you're selling
now and inside for a while, it'shas a lot to do with training
people, right? Is it yes, and I'm just curious,
you know, just from a, from a sales perspective and training
people, you know, it's, it's oneof the things that Kevin and I
(32:37):
care a lot about. But you know, how, how effective
is it for those types of things?Because there's certainly
knowledge, right, and information that I think AI is
really good at distilling down and summarizing and giving you
bullet points and things that you can consume.
Then of course, there's the nuances of the sale sales for
(32:59):
people themselves, which we've been talking about, right, which
I don't think it does a very good job of that, right?
So what in your mind what makes it for effective sales training
using these new platforms? Great.
Great question. So there is always a need, I
think to build that foundationalknowledge.
You know, whether it's reading, hearing, seeing videos, E
(33:21):
learnings, there's always a place to kind of build that
baseline. You know, over the last 10
years, I've seen one of the mostpopular courses from an
e-learning standpoint be situational leadership.
My opinion, you should have situational everything because
you can have all the theory in the world, but until you are in
that particular situation, you may not know how to react.
(33:42):
And that is something that I think we found that a sweet spot
where we put sales people in particular situations and they
have to find their way out, whether it's through a game and
it's all game based. So whether it's pick your own
adventure, what decisions will you make to win the deal went
(34:03):
over the customer or using conversational AI, how do you
deal with objections? You've read about it, but it's
almost like the Mike Tyson quote.
You know, everything changes once you get hit in the face.
What happens when someone is yelling at you, you know,
depending on what you're selling?
What if they are just not sayinganything and they're quiet?
So we can tweak different personalities and, and really
(34:25):
just put people in different situations that are relevant to
their business. It's relevant to the products
they're selling. And really that's what builds
confidence when going out into the real world because the
alternative is going in the realworld and potentially failing,
which is very, very costly to businesses or potential role
(34:47):
plays where again, are very expensive.
Typically leaders have to be evaluated by other senior
leaders. And you know, it's funny, we
have all this technology and youknow, we analyze everything.
But then when you, when you do arole play, we have this piece of
paper and we score it. And I, I have conversations
(35:07):
daily with organizations that spent millions on their training
tech stack. But then when it comes to things
like role plays and putting people in those situations, Oh
yeah, we have a recording on teams and this piece of paper
that we evaluated and the data goes nowhere.
So that's the particular gap that we're we're filling is just
(35:29):
exposing folks to different situations, not just from a
leadership perspective, but sales service, you know, and
pick something that is, you know, relevant, you know,
they're important to a company and we can create that scenario.
Yeah. I love that.
I'd never really thought of thatbefore, but you know, it's, it's
role-playing at scale. And I imagine that you can tune
(35:52):
these agents to, to throw out different types of things,
etcetera, as well. I remember, you know, back in,
back in the day, you know, my father worked for the State
Department. You know, it's the counselor's
office and embassies overseas and stuff like that.
You know, when people are tryingto get into that program, the
counselor program, the process is super complex and super
(36:15):
arduous and intensive. But it wasn't really about so
much. What you knew is like, how would
you respond in these situations?Right?
And I remember one of the questions my dad told me about,
it's just like when I was, you know, my teens, he's like, you
know, the question was, you know, you have limited amount of
air conditioners, window air conditioners, right?
And everyone's, there's a long queue for them.
(36:36):
And the ambassador wife comes toyou and says, I want an air
conditioner. How do you handle that?
Right? And it's like, that's the kind
of stuff where you just got to think there's no right or wrong
answer necessarily, right? I mean, there's protocol and
stuff, but there's no right. But like, what is your process
for dealing with this? A personal authority demanding
preferential treatment? There's a process.
(36:57):
How do you, what do you do? And I think for sales it's, it's
certainly applicable. So I, I love that aspect of that
because I, I think that it is something that's very scalable.
Yeah. And and that's really, you know,
when when we get asked like whatis the value prop, it's behavior
change at scale. How do we replicate the
behaviors? What does great look like?
(37:18):
And then how do we replicate those behaviors at scale?
And again, it doesn't have to besome enterprise sale.
It could be buying a cell phone.One of our clients is a hotel
chain and they took all the swear filters off.
They want a customer service Repat this hotel chain to really
feel what it's like when an irate customer who hasn't had
(37:40):
any sleep because of an issue with their hotel room.
They want to, they want to put them in that situation where
they're sweating because someoneis furious and screaming their
head off. And you know, they need to teach
them in that high pressure situation, how do you
deescalate? And and you know, for I guess to
be cheesy, turn that frown upside down.
(38:02):
Yeah, I worked night out at a hotel for years, 12 to 8 shift.
I know that pain very well. Well, it it's you have some.
Stories. One of the things we always talk
about in sales is you learn a lot more from your your failures
in many cases than you do from your successes because you have
to breakdown what went wrong andyou have to provide a different
(38:23):
lens and really systematically break that down.
What I love what about you're talking about, it's not just the
scale of what you're doing it. It's also it's mitigating
consequence and risk. Because to your point, you can
either learn it in the wild and if you get it wrong, you'll
learn the lesson, You'll learn what not to do, but the
consequences can be dire. But now you can do that at scale
(38:44):
where the opportunity, where theimpact and consequence and
ramifications of failure isn't going back to what you were
talking about at the beginning of our discussion today, people
in the hallway losing their jobs.
Yeah, Yeah. I mean, that's because as you
said, failure in sales can have,depending on the role, can have
some serious ripple effects. And that again, that was the
(39:06):
first lesson I had in that firstCo-op job.
