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Hosted by Stephen Saberin, Senior Partnership Manager at the world’s leading technical HubSpot consulting firm, Domin8 is your backstage pass to the world of HubSpot selling. Get insider stories on what drives success—how top professionals close deals, overcome challenges, and thrive in this competitive industry.
From aligning the perfect GTM tech stack to tackling real-world sales hurdles, Domin8 is packed with actionable insights and captivating stories to help you excel in today’s competitive sales landscape. Whether you’re in sales, partnerships, or leadership, tune in to sharpen your edge so you can Domin8.
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The nonprofit space.
They move at generally a slower pace
overall, and it's being attuned to
that and being understanding of that.
If you're thinking more about closing
the deal or more about your quota
than you are like what do they
need and when do they need it by?
That's how it's gonna come off.
Welcome to the Dominate podcast.
On the show, we talk with HubSpot's
sellers about their latest wins,
pulling back the curtain to explore
the challenges they ran into the sales
strategies they use to win the deal.
I'm Steven Saberin, Senior Partnership
manager for Aptitude eight, the world's
top technical HubSpot consulting firm.
Today on the Dominate podcast, I
have a guest who's mastered two
worlds most wooden try to mix.
He's known as the
funniest man in software.
Spent eight years on stage as a
comedian and even landing spots on
Comedy Central and making the finals
at the Boston Comedy Festival.
But.
What really makes this individual
stand out is what he's done off stage,
especially in the world of software.
He's one of the early hires at a little
startup we all know as HubSpot, 16
years ago when it was just an idea and
a company that fit inside a single room.
Over those 16 years, Dan seen it
grow into a global force, and he's
at a front row seat for all of it.
These days, Dan's still combining
strategy and storytelling and
comedy while selling HubSpot.
Dan, Sally, I am super excited
to have you here, and I've
gotta start with the obvious.
How does a standup comic end
up helping build one of the
biggest names in B2B SaaS?
That's a great question and
thank you for having me.
So I started in sales and standup at
the exact same time and I will tell you
like both take tenacity and both take
a very high tolerance for rejection.
And so they worked really well together.
And I will tell you like there has never
been any situation I've ever been in,
in a sales capacity that has been worse.
Than my worst gig.
I will tell you that.
Like a none.
Absolutely none.
So from that perspective, I am an
i I feel exceptionally safe where
I am now off the stage and selling.
Yeah, in standup I believe you have
seconds to read a room and adjust
and alter possibly that script.
Do you feel like that is something
that carried over to sales,
that made that feel easier?
Oh, big time.
Yeah, big time.
I mean, My dad, who was, he was a trial
attorney, so he had a lot of experience
in high pressure, public speaking And
the advice he gave me, this is what
I was doing standup, is he said they
don't know what you're gonna say.
So the only person who knows
if you messed up is you.
And yeah, I think the ability
to adjust the ability to.
Know when things maybe aren't going
in the right direction and pivot
and get people back on your side.
Those are all things I learned in
standup and things I still apply today.
that's super interesting.
I think also comedy in general.
It's essentially storytelling and if
you're up on stage, it's under pressure.
So how has that, component of, you
know, storytelling kind of shaped
the way you approach, sales and
then complex sales conversations.
one of the big things I learned
with standup, and I think one of
the things I apply in sales is
having an economy with my words.
So thinking about what is
the clearest, briefest way.
I can get a concept across.
I think with standup it's more about
keeping people engaged, getting to
the laughs, keeping the pace moving.
In sales, it's more like you're fighting
against people's attention spans.
And in, in the case of more complex
sales, especially now that HubSpot
is more like a platform sale,
you're throwing a lot at people.
In usually what's an hour's time.
And so the simpler you can convey that and
the simpler you can make that the better.
That's super interesting.
I think it's great advice.
One of the things I heard recently
is talk in sprints of no more than
10 to 15 seconds to make it a volley.
Yeah.
And I feel like that is
essentially what you've said there.
Yeah.
Yeah.
I think sometimes what happens is we
get so comfortable with what we're
selling, and this isn't just HubSpot.
This could be any product, service,
whatever, that you almost take
it for granted that the person on
the other end of the line, knows
everything you're talking about.
The reality is they're all brand new to
this, and so in a lot of cases you really
have to pace the conversation according
to the audience you're speaking with.
And we can even tie this back into
standup where once you get a sense of
the crowd you're speaking with, you know
exactly where you should be starting off.
And again more savvy.
Prospect, you're gonna be
able to move a little quicker.
You're not gonna have to explain things
as much, but maybe somebody who's brand
new to whatever it is you're selling
needs a little more time for education.
