Grant: People don't trust salespeople
just generally speaking, it's an uphill
battle that we constantly have to climb.
From the moment that you have that
first conversation with them, you
have to figure out a way to demonstrate
credibility and demonstrate transparency
and get them to overcome this
natural, just caution that they have.
To trust somebody.
Welcome to onboarding therapy.
I'm Kim and today, Cheryl and
I are sitting down with grant
Jones, arrows, head of sales.
We're having an honest chat about
the tension that can come up between
sales and onboarding, why blaming
sales doesn't help and how working
together makes everything better for
us and our customers let's get into it.
Kim: So Shirell is our head
of customer experience.
Grant is our head of sales.
I'm head of operations.
So we have three different kinds
of departments here, but we are
a small early stage startup, so
we work together very closely.
So we're all more aware of.
Each other's day to days and the
work and stuff that we're doing
than a lot of bigger teams.
But it's perfect timing because Cherelle
and Grant just got off of a call
together with a prospective customer
that is in the sales pipeline right now.
And would love to hear, maybe Grant,
share what drew you to even bring
Cherelle into that call or what came
up during the sales conversation.
And then I think we can get into.
How sales generally works with onboarding.
Grant: Yeah.
Yeah, totally.
So for this particular deal I brought
in Shirella, I asked Shirella to join
just because they, in this case, we're
selling an onboarding product to them.
And so these are onboarding people
who put a lot of value on onboarding.
And so they had a lot of questions
about how our onboarding worked
just generally and what to expect.
And they, in their case, they had
been burned by other companies in the
past and signed up for them expecting
one thing that we're not officially
committed to in agreements in terms
of support and that sort of thing.
And it's a medium sized deal for us.
So not something that we would.
Enter into like custom SLAs
for, but wanted to make sure
that they felt very confident.
And we're talking to the person that
they're going to be working with post
sale and being able to hear directly
from Shirelle, just because as you
guys know, sales reps have a bad
reputation of overselling things,
especially when it comes to here's
what our team is going to do for you.
So, yeah, ask Shirelle to come and it
was super valuable to have them there.
I don't think Shirelle that
you said anything that I would
have said differently, but just
hearing it come directly from you.
Was a huge value add and trail offered
to even meet with them tomorrow
because we have them in a small trial.
So he's going to meet
with them even without me.
And then maybe you'll say some
things that I wouldn't say.
Shareil: I'll tell them
the truth tomorrow.
Don't worry.
No, I, one, I really appreciate
being pulled into those things.
Not just in our case for a number of
reasons, one, because I'll be also
potentially working with these people
and it just gives me a leg up on starting
to build some of that relationship
and having some of that insight.
But I think also what we see very often
is in marketing, really wine and dine
people and sales were really wine and
dine people, and we're very hands on
and we're very professional, not we
arrows, but we, the general population.
And then it does often feel like.
You're thrown over this finish line where
all the buzz and excitement wears off.
And it's good luck.
You might be talking to Cheryl.
You might not be.
We don't know exactly
what's going to happen.
We don't know exactly what the next
steps look like, which is part of the
premise of arrows, the onboarding plans
in the first place, like having that
customer facing extension of what's next.
But in this example that we
just got off of, or with this
prospect, we just got off of.
It was like bringing
that what's next slide.
That's often in a sales deck to life.
And I think it really
landed well with them.
To Grant's point to the point
where they're going to actually
trial it and start building it.
And in that moment, I was also
able to make an audible and say,
why don't we just do it together?
If you're going to, if you're about to
go into our product and build an example
that you're going to use as a business
case for your CEO on Friday, I, and
we want to be involved in that thing.
So having the luxury to just pull
up my calendar really quickly and
not have to go back and forth.
And
Kim: You're taking steps out
of your onboarding process.
Like the steps that you were walking
them through right now are steps that you
would be walking them through post sale.
So if it is adding value and helping
to get them to trust us as a business,
you're doing extra work, sure.
But it's work that would
be done post sale anyway.
Shareil: And I feel like I'm potentially
speeding up activation because now you're,
it's going to be their real account,
it's a trial, but we'll turn it into a
real account when they're ready and now
we are one step closer to you having
something that's usable and we can launch
and you already have some buy in from
your internal teams on this concept.
So it really is advantageous.
To me and my day job to where
possible to offer that kind of help.
Grant: The it is interesting though,
because this, I do feel like is one
of my responsibilities in sales is
to protect your time because you, and
I think most CS people are generally
like this are just overly giving,
It's yeah, I'll absolutely
jump on calls with you.
I'll absolutely, do all of these things.
And these are people who
have not even paid yet.
And so I feel like part of my
responsibility is to be like,
Hey, I'm gating Shirell from you.
I don't want you to access Shirell.
I will bring him into a call, so that you
can meet him and you can get to know him.
And in this case, I think it'll be fine.
