Onboarding Therapy

In this episode of Onboarding Therapy, Kim and Shareil talk with Matthew Ruxton about his journey from implementation specialist to RevOps leader, challenging common misconceptions about customer onboarding along the way.

Highlights from the Episode:
  • The Overwhelm Myth: Matthew challenges the common fear of overwhelming customers and explains why under-preparing is the real risk.
  • Building Scalable Processes: Learn why having a prescriptive onboarding road is crucial, and how to balance structure with flexibility.
  • Starting Onboarding Earlier: Discover why successful onboarding begins during the sales process and how to make that transition smooth.
  • CRM as Your Secret Weapon: Matthew shares how bringing implementation into your CRM transforms team adoption and customer handoffs.
Whether you're an implementation manager looking to scale your processes or a RevOps leader trying to improve customer handoffs, this episode offers practical insights on building onboarding that actually works.

Key Resources:
👉 Don’t forget to subscribe for more actionable insights and strategies for onboarding and customer success!

What is Onboarding Therapy?

Customer onboarding in B2B SaaS is changing fast, but the resources for onboarding teams? Not so much. That's why we're kicking off Onboarding Therapy, a podcast that tackles the real challenges onboarding teams face every day.

Matthew: People try to make it
like it's different for every

customer and like this and that.

And I'm like, there's a prescriptive road.

They have to go down.

They have to plug this in,
turn this on, do this thing.

And then they get there.

And if you refuse to see that, you'll
never get anywhere with their customers.

Welcome to onboarding therapy.

I'm Kim and today's Cheryl and I are
joined by Matthew Rexton who shares his

journey from implementation specialist
to rep ops leader and my process beats

personalization and customer onboarding.

Let's get into it.

Kim: Okay.

So welcome to onboarding
therapy for this episode.

We have Matthew Ruxton on who's
been a long time friend of arrows.

We've known you for years at this point
and always love, we were just talking

about your hot takes on onboarding
and HubSpot and all the things.

To get started, I would love, if
you could give a background on you,

how you got into implementation
and what you've been able to do.

We're doing now.

Matthew: Yeah.

If we want to go way back, we can talk
about, as a young boy, I dreamed of

growing up in an implementation of,
I, so like my first foray into SAS, I

would say I did lots of years selling
coffee for various large coffee chains

that we will not name for legal reasons.

But I, leaving that, I was like,
it's time to not sell coffee anymore.

So I.

Ran into a company that was like, Hey,
we're starting up a support function.

And I was like, that sounds like fun.

So got into like customer support.

Then they're like, Hey, we need
to build an onboarding function.

And I'm like, I could do that.

And I've been sitting in support
this time and I'm going, wow, every

time you handle tickets, you're like.

This issue is resultant of you
having a terrible onboarding.

Like the fact that we're fixing this is
because it wasn't fixed at the start.

So let's do that.

And I was like, yeah, I want to
fix, I want to move up the channel.

Let's fix it early.

So we don't have the amount of
support tickets that we have today.

So like I moved into onboarding and
I climbed up the onboarding ladder as

like an onboarding associate, then an
onboarding specialist and implementation

manager, and then they're just going
to like slowly working my way up.

And then after that kind of.

Did a little bit of fun time in a
completely unrelated industry with doors

and then got into HubSpot and CRM is
started in Salesforce and then quickly

learned that, Salesforce is very diluted
with tech talent and there's lots of

great talented people in Salesforce, but
it's very hard to get out there and get

noticed and do really stand out above
the crowd because everyone's getting

trailhead certifications and you're just
one of 50 people who applied for a role.

And I was like, I really want to get
into the operational side of stuff

and understand, cool, we're doing this
process, but are we showing that process?

To, our leadership, do
they know what we're doing?

When we onboard found HubSpot and,
saw a couple LinkedIn posts about it.

I was like, okay, let me take the
dive and, Dove into HubSpot and

was working as an implementation
manager, ironically, when we were

using HubSpot and we were like, Hey,
who wants to help fix this process?

And I was like, I'm, hi.

And we went in and we started
messing around with pipelines.

And I was like, this is really cool.

And I just got way into it and then landed
a gig at an agency for a little bit.

And then after that.

Went from there and now working for a
company, we're doing some cool stuff

and really just getting to live HubSpot
every day, administer in that sense.

I think it's been awesome.

It's been a fun ride I think
there's a lot of value.

And I think this is not
new news by any means.

