The Revenue Engine

Rosalyn: Welcome to the
Revenue Engine Podcast.

I'm your host, Rosalyn Santa Elena,
and I am thrilled to bring you the

most inspirational stories from
revenue generators, innovators and

disruptors, revenue leaders in sales, in
marketing, and of course in operations.

Together we will unpack everything
that optimizes and powers the revenue

engine growth farm production.

Are you ready?

Let's get to it.

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Rosalyn: In this episode of the Revenue
Engine Podcast, Chris Waldron, the c e

o and Co-founder of Satellite addresses
these questions and so much more.

He also shares why it is so critical
to ensure that there is equality

of opportunity to all individuals
across diverse geographies.

Races, ages, and gender.

So please take a listen to this two-time
founder and long-time sales leader and

learn how to accelerate sales training
and coaching to help accelerate revenue.

So excited to be here today
with Chris Waldron, the c e o

and co-founder of Satellite.

Satellite is a decentralized
workplace training and placement

program that connects talented
professionals in up and coming.

Cities to remote roles in modern
technology sales organizations through

a better way to train and place sales
talent with high growth companies.

So welcome Chris, and thank
you so much for joining me.

I am super excited to unpack
your story and learn more about

you and what you're building.

Chris Waldron: Great.

Yeah, no, I appreciate you having me

Rosalyn: as well.

Thank you.

So let's dive into it.

I mean, let's talk a little bit about
your career journey and some of.

Story, right.

Leading to founding satellite.

I mean, you have just an incredible
background as a co-founder, a sales

leader, a mentor, and just so much more.

Um, can you share maybe more
about your career journey and

some of your experience, um,
you know, prior to satellite?

And I would love to hear more
about this door-to-door selling

Chris Waldron: too, that that always spurs
an interesting conversation with people.

So I, I appreciate you bringing that.

Um, yeah, I mean, when I think about
how I want others to think about me,

um, first and foremost, a founder
satellite's my, my second startup.

Uh, so my first startup
was take lessons.com.

Mm-hmm.

, uh, which is another talent marketplace
where we helped focus, well, we

focused on, uh, creators, mainly tutors
who wanna do what they love to do.

So teaching subjects like
piano, parkour, math.

But they were never able to
earn a decent income from it.

And we actually had a friend
who was a drummer who was living

paycheck to paycheck, um, yet the
most talented drummer in a band.

And he was going to quit his job
in the band, uh, because he had a

family, uh, a son that was on the way.

And so we decided to build, take lessons.

For him.

Mm-hmm.

. And basically what it was, uh, was a, um,
entire platform for scheduling, payments,

communication and marketing for tutors.

And luckily that was acquired by
LinkedIn, uh, about a year and a half ago.

And, uh, they rolled that
into their learning org.

But that was my first, uh, Uh,
entrepreneurial, uh, attempt

and really appreciated that.

But, uh, after I left take lessons,
I wanted to, uh, work within

operations at a different scale level.

Mm-hmm.

, and I loved the intersection between
operations and revenue, and so I knew

I wanted to be in a VP of sales role.

But I knew I wouldn't, I
couldn't get excited about just

selling a marketing automation
platform or something like that.

Mm-hmm.

And there were two
organizations on the east coast.

I was moving from San Diego to
New York, and I wanted to work,

uh, with either managed by q.

. Uh, and that was, uh, being led
by Dan Teran or um, Andela, which

was being led by Jeremy Johnson.

And I really appreciated both of
their missions and their product.

And then I also wanted to learn from
them as founders, cuz I wanted to be able

to scale a bigger and better business.

So, Uh, unfortunately, Dan Tarran
rejected me, , um, and did not

accept me at his head of sales.

Uh, but I finally sold Jeremy
after about three or four months

of a drip campaign and, uh, things
worked out and I came on right after

their series B from Spark Capital.

Um, we raised our series C from czi,
our Series D from generation, and at

that point they wanted to bring in a
professional C R O who's managed a hundred

million, uh, in, in revenue, p and l.

Mm-hmm.

, and that made sense.

But I had a lot of fun building,
uh, Andela with an amazing team and,

uh, I, you know, just fell in love.

What we are doing at ela and you
know, that led to satellite and happy

to share more on what satellite is.

But, um, my first foray into sales
was door-to-door knife sales.

And so, as you mentioned, um, you know,
back in college I sold knives, uh,

for a company called Vector Marketing.

Mm-hmm.

. And the reason why I started the job
was my mom worked part-time in a re.

Um, and she didn't have enough money
to be able to send me to college.

Uh, she, um, was a high school grad.

My stepdad was a garbage man
with a high school degree.

Mm-hmm.