But I do feel that as a responsibility
of mine to make sure that I'm
either not letting them request
meetings with you before they paid
and also not letting you offer it
because I can't be like, actually,
Shareil: yeah, that's fair.
And then I can't complain to Kim about
not having enough time for anything
and how my calendar is always full
Grant: in this case.
For me, I'm usually the one who's doing
those trial kickoffs, and I'm very upfront
Hey, I am not Shirelle, I'm going to get
you to a point where you can validate
some of the product expectations that you
have, the things you've seen in demos.
But I'm not going to help you
actually set up like your proper full
on templates and, be able to start
using this tool to its full capacity.
This is literally a seven day trial,
just meant to validate what you've seen
so that you feel confident enough in
the product that you can move forward.
And so usually I'm doing
those trial kickoffs.
So on the one hand, I'm like,
awesome, Cheryl wants to do this.
That frees me up to do some of
these other calls that I have to do.
But on the other hand, I'm like, I don't
want that to become a thing where you're
often entering deals before they're
closed and putting in a lot of effort.
Joining a call to talk through it.
I'm all for that.
And I should invite you more often
because I think it is a big enough
value ad that it would push people
to close more often than not.
Shareil: You say that now until I
get in there and start telling them
they were oversold and they don't
need all these premium features
and that we can start on the.
Grant: That's the other fear
that I just keep to myself.
Kim: I will say from the customer's
perspective, I had a call with
a potential vendor earlier this
morning, and we have been burned
in the past where we've had a
really excellent sales process.
And then it's Night and day, once
we sign or pay we've actually had
multiple experiences like that.
And so when I'm on sales calls
now as a prospective customer,
I have so much skepticism about
what the sales rep is telling me.
So just from my perspective,
having someone who is not.
In sales from like someone that we
would actually be working with, whether
it's on our team, it's just you sure.
All right now.
So it literally is you are the
person, but even just having another
person coming into, yeah, like
validate, especially for larger deals.
When there is that hesitation from people
who have been burned in the past, it
really makes such a difference to be
like, okay, this it's not just one person.
This other person is coming in and
telling me the exact same thing.
This is clearly, Not like scripted.
They stand by what they're saying and
it just gives a lot more confidence
to making the decision to move forward
and not being like overly sold.
Grant: Yeah.
We talk about a lot in sales, just in
general, the idea of multi threading.
And I think it does go both ways.
Most people focus on just like threading
into multiple contacts and roles and
stakeholders At the prospect, the buying
company, but I think there's a ton of
value in having it go both ways and
having them be, connected with multiple
people on our team, because it does
just add extra confidence that what I'm
being sold is what I'm going to get when
multiple people, like you say are sharing
the same sort of ton of value to that.
Shareil: I think it's
extra true in our case.
Like arrow specifically, because Kim
and I also have our face on a lot of
the content and the videos and the
YouTube stuff that's out in the world.
And we, I get this reaction a lot
on kickoff calls with customers.
And they'll be like, Oh, you're
the guy from those videos.
I watched this thing that
you and Kim talked about.
And so I think it also, when you then.
Not that we're like special in any
sort of way, but then when you talk
to us, it does validate that we had,
they are putting out this content and
they know what they're talking about.
And they're the people that are going
to help me through this process now.
And I feel a lot more comforted
that maybe Grant shared all these
marketing resources with me.
And it is a real set of people
behind here that are going to now
really take me over that finish line.
And I agree like with what you said,
I, to a fault at times I can offer more
time than I probably should to folks,
but that is coming from the lens of
like really fostering that environment
of you weren't just marketed to and
sold to this is your experience through
the rest of your journey with us.
Grant: Yeah.
Yeah.
It's actually it's interesting.
There, there have been a handful of deals
that I've had over the past year or so
where one of the big drivers is wanting
to work with you because of all the
content that people have engaged with.
Yeah.
I love the videos that
I've seen of Shirell.
Will I be able to work with him?
Is there any way you guys
could set me up with him?
And of course the answer
is yes, but it does.
Yeah.
The Shirell, the head, shoulders,
knees, and toes of CS at Eros.
No, the it does bring
up an interesting point.
I wonder how applicable that would
be to other companies to have.
Your CS leader or CS people, the people
that they would actually be working
with be in marketing more publicly, more
visibly, like it makes sense at Arrows.
It's very easy to do because we are
in an onboarding space, but yeah, I
wonder how well that would translate.
Shareil: It did come up actually at one
of my previous employer at sprout social.
I wasn't like the
customer facing bit of it.
I was more on the operations
and program side of it.
But every now and again, I would be
pulled into with the CS leaders or CS
like onboarding team managers to also
talk about not just the, like the tasks
you're completing, but the thought behind
how onboarding works at our business
and the philosophy of how we really
do internally collaborate and make
sure that experience is felt through
any of the pathways of onboarding.
It was valuable then too.