It's definitely the coldest of cold
takes, which is that HubSpot is more

than a sales CRM or marketing CRM.

It's definitely something you can
run your entire business out of.

And something that we do right now at
Ignite, we run almost every team in our

organization touches HubSpot in some way,
if they don't operate out of it daily.

With that on all that data,
there's so much you can do.

I think it's wild to not make the
CRM the center of what you do.

Kim: Totally.

I think it's obviously unique that
you also have the experience of what

onboarding and implementation actually is.

So then you're using that and
thinking proactively about

building that out inside the CRM.

I think that's super rare.

We're definitely seeing it more where
people are including in the CRM, but.

A few years ago when we started
talking about this, it was not

really happening very much.

And I just think rev ops generally as a
role or position, is thinking about sales

and marketing so much and mostly sales.

And so to have like customer success
and onboarding be thought of in

that way is so awesome and great.

So tell us some of the.

Like learnings or maybe struggles
that you noticed as you were climbing

the ranks in implementation and
kind of building that program out.

Was there anything that stands out?

Matthew: I always think
the biggest thing is that.

If you don't have a defined process
early on in your implement, if you're

starting with, if you're building an
implementation organization, you're

building an onboarding organization within
a company, you don't have here's the

steps we have to do to get someone live.

That's where you have to start.

People try to make it like it's different
for every customer and like this and that.

And I'm like, you still have,
there's a prescriptive road.

They have to go down.

They have to plug this in,
turn this on, do this thing.

And then they get there.

And if you refuse to see that, you'll
never get anywhere with their customers.

And that's when, I think like I've
been in organizations where there

is no process and it's just like we
just get customers live and we hope

for the best and they hopefully stay
but we have a big churn problem.

We don't know why.

And I think there's a lot of I
always think of the biggest in

like revenue operations and just
across the entire go to market org.

One of the biggest endpoints is
always like the marketing sales.

You always hear about it.

Ooh, marketing's like always like eating
up sales and sales, automatic marketing.

And I'm like, that can exist in some
extent from like sales to whatever

your customer success organization
looks like, whether it's you have

a dedicated onboarding team or you
don't, you have just a CS team that

kind of does some of that work.

there can be that similar kind
of argument and pushback, but

it's never called out enough.

I feel like nobody focuses on that handoff
nearly as much as they focus on like

how marketing brings a lead to sales.

I'm like, that's important.

But just because they signed the contract
doesn't mean they'll stay next year or

next month or next 3 years, whatever your
contract cycles are, people are super

excited when they close 1 and so many
places just don't capitalize on it at all.

They just let it fall off and they're
like you'll just get on board and

you'll do what you need to do.

And it's awful.

And when you've worked at onboarding.

For a while.

It's weird how you see
it in other industries.

And people don't realize, I think,
how much onboarding exists in

everything that we do nowadays.

I think back to my mom of the day
was getting set up with the internet

and I opened the box and I'm like,
wow, this is actually pretty easy.

Like it's got like color coded numbers.

And it tells me this is step
one and this is step two.

And this is step three.

And then we got to a point
where something didn't work.

And their solution was like, call us and
I call and it's a 40 minute wait, and

I cried, and I just stopped and we did
something else like that pain point is

something that you as a business need to
make sure like you can have the nicest

packaging in the world for a product.

But if you don't understand the
pain points that could happen in

that process and provide an equally
nice way to deal with them, It's

not any better, like you may as well
not have that nice package product.

once you have a process, and then
once okay, you can't solve for every

option that could go wrong, but you'll
know pretty quickly if they get to

this point, here's the things that
could go wrong, and here's how we're

going to preemptively solve them.

being very proactive in your
onboarding approach is so important.

customers see that.

they get annoyed when
you have to be reactive.

They are much happier and
delighted when you're proactive.

Shareil: You said so much gold in there.

So much resonates.

One, if you, I don't care if you have,
every customer is unique and different.

Then you need a lot of unique
and different processes.

Like you still need a document.

Things if your counter argument
is well, we do it a little bit

differently for everyone I think you
just need a lot more documentation,

which is a pain in and of itself.

Yeah, but what you were sharing Reminded
me of you know when you're first

starting to date someone or getting
into a relationship and it's That

honeymoon stage and everyone's excited,
and then you go on that one like trip

and you're like, Whoa, what was that?

That's what bad onboarding feels like.

It's we just had all this
fun and sales and marketing.