John, I really appreciate you. You really kind of brought some
interesting elements to the table today and this last one
being no exception. So I really appreciate the
perspective you've been bringingin here today and opening our
eyes to some other potential andsome some real positive things.
(39:27):
You know, we do have to start bringing our our session to a
close unfortunately. And I wanted to quickly ask you
if someone wanted to get startedthe industry, I mean, you
obviously you had the opportunity of bringing that up
through your university, but what advice would you give to
somebody who's trying to do thatthese days?
How? How would they get started?
I think it starts with finding areally good company.
(39:49):
You know, you are interviewing them as much as vice versa.
You know, just really look for some, you know, a company that
has a good culture and a leader that is you can learn a lot
from. A good coach essentially, those
are the two big factors that I've I've learned and I've, you
know, I, I've had some really good leaders, some really good
(40:09):
companies and, you know some, some maybe not as much in my
background. And so, you know, really find
those two things and just be open to learning, be curious and
make, make in nurture relationships.
That's one thing. I mean, Kevin, we, I was
(40:31):
looking, I mean, we met over 20 years ago at this point and I
was looking. We, we, we, we touch base like
every 5-6 years, right? You know, and again, that's
something I can do better is just nurture those
relationships. But when you're just starting
out, I mean, there's folks that,you know, I, I haven't worked
(40:56):
with in 20 years and but there'sstill that trust in connection
because 20 years ago, 25 years ago, we had some really good
conversations and we both kind of reflect on that.
And it's all about relationshipsinternally and learning from
each other. So really just focus on that.
(41:18):
Don't think of it as just a job,but thinking, think of it as I'm
getting to know some really goodpeople.
Find those people that you can learn from.
And if you can make that connection, I'm telling you in
you never know, in 20-30 years you may cross paths again.
And that's certainly the case, you know, even with with this
Kevin. So that would be my advice is
(41:40):
just, you know, be curious, makethose connections, learn from,
you know, mentors, as I'm not sure if any of us would be here
if we didn't have strong mentorsto really show us how to get to
the next level and level up our own games.
So yes, rambling on as usual, but you know, I, I really, I
really believe in that. As do I, So John, if someone
(42:05):
wanted to get some additional advice, maybe reach out to you
for some mentoring, what's the best way for them to connect
with you? Best way is probably on
LinkedIn. I am on it constantly at, you
know, connected with more people.
I was just at a networking eventlast week in an industry that
I'm concentrating on. Just really trying to make
connections and give myself credibility.
(42:27):
I'm going to another industry specific content conference in
two weeks to really just immersemyself in that, in that world as
well. Nothing to do with software
sales, but networking is super important to me.
I think that was part of my brand throughout the years is he
(42:47):
knows a lot of people, he's wellnetworked.
I do enjoy it. And you know, LinkedIn is the
best place to start and I will. I am super responsive on on
LinkedIn and happy to mentor or any others as I've been
fortunate enough to have many great mentors throughout my
career. Well, very much appreciated that
(43:09):
perspective. And yes, I, we've had, we've
shared some of those great mentors and people that we've
learned from along the way. I have one of them who I have
the benefit of being my Co host every week when we come in to do
these shows. And Speaking of which, Matt,
before we go and wrap up today, anything you'd like to add to
the conversation or the commentsthat John just made?
No, not really, other than it's been a pleasure.
(43:29):
John really enjoyed the conversation and hearing a
little bit about your approach. It's brought back a lot of
memories of different things in my life as well, so it's good
talking with you. Including crazy Brits that
really know how to sell software.
Common experience. Three of us, obviously.
Well, John, it is funny. It is absolutely a small world.
(43:52):
You know, that's an interesting thing.
And this is from I haven't worked with him since 2006,
maybe 2005. So we're talking 20 years ago.
And again, lasting impression ofsomeone who does things a bit
different, but it works. Absolutely, absolutely had his
own style in it when he knew howto work that style.
(44:13):
And everyone needs to go and find that to the point that you
just made. But ladies and gentlemen, as
much as I'm enjoying this conversation with John and I
appreciate you going and, and opening our eyes to a couple of
different things that maybe we hadn't considered and bring up
some points that we knew, but maybe giving us a different
angle on. So John, thank you so much for
being with us here today and being our guest and sharing your
experiences and your insight. It was really fantastic and
(44:37):
thank you again for coming in. And ladies and gentlemen, if you
like what you heard here today, please leave a comment like
follow, subscribe costs you nothing and it really helps out
the channel or go to our websiteand buy our methodology book
there that is outlines why Matt and I have been so successful in
the past on our journey with respect to software sales.
But until we see you again next week, thank you very much for
(44:58):
spending a little bit of time and we'll see you again soon.
Welcome to Software Sales Simplified Move to Success, your
weekly podcast for sales professionals who want to sell
better. Whether you're a seasoned
professional just starting out, make our podcast your go to
resource for the latest and greatest insights and trends in
the world of enterprise softwaresales.
My name is Kevin Donville, I have over 30 years experience in
(00:31):
software sales development implementation and I am joined
by my good friend and colleague Matt Long, who is also a veteran
of the industry. Matt, how are you doing today?
I'm doing fantastic today, Kevin.
Thank you. Well, it's great to see you and
a wonderful do I have you joining us all the way from the
wonderful world of Hawaii. We got a a guest on the show
(00:52):
today who's going to be sharing some of their perspective.
And before we end up talking with that person, I wanted to
ask you a quick question. Have you ever had a sales leader
that was really inspirational for you really knew how to get
the most out of you? And if you did, how much of what
you learned from that person carried over into your next job
and and when you eventually became a leader yourself?