And now I see it in a different
lens, but I think generally.
The more opportunities you give people to
be connected to you on a personal level,
I think just increases the likelihood
that you get a chance to activate them.
It doesn't guarantee any of that.
Just because we're nice people doesn't
mean you're going to use the product and
activate on it, but it gives you a chance
to build that relationship to then build
on that and train them and educate them
and get some more honest conversation.
Kim: I think, so I think part of the thing
about people wanting to work with Cherelle
too, obviously he is in our videos and
very visible at Arrows, which is great.
And it's also a big piece of it is
a thing that I am very opinionated
on, which is having customer success
people be subject matter experts.
And so I think that is the big
thing too, is Cherelle has,
he is an onboarding expert.
There aren't that many people
who know onboarding so well and
have worked in onboarding for 10
or whatever years, a long time.
And so I think there is also so much
value and Shrell adds so much value to
our customers on these calls, because
he's not just like a person that knows
our product and has learned our product
and has learned like how customers use it.
He has been in their shoes and.
Can relate.
And this is, again, this is where
onboarding therapy started, but it's can
relate on these are the general problems
I'm facing as an onboarding manager,
whether or not they relate to arrows.
And so that's why you can connect
with people and actually help them.
And that's why they want to talk
to you is because they're like,
Oh, this is the person who gets me.
Beyond just like helping
me set up this tool.
They understand my goals.
They understand my problems.
They understand my day to day on a
deeper level than just being like
trained up on it when you join a company.
Grant: Yeah, that's definitely
something that I have gotten comfortable
with and take for granted and I
could actually sell it even better.
Like when it comes up naturally in
conversations, I always mentioned like,
by the way, sure, I was going to be
very valuable beyond just onboarding.
You to arrows because he has all of this
experience prior to even joining arrows.
He has 10 years experience doing
building the things that you're
trying to accomplish with arrows,
but that's something that I could
sell more proactively better.
I think.
Kim: So I jump in for demos occasionally
and I'm always surprised how much.
People ask about what happens post sale,
like what the experience is like, what
kind of onboarding they get and yeah,
what that looks like on the first call.
That is a main question that people
are asking and are evaluating in
their decision making process,
almost to the extent that they
are evaluating the product.
So yeah, Grant, if you can speak to how
you think about laying out the onboarding
process beyond just Cherelle, let's say.
We had a team of CSMs.
What does the onboarding process,
what kind of value does that add
to you to be able to leverage
that in the sales process?
Grant: Yeah, tons.
I think you're, you alluded to this
earlier, but for better or worse, we
are at the mercy of just the general.
Ception of sales.
People don't trust salespeople just
generally speaking, like it's an uphill
battle that we constantly have to climb.
Like from the moment that you have
that first conversation with them,
like you have to figure out a way to
demonstrate credibility and demonstrate
transparency and get them to overcome
this natural, just caution that they have.
To trust somebody.
And I think it actually puts us, it
gives salespeople a unique opportunity
to separate themselves when you can be
very explicit and very transparent about
here's exactly what's going to happen.
In fact, I didn't even build this process.
I'm just showing it to you.
So we use arrows plans, of course,
to actually do the onboarding
where it outlines all of the tasks.
And I can just show that to them
earlier on in the sales process.
Here's what's going to happen.
Very obviously you're going to pay
for arrows is going to be step one.
Immediately.
You're going to schedule
your kickoff call.
And then I can show them the other
phases where they're going to be
configuring different things and
doing training and that sort of thing.
And it definitely adds a level
of I'm going to be taken care of.
And I'm not just going to be thrown
over the fence and I'm crossing my
fingers that this thing gets set up
and awesome people have had such bad
experience that it gives us a unique
opportunity to demonstrate that this
is going to be a great experience.
And the better we can sell that and.
And, prove that, then it
makes the sale a lot easier.
Shareil: I think it's that final
check box of what is my gut
telling me about these people?
Because usually by that point, for the
most part, if you're that far into a demo,
you know that the product's likely going
to solve for what you're trying to do.
You've normally signed off on
the technical bits, if you're
installing a product, you've
verified a lot of that stuff.
stuff.
And it's that last little hiccup of,
I don't know, there's this feeling I
have and I want some of that validated.
And to me, that feeling is normally
validated human connections and being
able to be like, Oh yeah, this is
if you've enjoyed the experience so
far with me, this is what it will
continue looking and feeling like.
And I imagine as a sales rep, that must
feel comforting to know that you're
handing people off to a place where
they're going to get decent service,
good service, good support along the way.
And from this side, it
feels the same knowing that.
Like I never actually worry
about you overselling things.
I joke about it, but I've
listened to your demos.
I can see the customers coming up.
There's actually a lot of transparent
conversation leading into onboarding,
which then makes my life so much easier
to go in and just verify what you said and
show them how and why they would use it.