. And so I had nobody that, um, could
help me with getting into college

and to be able to pay for it.

And so, Um, I had to work full-time
and I saw a flyer that told me I could

make $2,000 over a holiday break.

Mm-hmm.

. And so little did I know for the next four
years of college, I'd be selling knives,

door to door . Um, also didn't realize
that I, I would make a hundred thousand

dollars in my first year out of college.

Yeah.

As a sales manager, it's a very,
very lucrative opportunity.

. Um, and obviously I've got a lot of
crazy b2 B2C stories, , uh, from that,

but that's probably for another day.

um, and it's not part of my resume,
but I will say that I am, um, a

big, uh, advocate of parenting.

Mm-hmm.

. And so I'm also a dad and
co-parent to two amazing kids.

Uh, they inspire me all the
time to do great work and I'm

always excited to talk to.

About the students and learners who
are in our program, about the partners

we're working with, um, and, and
they really inspire me to, to make

a positive and big impact on others.

So that's awesome.

That's my background in a nutshell.

That's

Rosalyn: awesome.

I love that.

I love that.

Thank you fors.

Thank you for sharing that.

Um, you know, oftentimes when I talk to
founders, , you know, the company starts

as a result of trying to solve a problem.

Right.

As you mentioned, at your first
startup or your first, um, kind

of attempted entrepreneurship.

Right.

Um, but was this the case with satellite?

I mean, was there some kind of, you know,
aha moment or situation that led you

to start the business or was it more of
just sort of a gradual sort of a pull

Chris Waldron: to it?

Um, I, I think there, there,
uh, it was a little bit of both.

Mm-hmm.

. And so, um, I try to
journal and reflect a.

And so when I made a, a career
change multiple times in my

life, I always asked myself why.

And, um, one of the things that I
discovered only probably like in my

mid twenties, that was why I'm in
sales, um, was in the fourth grade

I wanted a University of Michigan's
starter jacket, Uhhuh . This was

the, this was in the nineties, right?

I'm in, uh, I'm in the fourth grade,
right, trying to make an impression and.

Um, while school shopping, um, I
pointed out to my mom the jacket

and I think it was like $99 at
the time or something like that.

And, you know, she pulled me aside and
we were there with a friend and his

mom who was getting a, a jacket and
she pulled me aside and just told me

like she could not afford the jacket.

Mm-hmm.

. And that day I, I realized
and internalized a few.

that I probably didn't understand
at, at a total like comprehension,

but like it planted a seed within me.

Mm-hmm.

is, agency is very important and people
want a sense of control over their

lives and over time, I learned as an
entrepreneur, I could always control my

destiny and, and that it is to a certain
degree also as a sales professional.

Um, because you could change your income.

There's always someone willing to hire.

Um, but as, as an entrepreneur, I
knew I could always be in control

and, and nobody was gonna tell
me what to do with my company.

Or the brand or anything like that.

Of course, I always wanna listen
to really smart people I've hired.

Um, but I like being the boss.

Yeah.

Um, and a another thing with the
starter jacket is like I just learned

that I needed to be a hunter and
to get outta my situation so that

like I never needed to count on
my mom to pay for anything for me.

Like I knew it was gonna
take hard work resiliency.

. Um, and one of my favorite
phrases is, you know, chips on

shoulders create chips in pockets.

And ah, I look back at that moment
and, and know that that was my, like,

molding of, of becoming an entrepreneur.

And then what led to like actual
satellite was, um, both a around 35

years old, I started a family and
I thought of myself as a self-made.

and I only realized that yes, like I
was driven, a goal setter, hardworking,

all good qualities that we all wanna see
in, in our friends and, and teammates.

Mm-hmm.

. Um, but the system was set up for me to
succeed, uh, as a white male from a, a top

10 or top 20 state school in the nation.

I was gonna get a job
offer anywhere I went.

And, you know, I moved from
Detroit, Michigan to San Diego,

California, and I had multiple job.

. Right.

And this was in 2004, 2005.

Mm-hmm.

I was young.

Um, but like the biases had me set up
and you know, there were definitely

mentors that helped orient me to my
career and also made introductions for me.

Those all accelerated my path.

and I, I realized not everybody
has the same experience

and lived experience as me.

And I always thought because I grew up
poor and because I was, you know, like

in a single household, like I had it hard
and, and statistically speaking, like I

shouldn't be in a place where I am today
as, as a venture backed c e o owning a

home, home here in Brooklyn, New York.

Mm-hmm.

, but like in a lot of different ways.

A lot of people have it a lot
harder than than I ever did, and.

That's always inspired me to be a
strong mentor and to give back to the

community of, um, you know, either
people from Detroit or people that

went to school at Michigan, or just
people trying to get into sales.