And so things have to be kept
briefer, more digestible, and you
really have to check in and make sure
they're following you along the way.
The one thing that's tougher
about sales than standup is.
Pretty quickly it'd stand up if
they're not getting what you're saying.
Because if the crowd isn't
laughing, that's a problem.
But sometimes on zoom calls, everybody's
just sitting there nodding at their heads.
And if you're not checking in and
getting a pulse for where they're,
where they are you might very well
be losing them and not even know it.
Yeah.
Yeah.
So something you said, making sure
that you're essentially checking the
room in standup to make sure that
they're getting and what you're saying.
How do you apply that to sales?
So how do you make that initial or that
early checkup to kind of test how much
they understand and are, their background
with either CRM or HubSpot specifically.
Yeah, a lot of times you can infer it.
So if they've already bought software
before, so for example, if this
is more of a competitive sale and
they have an incumbent provider,
you generally know they're already
familiar with the software itself.
They're familiar with what it does.
Industry can be a good indicator.
There are some industries that are just.
More tech forward than others.
And then of course there's the
individual as well, just getting a feel
for, have you bought software before?
Have you used this before?
Is this your first time?
Second time.
Third time?
And so on.
And in some cases, you'd be speaking
with a group of people, in which case you
really have to move according to maybe
the slowest quartile of the audience
to make sure you're not missing them.
Yeah you also, you mentioned,
hubSpot has changed a lot over time.
How have you, how has that changed?
You've been here for 16 years,
so it's changed a massive amount.
How has that changed, the evolution
of how you're selling, the
problems you're selling and that
Whoa.
Yeah.
Yeah.
I mean we were really like, we were really
sm a much simpler tool when I started.
So first off, I think I, I wanna say
this because we're recording this.
I found out about HubSpot on Craigslist,
so that's how early days it was.
There was a job posting on Craigslist
and I looked it up and I was
like, this tech is pretty cool.
I've always been attracted
to the technology first, and
I, I saw what HubSpot did.
I instantly got the value
and then I had an interview
and I think was in there like a month
after I started talking with them.
They moved pretty fast, when I
started HubSpot, we were more or less
an SEO tool with a blog attached,
a landing page creator, and a
little email and some analytics.
And I had the fortune of being able
to learn the platform as we grew.
So when we started incorporating
sales tools in the CRMI was able to
learn that when we brought in Service
Hub, I was able to learn that I was
able to learn it piece by piece.
And so the advantage there is I'm
pretty proficient across the platform.
I think terms of selling it can
make qualification a little more
challenging because you're dealing with
a really broad cross section of needs.
I think that also when you're speaking
with multiple teams, it can be a
challenge to figure out, okay, how do I
present this in the best possible way?
And like in a lot of cases, we might
be dealing with a marketing team,
a sales team, and a service team.
In which case you really have to decide,
am I gonna try to do this in one marathon
call, or am I gonna break it up into
individual audience specific calls?
I'm a fan of the audience specific calls.
Because again, nobody, like
nobody has the attention span
for a two hour call in my mind,
even me, when I'm doing the demo.
Yeah.
so I think overall it's, it gets
back to what we talked about
earlier, which is you've got this
big, large, comprehensive platform.
How do you boil down what it
does in the simplest possible
terms so people understand?
Why we should be going this way
instead of maybe just bolting together
a bunch of different solutions.
For the sellers, right?
There's a lot of sellers that.
Don't have the advantage of,
we'll say growing up and, that
longer path and just learning the
platform as it grew up essentially.
What would your advice be to them that
are going from small biz to mid-market
or mid-market to an enterprise seller?
And what would your advice be to
them trying to make that switch
and what has to happen there?
Don't try to learn the
whole platform at once.
Like I think you can still
learn it piece by piece.
And a lot of times when we launch a
new feature, really the way I learn
it is when I have a chance to sell it.
So when a demo, I'm actually doing this,
I was actually doing this afternoon where
there are some new AI enabled features I'm
less familiar with that are gonna
be part of a column I'm on tomorrow.
And so I'll just sit for an hour
and play around with the tools and
figure out what they do and go into
our knowledge base and get myself
familiar with that little subsection.
So I think for folks who
might be a little bit newer.
Might be, again, moving
up to more complex sales.
I think number one, it's just give
yourself time before a demo to learn
parts of the platform you don't know.
I think that the other thing I'd say
too is in a lot of cases it's not that
complex because even though we do a
lot, generally what I find is the use
cases across teams are pretty universal.
So every now and then you get
an edge case that maybe is using
some particular functionality.
That isn't, I isn't one that
the majority of use cases need,
but for the most part, it's
like the same set of tools.