And then the other thing that I've
seen way too often that I don't
think is smart is it's easy to
throw the salesperson under the bus
when you run into something that.
Because in that moment,
you're probably frustrated.
You're like, God, this
project doesn't work this way.
Why would I, why would he say this
or why would she sell it that way?
But that maybe makes you
feel better in that moment.
But now you have built more distrust
in that person, in that client, that
newly acquired customer, and it.
I don't know.
It just makes it so much harder
going forward from there.
Now they're always going to think,
what else was I lied to about or misled
about or expectations were missed that
it starts to put weird thoughts in
your head about potentially growing or
expanding your business with that team.
So even in the rare events where
someone says, Oh, Grant said this.
And I just think there's no
way that's how that works.
Nor do I think Grant actually
said that in that moment.
I'm not like, Oh yeah, Grant's dumb.
I can't believe he said that to you.
I'll usually just say.
That's interesting.
I'll check with him to see if he meant
something different, or we can, I can
look into that and get you a more clear
answer because maybe I misunderstand it.
So acknowledging those moments too,
to protect that customer experience, I
think is critical to building a better
cycle management of customers and then
internally go talk to Grant, did you
say that you've seen me do this a lot?
I'll message him.
I'm like, Hey, this customer thinks this.
Is that actually what you said?
Sometimes you'll say, no, sometimes
you'll say, this is how I said it.
But my point is like, protect the
integrity of your team to that
customer or to that experience
that they're about to go on.
Kim: This is not a topic that we
have talked about talking about, but
maybe take your arrows experience
out of it and go on past experience.
So let's say there's a scenario
where we have a new customer and two
months after they close, they churn.
Or to say they're going to cancel.
So my, I've been in sales and onboarding,
so I can anticipate the kind of
reaction from both teams a little bit.
There's some level of onboarding
being like, this customer is never
a good fit, they should have never
been sold, we've all run into
that experience at some point.
And on the sales side, it's like
they weren't onboarded properly.
So I feel like that situation
is such a tough thing that
just happens at companies.
I think ultimately it's.
Probably some bit of a little bit of
everyone's fault and potentially no one's
fault, but I'm curious if you guys have
specific thoughts on the topic generally
of like how that feels on both sides.
Grant: Yeah.
It sucks.
Shareil: It's very annoying.
Yeah.
Generally.
Grant: Yeah.
Generally it sucks.
Thinking, it, it especially
sucks if you're a salesperson,
if you have a clawback.
Which most that's like the
big thing is it's I put in all
this work to sell this deal.
And then if I genuinely believe
like this is someone who should be
successful using it, why were they not?
Then?
Yeah, that definitely feels
like I did all this work and the
onboarding team dropped the ball.
And now I'm getting money
taken out of my pocket.
There definitely are times though, where
it's I think this could work, and it's
those ones, maybe it's a little more like
you've got to have a good relationship
internally to be to the onboarding person,
to be able to be like, Hey, this I think
this can work, this is why I'm skeptical.
How can I help you make
sure this is successful?
Because obviously I want them to be
successful too, but it requires a
good internal relationship to do that.
Shareil: Yeah, it sucks, especially in
like more high volume onboarding worlds
where you're just going through customers.
And it sucks in that reason, because one,
you're frustrated now that you potentially
spent time on something that might affect
your targets or might impact your targets.
But also you likely can't give that person
the right amount of attention because
you're so jam packed with new calls and
other customers that you're helping.
And so they churn that part sucks.
The clawback happens.
Now the sales rep is frustrated.
And if you in that onboarding world
or in that onboarding seat are in that
mentality of that person just sucks, or
I'm frustrated with that and don't give
any feedback, then it's also going to
just keep happening over and over again.
And that's where it's really
easy to get mad at the sales rep.
Which, fine, be mad at the sales rep.
But everyone
Grant: We can take it.
Shareil: First of all,
everyone makes mistakes, right?
You might have just said the wrong
thing, or you might have had an off day.
Or, it might not be your fault at all!
You could say the exact words and
read the exact script, and someone
might just receive it differently,
and we've seen this happen where
Oh, I thought arrows could do this.
And it's no, it can't.
And Grant didn't say that.
And I didn't say that.
And none of our marketing says
that you just thought wrong.
And it's just
Kim: You make an assumption.
We all do it.
It's Oh, when you said this,
I assumed it meant this.
And so I never even thought to ask
the deeper question to make sure.
Shareil: But if Grant kept missetting
the same expectation over and over
again, and I keep seeing it, and not
doing anything about it, then that's my
problem, ultimately, to have to deal with.
But, if Grant keeps saying Arrows does
X, Y, Z, and it just simply doesn't, and
if I'm not talking to him about it or
addressing that, then why or how would
he learn to potentially change that?
Or, if I'm just getting mad and
internalizing that and being
frustrated, which, again, you have
the right to do, But that is where
you can be a better partner to your
teams and build that relationship.