And now you're thrown over and it's good
luck, Cheryl, figure it out on that side.

And it is night and day.

And you're like, what just happened?

And now it's good luck, figure
it out on your own ones I paid.

And that's such a bad experience
and such a bad way to continue that.

What could be super high engagement
and high initial momentum then gets

turned into The actual opposite.

And to your point, whenever I hear
we have a churn problem at day 30 or

day 60, you have a really bad handoff
and onboarding and implementation

problem and the output is what
looks like a churn result at day 30

Kim: I love the AT& T example.

And I think a lot of people don't think
about onboarding in that way, but It's so

true where a lot of people are, if they're
doing onboarding, it's like a handoff

email to a customer success manager.

That's Hey, here's your
new point of contact.

Do these six things in an
email or whatever it is.

as a customer, I'm receiving that.

And I'm like, okay, great.

Six things.

I can do this.

Maybe I'll do number one, log in,
whatever it is, do number two.

And then there's inevitably
a step where I get stuck.

And that stuck point is
I'm a goner at that point.

I had just dedicated time to
getting up and running with this.

And I said, okay, I'm going
to work through it right now.

And now I'm stuck.

I can't get ahold of anyone.

I don't know what to do.

There's no resources.

And now I'm just completely stuck.

And who knows how long it's going
to be until you get me back?

Cause I maybe was planning on
just that day, getting it set up.

And now it might be two more weeks.

And I think people just don't
think about the customers.

perspective on what they're experiencing
when there are roadblocks like that

and how much of a blocker it is and
how like mentally devastating it

is to be like, I thought this was
going to be a quick and easy thing.

And now I don't know
what's going to happen.

Matthew: there's so many examples
of stuff that you do where it's just

there'll be something you stop and
you're like, I am done with this.

I'm going to go do something else.

Like you build furniture.

It's the same thing.

Like you get to step is you need a hammer.

And I'm like, I, why did you not tell
me the getting any of the hammer?

Now I've got to go find a hammer.

I don't have a hammer.

I am done.

I'm going to go make dinner.

And then you have a half
assembled bed in your office.

I'm amazed at the amount of
like processes and onboarding.

And I think it happens in SAS.

It happens in every industry, but
there's any sort of like process to

get you started where like so many
businesses just don't think about.

How am I going?

What do I need first?

And you always see people like
they're like, Oh, it's so annoying

when I open a booklet and it's
you'll need these nine tools.

You're like, do I need these nine tools?

And it's no, you need
eight of these tools.

This ninth tool.

I just know you might need by rally.

You have it now because then you
can get this done in an hour because

you already have the tools you need.

And I think there's so
much in onboarding process.

They're like I don't
want to overwhelm them.

I don't want to give
them too much at once.

I'm like.

Yeah.

there's overwhelming and there's just
preparing and they're not the same thing.

And I think so many people are scared
to overwhelm their new customer.

They just signed, they
gave you their money.

They're not, realistically, they're not
going to go anywhere for maybe 30 days.

So it's okay to be like, these
are all the things we need.

did you have this conversation with them?

Pre closed what?

So many businesses wait till
the closed one has happened

to have these conversations.

Inform them before closed one, say,
Hey, if you want to do this launch

day, if you want to launch this in 30
days, we can help you out with that.

But I just know as a sales rep, you're
going to need X, Y, and Z successful

customers have X, Y, and Z ready to go.

If we want to launch in 30
days, we can do that for you.

We recommend 45, but we can do 30.

If you have these three
things you do great.

Let me get you going.

I think that is where that kind of
the handoff is less like a singular

point where it's I am done and
now this person will take over.

It is, how can we layer that
handoff a little bit better?

We're going through that right now.

It's like, how do we layer that?

At what point do we bring this
person into the conversation?

So that it's not this sort of jarring
experience where you go, Okay.

I'm being, wined and dined and
all this stuff and suddenly here's

this new person that's just yelling
at me for six different things.

Kim: Was there anything that you did
when you were working specifically

in onboarding implementation to
collaborate with the sales team

in that way to make it better?

Or was there specific things you
had to overcome working with them?

Matthew: think there's always like this
sales, it's like, why are you in my space?

Which is always hard, but I can't remember
who, I think it was RJ you had on a

couple weeks ago you guys were talking
about how, as an onboarding person I

have a vested interest in seeing how
you close the sale, because there's

so much gold in that closing argument.