(01:14):
Sure. Yeah.
I mean, I can think, I can thinkof a couple.
I've been fortunate to have pretty good sales leaders at
companies that have been at. And I think one of the qualities
that goes across all of them is that they really understood
every individual separately, as you know, in terms of what their
strengths were, what their weaknesses were, where they can
(01:35):
apply them, where they needed help.
And I think that's really critical because a lot of times
if you have a, a blanket approach to just training people
or managing people or, or pushing people, right, right.
It doesn't work the same for everyone.
People are motivated by different things.
So I think that's one of the biggest things they took out of
it is the motivation for for everyone is different.
(01:57):
And you really need to understand what that is to get
the most of them. And for sales, of course, that's
critical. So.
No, wholeheartedly agree and I've worked for you in the past.
You've been my boss. You were inspirational for the
career path that I took. So thank you very much for that.
And a lot of what I try to bringto the table reflects what you
taught me. And in order to kind of pass
(02:17):
that along, we're going to be talking with the gentleman who
not only is a top seller in his own right and has had the
opportunity had each so chosen to sit in the captain's chair,
as it were, but he also is a lotof experience with respect to
those training and passing on ofskills as well.
We're joined today by an old colleague of mine, John
Kavanaugh. John, how are you doing today?
(02:39):
I'm doing well. I really appreciate the invite
and happy to talk about my career journey here.
And you know, this has been, this is great.
No, I really appreciate you coming on board.
We're going to be talking about that in a little bit about where
you are now. You know, I'm very familiar with
your, your work history and, andyour trajectory and success over
(02:59):
the years, but our audience probably is not.
So if you wouldn't mind, take a moment, take the floor and tell
everybody a little bit about yourself, where you been, how
you got there and the things youdo and how you do it.
Perfect, perfect. What a what a loaded question
so. I designed by design.
Yes, yes, yes. I guess that's why you have a
podcast here. So essentially when I was
(03:21):
looking at colleges, so we're going way back to 1718 years
old, I had, you know, I have, I got accepted into a few colleges
and I chose a college that had aCo-op program.
I think my theory was what's going to differentiate myself
(03:41):
versus all of these other folks that are going through college?
And I think I recognized early Iwasn't the brightest, I wasn't
the most suave. I need to do something to
differentiate myself and that was why I I chose a college with
a Co-op program and one that wasnot as rigid as like a
(04:02):
Northeastern which I did get into but and not a knock but
they are fairly rigid with theirCo-op.
I ended up going to Merrimack College, which was a smaller
Catholic school in Andover, MA, and they had some flexibility,
which I really liked because I just didn't know what I wanted
(04:22):
to do other than I wanted to go into business.
John, for for those of us that don't understand the term, what
is a Co-op college or program? Yeah, yeah, great question.
So a Co-op, a Co-op program essentially you take semesters
off as part of your college experience.
You take semesters off and you do a Co-op job.
(04:46):
And so you try, you can try out different industries, different
roles. It's a partnership between the
college and many institutions. Or organize business businesses.
And then when you graduate, you know you have some real life
work experience as well as a college degree.
OK. Yeah, fascinating.
So it's almost like a a plan forinternship in that's kind of
(05:09):
interwoven into the curriculum. Interesting.
It is. It is typically it's a five year
program. I had completed my freshman and
sophomore years. I knew at a younger age I wanted
to go into business. I was always fascinated.
I subscribed to Ink magazine in high school.
I was just always really enamored with business and how
(05:29):
transactions get done, innovation, all those things.
And I ended up going my first intern and my first Co-op was at
a company called Salience Associates.
So it's 2002 at this point. the.com bubble had burst.
What Salience did was offer turnkey sales teams.
(05:52):
Essentially they would outsourcethe a particular sector or the
entire sales teamtoa.com. So when I had got there, a lot
of their clients had gone belly up.
It was actually a really tough time my first day.
You know, I have zero business experience and the CEO was
(06:13):
outlining strategy and then lookto me and one other to
understand the value prop of this organization, how to
target, why we should be target targeting it, you know, and and
come up with the point of view. So it was pretty daunting until
I really started understanding why organizations would bring on
(06:34):
a a third party and partner withsalience associates.
What I learned was I did not like that model.
They were not selling. I mean, these were typically
multi, you know, $1,000,000 deals and it was a very tough
market, but it gave me some really important skills.
(06:57):
They taught me how to read 10 KSand read annual reports and find
which organizations we should goafter and where there might be a
good fit for an outsourced salesteam.
What were you looking for in thein the 10 KS?
Was it their strategy or gaps intheir in their business or what?
(07:17):
What kind of things would indicate to you that they were a
good candidate? You know, if they were entering
a new market or expanding into anew market or geographic region
that was, hey, this is a great fit for what we do.
We can hire from your competitors.
We, we probably have a lot of them in our database and then we
(07:38):
can, instead of you partnering with HR and let's say spending
six months to ramp up an entire sales team, we can do it in a
matter of weeks. The challenge was these were
very, very big ticket items and a lot of our client base we're
starting to, to churn. It really taught me how to look
(08:00):
for, you know, how to create a point of view and not just go in
with a widget. You really have to read, study,
get into the customer's mind andread articles.
That was my first Co-op. It ended up, and that was the
summer after my sophomore year. It was the culture there.
(08:20):
It was older, older demographic.Yeah, I remember my manager.
He just became a grandfather. And as someone who's 20, I had,
I could not find common ground with the gentleman.