And if you have enough data,
it might make the conversation
a little less confrontational.
I'm not trying to say, Hey,
Grant, you suck at sales.
What I'm trying to say
is this happened twice.
Is it because you're saying it this way?
Or is it because they're
misunderstanding it?
Or do we even touch on
this part in the demo?
Yes or no.
And I think that enough of those moments.
If you catch enough of those,
we talk about doing every step
a little bit more proactively.
So if in onboarding you see the same miss
expectation over and over again Maybe
it's an opportunity to talk to the sales
team about are we saying it this way?
And then maybe sales is just saying it
that way because it's being marketed
that way and none of this is pointing
fingers Although it feels like it What
it really should be is we're trying
to improve this customer experience.
And we keep running into this
thing and now it's actually
affecting all of our targets and
revenue and customer attention.
Can we figure out where it's
breaking or where in that process,
it's the gap is happening.
Grant: Yeah.
I feel like one of the, one of the big
things, and it's super obvious in small
companies like we are, and it can get
swept under the rug a little bit more or
a little bit more hidden in big companies.
But.
It's like the way that you have
those conver those conversations
have to be had, for sure.
If I think that you're doing
something wrong, the conversation
has to be had in all directions.
And it's like, when you are, when
you're able to present the data
and say hey, I think that we need
to change the way something is
happening for the sake of the team.
It's that mentality that works.
When it's you're screwing me over,
you're passing me bad deals, and
it's making my number look bad,
that's when it's not helpful.
And not productive.
But when it's like, Hey,
we have this team goal.
We need to get there.
This is where it's challenging.
And this is an idea that I have to
help whatever sales process or in
the post sale process, then it's
like a productive conversation.
But so much of it is just psychological
and not even necessarily in the
way that you present, but the
way that you individually think,
like I'm thinking about the team
goals and the company goals.
And that's how I'm.
Approaching you with this,
not you're making me look bad.
That's not it.
Yeah.
Shareil: And make it about the customer.
Like I agree with all that
and ultimately who's going to
suffer the most is our customer.
Like I actually tell this, I say this
verbatim to our customers because I mean
it in the context of arrows, the product,
but ultimately they don't care what me and
you or Kim are doing behind the scenes.
They don't know, should they care?
They don't care what property you filled
out, or if I like your notes or not, or if
you like my handoff email or not, that's
for us to figure out internally, not for
them to have to think or worry about.
And the more that they get exposed to it.
And that's why we say protect the
customer experience because those internal
friction points ultimately impact them.
It might mean they get their
onboarding plan a couple of days later.
It might mean they end up getting
misinformed on how something works
that they were planning to do.
And now they're setting
up and I've wasted time.
So all of that ultimately
impacts their experience.
Yes, churn is the most like clear
outcome of it, but along the way,
as little internal frustrations that
build, it's mistrust in the product.
It's mistrust in sales.
It's just not a good overall experience.
And that could be the thing that
then causes them to not refer a
new, or refer one of their people
over to you, more expand with you.
So yeah, it's frustrating to Kim's
question and it happens all the time.
And it's just.
Probably going to keep happening.
We are all humans.
Everyone is trying to hit their targets
and hit their numbers and do their
bits, but have some accountability
when it does happen and try to reach
out to your counterparts and try
to have those conversations before
it feels like so frustrating that
you don't even want to address it.
Grant: What's your what's your take
on full cycle rep, someone who sells
and then onboards success contact
throughout the whole life cycle?
Shareil: I've never actually
been in a world where that's the
case, so I don't know if I have a
strong opinion one way or another.
I don't think it's a bad thing, as
long as that person knows the Knows
how to sell and knows how to onboard
and knows how to support a customer.
It sounds wildly hard and busy
and hard to manage all of that.
I wouldn't want to do it.
Kim: I did that at my last company.
I was in sales and sales reps were
responsible for onboarding customers.
And so we would get them on
boarded and then we would hand
them off to customer support.
And that's why I started an onboarding
department because it was a series a
company and we were as with any company,
like new business was the entire focus.
And so the metrics that we were tied
to as a sales team was closing deals.
But we also got clawbacks
if customers churned.
And so we had to onboard them, but we
weren't really like we were incentivized,
by the clawbacks, but it was just like
such mixed messages in terms of where
we should be spending our time because
at that time we were cold calling.
We were generating our own business and
holding demos and onboarding customers.
And we were responsible
for a fairly high volume.
And it just became clear.
I was doing that for a year.
They had.
been decent sized sales
team for a year prior.
And at the end of that first year, it
was just clear that you can't continue.
And it's just a, it's a very
different skillset to be in
sales versus an onboarding.
I luckily, like I had been in sales most
of my career and had been spending most
of my career trying to get out of sales.
So for me, it was like the perfect
opportunity to be like, Oh, I just
learned what onboarding is because I have
to do that as a part of my sales role.