What convinced them to come to us?

Because you have this integration.

Great.

As an onboarder, I need to know
we need to focus on getting that

we can suck at everything else.

We don't want to do that, but like we
could suck at everything else, but you

bought because of this integration.

Let's make sure that is our number
one priority coming into onboarding.

And I think that taking that time to
go sit with an AE or go sit with your

closing sales rep or whoever that is in
your organization and just see how they

close and what is getting people across
the line, can help drive your focus goals.

So much effort I think is put
in by sales reps to be like,

What are your three goals?

You'll hear CROs and heads of sales.

What are the three main goals
that you got people to buy on?

What are the three
things you got to buy on?

And then they hold that
information and never give it up.

And I'm like, that is
gold for an onboarder.

If we know your motivations, like we want
to capitalize on your motivations and make

sure that's what gets you across the line.

HubSpot does that with
their onboarding process.

So what are the three things
you wanted to achieve in sales?

Okay.

These are the three things we're
going to work on first because we

want to get that time to value.

Like you bought it, we want
you to see it right away.

And especially if you have a product
that is long time to value, just by the

nature of what it is, you want to find
that thing that, what was the thing

that got them across the finish line?

And let's make sure we prioritize
that over anything else.

Shareil: So you said that really stood
out to me about, overwhelming customers.

One of the.

If not every single customer, almost
every single customer that signs up for

arrows and starts building out their
onboarding process with me always asks,

is there such a thing as too many tasks?

And I never answer that question.

I always follow up with what
did marketing and sales promise?

Because if they told you it's going to
be a quick deployment and a few weeks

to set this up, but actually it is a six
month process, then there's a way bigger

problem than overwhelming customers
because you shouldn't shy away from.

Yeah.

200 tasks, if those 200 tasks
are the thing that's going to

get me the value I paid for.

Now, if half of them are selfish tasks,
as I call them, tasks that we might

want you to do, but don't really get you
closer to activating for your goals and

needs, then yeah, that is overwhelming
and maybe feel counterintuitive

to the expectations that were just
set from marketing and from sales.

But I think part of the challenge is,
and I see this across, especially in

SaaS, across marketing sites, you read
it all the time in the headlines, super

easy to set up, start sending your report
within minutes, XYZ can happen overnight.

And it's no, that's not
actually what happens.

And now you have really set these
onboarding reps, CS reps, support

reps up for failure because you're
never going to be able to deliver

on that promise if the reality is
a long, complex product is set up.

Yes, there can obviously be such a thing
as overwhelming customers, but if they

are tasks and you communicate it in the
right way, and I'm seeing value from

that, then I wouldn't worry so much about
the pure number and worry more about

the tasks themselves and what you're
asking people to do in that moment.

Yeah, it's so true.

Kim: And I think it goes back to,
again, if I'm the customer, I want to

know how long it's going to take me.

So I can, cause I like, realistically,
I'm blocking the time on my calendar.

I am saying during this.

Whatever time period I've been told it's
going to take, I am blocking this time.

I am allocating this time and my
mental resources to get this done.

So if you say it's going to take me
15 minutes and then I really don't get

anything done in 15 minutes, I'm now
annoyed and I have to find another time.

And I have to like, try to
figure out myself how long

it's actually going to take.

So I think if there's so much
internal management that has to be

done around how long it actually
takes and setting those expectations,

but then also communicating to the
customer Hey, this is going to take.

Two weeks.

And in those two weeks,
this is what's happening.

This is how much time you're going to need
to spend to set up your internal kind of

processes versus how much time we're going
to spend coordinating things on our end.

Like people are afraid to overwhelm
customers, but it's customers

just want the information.

They just want to know what's needed.

And then they will.

They'll allocate their time.

They'll figure it out, but not telling
them and hiding that information is

just making it worse for everyone.

Matthew: But I think it's like the fastest
way to lose a champion for your product.

There's been someone in that buying
committee that has been like the one

that said I want us to pick this one.

And if that person is they're the person
that's going to advocate for its use,

Long after onboarding, but if you don't
let them be aware of that, like they're

not, they're going to lose that passion
and they're going to lose that sort of

want for that product because they're
like oh shoot, I said we wanted this.

And it's 40, 45 days to get done.

So I don't have time for that.

That's the thing that like, as someone
now, like on the opposite side of the

thing, as someone like in operations,
who's like shopping for stuff and

looking for tools and getting demos
all the time, the one of the questions,

the first question I ask is okay,
but how quickly can I be set up?

