Parallel Entrepreneur with Mark Cleveland

In this episode of the Parallel Entrepreneur, Innovation Series, Mark Cleveland and Johnny Anderson sit down with Amy Henderson, Director of Infrastructure at HCA Healthcare Physician Services.

Amy operates at the intersection of technical viability and business outcomes, aligning talent, technology, and data to drive enterprise growth inside one of the largest healthcare systems in the country.

But this conversation isn’t just about infrastructure.

It’s about what it really takes to connect strategy to execution. To build teams that understand both the financial model and the human one. And to develop workforce pipelines that strengthen an entire region.

Amy also reflects on her decade of service with the Nashville Technology Council, including her time as Board Chair, where she helped advocate for technology-focused workforce development across Tennessee, from K-12 to career changers.

This episode explores:
• Why strategic alignment is a leadership discipline
• Operating technical teams inside financial guardrails
• Building culture while scaling enterprise systems
• Workforce development as a long-term investment
• The role Nashville plays in shaping tech leadership

If you care about the future of enterprise leadership — especially where technology meets execution — this conversation is worth your time.

About Amy Henderson

Amy Henderson is Director of Infrastructure at HCA Healthcare Physician Services, where she aligns talent, technology, and data to drive enterprise performance in complex healthcare environments. With a focus on connecting technical strategy to business outcomes, she builds high-performing teams that operate with both financial discipline and cultural strength. Amy also served for a decade on the Nashville Technology Council Board, including as Chair, where she championed workforce development across Tennessee’s tech ecosystem.
https://www.linkedin.com/in/henderson-amy/

About the Hosts

Mark A. Cleveland
Managing Director at Kensington Park Capital, entrepreneur, M&A advisor, and host of the Parallel Entrepreneur Network
https://www.linkedin.com/in/macleveland/

Johnny Anderson
Nashville tech leader, GNTC board member, Entrepreneur-in-Residence at the Entrepreneurship & Innovation Center, and host of The Impodsters™
https://www.linkedin.com/in/johnnyonbrand/

Links & Resources

👉 Learn more about the Entrepreneurship & Innovation Center (EIC):
https://www.wcs.edu/secondary/entrepreneurship-innovation-center-eic

👉 Join the Parallel Entrepreneur Network:
https://www.parallelentrepreneur.com/#about-me

👉 Subscribe for more conversations with leaders building aligned systems across business, education, and community.

👍 If this episode resonated, leave a comment or share it with someone shaping the future of leadership.


Chapters
00:00:00 The intersection of tech viability and business goals
00:00:41 Episode introduction + Amy’s leadership focus
00:01:07 Amy’s role at HCA Healthcare Physician Services
00:01:54 Aligning talent, tech, and data inside enterprise systems
00:02:48 Operating to a financial model while scaling teams
00:03:39 Building culture within infrastructure organizations
00:04:28 Why workforce development matters in Tennessee
00:05:27 Serving on the Nashville Technology Council
00:06:18 Developing talent pipelines from K-12 to career changers
00:07:32 Leadership lessons from board service and enterprise growth
00:08:36 Episode close

What is Parallel Entrepreneur with Mark Cleveland?

Mark explores the minds of visionary entrepreneurs who refuse to limit themselves to a single venture to learn how these trailblazers manage risks, innovate across industries, and turn ideas into impact.

Whether you’re scaling your first business or juggling several, this podcast is your ultimate guide to thriving as a parallel entrepreneur.

Folks are asking better questions to find out

and probably through that process

encouraging people to know more about themselves.

What motivates them? How do they succeed?

What kind of recognition do they want?

Growth gets over simplified

more often than we'd like to admit.

Amy Henderson is an experienced executive,

who helps organizations drive enterprise growth

by aligning, talent, technology and data.

All while operating with financial discipline.

Her work focuses on designing strategies

that can actually be executed.

And building the culture

and leadership capacity required to sustain them.

What sets Amy apart, is how deeply she understands

the gap between strategy and reality.

She spent her career working inside that space.

Translating vision into action

balancing ambition with rigor

and ensuring growth doesn't outpace

the organization's capacity to deliver.

In this episode we unpack why misalignment

not lack of ideas is what stalls growth

and why sustainable scale only happens when culture,

talent, and technology are built together from the start.

So let's dive right in.