And so I can start up this new onboarding
department and kind of, Get sales reps to
focus on their goals of closing business.
And then I can onboard the new customers.
And it was just me onboarding all of
the sales team customers for a while.
And then we ended up bringing on more
team members, but I think it just
doesn't, the incentives don't match.
I think it's a great thing for a very
early stage company to do, to have you
sell and onboard the first customers
to get the experience and understand
what customers are going through.
And I think it's not bad to have
salespeople experience what it's
like to actually get a customer.
Onboarded to the company, but
I just think it's a different
skill set and true salespeople.
You don't want onboarding your customers
and onboarding people are not going
to be good at selling your customers.
So I just think it's yeah, it
doesn't actually make sense.
Shareil: Yeah.
I feel like there's different character
types that end up in those roles and
their strengths are not one or the
Grant: other.
Yeah.
Yeah.
I think it's like it's just different
problems that are being solved, like the
problem that I'm trying to figure out
how to solve is how to demonstrate value.
Like that, that, that you haven't
yet gotten, but that you will get,
it's like a very unique problem
compared to what you're trying to
do and onboarding scenario, which is
like ultimate actual outcomes, like
achieving those outcomes and taking
into account all of the nuances of their
business and their current processes
and the challenges that they have.
It's a, I think it's just a
different set of problems that
require a different skill set.
So I appreciate the way
that we have it set up now.
We're basically like if any money
discussion comes up, you could just throw
it back over to me and they already know
me because I sold them the original deal.
So we have a level of relationship
and it feels natural enough and I
don't think it feels like a joltee.
Is that a word?
To them?
Shareil: We make up
words here all the time.
Grant: Do you know what I mean?
Shareil: At least I do.
Kim: Grant have you felt across
your sales career that there's
a lot of blame on sales reps?
Do you feel that generally?
Grant: Yeah.
I I wouldn't say a lot of blame,
but there is always going to be
errors is probably the place where
I felt at the absolute least.
But there's always going to be some
level of sales shouldn't have sold this
deal, and unfortunately a lot of orgs,
it's like you've got this pressure put
on you by quotas and other things that
are like, I'm trying to find any way
that I can to close business because
that's what I'm being asked to do.
But then when I do, it's ah,
you didn't sell a perfect deal.
Shareil: Yeah.
Grant: That can be a super
frustrating position to be in.
And I think it's always present.
You just got to try to minimize
it as much as you can with the
right incentives and just the right
relationships between orgs to where
you can just talk about things openly
and not feel like it's a blame game.
One of the funny things that sometimes
happens, I think is people generally are
adverse to being sold to, and they don't
want to feel like they're being sold to.
And I think my selling style
is very not pressure not salesy
in like the traditional sense.
And so I try to be super upfront
with people about what it's designed
for and what it's not and why I
think this would be a good use case.
There have been several occasions
where like someone, we're doing the
discovery and they're describing their
challenges and what they're trying to do.
And I'll going into my now pitch of
arrows and the demo that I'm going to
provide on that same first call, say,
I'll be honest, I don't think arrows is
likely a good fit for you, or I don't
think it's the best option in the market
for you and something psychologically
people are like, no, but I already
thought it was when I saw your stuff.
And so I'm going to prove you wrong.
And then they really want it.
And they, and it's this sort of
psychological thing that happened and.
In some cases I'm like, great.
Yeah.
You're selling yourself,
which is what I want.
And then in other cases, I'm like,
no, I genuinely think that you are
not going to be successful with this.
And some people just
want to get it anyway.
And who am I to stand in their way?
And maybe they'll find a way to make it
work, but it doesn't make it an awesome
experience for the onboarding team.
Shareil: But even when that has happened
here, you at least leave a little note.
Inside of the CRM notes where you're
like, they're trying to do this with it.
And I let them know this isn't
the greatest application.
So at least you're aware of it.
And then trying to give a heads up,
which is often what the onboarding
rep wrote, that frustration that we
were chatting about earlier with Kim's
question, I think it really is just
frustrating because you feel like you're
being blindsided or caught off guard.
Whereas if I know.
And you do a good job of this.
You'll say yeah, they're, they bought
this product, but their main use case is
this, or we talked about this use case
and they know this isn't a thing, but it
still might come up in the conversation.
So you're at least
prepping me with that info.
And then inevitably when it does, I
just double down on what you said.
And again, it.
Actually makes it feel like a, it
makes them, I think, feel like, yeah
internally they're talking and I, I'm
always referring to, I read Grant's
notes, I watched the demo clips.
I did the things that Grant shared
to again, make them feel heard and
valued and that they're the things
they said were confirmed and to double
down on things that you have called
out of yeah, no, he wasn't getting it.
Can't do this thing.
Or you're going to run into challenges
with this bit, but it's when you're
in that grind and to your point,
everyone's got metrics and leave
monthly goals that they're trying
to hit and everything's fast paced.