And I always judge the answer because
there's certain sales reps that will

say, we can get you set up in minutes.

And I'm like, you're lying.

Because you're just wanting
me to close the deal.

And I'm like, it's not, I don't
want you to tell me it's going

to take me minutes to get set up.

I want you to be realistic.

Ask me that follow up question of what
do you want to get done in 30 days?

If it's a case of, I want to, we're going
through this right now with e signature.

It's I want to be able to at least
send out my existing contracts within

14 days of getting onto your platform.

Great.

If you already have your contracts,
we can get you done in 7 days.

Versus, hey, I may have said in
the sales process, we also want

to overhaul our product tracks
and do all this other stuff.

But ultimately, to get me going,
I'm happy to just get this

our existing process in place.

And then we can work on making our
new process so much better with your

tool, because your tool gives us all
these functionality, this ability to

do this, and I can put properties in
host bar whatever, I think there's that

sort of like level of conversation has
to happen early in the sales process.

And I think there's some organizations
are doing a really good job of that.

And I think if you have the
budget for a solution, engineers

solution, and you should work
so closely with onboarding reps.

some of the best solutions I've worked
with have been in onboarding because

they know what is doable in 30 days,
they know what is doable in 60 days,

and they don't sell the customer
something that isn't really there yet.

The other thing I love

Shareil: that you said earlier
is the proactive piece.

Let me know proactively how
long it's going to take.

if I have to ask questions, That is.

A quick way to delay the process because
now I have to wait for you to answer.

Odds are I have to process the answer.

Odds are I'm not going to like the answer.

And then I'm going to have to go think
and know, now what do I do with this

answer and this yet found knowledge?

Whereas if you proactively tell somebody,
We're going to review your documents and

it's going to take us up to two weeks.

Now you have an answer and you
have a little bit of more insight

into what I might be doing.

You can go on and build your Ikea
furniture in those two weeks while

you wait, but you know that you
don't have to sit here and wait.

For me to communicate that or you
have to ask and then get frustrated

and ask again and get frustrated.

It's just so the proactive piece
feels very missing and I understand

it's not, I don't think people
are trying to not be proactive.

You just get hung up in 10 calls a day and
multiple follow ups and that cycle just

becomes very hard to maintain, especially
In sales and onboarding and support.

Kim: This is my first time in an ops role.

So I've been on the buying side
and the implementation side

a lot more as a customer now.

And I really feel like it's the
norm to be let down post sale.

Like I hate to say it, but it
just is I have so little trust in

the sales process for any tools
anymore, because I'm like, I don't.

Believe you.

I don't, I just healthy

Matthew: distrust.

you're doing good in the ops world where
you're just like, you just trust no one.

Kim: I will say the bar is low.

And so if you can be upfront, like
these are really small things.

They're actually small tweaks
that you can make that really

change people's perspective.

Because if you have someone in sales
who is being honest and being upfront

and setting clear expectations,
that is such a big differentiator

because no one is doing it.

So that's just such a great
way to stand out as a vendor.

Matthew: I always think of the phrase,
you polish a turd, it's still a turd.

I think I've used this several
companies where I'm nobody likes

internet service providers.

We all equally disdain on all of them.

And for most of us, you have one, maybe
two, if you're lucky, three options

in your area for service providers.

And They have these fancy J.

D.

Power Awards, and I'm like, oh yeah
Comcast won it seven years in a row,

and I'm like, yeah, but they suck.

but when you suck the least
amount of group of people that

suck, you win an award for it.

And that is my I've always said,
do you want to be, the least sucky,

or do you want to be the best?

And that is I think that's a
differentiator a lot of businesses, Really

struggle with customer success in an
onboarding is they're like, yeah, but we

just need better than our competitors.

And I'm like, no, don't just be
better than your competitors.

Be the best in your area.

If you can prove that, like we're
gonna get customers onboarded

and get that sort of stuff.

You don't see that many businesses that
will have testimonials of people that went

through about their onboarding experience.

They always say the product's great.

Or, we were able to solve this
problem with our product, but nobody

ever wants to get a testimonial.

I will give a testimonial about the
onboarding experience if it was good,

because like that, I think like that's
going to resonate with me as a buyer.

Like it may not resonate with the
top buyer person, but there's someone

on every buying committee that is
going to have to put this together.