Like on marketing, you've got marketing
automation, email and analytics on
sales, you've got, deals and sequences
and of course reporting as well.
And on services, you've got tickets
and again, reporting and live chats.
So there's there there are a couple
of core tools that I think show
up in every demo, but again, every
now and then you get a fringe case
that you really need to adjust for.
I think the other thing I'd say
more than the feature side is
also really understanding how
to deal with a larger team.
Because a lot of times we're looking at.
The demo for, a specific
persona's problem.
And in a lot of cases you have people
with a bunch of different concerns.
So for example, the concern of a marketing
manager is gonna be different from the
concerns of A CMO and that's gonna be
different than the concerns of a sales
rep. And that's gonna be different than
the concerns of it and InfoSec folks.
And so it's making sure that your.
Addressing all the different needs and
all the different personas in the room
in order to make sure that it lands.
And I think beyond that also getting
used to doing that like post call and
throughout the sales process, like
checking in with all those individual
people and making sure what you're saying
to them is personalized to their role
and what they're most concerned about.
Just a great example is, it doesn't
really care if a tool's easy to use.
It doesn't really care
if a tool unifies data.
What they care about is this gonna make
more work for me and is this secure?
And so in my communications with it, I'm
really talking more about that where,
again, in my conversations with, let's
say a marketing manager, I'm focused
more on the ease of use side of things or
the ease of reporting, things like that.
Yeah.
I think the other big factor that
comes into play is nomenclature.
What there's, you can have the same
use cases, but nomenclature is one of
those things that kind of makes it.
Real to the prospect of the
customer that you're speaking with.
It's the connector piece, right?
If we're trying to gauge
that that piece there.
Yeah.
Yeah.
I think one of the things
I do, and I would say like
Okay.
some people might disagree with the way
I approach demos, but I spend a good
two hours prepping my demo portals.
A specific use case.
So I really like to make sure
that this looks as close to
what it's gonna look like
when the customer's actually
using their own HubSpot portal as
possible.
And that gets, and I don't know if
this is what you meant by nomenclature
but just like using the prospect's
terminology and incorporating
that directly into the portal.
So there's no gray area there.
They don't have to do, they don't
have to use their imagination at all.
They can just come right in and say, okay,
this is what we look like using HubSpot.
Yeah.
Yeah.
I think some of what I was talking about
and the deal that I think we recently
won together, it was a nonprofit.
So in, the nonprofit world, right?
They don't have contacts and deals
that tend to be members and, it's
a different set of nomenclature
than, a B2B or B2C company, right?
Oh yeah, for sure.
For sure.
And definitely speaking their
language too, because to your
point, it's definitely a different space.
They have a different set of concerns
and different set of priorities.
So things like ROI I mean, they're
important, but they're not as
important in the nonprofit space.
And so yeah, you really have to know how
to position it specific to that industry.
Yeah.
I would say that's not unique
to the nonprofit space.
I think every industry you have
to approach a little differently,
there's a key difference between
like nonprofit and let's say your
standard B2B or B2C prospect.
There's some key differences buying
cycle, being one of 'em, but,
I think the recent win, I believe it was
one of those ones, it wasn't a single
team, single tool evaluation here.
give us some background on, how they came
in, the challenges and, what that looked
like and how you ended up navigating
that initial conversation with them.
Yeah.
For the sake of this conversation,
for the sake of confidentiality we'll
allude to the company, but this is a
major nonprofit we were working with.
They actually had worked with
us on a smaller scale before,
so they already were familiar
with us on the marketing side of
Okay.
Okay.
and we were included in a CRM eval,
and it was between us and Salesforce.
Yeah I think we're
still like, very much the
upstart in the CRM space.
I think I think Salesforce
is, has an overwhelmingly
large amount of market share.
So
It's just, it's great.
Again, as somebody who worked here
when we were in an incubator, it's
great to see us now at the, brought
to the table with Salesforce.
But anyway that aside, when we started
the conversation, it was very clear that
this was more of an internal comms play,
than it was like, donor marketing or
volunteer engagement, like things that
we, things that very often we're
pulled into in the nonprofits space
on the marketing side of things.
That was number one.
Number two, it was very clear,
lots of different constituencies
like we talked about before.
So we had the system admins,
we had the the InfoSec folks.
We had the folks who were actually
in charge of working with different
partners outside of the nonprofit.
And so it was again, a matter of
telling a story that resonated with
the core user, but also addressed
some of the bigger problems they were
having on the, the system side and the
the data consistency side of things.
When you first got involved, what did
you find was broken or missing, I guess
from their perspective and what did
they think they needed versus what they
actually needed in the end that you
were able to take them down that path?