And now you run into that in real time.
It's just frustrating.
It's easy to blame the sales rep
or blame the onboarding, right?
But find a way to talk through it.
Yeah.
I appreciate that with you for sure.
Just having a quick slack
or quick heads up on things.
Grant: So much of it just has
to do with the like incentives
and the pressure that's applied.
Like when you start to get desperate,
then you start doing things that, are
going to not be awesome for the next
person down the line and sales case
it's onboarding and onboarding cases.
Kim: Yeah.
I think that's what I was getting at
with when I asked if you feel like
there people get upset at sales or if
you've had the experience I, so a couple
jobs ago I was not selling software.
I was selling trade show
exhibits that we had to produce.
So it was a big.
Lift for our team.
So I would sell something.
And then it was like, everyone
was like, I'm so excited.
I'm helping our business
hit our financial goals.
I just closed this huge deal.
And then everyone's okay,
now we have to go do it.
And it was so frustrating to me.
Cause I'm like, guys, this is the
whole reason you have a business.
If I didn't sell this.
We don't have a job yet.
And I totally get it.
So I had a lot of that
experience as a seller and it
was always really frustrating.
Cause like he and the CEO would be like
celebrating yay, we just got this big
deal and everyone else was like pissed.
And then when I went into onboarding, I
feel like I had the sellers perspective
and I was like super trying to make sure
there was a lot of times where literally
people were selling, especially new
sales reps were selling a completely
different product, truly it was wild.
And I was like very much
trying to educate and help.
Let's figure out where things went wrong
and let me show you how our product
actually works, that kind of a thing.
And then when I hired someone who
hadn't had the experience of being a
seller and having that pressure and
experiencing what it's like to have the
post sale team be annoyed at you, it
was a really interesting perspective.
Cause it was a lot of me having
to talk them down of hating the
sales team for giving them problems.
And it's inevitable again, back
to what we keep saying is some of
it sometimes can be things that
the sales team could do better.
And some of it is just like people
perceiving things wrong, people making
assumptions about the product or just
not asking questions and not realizing.
And it's a super honest mistake.
And I think it's just so easy to
say salespeople get commissioned,
salespeople get a flexible schedule.
schedule, whatever the kind of thing
is and being frustrated as like an
onboarding or CS person at the sales reps.
And I get it.
It's frustrating, especially like the end
of month deals and the weird kind of stuff
that gets thrown at the onboarding team.
I am 100 percent get it.
It is frustrating and sales teams
are under a ton of pressure.
And if you have no sales, you have
no job as an operating person.
So I just think there's a lot of
empathy that needs to be had across
both teams to understand the position
that both teams are in and both teams
are making it harder for each other
and nothing works without each other.
Like it just has to be a thing that
works together and you have to understand
where the other team members coming from.
And I think without that, it's so easy
to have contention between the teams.
I think.
Grant: Yeah.
What you really need to do is
have everybody switch for a month.
Kim: Yeah, do you guys want to do that?
Grant: Terrible for the business, I
think, but great for camaraderie and
like being able to work together.
Shareil: Yeah.
I love that you said that though,
Kim, because I've definitely heard
that, and I've thought that too in
past worlds of like, why is that rep
getting paid so much to sell this shit?
And now I have to clean
it, clean up the mess.
And it's wow, put yourself in
their shoes for a split second.
Their job is really hard.
It is a grind.
It's transactional.
They don't get the friendly conversations
you get on those onboarding calls where
they're already excited to be here.
So it is a very difficult job.
And I do think more onboarding reps and
everyone should do a few sales calls, do
a few demos, at least listen to them to
see what those folks are going through.
Because it's easy to hold.
and have feelings of frustration because
of that, and then they're compounded
because now you're also bringing money
into it, and you think you're doing the
same job, and it's just not the same job.
It's very different.
It's very hard.
Go try it.
If you really want to be a go salesman,
go try it, and I promise you, if
you're If your characters are more
suited towards onboarding, you're
not going to enjoy doing sales and
it's going to be a difficult world.
Kim: I think that's the thing is
people who do onboarding and customer
success are also customer facing
and they're thinking I'm showing
my customers value all the time.
How hard is sales?
What you realize quickly is when
you get into those demos, it's a lot
more than just showing people how
cool it is and how valuable it is.
There's like a lot of art and
science that goes into being
an actual good salesperson.
It doesn't just happen.
It happens for some people, but
like Grant truly loves sales.
Like he he's a salesperson and I
was in sales for most of my career.
I never loved sales.
I always hated it.
And I think that's just a thing.
You can maybe get by just talking
to customers if you're like, have
a good rapport and all that stuff.
But I think a truly good sales rep just is
a different skill set and a different type
of brain and a different type of person.
Shareil: You're also in onboarding.
You get to show them value that
they've already been convinced is real.
That's easy to do.
I'm just convinced.