And if they get like a, Hey, I'm you.

I'm in your position.

Darrell was awesome.

He led me through this process and
he gave me all the tools I needed.

And I didn't feel like I was struggling.

That is the best kind of testimonial
I think over your product could suck,

but if the onboarding experience is
amazing, people remember that, and that's

I think that goes back to anything.

If you create that really nice
experience that people will remember

and differentiate from, you will keep
customers a lot longer and they will talk

about how awesome it was to their peers.

Kim: Yeah.

And make the person buying
and implementing the

software look like a genius.

I think that's a thing too.

the company should feel like, Oh my gosh,
Matthew just implemented that software.

I chose to buy that software
and it went so smooth.

And that was the smartest
decision we ever made.

Whereas again, the norm is like,
Oh, this was a rocky decision

and we don't really like this.

And you're just neutral at
best about the decision made.

So I think like thinking about it through
like the customers, there's a lot of like

goals in there, but like the individual
buyer wants to look like they are so

smart for the decision that they made.

And they made the right choice,
especially that most people are

evaluating competitors and making a
specific decision one over the other.

They want to look like, I did
this and this was like my call

and I made the right call here.

Matthew: Yeah.

I feel like that's a pretty good example
of what a lot of people do with their CRM.

a lot of the tools they buy, they
go I didn't do what we wanted it

to do, but it's doing it enough.

So we'll say, and that is the
sort of slow churn that eats me in

the back of my mind all the time.

people that are not unhappy, I always.

Using the example of NPS is a great
tool, but it has its flaws, and it

doesn't focus on why are people passive.

And that is always something that's
dawned on me, really, detractors are

a problem, they're often a sign of
someone who's going to churn soon.

Then your positive, I can't remember
the name of the positive ones, are,

I'm like, your protractors, I'm
like, no, that's a mathematical tool.

Promoters, there it is.

Your promoters are like people that are
evangelists and they're going to talk

about your product, but like the passive
people, like I think sometimes are the

ones you want to spend your time on
because they're the ones that are not

fully bought in yet, but they're also not.

upset, but there's, it could just take
one thing to throw them either way.

And like NPS is a wonderful scoring tool,
but those are the ones I always tell

people, these are the people we need to
watch because they are in the middle.

They're on the median.

We need to figure out why
they're not going either way.

A lot of times it's they had
a bad onboarding experience.

They had like during setup, something
didn't work the way they wanted it to.

So now they're just
going They're doing fine.

It's a solid B minus for them.

They're like, it's working,
but it's not working great.

That's the issue we have right now
with our current e signature provider.

Is it like, it works, but it
doesn't work the way I want it to.

But I was like, last year when we
did a renewal, I'm like, the pain to

switch to another one is just so much.

It's I couldn't it was not
enough to overcome that.

And then now this year
there's a cost difference.

So I'm like, that suddenly
the pain has shifted.

And I'm like, cool.

Now I have a reason to
switch to another provider.

if it only takes the pricing change to
have someone leave and then you're all

these passive people switch to detractors.

I think that if you give them
such a good onboarding experience,

they are less likely to move.

They're less likely to
go find a competitor.

But at that point, if you've informed
them early on, what they're going to

get, then I think they will want to stay,
that they want to make the decision.

Because I'll be honest with an ops person.

I don't want to go shopping
for products every year.

Like it's painful.

It's no fun.

I much rather shop for
presents for myself.

Like it's not a fun time to go shopping
because you know you're gonna get

bombarded with AEs and they're gonna
message you on LinkedIn and they're

gonna ask you like all these things.

I just think there needs to be more.

If a company was to be like, hey, we're
going to invest all our time in showing

you that you're going to get value
quickly from our product, show it in the

onboarding process, not in the product.

The product, your product is going
to be, it's either going to be

great or it's not going to be great.

But you can have a terrible product
and a great onboarding experience.

People will stay with you because
they're like the onboarding was amazing.

So I think there's so much value
in highlighting the onboarding

process more with your future
customers and as early as possible.

Shareil: Those quiet quitters
you described are also dangerous

because one, they're not using
the product or activating.

When you ask them for feedback or thoughts
or exit interviews, you tend to get

answers like you guys were a good team.

You have a good product that
just didn't work for me.

And it's what part of
it didn't work for you?

It might've worked for you actually.

Had we gone into your pains and into
your challenges and to your point, nobody

wants to actually switch providers.