The issue they had is they had a
bunch of different divisions that were
involved in connecting with partner
organizations that they worked with.
And each of these divisions had their own
CRM or their own system, whatever it was,
like Airtable spreadsheets monday.com.
A couple were using Salesforce,
one was using us and the issues
that they were running into was,
were primarily around coordination.
Because what would happen is, let's say
two teams were in touch with the same
outside partner, they would both be
communicating with that person unaware
of the other person's And so very often
they were stepping on each other's toes.
They were creating confusion,
it over communicating it wasn't
the best look, and so they really
wanted to consolidate that under
one platform to solve the issue.
I think one of the things I've
noticed about the CRM space in
general is that even today for
a lot of larger organizations,
it's still an IT driven process.
And so in a lot of cases.
You have people looking at it from
more of an IT perspective and more
of an issue of does this solve
the problem of unifying data?
How do we deal with security?
How do we deal with user permissions?
All that stuff.
A lot of times what they miss in that
process is this something the team
is actually gonna be able to use?
And the good news here is they
were already aware that user
adoption was gonna be a big deal.
And so that was really where we were
able to come in and ultimately win this.
Because, from a, just a clear nuts and
bolts functional perspective, Salesforce
or HubSpot could do the job, but
Salesforce was gonna require 10 more
admins, a hundred additional clicks
to get the same thing done in HubSpot.
And I think ultimately where we
went out was just number one.
It was gonna be way easier to administer
it, way easier to implement it.
And it was also going to be way
easier for the end users to adopt.
We weren't talking about non-technical
folks, but we weren't talking
about folks who necessarily wanted
to live and breathe in A CRM.
Either.
They just wanted something easy that
they could get their job done In.
Was the ease of use sale, is that what
they came in with, or is that something
that you guys directed them towards?
Or was it, did they come
in with that expectation?
They came in with concerns
more about adoption.
Okay.
And I, think ease of use, we were
able to bridge that into ease of use.
Everybody has a story about this
particular platform or piece of
software that they purchased,
and then nobody ever used it.
It's like the proverbial, piece
of exercise equipment with
your laundry hanging off it.
Everybody always has an adoption problem
or an adoption story with some software.
We bought this, nobody ever used it.
And sometimes people understand
that means ease of use.
Sometimes people don't.
And so I think a lot of times
it's up to us to say, Hey.
The big issue you're gonna have
with adoption is making sure
people understand how to use it.
I think they were a little friendlier to
it because they already had teams that
were in quote unquote easy to use tools.
So monday.com, for example,
really easy to use, or
Pipedrive really easy to use.
And it's just, the problem with
those tools is they just don't scale.
So I think, one of the advantages we have,
I don't want this to turn to a HubSpot
infomercial, but you can't stop me.
I'm hardwired for it.
One of the advantages we have is
that we have that ease of use, but
we're, we also allow folks to scale.
Yep.
I know different stakeholders in the deal.
Ease of use and adoption, right?
Communicating how that translates
to platforms depending on
where that stakeholder sits
can mean different things.
Walk me through, I guess, what that
stakeholder mix was and, who was,
the final decision maker and what
the challenges were with the mix of,
folks that you were chatting with.
I'm gonna come out and
confess right off the bat.
I have no idea who the
final decision maker was.
I really I have zero idea.
I tried to suss that out.
I think it was a decision by committee,
and I think that's a, that's again,
something different about nonprofit.
I think they tend to be a little bit more
consensus driven than, think B2B orgs B,
B2C orgs private companies, which again,
will work by committee, but ultimately,
typically there's somebody who's gonna
put their stamp of approval on it.
These folks were definitely
way more consensus driven.
And the mix was project managers.
So folks who are actually
gonna be in charge of in charge
of getting people onboarded.
That was number one.
Number two, we had your IT InfoSec folks
and they were most concerned with how is
this gonna integrate with our systems?
What kind of user permissioning was there,
data protection, all that good stuff.
And then we had folks in the middle who
were let's call 'em like systems admins.
And these were the folks who were
ultimately gonna be responsible
for keeping the thing humming.
And so.
We, what we did with this particular
deal is we really broke that up
into a couple of different calls.
So like it InfoSec had their
own call, had their own call
to answer all their questions.
Oddly enough, we had more calls
over their concerns than we
did with the project managers.
The CRM side of things was
pretty easy to get done.
And then it turned into
the wiring underneath.
So things like user permissions,
integration, stuff like that.
Interesting.
Any champions on the IT side or was that,
did you have champions in other areas?
Yeah, they were all, they were
really great to work with.
they were so overall, like they were
all very amenable to what we had to say.