He was super nice. But you know, it, it, it, it was
a suit and tie culture. And also like 9 to 5 where as
(08:43):
soon as 5:00 hit, people just lined up and went out the door.
It wasn't really for me. I was thinking about leaving and
they ended up going through a reduction in force and then
filing for bankruptcy not too long after that.
But, you know, it was my first kind of time seeing that type
of, you know, emotional impact that it had on people.
(09:05):
People that have been there for a number of years were let go
and you saw a kind of, oh, man, this, this is serious.
You know, people are crying in the hallway.
And you know, it's it's not a decision they took lightly.
I'm sure as business is business, if you don't have
customers, that many customers, you have to adapt.
(09:26):
And unfortunately, that meant reducing the company and then
eventually filing for for bankruptcy.
Yeah, I remember, you know, we're both Kevin and I started
in the.com, you know, in the late 90s, two thousand.
And then that's where I experienced my first round of
layoffs, right. I never experienced that before.
(09:46):
And so it's kind of started thatwhole process of like, wow, this
is a part of the business is that there's the upside and
there's a downside, right. And it does help you prepare a
little bit, but you never quite prepared, you know, when it
happens to you. Absolutely.
I mean it, it it just it it bring it brought some of the
human side of it of OK, it's I never saw a business grow
(10:09):
because it was my first job in in a in a corporate setting.
But you know, it also may realize, OK, there are some
serious like when a customer when you lose a customer, it's
not just, Oh, you know, that stinks.
I wish we could have done something different.
There's real impact to head count and PNL.
That's a great point. Also, it you can study business
(10:32):
all you want and you know, on paper it seems easy, but when I
was there, I think it certainly left an impression on me where I
was like, like sales is so important that if it doesn't
work out, all of these other folks, you know, are out of a
job and they have to figure out what they're going to do next.
(10:53):
So you were, you started out in that marketing world and then
you made that epiphany about howsales really feeds the machine,
right? It and it all starts with sales.
So was that when you decided when you came back in?
Because that's when I, when I first met up with you, that was
the role that you were, you weretaking on.
You were starting that journey in sales when you were making
(11:16):
that, was it a major challenge? Where did you take the sales
immediately? And if so, how did you manage to
fit into that mold so easily andso quickly?
Yeah, yeah. Great, Great question.
So my second Co-op job was at a company called Centra Software
and it could not be more opposite in a good way than
(11:38):
where I had come from. I remember my first day, I'm not
sure if you remember Joe Gordadaria, but he was walking
around in flip flops, a polo anda hemp rope necklace.
And he was the VP of professional services at Centro
when I started. And I was like with that, that's
(11:59):
AVP because I came from a place that was suit and tie.
I saw folks on, you know, scooters around the office.
We had cocktail Thursdays. And so the reason I went there,
I, I had gone back to my Co-op and said I need to do something
like, I just want to be in charge of something.
I felt like I was researching and then I was organizing filing
(12:23):
cabinets like it, it was not very I, I just did not enjoy the
work as much. I liked the research, but it
wasn't paying off. And so there was no, there was
limited satisfaction, right? If we won something, yes, I'm
sure that would be great. But I feel like I, I did all
this time, spent all this time teed it up and it, it never
(12:44):
really went anywhere. And, and again, it's no fault to
the folks on the business side. It was just a tough market
market. I ended up taking a job at
Centra Software. It actually paid $2.00 less an
hour. But they said your day will be
basically using this cutting edge virtual classroom software
(13:08):
and your role will be to interact with different sales
reps all over the world. And it also involves role plays.
You might be helping building out presentations and really
showing that this technology works.
I mean, 2002, that was the days of 56 K dial up and that was our
(13:30):
that was part of the value prop of Centra software was hey, we
download a lot of the content and the application prior to
launch so that it can operate ona 56 K dial up.
And I feel like a lot of those early meetings were just proving
that the technology works. And for me, I just thought
(13:51):
immediately, this is the future.I mean, using your computer to
see one another to share an application, you know, breakout
rooms when that came out, I was like, this is this is crazy.
It was such a pioneering technology.
And again, this is we were bigger than Webex back then.
(14:13):
You know, we were one of The Pioneers in that space targeted
towards learning and so. I think so Central was kind of a
communication type software thatyou could do with teams and
share, share documents and things like that.
Is that correct? Yeah, Yeah.
Yeah, I will. I would have the caveat that we
(14:34):
were a learning company. So Webex came at it with as
we're a meeting platform. We had an E meeting products,
but our core competency was e-learning and and virtual
classroom training, replicating the physical classroom on APC
(14:55):
with the webcam. And it really, you know, it's,
it's more of a niche, right, Because what you know, meetings,
everyone has meetings. When you get into e-learning and
training, it's a narrower focus.But that was really, you know,
our secret sauce, I think. You actually use your platform
to train the sales people, whichessentially was helping them
(15:15):
understand the value of it. But I imagine for you that was
great experience, right? Because you saw first hand how
this could move the needle, whatthe value was and the benefits
and all these things that you can articulate very well.
Absolutely. I mean we would and so
technically it was pre sales, right.
So I would be sitting in Lexington, MA and I would work
(15:38):
late. Sometimes we would have meetings
in California and then I would stay really late and help out
Australia. And for me, I'm like, I just met
with three Fortune 5. And you'd have kind of the
capabilities demos and then you'd have the role plays of
here's how you do executive leadership training on the
virtual classroom versus the, instead of flying all of your
(16:01):
leaders to one location and doing this.
And you know, we had ROI calculators and this was the
alternative was computer based training, send out ACD ROM.
I mean, it's not interactive. It's that didn't really catch
you on too well, as you can imagine.