Like I would rather you
monopolize my whole business.

I would rather call one customer success
person who can handle everything and

it handles it so well that I don't need
to call around to a million places.

But that's not the reality.

And to a lot of Kim's experiences
recently, most CSMs, unfortunately

are just checking boxes on the other
side and doing their, I did it.

I did my activities.

I did my calls.

I did my check ins.

Yeah, but did you add any value?

Matthew: I think a lot about, what
I was doing, when I was project

managing as implementation, manager.

The amount of times I would say,
I have no stake in if you upgrade,

I have no stake in if you do.

I am paid a salary and I can
bonus on the company growth.

I don't get paid if I get you to
upgrade, but I'm letting you know

that you need more, in that case
of you need to buy more contacts.

Like you are not going to be able to
market to enough people quickly enough

on the ramp that you want to do.

And I feel like they appreciate that
just like honesty in the onboarding

process of I am working as I want to
be a thought partner for you, not You

know, just a taskmaster that's telling
you to do things, I think that's huge

and I always worry people talk a lot
about I think I've seen like a couple

like Whisperings of like, how do we
comp plan onboarding managers and should

they have quotas and this sort of stuff?

And I'm like, I don't know my hot take
is I don't think onboarding should have

any form of sales based quota, because
I think that's just going to make them

like thinking of the wrong motivation.

But you need someone who's I want
to be your friend in this process,

not like someone who's just actually
trying to get you to buy more things.

And I can show you to your point, I can
show you a feature that you didn't pay for

and be like you have this pain and this
would probably solve for it, or here's

how X company did it and solve for it.

But I think that relationship has to be
one of like mutual respect and not one

that's coming from a place of, I'm still
trying to get you to buy more things.

I don't think you should
have quotas in onboarding

Shareil: But what I've seen work well
is like incentivizing discovery of

growth opportunities in onboarding.

So if I.

Talk to you about a
potential premium feature.

And then three months from now you upgrade
into it or whatever timeframe you set.

Cool.

Maybe you can get a hundred dollars
spent for something to keep you

excited about discovering those.

But to straight up have
people selling in that world.

It just feels like a sticky or a
slimy extension of the sales process.

Kim: Okay, so we are nearing the end,
but I would love to get some of your

takes now that you, because you've been
in ops for a couple years at least.

Matthew: Yeah.

Kim: And in all or most of those
roles, you have been working with

customer success and onboarding teams
and getting ops set up inside the CRM.

Matthew: So like I was subverted,
like it's coming from a space

of using HubSpot primarily.

So there's some slant in this
conversation a little bit to that.

I think there's a lot of value in having
your CST just be able to see product data.

And I think it's wild if you
don't factor product health and

product usage into your like health
scoring metrics and in your CRM.

I think a lot of people don't utilize.

The tools inside of HubSpot for CS
and nearly as much as they should,

like there's so much value in
like using the meetings scheduler.

There's so much value in like using
documents and having your team view

documents that are technically like sales
documents, because then you can start to

see like, where are they viewing them?

Where are they clicking?

Where are they stopping reading?

That is, there's a lot of like stuff
that's in there that's important.

And I think that one of the biggest
things that we did recently was we started

giving each department in CS their own
object, at least they are responsible for.

But we have custom objects for
certain parts of our process.

And I'm like, this UCS never
responsible for this object.

This is your home, you bake it when you
want it to be your here implementation

associate, this is your home over here,
you're going to build it and we let those

teams control how that looks what it looks
like, what is their day to day use of it.

And that drove adoption much
faster than me coming in

saying you need this and this.

Because when the people
that work in it day to day.

get to have some say in how it's built.

they will adopt that thing like crazy.

And this is coming from a team
that was like spreadsheet city.

So they were so excited to get out of
spreadsheets, but we're actually nervous.

What does that look like?

I'm like, we can build whatever you want.

We can build you like what you
need and what you want to see.

There's just so much functionality
and letting your team see each

other's data and be able to
interact with it in some way.

And that should be no different.

I should be able to see like
our deals are coming our way.

What are our sales team doing?

What is marketing doing?

I've seen a team has such a good
relationship with marketing because

we're like, Hey, these customers
won't shut up about how good services

and how it's impacting their kids.

they want to tell people about it and
we're like, marketing here you go.

It's wild to see somewhere where
we actually see, the flywheel work.

everything is going around in a
circle, and I think that removing

them from the CRM would be terrible
in that sense, because then

all that data stays out of it.