I would say they kept us at arms
length, but they were very clear
that this was a level playing field
between vendors and so I wouldn't
say we necessarily had a quote
unquote champion or somebody who
was really like pushing for us.
I think it was really up to us to prove.
The value and prove why we were
a fed it, we needed to win over.
One of the things I would say to
anybody selling to a mix of IT
folks, and then maybe end users
or project admins or whatnot.
Is that you also have to
be good at selling to it.
And it is familiar with a
small subset of vendors.
So for example the easy button for
it is like Salesforce or Dynamics.
It is way easier for it just to say
yes to those two because they're
just familiar with them because to be
frank, those two organizations do a
lot of work marketing to that persona.
With us, we really had to win
them over from that perspective.
'cause that's one I think.
One area where we're not as well known
yet is on that side of the fence.
And part of the reason is
because, the software's designed
to make it's job easier.
So the software I ideally hubSpot
doesn't have any involvement from it,
or it just has to do very minimal work.
Whereas if they take on a
Salesforce, they take on a dynamics
that's like part of their job.
Like they're married
to that system forever.
And yeah.
But to, again, to give you the longest
possible answer to that very simple
question I think we had to go in
and maybe win over it more than any
other constituency in the process.
And again, it wasn't necessarily averse
and they weren't they weren't necessarily
gunning for any particular vendor.
I think there were just more gray
areas with us than there were with
Salesforce, and they just had to
make sure they were exploring those.
Definitely experienced the same thing,
dynamics, Salesforce, particularly
Dynamics in a very high, security
environment, it's the easy play.
So it's always selling
against almost the incumbent.
There.
Did you guys approach that in order
to make sure that you addressed it?
Because I would love to double click
a little bit more and get even more
detail there, because I feel like
we've all encountered that and that is
one of the biggest.
Challenges is selling to it and then,
demonstrating that, we can support,
HubSpot can support their needs.
Yeah, I think a lot of it was, a lot of it
was being very detailed with understanding
their questions, understanding their
concerns, and providing answers.
With IT folks, the details are
super important, whereas a lot
of, with other folks you can speak
in in, in broader brush terms, I
think our trust center really helps
a lot that has all the documentation
IT folks are typically looking for.
And once they see you have all that.
That tends to put them at ease.
And then of course, having a partner,
having a good partner who is highly
technical and can talk the talk.
' Beause that is where
my experience tops out.
So I think that's a big deal.
But I think ultimately the
other thing is to understand
what their core concerns are.
And their big concerns
are, is this gonna break?
Is this gonna create a lot of
extra work for me and my team?
And is this secure?
Is this gonna result in a data breach
or some other tech catastrophe?
And so I think it's just being very
empathetic to that and to those concerns
and making sure that you are giving
very clear, very thorough answers
and backing it up with documentation.
Okay.
So making sure that detailed
responses address very specific
concerns that they may have.
Having partners that, can speak
the language and are, familiar
in these technical environments.
How do you get ahead of some of those?
Because I know that often in these,
in a complex selling scenario.
If you don't address that early often you
can get through an entire sales process.
You feel like you're ahead and then
all of a sudden they're like, oh,
and also you have to talk to our it,
and sometimes it could throw you off.
If you didn't get ahead of that.
How do you make sure that
you get ahead of that?
Yeah.
So the first thing I typically
do in a discovery is I get an
understanding as to what do things
look like from beginning to end.
What we like to do is work backwards and
say, okay, so your ideal implementation
data is X, so let's talk about how long
it's gonna take to get this set up.
And then from there we determine
when exactly they need to start by.
And then at that point we can work
backwards and say, okay, what does
the approval process look like?
What does the InfoSec
Look like?
What does the procurement
process look like?
Legal, and we really cover all the
bases so we can start to tee up
What we're gonna need
to speak to and when.
And in some cases you have it
along for the ride from the get go.
I actually prefer that.
To the
alternate to the other side,
which is they decide they want
it and then they bring in it.
And part of the reason is again,
speaking with empathy to the IT
persona, they're dealing with people
breaking stuff all the time, or people
clicking on links they shouldn't
have clicked or something else.
That's their whole job.
And so a lot of times when they
hear, Hey, we wanna go with this
vendor and we need to get started
in two months, like they're.
they're.
like pumping the brakes right away
because if they're hearing about this
for the first time, they've got all those
questions, all those concerns popping up.
And so I think the earlier you can
get them into the process, the better.
But that out of the way it's.
Yeah, I've had success with either.
It's really just a matter of making sure,
like when you have that call with them,
that you have somebody who can speak
competently to the technical concerns.