Um, and the other thing that
led to satellite was andela and.

. I was working with executives like
Jessica Hunt and Evan Green Low,

and I was moved by what Adela was
building, like I mentioned earlier.

Mm-hmm.

and I would spend weeks in Africa
meeting engineers in our program who

were brilliant individuals, um, whose
professional options were becoming

fishermen because their grandparent was
a fisherman and their dad was a fisher.

And so through our training that we did
at Adela and through like the managed

services program we had, we were able
to help people in five x their income

in six months and to save 20 x more,
you know, over the next two years.

And like I just came back from Africa
every time, more and more fired up

about what we were doing in at ela.

And then when it was time for
me to leave, like I combined all

of those experiences of being.

getting into sales and having
strong mentorship and network, and

then like believing in the, the
concept that intelligence is evenly

distributed and you know, like I
didn't reinvent the wheel like.

Satellite is here to help people gain
bridge and have equal access to meaningful

and lucrative careers regardless
of their socioeconomic background.

And it's my job to create a brand
that sales leaders and CEOs and our

industry more broadly trust that
they're going to get a high quality.

By recruiting out of our platform.

Oh,

Rosalyn: I love that.

I love that.

There's so much there to unpack , but
I mean, what a great story and

just great journey to get here.

I mean, it's just so.

I am truly just kind of inspired
by what you've just shared.

I mean, even your, even your, uh,
quote around, you know, chips on

shoulders become chips in pockets.

Is that what the quote was?

That's, I actually wrote that down
because it actually, um, it's quite

meaningful and even to me, yeah.

It's quite

Chris Waldron: meaningful to me.

I, I, I, I just want, I just wanna
make sure, uh, to give credit, there's

a VC Josh at Luxe Capital Yeah.

Who says that, and so, , um, I
borrowed from him with Pride, but

like wrote it down the first time
I heard it as well, and, and have

definitely thought about it a lot.

Yeah.

Rosalyn: Yeah.

That's great.

Um, so you touched on this a little bit.

You talked about the vision for satellite.

You talked about sort of that
equality of opportunity, right?

And sort of the access to
those lucrative sales careers.

Um, in, at satellite, you offer
training right along with that.

Support and then that access
to that career development

coaching that you mentioned.

Um, can you maybe talk a little bit
more about the business, you know,

kinda the business model and maybe
how both companies and individuals can

Chris Waldron: benefit?

Yeah, um, definitely.

And so my firsthand experience of
building a sales development org.

Um, was not pretty.

And at, at ELA we had raised a around,
needed to generate a lot of MQs or, or

sales qualified leads and we just weren't
hitting our, our top of funnel numbers.

And I went to my cfo, Isaac, and
said basically we need to build a 25,

30 person SDR team in the next 90.

or with our sales cycle and our
win rates, we're not gonna hit our

numbers three quarters from now.

Mm-hmm.

, and they gave me the budget
and I made a ton of mistakes.

Mm-hmm.

. And what I realized is that,
um, hiring for, for sales

development is, is really hard.

Like there's no shortage of people.

Mm-hmm.

, like there's 60 million
people who are underemployed.

And so the problem.

just getting applicants right, like
even in this bad market, like you could

post a job and get 200 applicants.

Um, you could spend any amount of
time on, on LinkedIn and you'll

trip over 10 people that are
looking for getting into tech sales.

The problem is that with hiring for SDR
and entry level, what I like to call

emerging roles, it's hard for a sales
leader to translate the skills from

previous roles into matching them against.

, both your sales culture and then the
role and responsibility of an sdr.

Mm-hmm.

. And so what happens is, as managers,
when I interviewed a bunch of sales

leaders to figure out how to build this
SDR org, all of them basically said some

version of higher white males who went
to liberal art colleges and played on the

lacrosse team and you're gonna do well.

And like I knew that was full of
biases and, and, and bad approach to.

. And of course, uh, uh, an NCAA athlete
is going to be more successful than

some in a sales development role,
but it's not the only type of, of

persona that's going to succeed.

And as, as a function, like 50% of
hires don't make it nine months.

Mm-hmm.

. And so I just looked at that and.

There's gotta be a better way.

And, and so I thought about like,
what if we flipped the script?

And obviously there's a lot of boot
camps out there and I wasn't coming

up with some novel type of idea, but
how we thought about it was different.

And you know what I mean by that is
first of all is, you know, when you think

about sales boot camps, Particularly,
um, and I don't mean everybody, and

I don't know the whole landscape.

It seems like a new bootcamp pops
up every week or every month.

Mm-hmm.