And so, so you could have a capabilities demo where you're
just walking through functionality and then the
(16:22):
really good reps, which was probably the best part was just
getting exposed to all the different personalities.
You could have folks that were really smart, some that were
really funny, charismatic, others that were just into more
of the analytical side. And it just gave me some great
exposure of all of the differentpersonalities that were
(16:44):
successful or could be successful and how they kind of
get the customer to understand how this could fit in their
ecosystem. And that was really, you know,
just one of my, I loved going towork every day, let's put it
that way, because I was learning, I was seeing business
in real time. We're talking about real issues,
real business challenges that could be solved by this.
(17:05):
And you know, they were enterprise type deals for in a
corporate setting. Did you formulate an opinion at
that point as to which personality type or approach
worked best or and and did that change over time or was it just,
you know, you just got to see a lot of different approaches?
Great question. I think I tried to emulate
(17:28):
others for a period of time until I found my own voice.
I think that's, that's somethingthat, you know, it took me a
little while. You know, I, I won't mention his
name, but there was a British fellow and Kevin, you may
remember, and he he was hilarious.
He knows him. He knows him.
OK. Yes.
(17:49):
Name shall remain nameless to protect the innocent.
But yes, Hilarious. Wonderful chap.
Great biting. That's true.
Very true. Yeah.
So I knew and he would go in a room and he would swear and he
would have dirty stories and have everyone rolling.
I mean it was like a stand up special every time he presented
(18:13):
and people loved him and he was successful.
And then others, you know, were a little more serious, business
oriented, but there was a level of trust.
So I kind of saw both sides of, you know, OK, like you don't
have to fit into a corporate mold.
Be yourself. If you're funny, be funny if
(18:34):
you're more of an analytical person, just be that.
Whatever's you know, whatever you are and how you, your
approach to things, just be that.
And I think that was the lesson I, I learned was you don't have
to be XY or Z to be successful. It's all about human connection.
And the only way to do that is to be yourself.
So that I think was a unique kind of training experience
(18:58):
because every day I was, I was meeting with different folks and
executives, training leaders around the world.
And it was just a, an unbelievable training ground to
start out when I, when I, when Iwas there.
So you got, you had this wonderful kind of introduction
(19:20):
into the world. You got exposed to all kinds of
different styles and you found that there's not just one way,
right? There's multiple different paths
of someone can go down. Let's spin the clock forward.
You're now a veteran of selling in the marketplace is
particularly in your own space. How much of what you saw then is
true today with respect to what makes a good seller?
(19:44):
Is it that ability to understandwhat you're good at and to be
comfortable in your own skin? Or are there is there a little
bit more of a nuance around tactics and methodologies as
well? I would argue the first
statement that it is the most important, making those
connections, striving to understand what the customer
(20:05):
cares about. Methodologies are important, but
a good methodology without connection and trust and really
making those connections, it's going to fall flat.
And so that was that. That's something I think I don't
care where technology and AI goes.
We are still humans. And we need to connect with each
(20:26):
other as humans. And each of those personalities
or personas that I had mentionedearlier, they had that ability
to really connect, understand, put themselves in the customer's
shoes and have a level of empathy too, with maybe some of
the challenges they had, ask those second level questions and
then present how we can potentially solve that together.
(20:48):
Yeah, fantastic. I make I, I really think you
just put together a recipe book in that little, that little
description there about how folks are going to be able to be
successful. Because Matt and I are very big
on being able to understand if you can figure out what is the
problem that's keeping the customer up at night, that's
preventing them from being successful and keeping them from
(21:10):
their objective and then presentto that person.
Here's the path to to remedying that you gone and taken this
from being a conversation about selling something and all about
partnering towards success and solution and relief going
forward. How let's flip that around a
(21:32):
little bit. So now we understand Kate, what
what makes it good for a seller?What kind of leaders are the
best at being able to bring thatout of people?
Do you think with respect to of sales teams, because we've
worked for a lot of different kinds of personalities over the
years? Yeah, yeah.
And you know, I've been super fortunate in almost every role
(21:55):
to have a really good leader that to really.
And what I look for is someone Ican learn from, whether it's
skills, approach, how do I get better in in my job?
What don't I know? And I think a part of that is
checking the ego at the door. It's something that probably
took me a little while to do. A level of hubris, especially if
(22:17):
you've had success of I know what I'm doing and I've done
this before. Just, you know, for folks just
starting out, just try to take that out of it and just learn.
Always be a student and if thereis something you can learn from
a leader, embrace it. Don't look at it as a threat or
get defensive. Embrace criticism.
(22:39):
Certainly, you know, that that'ssomething that I think it takes
some years and some thicker skinto realize like, hey, they're
doing this to to help me insteadof, you know, as long as they do
it in the correct way. And, and that's really what I
look for someone who's a, you know, being a great sales leader
in all of the attributes that I mentioned across all of these
different leaders that I've worked for, all of them, one had
(23:01):
trusted me. They were not micromanaging, you
know, they were, they were therewas a level of trust.
There was a level of coaching and hey, maybe you should think
of, you know, building this particular skill at, you know,
(23:23):
in your job, so kind of challenging you to get better.
That's something I think that asI look at and some of them, you
know, would teach me a, a skill,something I, you know, I, I can
learn. So I'm actually learning too.
I'm not just, they're not just saying, you know, you need to
brush up on how to leverage AI in your sales process, right?
(23:43):
They're saying, hey, here's how I do it.
Here's what some of the innovators in this space are
doing. You know, why why don't we sit
down for a little bit and I'll show you some practical examples
of how this can help as you're, as you're doing your job.