And then again, you have all the
documentation ready to back that up.
And thankfully we do.
Yeah.
I love the idea of backing into,
working backwards from, implementation
and then backing all the way through.
I know we.
Go all the way through, planning
out what that discovery needs to
look like as we're co-selling.
Who needs to be involved along the way?
What calls do we need to have, what
departments need to be involved, right?
Which then starts to bleed into giving
them that confidence and, it, the
confidence and all the other departments
that, hey, like we've done this before.
We're gonna get all the information and
take everybody's needs into account.
Since it's a complex deal.
Yeah, and it makes it a lot easier
in the back end too, because
if you have a date when they.
Need to get started by, or you can anchor
that to something that's critical to them,
then it's a whole lot easier to move the
process along because if you understand
all the different steps we need to
Before you can get started, then
it's a lot easier to progress the
deal along.
I think one of the potholes
I see a lot of folks.
Get into who are either new to sales or
just starting out with more complex sales
is they don't get that, understanding.
And instead are moving with
this sort of assumed timeline
of demo security, call, sale.
And that can lead to a lot of, friction.
Mm-hmm.
a lot of, tone deaf messaging and a
lot of things that just make the sales
experience unpleasant for the buyer.
And especially in the nonprofit space.
They move at generally a slower pace
overall, and it's being attuned to
that and being understanding of that.
If you're thinking more about closing
the deal or more about your quota
than you are like what do they
need and when do they need it by?
That's how it's gonna come off.
With this one in particular, was there
any point through the discovery, right?
I know this was a, something that we
planned out, but was there any point in
that that you had to slow the deal or
slow the discovery down intentionally
to make sure that didn't break down,
further down in the discovery process?
For these folks, no.
They were ready to be really
thorough and really methodical.
I think just to offer a contrast to that,
you do get some situations where folks
just wanna jump right into the demo,
or let me just see the software those are
conversations you have to finesse a bit.
I never wanna appear, like I don't
wanna show the software, but on
the same token, I also don't wanna
waste everybody's time either.
And so in a lot of cases, when you have
those people who just want to get to the
demo, it's really a matter of telling
them like, Hey, we can spend an hour,
we can spend all day looking at all
the features, but if I don't understand
what matters to you, I could hit every
feature that you don't care about.
So let's save time, and rather than
doing three demos to get to the one
you want, let's do one discovery
call and then one demo that's
really gonna nail the use case.
I love that approach.
Would there be any scenario where
you would have, possibly two demos
where the first demo, you give them
a taste and a feel for the platform.
And then the second demo you've
tailored it to what they need.
Yeah, a hundred percent.
I wouldn't, it's not sales best
practice, so I'm not gonna give
advice to people about this.
But you do have to feel it out.
There are some cases where folks wanna
see it before they pull in their entire
team.
a lot of it's a question of, economizing
your time for the opportunity.
So in my mind, if we have an opportunity
where somebody's interested, but we're
gonna need to pull in other stakeholders
in order to get approval, and we may not
get those stakeholders in without showing
something, then I'll show something.
I will do some.
I'll do some high level discovery
with the understanding we're
gonna do a deeper disco call after
that, and that generally works.
And if it doesn't work, it usually
means it wasn't going anywhere anyway.
So yeah, there are cases like
that it's very situational.
I think if I were advising anyone new
to sales, I would say don't do that.
But after a while, you get a
nose for when to go off script.
I don't wanna say I'm a special person,
I don't wanna mislead anybody either.
So
Well, 16 years, you start to learn a thing
or two about a thing or two and, you know,
there's, you can make the exceptions,
I've earned it.
I think I've earned it.
So most complex deals maybe
most is a strong word, but I
would say many complex deals.
They have the, moments
where it's pivotal, right?
It could go sideways.
Was there a point in this
that had the most risk?
For this particular uh, you know, cycle?
think for us there wasn't necessarily
any areas where things would go sideways
with this specific deal because they
were very forthcoming about their
needs and they were very forthcoming
about their evaluation criteria.
So in that respect we knew
what we were speaking to.
I guess the risk for us was that they were
definitely very vendor neutral throughout
the process, and I was cool with that.
Like I definitely respected the
fact that they wanted to run a
fair and level evaluation process.
Obviously I would've preferred
it if we were the shoe in and.
Whatever.
I would've preferred knowing that
would've made me feel better.
But I would say for us, the risk
was getting into, as involved of
a sales process as we did without
a full understanding as to where
we stood against the competition.
Because I think when it's just us
versus an RFP or us versus a list
of requirements, we could say, okay,
we meet all these requirements.
Great.