. Um, but a lot of them design
it in a way that learning is

asynchronous content heavy.

Maybe some lecture style events where
like a well-known sales persona is talking

to people in a lecture style environment
and then they commercialize it.

Attaching an income share agreement or
a deferred tuition plan, which is where

basically you pay 10% of your income
for the next three years up to 7, 9, 12.

There's programs that charge upwards of 25
or $30,000 for their program, and I just,

no matter what on paper, how people think
ISAs align incentives of boot camps to.

the learners.

I disagree because when I
interviewed 50 people back in 2000,

they didn't need the learning.

We all know there's hundreds
of hours of learning online on

YouTube and LinkedIn every day.

Mm-hmm.

, what they needed was to be oriented
to the job of what an actual s d.

looks like, and they need to be able
to be given the network and that last

mile of access to hiring partners and
they need someone to vouch for them.

And so an income share agreement
incentive, like I think the

world is run by incentives.

Mm-hmm.

. And if I'm running a business
with an income share agreement.

My job is to get as many people to sign
that contract as possible, scale that

learning one to a thousand as quickly
as possible, and then have the money

come pouring in with, you know, the same
margins as a traditional SaaS company.

And I'll raise all kinds of venture
capital and people think I'm a

genius , and I just don't think
that's the way that it works.

Like an income share agreement might
be a good way to defer the payment.

. But if you're in service of helping
B2B partners hire the best talent,

like you can't tell me you're
putting the best talent through

your program if you're monetizing it
through an income share agreement.

And so I know I've said a lot there.

Um, what satellite is, is an
immersive case-based approach

with heavy coaching and mentor.

And I don't want to get into the weeds
and bore everybody with what all of

that, that looks like, like if anyone's
interested, my program leader is a

former Teach for America executive, and
he has designed it in a way that where

we focus on frameworks and mindsets.

Yeah.

And then we're able to actually
practice the work and, and,

and responsibilities of an SD.

and we see our learners go
through an amazing journey over

about seven to eight weeks.

Um, some of them come in with
a strong foundation, right?

They sold insurance for two years.

And they hate the industry and they
want to get into tech sales and we

really just need to polish their skills.

Mm-hmm.

. But they come, they, the, in their csat
um, feedback, they talk about how they

were arrogant and they thought they were
gonna know it all and, and how we helped

reframe how you should think about, um,
the role and responsibilities of an sdr.

And I'm really proud of that.

They get a lot out of our program,
but then we see individuals who are

former teachers, police officer.

working in nonprofits and, and
they come through our program.

We break all the myths
that you can think about.

The alpha bro, you know,
cold call sales environment.

Mm-hmm.

, and then we're able to give them access
to rewarding careers and we're able to

help increase their financial stability.

And in the short term, we're able
to get our learners anywhere from

a 20 to 40% bump in, in their pay.

but over a 20 year career, as you and
I both know, the trajectory that one

can be on in working in tech sales,
they can make anywhere from the next

1 million to 1.5 million compared to
their previous, um, industry and career.

Mm-hmm.

. And so that shifts.

Some of these entire socioeconomic
standing, and that's a home that's

diapers from when they start having kids.

That's a college education for, for
a child who maybe otherwise wouldn't

have been able to go to college
cuz they didn't have access or, or

they never, you know, had had the
ability to pay for it otherwise.

. Mm-hmm.

. And so a, as a company, we are a training
and mentoring platform on the B2C side,

and it's extremely rigorous and immersive.

And what that allows us to do is to
build the confidence that our buyers,

our B2B enterprise companies, know
that when they're paying for access

to our talent, they're gaining access
to a hidden, diverse pool of talent.

Mm-hmm.

that they otherwise
could not get on their.

and we're, we're
recruiting at scale always.

And so we get over 2,500 people applying
to our program every single month.

Wow.

And so if a series B company comes
to us and needs to hire six people,

it sometimes takes them three months
and it's really hard to like line

up all six of those people into one
training cohort and they talk to 30

people who are like way off the mark.

And somebody could come to our, our, our.

and if they want to interview six
people, they could have 12 interviews.

Within 72 hours.

And that's the power of, of
recruiting outta satellite.

Wow.

Wow.

Rosalyn: Yeah.

Recruiting is really, really tough.

Right.

And I think about in the market
today, you know, on one hand we have,

you know, talent shortage, right?

In sales.

But then with the last, you know,
several months or last couple

months, we've been seeing a lot of
folks come on the market because of.

Tech, la, you know, all these layoffs,
especially in technology, but regardless

of sort of where the market falls, I think
there's just this constant battle, right?

To have strong experience and
expertise, especially in sales.

Um, what are you seeing, I guess,
in the market today in terms of

sort of talent around the sales?