I think a lot more people need
to realize that centralizing that

around 1 system can be scary.

It's a hundred percent worth it because
just so much faster to pull data and so

much faster to pull what you need to see.

Kim: So I ran an onboarding
team in my previous company.

We were using Salesforce for our CRM.

Only sales was in there.

We had some kind of basic tracking
in there for onboarding, but I

wasn't as an onboarding manager
living in there day to day.

My day to day was in Trello is what we
used, to manage onboarding at the time.

And then every once in a while, I
would have an issue with the customer.

And I'd be like, okay, what it sales.

Tell them, and then I'd have to
go log into Salesforce, try to

reorient my brain around how does
Salesforce work, where would this.

Information be stored.

And so there's also just that
difficulty of I need to go reference

information and I'm not used to
this cause I'm used to my system.

Whereas if all teams are working together,
I already know how the objects work.

I know what record to go to.

I know where the sales deal
and ideally it's connected

to the object I'm working on.

Inside HubSpot and having all the teams in
the same interface where they know I can

look this up and I have access to the same
kind of information for the individual

onboarding or implementation team member.

Matthew: A hundred percent.

I think you have to make a, by
having everyone in the same platform,

they, you can, there's a lot shorter
learning curve for people coming in.

And like in my current org,
we are hiring it feels like

exclusively like ex teachers.

People that are coming from
places that don't use CRMs.

This is their first CRM that they've
ever encountered in their life.

And they're coming in and they're
seeing this and they're like scared

and I'm like, it's not that scary.

Let me walk you through it.

And we did that this year.

Actually, we launched like a little
like HubSpot 101 course that we

like customize to our portals.

Here's where everything is
and here's what it means.

And so many people, like the amount of
ticket volume that I get for basic stuff

has decreased like 80 percent Because
like they can self serve now they know

where to go and get the information
they're looking for and they're not

afraid to leave a note on an onboarding
person's object that are afraid to leave

a note for a sales rep, like they will
go have those conversations like in the

platform and I just cry in the background.

I'm like, this isn't a spreadsheet
somewhere or an email chain.

they're actively participating.

And I think that is the hardest
part of adoption in any theorem

platform is getting people to
use it for day to day stuff.

And when that starts
happening, it's magical Okay.

You just got to let them get what
they want out of it, instead of

trying to force them down into this
is what the industry says you need.

It's no, listen to them and see
what you can build to accommodate.

Shareil: I think that last part you
said is important in that actually

listen to them, like what are their
day to days, like what's their pain?

And that makes CS folks feel so heard
for one and as part of the team because

they've always been, they've always
had to use spreadsheets and emails

and you're actually using all the
components of a CRM, they're just all

over the place and poorly integrated.

And that's why you're frustrated because
you're having to do Not just double,

but triple, quadruple the amount of work
because of this disjointed system of

crap when the answer actually is the CRM.

But also to Kim's point and your point
if you're just going to jam me into the

same deal object that sales is using,
yeah, that's probably going to feel worse

compared to what I'm used to when, if
we spend some time and build something

a little bit more focused on my job.

I'm going to lean in a little bit more.

I'm going to see the activity
that I want out of it.

You're going to see the
activity that I want out of it.

And then you're going to invest
more in time and money and effort

to make it work even further.

Kim: Thank you so much for
coming on and joining us.

Any final thoughts that you want to
share before we sign off, Matthew?

Matthew: I think the most important
thing is to really mirror what Shirelle

said, if you're getting into, operations,
your first operations job, managing a

CRM, or you're an accidental admin, the
best thing you can do is just listen, I

think that if you take the time, it's so
easy to get into a new role, and you're

like, I want to make change on day one,
and I want to do this, and I'm going to

change this, and we're going to do this,
That is the runway trip to Burnout City.

I'm like, take the time to just listen.

Live in your people's processes, see
what their pain is, hear what they're

going through on a daily basis.

Because then that will help you
build much better integrated systems.

If you just go in you need a pipeline
and you need an object and you need this,

you're going to build a bunch of stuff
that's just going to end up not being

maintained, doesn't get used properly.

A year from now, you have
to do a maintenance project.

You can be like, we're not using
30 percent of our properties.

That sucks.

why we've been collecting this
data or one CSM is entering into

this field for their customers.

No one else is using it.

I think there's value in just taking
the time to listen and build a

tool that they are excited to use.