And then the risk is mitigated when
there's a competitor in there, you're
just never quite sure where you are.
And I think the one thing I've learned
to do over time is really allocate
my time to where I feel the greatest
opportunity is gonna be or where
I'm gonna get the greatest leverage.
And I think part of that is understanding
exactly where we are in terms of
vendor of choice, or exactly how
far we are away from being vendor
of choice or how close we are.
Because at that point, if I know where a
little, maybe further behind, maybe we're
second or third choice, then I know, okay,
I'm not gonna allocate the same amount
of time I would if we were first choice.
But in this case, we were always competing
for first place, so there was never
a sense as to where we stood and and
that again, we could have potentially
invested a lot of time and gotten to
know, and and that's the risk you take.
But I feel like with this one, it was
worth it, especially since we won it.
Who are they looking
at outside of HubSpot.
So it was just HubSpot and Salesforce.
That was it.
And then they had, yeah, and then, they
did have some incumbents like Airtable.
I think it Monday was in there.
I don't think they ever were seriously
entertaining those, I think they knew
they needed something with scale,
and that was us and Salesforce force.
Were they replacing, did they keep Monday
or were you integrating with that, or
were they truly using that as a CRM
We were, they were using it as a CRM.
Interesting.
Okay.
Oh yeah.
Yeah.
I mean
you'd be shocked at some of the
size of some of the orgs I speak
with who are using this sort
of mishmash of different tools.
In this particular ORs case, it made
a lot of sense 'cause there were
some autonomy to the different teams.
But, I've seen teams with like sales
reps. I've seen sales teams of a
thousand people working off spreadsheets.
That's sometimes
wild.
Yeah.
So it's good.
I know I've got job as long as people
are doing that, I've got job security,
so I'm feeling okay about that.
I know particularly nonprofits can
be sometimes difficult to get a
temperature check as you are, going
through the sales process and really
understanding or getting a, getting a
feel for, are we the leading contender.
Was there any point during this where you
felt a tip from Hey, we're a really strong
contender to like we are the contender
and this is likely to move forward?
Yeah, like at the very end, I hope when
I say this, it comes off as an extreme
compliment to these folks because they ran
such a professional evaluation process.
I don't think I knew until maybe two
weeks before we got the official thumbs
up that we were getting the thumbs up, and
that was after all the calls were done.
like we had already done all the work
we were gonna need to do in there and
then they were like, Hey, we don't wanna
say anything just yet, but we think you
all are in a pretty strong position.
And I would ask them constantly.
I'd say, listen, I wouldn't be
doing my job if I didn't ask.
Like, how are we, where do we stand?
you gotta ask
They gave me the Heisman every single
time until that, until the last moment.
I know we're coming up on time a bit,
but looking back at that deal, is
there any, anything you would've done
differently or approached differently?
What are the reflections.
great question.
I hate to say this because I know
this is supposed to be a learning
moment, but with this specific deal.
I think we did everything we should have
done and did it all in the right sequence.
I think and maybe to make this a
little more informative, it's funny
getting back to my roots in standup.
Nobody ever wants to hear about the show.
When you kill it.
Everybody wants to hear about
when you bomb the worst.
This is the thing about standup comics.
When you see a comic bombing up there,
just know that in the back of their
mind, they're thinking about how they're
gonna talk to all their standup friends
about this afterwards, because those
are the stories people want to hear.
And in this particular case,
this was one where we nailed it.
I think again, there was some vagueness
around where we stood as vendor of choice.
But on the whole the
process was pretty solid.
If I had to offer something though
that was a little more prescriptive
or maybe a little more educational
for anyone listening, what I would
say is that in a lot of cases, we
view our sales process almost as a set
of requirements, almost like an RFP.
Where if I get this, then I give that.
If I get this, then I give
that, and so on and so forth.
So if I get all the stakeholders,
then I give a demo and I need to know
timeline, and I need to know who signs,
and I need to know all this, right?
And all that's true and all that sound.
And you should be getting
all that information.
And you also have to understand
that all that information
exists to make you feel better.
It doesn't deliver any value.
To your prospect at all.
Your prospect knows this, right?
they don't need to have that information.
You need that information.
And so I think what's really important to
understand about any sales process, but
especially ones that are more complex,
is you really have to view it almost
as an exercise in risk management.
And the thing you're managing
is your limited time.
And the risks are any
vagueness in the process.
Those check boxes you're supposed to mark
off before you proceed to the next step.
Those are all designed to keep you from.
Spending too much time on
folks who aren't qualified.
'cause that will be the kiss of death.
In this specific instance, I think there
was an acceptable level of vagueness
that we had to navigate through, and
that was the toughest part of it.