The sales

Chris Waldron: role.

Yeah.

Um, you know, it's funny because I
would've answered that question very

differently just a few quarters ago.

. Mm-hmm.

. Yeah.

There, as I mentioned earlier, there,
there's no shortage of people, um,

you know, with, uh, people being
underemployed or, um, interested

in, in getting into new careers.

But I think the problem specific
to the market that I play in,

and this may not be the same.

More senior roles or, or maybe a different
function is, um, I have found that

sales leaders for the sales development
function see them as a fungible role.

Hmm.

And are easy to, uh, fire and,
and to get rid of and pretend

like they never existed.

And I don't want that to sound dark
or, or like a blanket statement

across the entire industry.

Um, , it's, I see it
just time and time again.

And I know part of it is, is revenue
leaders are having a hard time, um,

putting an ROI to the SDR function.

Mm-hmm.

. Um, but I can remember at take lessons cuz
we, we had a, it wasn't an SDR team, it

was actually more of a customer support
or customer success on the B2C side.

And I remember sitting in a
meeting with all of our executive.

And I'd made a passive comment, um, about
somebody's performance and, and my VP of

product actually chimed in and, and shared
with me like how important those people

are to the success, overall success and
growth o of take lessons at the time.

And that I, he, and this guy's a tech
person who's managing the technology as,

as a product, but he genuinely was more
passionate about the people and that.

The customer service that we
were giving than, than I was.

Um, I just realized that like,
just because somebody is, is junior

or they're less experienced or
they're not carrying a quota mm-hmm.

makes them know less important.

And from that day four, like I
always knew that my frontline

team was super important to me.

And I, I find that a lot of revenue
leaders, especially in tough times, like

right now, are, um, easily blaming SDRs.

and, or like, um, getting rid of teams
and, uh, it's just, it's discouraging.

So I'll leave it

Rosalyn: at that.

Yeah, yeah.

Yeah.

And I think, you know, I can maybe along
the same lines, I mean, it's, you've

touched on this a little bit around
sort of what people are doing sort of

right, and what they're doing wrong.

You know, are you, are there any things
that you would like to highlight around

sort of when it comes to sourcing and
then retaining Right, that sales talent.

Are there any things that
you're seeing that, you know

companies are actually doing?

Chris Waldron: Right.

Yeah, for sure.

Yeah, definitely.

And I, yeah, definitely.

If I was morbid before, I apologize.

Um, , I think there's a lot of companies
that are doing things really well.

Um, you know, this is something that.

Um, I'm biased about, and it also benefits
my company, but I hear a lot more teams

talking about building diverse orgs.

Yeah.

And so that's diversity of, um,
obviously rage, uh, race, age,

ethnicity, um, um, gender, but it's
also like geographic experiential.

And, and they're open to people that
don't have a four year college degree.

And, and that's super exciting.

Like, I barely graduated from college.

Mm-hmm.

and my degree has never been the
reason why I've been successful

in, in sales or, or in life.

Uh, another thing is, uh, I see
some people doing really well, and

I shared this actually on LinkedIn
recently, is good feedback loops.

And in my own personal experience, I
can remember my first HR leader at Take

Lessons who was like, oh, we can't share.

Hmm.

And I was like, we were in California.

And so like she explained to me
that the reasons why, and I was

like, oh yeah, that makes sense.

But like I never put myself in the
shoes of the Canada, especially

a junior emerging talent type of
individual who's maybe interviewing

or trying to apply a 40 or 50 places
and they're getting no feedback.

and, and, and so like, I think
companies, uh, there's some really

good companies that like take a
minute and give good feedback.

One of our sdr uh, managers, like in all
of her rejection emails, there was like

a Calendly link for a 15 minute call
where like, if they wanted to actually.

take the effort and schedule it.

Um, they would give the
candidates feedback.

Um, and I thought that, I just loved that.

Mm-hmm.

? Um, I think a few other things that
people are doing really, really

well is, um, we have seen sales
development orgs thrive under CMOs.

Hmm.

And, um, you know, I, it was, it's very
interesting to me because the skills

and the mindset of the marketing.

Are overlapping with the sales org.

Mm-hmm.

, but not a hundred percent.

And we have partners like naia,
um, in HR tech, uh, SaaS Company.

And our, our placements have really
thrived under them and they're obviously

hiring and recruiting more out of our,
our platform right now as we speak.

And I feel like, um, the marketing
org helps BDRs have more of

an account based strategy.

More of a product and product marketing
point of view, and often rightfully

so, because back to incentives,
they, they rule our behaviors.

Sales leaders are sometimes shortsighted
and they're only driving towards.