That is the number one thing is just, you know, having your back
and being a really collaborativecoach.
(24:05):
Yeah. Getting back to that trust
though, because that's a common theme, you know, in any
relationship, right? I'm curious, do you think that
you earned that trust, This is why he gave it to you or that
leader was just a general genuinely trustworthy person or
how did that come about? And if you, if you did earn it,
what was it about you or your approach that that warranted
that? Great, great question.
(24:27):
I think trust is earned, right? It's it's tough on day one to
say, you know, let me let me do my thing.
You know, it, it comes with it'sa gradual process to really
build that trust. And some leaders I've worked
with, you know, adjacent for a while.
So when they became my particular leader, there was
already that level of trust. It could because we were
(24:49):
colleagues and then they were, you know, potentially promoted
or just org, org shifts and theywere above me.
And, you know, it's almost like leading from the front where,
you know, hey, here's how to here's my approach, here's how
we do it together. So yeah, definitely, you know,
positive influence with all the leaders I've worked.
(25:10):
With yeah, definitely. I know there are a lot of
different kinds of management styles.
There's those that delegate and there's those, as you say, lead
from the front. I know which style I prefer.
I much prefer someone sitting next to me in the trenches,
someone I can learn from, observe and pick up those skills
passively and actively from. But not everybody, you know, has
(25:30):
that particular makeup in their in their repertoire.
But nonetheless, I follow what you're saying.
If I can paraphrase and tell me if I'm getting this right, a
good sales leader is as much coach and teacher as they are
executor of the sales strategy out in the field as well.
And they invite that trust. Is that a fair representation of
(25:53):
what you're saying? Makes up the, in your mind, an
ideal sales leader? Kevin, you that is the succinct
answer that I was hoping to give, but I rambled on.
But yes, that that exactly is what we're you know, to to
really paraphrase down to 2 words coach and close, you know,
coach me on being better help meclose business.
(26:16):
That that is the the two word answer to even make your your
answer even more succinct. Totally believe that.
That's what I look for, especially as, you know, I may
want more if I'm just starting out, but as someone who's been
doing this for a period of time,you know, coaching and closing
that, that's what I look for in leadership.
Yeah, someone who sat on both sides of that equation, both
(26:39):
being and by the way, that the whole ability to develop and
build people and and and make them better sellers is largely
what drove drew me into sales leadership and what was my
motivation. So I I understand that
perspective. It's interesting though, in
today's day and age, we've got asituation where those abilities
(27:01):
to have that kind of exchange asboth the individual contributor
and the manager can sometimes becompromised, right, because of
just the demands of the job and doing less with more.
In your industry in particular, I mean, you guys focus and
specialize. The tool you're working with now
is all about training, all aboutskills development, right?
(27:21):
There's a lot of pressure in themarketplace now to do less with
more, and AI seems to be complicating things,
particularly in your space. How are you seeing that, both
with respect to what you're trying to sell and also with
respect to your ability to get what you need from your sales
(27:43):
leaders? Now that's a pretty broad
question, but you know, I'm curious.
You know, AI is in every industry.
It's a big buzzword. I think people have a hard time
deciphering how AI can help themin particular, because every
vendor, you know, everyone is just AIAIAII think that as I
(28:11):
look, there's there's a couple things that are happening that I
see. One, the pace of innovation is
skyrocketing. I mean, you know, in our, I'm at
a company named called the Tennessee where we can have, and
it came out maybe a little over a year ago, virtual AI
conversations with a, with an avatar, right?
(28:34):
And it's using a Gentek AI to look at all of these multiple
areas of trying to replicate an authentic human conversation.
So from that, from that standpoint, it's making the pace
of innovation shorten. I mean, it's, it's, it's amazing
just how advance has been. I, I've been at the organization
(28:56):
for six months and I mean it's revolutionizing everything.
We're incorporating it in other e-learning products and really,
you know, just on sitting on that bleeding edge of what is
possible within corporate learning.
I think on the other side of howit's been a challenge from a
customer standpoint, there's so much automation and AI, it
(29:21):
allows reps to cast a wider net,make it more relevant.
And just the sheer amount of messaging, whether it's through
LinkedIn, e-mail, it's, I think it makes it a bit tough for a
potential customer to sift through.
What is everyone saying, AI? How do I sift through all of
(29:42):
these, all this different messaging that I'm getting?
And I, you know, my point of view is just the level of
outreach, you know, to executives is just exponentially
higher than it was maybe 10 years ago.
Do you think that even with it'sfunny that you're mentioning
this and it actually coincides with some things we've heard
from some of our most recent guests on here.
(30:04):
It's like we're getting more, but it's actually in many cases
less actionable because of the fact that there's this this
deluge. And even though AI purports to
being able to help you sift through it, if AI is creating
it, are you, are you coming out with a net neutral at the end of
the day? So how do you how do sellers
(30:24):
like you then engage with your prospects and help them make
sense of just the sheer noise toto really get to here's my
problem and here's what I need, how I need to solve it.
Yeah. And we've had these discussions
internally too, because some of the traditional ways of selling
calls, emails, LinkedIn, it's tough to breakthrough,
(30:47):
especially to a certain industries that are really tight
knit. So one of the things that we're
doing is really just being of the industry.
So we're looking at where we've had success, how do we turn
customers into advocates and share their story?
Because that is, and it's going back to basics, right?