But I would also say again, just as advice
to anyone selling, really think of those
qualification questions and think of,
everything from timeline to compelling
event, as little pieces of evidence
as to how much time to invest in that.
And I think if you do that you're gonna
gear your process much more to the
prospect, to the person looking at it.
You're gonna be able to frame those
questions in a way that matters to
them, rather than matters to you.
And you are also going to be
able to know exactly where you
should be spending your time.
I love it if somebody is listening, and I
feel like you might have already answered
this one, but if somebody's listening
who's early in their HubSpot sales career.
What's the biggest mistake they
should avoid on deals like this?
Oh, I'm gonna flip, I'm gonna say the
exact opposite of what I said, I would say
that the biggest mistakes are number one.
Not having a clear understanding
as to the prospect's timeline and
why that timeline is important.
If you understand when and why you
understand most of what you need
to know about whether that deal's
gonna close or not.
And I think if the when and why are
compelling, then you can backfill the rest
if you don't understand the when and why.
Then you really run the
risk of wasting your time.
And with a complex deal, these
are a lot of calls, there's a
lot of prep time and they're long
processes and you can burn up.
And I've done it, I've burned
up a lot of time with deals
that weren't going anywhere.
And that sets you back because for every
hour you're spending on a deal that
isn't going anywhere, that's an hour
you could spend LinkedIn prospecting for
new deals or in your database, or maybe
prepping for deals that have some legs.
And so I would say really gain an
understanding as to why the prospect
is looking, why that's important, when
that problem needs to be solved by.
And then, like I said, you can
backfill the rest from there.
That's perfect.
Last question before we wrap it all up.
What is something about you personally,
professionally that most people
either don't know or wouldn't expect?
I don't know or wouldn't expect.
Oh, I'm full of surprises, Steven.
I'm full of surprises.
I'll tell you something now.
So I'm a big language geek.
I actually, when I started at
HubSpot, we had, we only had the
office in Cambridge and we had a ton
of leads coming in from overseas.
And so they needed somebody who
was willing to get up early in the
morning and talk with folks in Europe.
And now, at the time I had a bunch
of small kids and I hadn't slept
through the night since 2007.
Anyway, so I was like,
fine I'll go and do it.
And it worked very well with my schedule.
'cause I was working from five,
usually till about like noon one or
Mm-hmm.
Really child-friendly hours.
And I really got used
to it, really liked it.
And then I got to a point where I thought.
If I'm gonna stay in this role, I
really should know another language.
So I talked to our international
recruiter and he was like Brazilian,
Portuguese is in high demand,
so I taught myself Brazilian,
Portuguese got competent enough.
Like I can have a conversation.
I can't sell HubSpot in
Portuguese, I can get around.
Okay.
I fell in love with learning languages.
And so right now.
I'm actually, my, my, my side project is
I am building an app to learn Hungarian
using a lot of different, a lot of
different AI tools, a lot of vibe, coding
tools, and really using it as a dual.
I don't think we have time for me to
explain why I wanna learn Hungarian,
but just as you might imagine, not a
lot of resources to learn Hungarian.
So I just decided to build my own and it
also allowed me to get really familiar.
The potential for AI to do
custom coding and build apps.
They've gotten to do some API work,
so it's just really helped me better
understand the full potential.
I could speak more
intelligently about it at work.
And I also, I think my technical chops
have gone up quite a bit, so now.
When my sales engineer and the IT
person, one of my prospect companies
starts talking about API, I don't have
to put myself on mute and zone out.
I actually know what they're talking
about and can add some value there.
So that's my surprise.
Is that
I love it.
Okay, so Portuguese, so funny enough,
we, some of our best friends are
Brazilian and we don't speak Portuguese.
They do.
So I'm familiar with it.
I don't think I know a single word, but,
yeah
That's pretty interesting.
well
Send
that to your friends.
Send that to your Brazilian
friend, so they'll
they'll translate for you.
I feel like we should have had some
sort of standup, portion of this to
take advantage of your, the comedy here.
But
I tried to
maybe for next time,
time, Yeah.
next time,
Awesome.
Dan, thanks for joining us.
This was really fun.
This was a fun one.
I really appreciate you breaking
down how everything worked, why it
worked, and, selling in this complex
environment with larger nonprofits.
So appreciate you being here.
likewise.
Thanks for having me.
Thanks for listening.
You can find me, Steven
Sareen on LinkedIn.
If you want to keep the conversation
going, check out aptitude eight.com
to learn how we're helping
HubSpot sellers and solutions
teams win more complex deals.
Until next time, keep selling,
keep learning, and keep dominating.