An activity, uh, kpi, like call volume.

Mm-hmm.

or meetings booked.

And, and sometimes I think rightfully
so, uh, marketing has a, a more holistic,

broad viewpoint, um, on lead gen and,
and how we're working at accounts.

Um, so that, that, that's something
orgs are doing really, really well.

Um, and then finally, like I see some
teams, you know, even with declining

response rates, um, and longer sales
cycle, like advocating for the r sdr

org and you know, on LinkedIn, you
know, there's the sales leaders who

are always recognizing their SDRs.

And then there's the one who shared the
bad outreach from some other company.

Mm-hmm.

. And, um, I feel like,
you know, it's our job.

Just like raising my own children, like
when they walk in the neighborhood,

like I want other parents to help
teach the values and what good behavior

looks like and support my kids and
help stand them up as good citizens.

And, um, there's a lot of really
great revenue leaders who I feel are

advocating really well for SDRs, and I'm
excited for it because I don't think.

Believes in the function,
um, as a good roi.

Yeah, I love that.

I do

Rosalyn: see a lot, you know, having
spent spending a lot of time on

LinkedIn, I see a lot of really great
advice also given and good examples

of, you know, what good looks like.

So that's great.

Um, you know, if I think about for
individuals who may be thinking

about starting a career in sales, do
you have any advice maybe for them,

like how do they know if sales is.

Career path for them and
maybe what questions should

they be asking themselves?

Chris Waldron: Yeah, I mean, the short and
easy answers check out join satellite.io

Yeah.

Um, through our, through our admissions
process, you know, we, we definitely

help orient people to the role in, in
responsibility, um, of what an SDR is.

But other than that, um, I have found
that writing and reflecting on my.

Is extremely beneficial.

And sometimes people are overwhelmed
with buying the calendar or buying the

journal and doing it every single day.

Um, but you could start with a
post-it, like, and, and every day,

um, write just one emotion and, uh,
that you feel about a career change.

And then one topic that you're going
to research related to becoming a

sales professional, and then one
person that you could reach out.

Who could be either pro or, or
co uh, anti becoming a, a sales

professional and interview them.

And, you know, I feel like we talk
in our heads a lot and it's better

to get things out into the world.

Um, especially when you are, you
don't know what you don't know.

And I think that as a physical
therapist, you're questioning

your career all the time.

And if you're not excited
when you wake up in the.

Maybe tech sales could be a
really good opportunity for you.

Yeah, that's really great

Rosalyn: advice.

I never thought about that.

That's actually very practical

Chris Waldron: advice.

I go through a lot of
post-its in my office,

.
Rosalyn: I was talking to, uh, another,
uh, rev ops leader yesterday and he said

that he had Post-Its everywhere of all
the notes of things he needed to go do.

Which I'm also sometimes
guilty of, so, okay.

Yes.

Let's talk about something else.

I think on your LinkedIn profile, I saw
that you share that at the end of the

day, only a few things matter, right?

To achieve success, and you
share these three things.

One, prioritization of your
talent development, right?

Composed of individuals across diverse
geographies, races, ages, and gender.

Two, you talk about product
and go-to-market, execut.

. And then three, you talk about
balance of high growth and

best in class SaaS metrics.

So to me, when I read that, I'm
like, okay, simple, straightforward,

makes sense, but can we talk through
these and maybe learn more about,

you know, your perspective here?

Chris Waldron: Yeah, for sure.

I need to go back and, and
review my, my LinkedIn , um,

and, and probably update that.

I was, I was probably trying to
be performative at some point

and, and sound smart on LinkedIn,
but I'm gonna refresh that.

Um, with, with the, the talent, um, uh,
I'm biased, um, because I'm obviously

selling this product, but I, I think
hiring good talent is always going to

outperform a really well written playbook.

Mm-hmm.

and, um, or a bad culture.

And I'm not a traditional sales leader,
meaning like there are hundreds of sales

leaders in, in organizations like Pav.

That are way better at
closing deals than me.

And, and I'm very much more
of a sales ops and, and, and

playbook, um, type of sales leader.

But even with that, like, I just
believe if you don't hire good

talent and then give them room to
grow and, um, your culture in, in

your revenues are just going to be
okay, but they're not going to be.

And so I believe in a, a product
playbook or, or go-to-market playbook.

But if you're overinvesting in
that area and you don't have a

system to how you recruit, you're
not reporting on your diversity

numbers even within a small team.

Um, and if you're not making sure
that you're like coaching and

developing them, it gets crazy.

When I graduated from.

, like IBM would hire someone and
put them in a shadowing role for

like eight months to to a year
before they would carry a quota.

And now I talk to CFOs who are like,
is your SDR going to ramp in 30 days?