I'm not even convincing him anything.
I'm just basically validating what
you've already been led to believe.
Grant: It's an interesting thing.
People have asked me occasionally Oh,
what made you want to do software sales?
Like, how did you get into it?
And.
I don't, nothing made me want to do it.
Like it wasn't like I'm super passionate
about sales and I love software.
It was like, I have a
lifestyle that I want to live.
And a lot of that has to
do with work life balance.
I guess I got to get good
at this and practice this.
And that was just, and I have grown
to really enjoy it because I feel like
the challenges are things that I've.
Gotten better at some of those
things that I was not good at early.
And so it's very fulfilling in that way.
And so it's become fun to me, but
definitely wasn't fun in the beginning.
Shareil: What's your least
favorite thing about sales?
Grant: My least favorite
thing about sales.
I love every aspect of it.
Shareil: There's just no way.
Grant: No, I think my least favorite
thing about sales is probably the
lack of control, like in every
scenario when all is said and done,
I have no power to close these deals.
Like it is the buyer and oftentimes people
that I'm not even connected to, not even
talking to who are influencing this deal.
And it always feels like it's at an
arm's length and all that I can control
is like the probability that it will
close, but whether it actually closes
or not is completely out of my control.
And that's that'll drive
you crazy and you feel that
Shareil: after every call.
That's yeah, that's an interesting.
Grant: I don't feel it after every call,
but I feel it anytime I'm thinking about
Metrics and like a quota, especially,
and it's made a thousand times worse.
If you have a quota, that's unachievable
or a quota that feels very hard to
attain, or a team that doesn't that
isn't like understanding about,
the realisticness of the quota
that you set, it's like day to day.
I don't necessarily feel it, but
it's when you're talking about okay,
I've got to find a hundred more K.
In this next week to close, there's
some things I can do to increase
the probability that these, some of
these deals in pipeline might close,
but I can't just make them close.
It's so frustrating.
Yeah.
It's a good sales is good.
It sells.
It can be awesome.
If you're at the right company
with the right products, it makes
all the difference in the world.
There's a lot of people who I talked to.
They're like, I tried sales.
I could never do it.
I'm like, yeah, you probably
had a crappy company or culture
or experience or product.
You could absolutely do it if
you were at a company like I'm at
now is how I feel a lot of time.
Kim: Yeah.
Trell, what do you hate most about
customer success and onboarding?
Shareil: What I really hate
is when customers churn.
And they don't give you a real reason,
especially when, you're trying and
you're putting an effort and you think
you're doing the right things and you're
iterating on your processes and you're
like, just give me some real feedback.
And they'll say things like, you have a
great product and you're a great team.
Just didn't work out.
And it's why?
Because we're trying to really learn
both at arrows, but at other places.
So that's frustrating.
And then the second thing is, and this is
usually the onboarding team's response.
Not usually this is 100 percent the
onboarding team's responsibility to
own and to convey, but when other
departments don't understand the,
your day to day or your job or the
value you're providing, and then you
become this reactive transactional
motion of just do X number of calls
or do X number of email check ins.
And it becomes very, I don't know,
robotic, because there is a lack
of understanding of what is the
value you're actually providing.
And like I said, that's on you to
normally be able to share and convey.
But I've worked at places where when
I try that and it's just not received
at all or there's just no care from
executives on that topic, it's just hard.
It's hard to stay motivated when
you're already feeling like you're in
this daily grind of, Keeping up with
phone calls, keeping up with emails,
keeping up with customer check ins.
So those two things grind my gears a bit.
Grant: Kim, what's your least
favorite part about Ops?
I
Kim: don't know.
I'm probably not going to
have a good answer for that.
I think maybe the toughest thing about
Ops is I'm so closely tied to your teams
and your roles and also have, there's
an impact and I can help with things.
And There's only so much I can do to help.
So I think for me right now at
this stage too, I'm really keeping
such a close eye on like everyone's
metrics, everyone's goals, how we're
pacing toward them, all of that.
And I feel bad a lot that I don't
have a metric that it's like,
if I do this and hit this goal,
then our team will be successful.
It's like a broad general thing.
And that feels bad sometimes just
because I think a big part of my
role is supporting and lifting up.
Each of the individual teams to help
us reach our go to market goals or
customer team goals, we call it.
And yeah, I don't know.
It's the thing I'm still working out.
Grant: Yeah, that would be hard.
It feels good to be able to look at a
number and be like, I'm doing a great job.
It also feels bad to look at a number
and say, I'm not doing a great job.
Kim: Yeah, exactly.
By the way, this is my
first time in operations.
I absolutely love it.
It's so fun, but that's just a thing that
I just generally feel bad about yeah.
Wow.
This was like really therapy guys.
So at the end,
Grant: I told you guys, I didn't
know what I signed up for.
Shareil: We
Kim: know
Grant: real therapy.
And so that's what I got out of it.