(31:08):
This hasn't changed. If I'm buying a Ford F-150 or
I'm thinking about buying a FordF-150, I might call my two
friends that have Ford F1 fifties to see what their
thoughts are. It's the same type of, you know,
basic human connection that we're that we're trying to
leverage, right? Is how do we get into those
networks, become a, you know, become of the industry?
(31:30):
We're not just selling, but we're trying to give something,
whether it's knowledge or insight, Hey, here's how you
know, so and so who's very similar to you is approaching
this potential problem. And now we're adding value.
And we're not just, you know, trying to sell.
You're right. We're, we're, we're adding value
along the way, hopefully. And when they are ready to buy,
(31:54):
we'll be, we'll be top of mind. And if they call colleagues,
hey, I'm having this challenge. Hopefully their colleague, if
we're doing the, if we're doing things the right way, will say,
hey, you got to call this this organization.
I've had two friends or two folks in the industry that I'm
connected with that have had really good results by
(32:17):
partnering with said organization.
Yeah, I, I go ahead, go ahead. I'm.
Sorry, so you're. The software that you're selling
now and inside for a while, it'shas a lot to do with training
people, right? Is it yes, and I'm just curious,
you know, just from a, from a sales perspective and training
people, you know, it's, it's oneof the things that Kevin and I
(32:37):
care a lot about. But you know, how, how effective
is it for those types of things?Because there's certainly
knowledge, right, and information that I think AI is
really good at distilling down and summarizing and giving you
bullet points and things that you can consume.
Then of course, there's the nuances of the sale sales for
(32:59):
people themselves, which we've been talking about, right, which
I don't think it does a very good job of that, right?
So what in your mind what makes it for effective sales training
using these new platforms? Great.
Great question. So there is always a need, I
think to build that foundationalknowledge.
You know, whether it's reading, hearing, seeing videos, E
(33:21):
learnings, there's always a place to kind of build that
baseline. You know, over the last 10
years, I've seen one of the mostpopular courses from an
e-learning standpoint be situational leadership.
My opinion, you should have situational everything because
you can have all the theory in the world, but until you are in
that particular situation, you may not know how to react.
(33:42):
And that is something that I think we found that a sweet spot
where we put sales people in particular situations and they
have to find their way out, whether it's through a game and
it's all game based. So whether it's pick your own
adventure, what decisions will you make to win the deal went
(34:03):
over the customer or using conversational AI, how do you
deal with objections? You've read about it, but it's
almost like the Mike Tyson quote.
You know, everything changes once you get hit in the face.
What happens when someone is yelling at you, you know,
depending on what you're selling?
What if they are just not sayinganything and they're quiet?
So we can tweak different personalities and, and really
(34:25):
just put people in different situations that are relevant to
their business. It's relevant to the products
they're selling. And really that's what builds
confidence when going out into the real world because the
alternative is going in the realworld and potentially failing,
which is very, very costly to businesses or potential role
(34:47):
plays where again, are very expensive.
Typically leaders have to be evaluated by other senior
leaders. And you know, it's funny, we
have all this technology and youknow, we analyze everything.
But then when you, when you do arole play, we have this piece of
paper and we score it. And I, I have conversations
(35:07):
daily with organizations that spent millions on their training
tech stack. But then when it comes to things
like role plays and putting people in those situations, Oh
yeah, we have a recording on teams and this piece of paper
that we evaluated and the data goes nowhere.
So that's the particular gap that we're we're filling is just
(35:29):
exposing folks to different situations, not just from a
leadership perspective, but sales service, you know, and
pick something that is, you know, relevant, you know,
they're important to a company and we can create that scenario.
Yeah. I love that.
I'd never really thought of thatbefore, but you know, it's, it's
role-playing at scale. And I imagine that you can tune
(35:52):
these agents to, to throw out different types of things,
etcetera, as well. I remember, you know, back in,
back in the day, you know, my father worked for the State
Department. You know, it's the counselor's
office and embassies overseas and stuff like that.
You know, when people are tryingto get into that program, the
counselor program, the process is super complex and super
(36:15):
arduous and intensive. But it wasn't really about so
much. What you knew is like, how would
you respond in these situations?Right?
And I remember one of the questions my dad told me about,
it's just like when I was, you know, my teens, he's like, you
know, the question was, you know, you have limited amount of
air conditioners, window air conditioners, right?
And everyone's, there's a long queue for them.
(36:36):
And the ambassador wife comes toyou and says, I want an air
conditioner. How do you handle that?
Right? And it's like, that's the kind
of stuff where you just got to think there's no right or wrong
answer necessarily, right? I mean, there's protocol and
stuff, but there's no right. But like, what is your process
for dealing with this? A personal authority demanding
preferential treatment? There's a process.
(36:57):
How do you, what do you do? And I think for sales it's, it's
certainly applicable. So I, I love that aspect of that
because I, I think that it is something that's very scalable.
Yeah. And and that's really, you know,
when when we get asked like whatis the value prop, it's behavior
change at scale. How do we replicate the
behaviors? What does great look like?
(37:18):
And then how do we replicate those behaviors at scale?
And again, it doesn't have to besome enterprise sale.
It could be buying a cell phone.One of our clients is a hotel
chain and they took all the swear filters off.
They want a customer service Repat this hotel chain to really
feel what it's like when an irate customer who hasn't had
(37:40):
any sleep because of an issue with their hotel room.
They want to, they want to put them in that situation where
they're sweating because someoneis furious and screaming their
head off. And you know, they need to teach
them in that high pressure situation, how do you
deescalate? And and you know, for I guess to
be cheesy, turn that frown upside down.
(38:02):
Yeah, I worked night out at a hotel for years, 12 to 8 shift.
I know that pain very well. Well, it it's you have some.