Mm-hmm.

like, can, can, can, cause you know,
that's part of our value prop is

like, are our people are smarter,
so they're going to learn faster.

They're gonna.

And the CFO will be like, I'm
gonna, I'll pay this big amount of

money, but like, can you promise
me they're gonna ramp in 30 days?

And I'm like, no, , I cannot.

Right?

Yeah.

Like we, we can't guarantee that.

But if, if success is 50% of
the time you're hiring the right

person, you know, satellite's gonna
help you do it 85% of the time.

Um, the second thing is about
product and go to market execution.

Like I remind myself all the
time to be customer centric.

and then I go do something that
only benefits me and is at the

cost of the customer experience.

Even I think it was last week, I was
talking to my co-founder in ctl, right?

Mm-hmm.

and stereotypical like you would not
think a CTO is so customer driven,

but like I love my co-founder and
we were talking about some changes

to our service agreement and I
was like, oh, well we should do.

and he was like, really?

Tell me why.

And like the three bullets
were all benefits for us.

Mm-hmm.

, and it did not improve the,
the customer experience at all.

And he was like, I disagree.

Mm-hmm.

, and I love that he called me out on
it because it was a reminder that like

being customer-centric and thinking
about your product and the pain that

you're solving for them, like always
needs to be at the core of what you do.

if you can't make enough money doing
it without charging somebody an extra

fee or a tax or, or manipulating
them somehow, like maybe your product

isn't as good as it needs to be.

Mm-hmm.

, right?

Yep.

And then the third thing is just
the balance of high growth and best

in class SA metrics like, I went to
Andela because I wanted to be an A

grinder and take lessons was also,
but like I wanted to make it to

a hundred million in, in revenue.

And um, you know, that's important and
it's a great experience, but growth at

all cost, um, is not always worth it.

Mm-hmm.

and.

You know, at Take lessons we, we had a
choice and we chose let's get good at all

of our metrics as a two-sided marketplace
and not keep overinvesting in these

areas where it would help us continue
to be classified as a tech company.

It would make sure we're growing
200% a year, but if anyone

peeled back the onion two.

you would see that they're not
adopting these features and it's

costing us just as much money to
grow as we're generating in revenue.

Mm-hmm.

. And so, in hindsight, I'm glad we
chose best in class metrics and, and

becoming really good because we ended
up getting acquired six years later.

But it just took us a while
to get to that acquisition.

Um, but had we chosen the other path,
we would've burned and run outta money.

Mm-hmm.

and so, . Everyone right now is focused
on, you know, best in class SAS metrics.

I came out of the CRO summit and everyone
was like, all about efficiency and

that's great and, and you know, it took
the market change to make that happen.

But like we all know, like boiling a
frog, it's gonna go back the other way.

Whether it takes two years or or five
years, it's gonna go back the other way.

And like, I just encourage everyone
to like always ask yourself.

, why?

Right?

Like why are you trying to
grow at these, these rates?

And if you have a good
reason, then you should do it.

At ela, we had reasons and
we did it, and it was great.

Um, but it's not, it's
not the only way to grow.

Yeah.

I love

Rosalyn: that.

That's great.

And it's the, the market kind
of flip flops constantly, right?

Over the last couple of decades.

You can just kind of see, we all kind of
come out of it at the other other end,

and then the pendulum tends to swing,
you know, full force the other direction.

I mean, just the last few years even,
it's been a quite a rollercoaster.

Um, yeah.

, you know, so as I think about the revenue
engine, I think about this podcast.

I'm always hoping others will,
you know, be able to learn how to

accelerate revenue growth and also
in this market retain revenue, but

really power that revenue engine.

So maybe as a ceo, a two-time founder,
a long-time sales leader, you know,

from your perspective, you know what?

At the top.

Two or three things that you think
all leaders should really be thinking

about today to help drive and retain

Chris Waldron: revenue?

So, uh, one thing that I recommend that
maybe sounds counterintuitive, but Sam

Jacobs always talked about creating
value in leaving some on the table.

And he even brought it up
recently at a, uh, pavilion event.

And I think it's a good
long-term view of the world.

Um, and one that I encourage and.

I have found even in our, our
business as satellite is, you know,

not trying to get a hundred percent
of the contract right away has, has

benefited me in ways, um, downstream
that ended up generating more revenue.

And in our space, a lot of people refer
us to their friends and and peers, and

I've found that, you know, creating
a little bit of extra space and, and

just leaving something on the table.

Has benefited me.

And then, uh, another thing I
just was, um, speaking to the

founders of, um, forum Ventures.

Uh, they run a really interesting
program there and I was sharing with

them, like, I recommend them to stay
close to the buyer, the customer.

as long as humanly possible.

And it's so easy to convince ourselves,
um, that we have other priorities, right?

Like writing an employee handbook
or, you know, I hired that sales

leader so she can take it over now,
and I don't have to do that anymore.

Um, but, and I know I won't have
the heartbeat of the market forever.

but I love founders and CEOs like
Pete, um, CEO from Atrium, like he is

still actively involved in cadences.

He had tweeted out like a
week or two ago about like the

productivity and out outputs of
a, a, a cadence he put together.

Mm-hmm.

, um, reaching out to maybe some
accounts and like, I love that.

Mm-hmm.

and, and I constantly remind myself,
stay close to your buyer and, and

understand them as much as possible and.

I'm actually trying to think about how
to build a customer advisory board.

So if anyone listening to this has
done that and you wanna reach out to

me and gimme five tips on, on how to
do that, I would love that in return.

Rosalyn: Is there anything, you know,
as you kind of look back, is there

anything that maybe you wish you knew
earlier or maybe you would do differently

if you could kind of hit that reset
button and do it all over again?

Yes.

. And I think you touched on
some of the things kind of

throughout the conversation.

Chris Waldron: Yeah.

But the, the one thing that
I would do is, um, I would

treat people with more empathy.

Hmm.

And, um, in sales, often I think we
operate with this mindset that like,

Salespeople are, are gritty and they can
just deal with direct conversations and I

can be radically, uh, mean to them, right?

Like all that kinda like b, BS.

And, um, going back to Andela, like
it was an amazing ex experience in

two years, going from 5 million to 50
million in, in, uh, reoccurring revenue.

I just wish I'd been more present with
the team and in the one-on-ones not always

focused on the metrics and the results.

And I think I was decent
at getting to know them.

Um, but it was just an amazing
experience in my life and I

wish I had been more present.

And even now with like my
kids, like when I hug them.

I make sure it's a real hug with both
arms and, and I'm thinking about it.

Yeah, hopefully.

And I'm not gonna hug all my
employees all the time unless

that's what they want me to do.

Cause I don't wanna get in trouble
with HR . Um, but like, I just wish

I treated people with more empathy.

I, I actually, quick story.

I reached out to one of my buyers
recently, not recently, about a year

ago, and he was at a new company.

He interviewed with me at ela.

And he shared with me that after the
interview, he went home and cried.

Oh, and I was blown away that this
individual was, was comfortable

enough to share this with me.

And I remember the day and
I did not handle myself

professionally during an interview.

He was someone who came highly, um,
scored in, in our interview process.

Everyone loved.

and there were some things that happened
during the interview and I was just

like a flat out no and had checked out.

I'm not making excuse for my behavior,
but like I'm, I'm sure I was burned out

at that point in time as a sales leader,
and I just wish I would've been more

present and treated him with more empathy.

And luckily because he gave me the gift
of, of knowledge, like I was able to

hopefully repair that after the fact.

Um, but I encourage you as sales
leaders, Not to put yourself in,

in, in that situation and and to
remain empathetic to your team.

Wow.

I

Rosalyn: love that.

That's great advice and
that's a great story too.

There's, I, you know, I can't wait till I
go back and listen to all of this, Chris

, cause I feel like you're just dropping all
kinds of, you know, all kinds of really

great advice, very insightful and just
very based upon, you know, real life ex.

Experience.

So definitely there's just
so much to learn from you.

Um, so thank you for, for
so much for joining me.

Um, but as we wrap up, before I let you
go, I always ask every guest two things.

One, you know, what is that
one thing about you that others

might be surprised to learn?

and two, what is the one thing
that you really want everyone to

Chris Waldron: know about you?

I appreciate you letting me know.

These were gonna be
questions . Cause I would've said

something even more ridiculous.

Um, but, uh, I'm pretty boring, but
I love bowling and Oh, so again,

I live, I live here in Brooklyn.

Mm-hmm.

. So if anyone needs a bowling teammate this
winter, totally available and, and would

love to get that surprising email in my.

Um, and then one thing I'd want everyone
to know about me, um, I hate to lose and.

You know, I try to balance that in my
personal life and, and, and not letting

it negatively affect, um, how I, I
operate with my kids or my friends or

anyone, but like, I'm super competitive.

Rosalyn: Well, great.

Well, thank you so much
Chris, for joining me.

I'm so happy to have done this
inter this podcast with you and just

learn so much about you and about
your business and learn from you.

Yeah,

Chris Waldron: I appreciate
having me on it as well, and,

and o obviously, hopefully.

We get to connect again.

That's awesome.

Thank you, Chris.

Good night.