Stories. One of the things we always talk
about in sales is you learn a lot more from your your failures
in many cases than you do from your successes because you have
to breakdown what went wrong andyou have to provide a different
(38:23):
lens and really systematically break that down.
What I love what about you're talking about, it's not just the
scale of what you're doing it. It's also it's mitigating
consequence and risk. Because to your point, you can
either learn it in the wild and if you get it wrong, you'll
learn the lesson, You'll learn what not to do, but the
consequences can be dire. But now you can do that at scale
(38:44):
where the opportunity, where theimpact and consequence and
ramifications of failure isn't going back to what you were
talking about at the beginning of our discussion today, people
in the hallway losing their jobs.
Yeah, Yeah. I mean, that's because as you
said, failure in sales can have,depending on the role, can have
some serious ripple effects. And that again, that was the
(39:06):
first lesson I had in that firstCo-op job.
John, I really appreciate you. You really kind of brought some
interesting elements to the table today and this last one
being no exception. So I really appreciate the
perspective you've been bringingin here today and opening our
eyes to some other potential andsome some real positive things.
(39:27):
You know, we do have to start bringing our our session to a
close unfortunately. And I wanted to quickly ask you
if someone wanted to get startedthe industry, I mean, you
obviously you had the opportunity of bringing that up
through your university, but what advice would you give to
somebody who's trying to do thatthese days?
How? How would they get started?
I think it starts with finding areally good company.
(39:49):
You know, you are interviewing them as much as vice versa.
You know, just really look for some, you know, a company that
has a good culture and a leader that is you can learn a lot
from. A good coach essentially, those
are the two big factors that I've I've learned and I've, you
know, I, I've had some really good leaders, some really good
(40:09):
companies and, you know some, some maybe not as much in my
background. And so, you know, really find
those two things and just be open to learning, be curious and
make, make in nurture relationships.
That's one thing. I mean, Kevin, we, I was
(40:31):
looking, I mean, we met over 20 years ago at this point and I
was looking. We, we, we, we touch base like
every 5-6 years, right? You know, and again, that's
something I can do better is just nurture those
relationships. But when you're just starting
out, I mean, there's folks that,you know, I, I haven't worked
(40:56):
with in 20 years and but there'sstill that trust in connection
because 20 years ago, 25 years ago, we had some really good
conversations and we both kind of reflect on that.
And it's all about relationshipsinternally and learning from
each other. So really just focus on that.
(41:18):
Don't think of it as just a job,but thinking, think of it as I'm
getting to know some really goodpeople.
Find those people that you can learn from.
And if you can make that connection, I'm telling you in
you never know, in 20-30 years you may cross paths again.
And that's certainly the case, you know, even with with this
Kevin. So that would be my advice is
(41:40):
just, you know, be curious, makethose connections, learn from,
you know, mentors, as I'm not sure if any of us would be here
if we didn't have strong mentorsto really show us how to get to
the next level and level up our own games.
So yes, rambling on as usual, but you know, I, I really, I
really believe in that. As do I, So John, if someone
(42:05):
wanted to get some additional advice, maybe reach out to you
for some mentoring, what's the best way for them to connect
with you? Best way is probably on
LinkedIn. I am on it constantly at, you
know, connected with more people.
I was just at a networking eventlast week in an industry that
I'm concentrating on. Just really trying to make
connections and give myself credibility.
(42:27):
I'm going to another industry specific content conference in
two weeks to really just immersemyself in that, in that world as
well. Nothing to do with software
sales, but networking is super important to me.
I think that was part of my brand throughout the years is he
(42:47):
knows a lot of people, he's wellnetworked.
I do enjoy it. And you know, LinkedIn is the
best place to start and I will. I am super responsive on on
LinkedIn and happy to mentor or any others as I've been
fortunate enough to have many great mentors throughout my
career. Well, very much appreciated that
(43:09):
perspective. And yes, I, we've had, we've
shared some of those great mentors and people that we've
learned from along the way. I have one of them who I have
the benefit of being my Co host every week when we come in to do
these shows. And Speaking of which, Matt,
before we go and wrap up today, anything you'd like to add to
the conversation or the commentsthat John just made?
No, not really, other than it's been a pleasure.
(43:29):
John really enjoyed the conversation and hearing a
little bit about your approach. It's brought back a lot of
memories of different things in my life as well, so it's good
talking with you. Including crazy Brits that
really know how to sell software.
Common experience. Three of us, obviously.
Well, John, it is funny. It is absolutely a small world.
(43:52):
You know, that's an interesting thing.
And this is from I haven't worked with him since 2006,
maybe 2005. So we're talking 20 years ago.
And again, lasting impression ofsomeone who does things a bit
different, but it works. Absolutely, absolutely had his
own style in it when he knew howto work that style.
(44:13):
And everyone needs to go and find that to the point that you
just made. But ladies and gentlemen, as
much as I'm enjoying this conversation with John and I
appreciate you going and, and opening our eyes to a couple of
different things that maybe we hadn't considered and bring up
some points that we knew, but maybe giving us a different
angle on. So John, thank you so much for
being with us here today and being our guest and sharing your
experiences and your insight. It was really fantastic and
(44:37):
thank you again for coming in. And ladies and gentlemen, if you
like what you heard here today, please leave a comment like
follow, subscribe costs you nothing and it really helps out
the channel or go to our websiteand buy our methodology book
there that is outlines why Matt and I have been so successful in
the past on our journey with respect to software sales.
But until we see you again next week, thank you very much for
(44:58):
spending a little bit of time and we'll see you again soon.
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