You know

I wonder if chaos isn't the standard and organization

is the exception

in almost everything. So, you

when you

step into an organization and contribute

like you have, it to

at one moment it might feel like chaos

and then you get this sense of we're

we've we've got direction and we've got organization

and we're getting the right people involved

talk talk to us about something you're celebrating

when you've gone from chaos to order

chaos to order it's more like chaos to organize chaos

I feel like a lot of times

when you're in that fast paced

um you know

business that we're that we're in

I I feel like honestly celebrating teamwork right when

when all of that has come together

it's because people on the team

folks on the team have played their part

they've engaged they've understood the direction

there's been clear leadership

and that that is not simple

that is not easy you guys both know that

I know a little bit about your backgrounds and um

that that is something to tremendously celebrate and

you know people uh

can be the biggest obstacle

but they can also be

the biggest contributors to success

and um

and yeah I

I think I think it comes back to people

in AI and we talked about chaos and ever changing

and ever evolving the

the necessity to to unlearn

mm hmm what does unlearn mean

yeah that unpack that

oh yeah

that's a that is a really tough one unlearn

I think it's you know

stopping yourself

from approaching things in the same way

and it and it's

you know

if you've been a leader and you know

organized teams in a certain way for so long

like

just imagine that you're not gonna do that anymore

you're gonna have you're gonna organize by skill sets

and you're gonna pull people together

inside your organization according to

the skills and the expertise that those folks have

I mean what does that mean for your

you know managers

what does that mean for your

you know all of a sudden

they don't have that person on their team or

you know it's

it's really fascinating um

and yeah I unlearn I think it's

it's stopping habits stopping

stopping your way of thinking

and recognizing your stuff

right'cause your mind is just gonna go that way

automatically

it's interesting I'm

we all grew up in an era where we did a disc profile

or we did a Myers Briggs

or we did some sort of a psychographic profile

and then the organization would say well

this person's gonna be a good cultural fit

then they would put you in a job that is a drainer

or maybe they put you in a role that was energizing

but you know

we keep doing these things that we're accustomed to

we sort of trained to suffer a little bit as humans

and then we could just like set that down

and what I've seen recently is

companies evaluating the role

the the

the the job itself

and putting a psychographic

profile together for that role

cause it's a human role in a human organization

and then fitting

the people to the demands and requirements

of that role where it's flexibility

etcetera and I'm wondering

this is people are rapidly becoming far more aware

of their own things that feed them and yes

and where they're getting energy

and how they're contributing energy

so it's not just leaders

but it's us individuals that are being

I think speak a little bit to that

is that is that because the technology is available

is that because we're more open

what do you think that's about

folks are asking better questions to find out and

and probably through that process

encouraging people to know more about themselves

and what how

what motivates them how do they succeed

um what kind of uh

recognition do they want

that was one of the things that Derek talked

about earlier um

taco bar taco bar

that's right hey

I think we're all motivated a little by taco bars

I don't know anybody that wouldn't be but um

but yeah it was a Nashville hot chicken bar

that hot chicken bar oh

that's interesting yeah yeah

um but yeah

I I feel like there is this real push

you know the teams right now with what's going on

you know are generally smaller

they're expecting more from fewer folks

so you want to still maintain that trust that um

relationship that teamwork

even though those folks may be managing

you know uh

agents right

rather than than people

but you you

in order to make an organization work

you still have to have all of those human components

um in there

and I do think there's a deeper exploration of

what makes someone successful

and what might motivate you to be a

you know top performer for our team

and it's it's a two way kind of conversation

it's interesting you said people may be managing agents

um wow

right yeah

just rewind just a few years

and that would not be in our conversation

what are you doing well

I manage a team of agents

that's right today

and there's 35 of them

and individual roles look like this and sound like that

um are people

are people adapting to managing agents

is this something that you see

just a subset of people being successful

this is part of this evolution

right of where instead of a dev lead has

you know four folks on their team

they're now they now have

are running AI agents um

of you know seven

so what do you see in education

changes that might happen

oh my goodness um

that's a tough question I'm not a total expert on that

but I I think

this human component and making sure things stay human

that's gonna become the rare thing

right if I go to school

and I learn math or I learn computer science or I

you know

dig in on one of these really technical degrees

you know

am I also getting the foundation for that people aspect

and you know

you now only have I don't know

maybe you only have 10 people on your

on your team who are all doing very different tasks

or owning very different parts of the business

you know that can enter cross Silo communication is a

is vital for that to be a

a success so there is

there is this people psychology

I think it was it Derek this morning that said um

you know don't you after years of managing people

don't you wish you had studied psychology

and yes I was one of the ones that raised their hand

so Simon Sinek says people that don't understand

people don't understand business

yeah and I agree with that completely

more and more every day

well problem solving right

I mean we probably

if you look at

the fun part about everything that's true

is that you're unbelievably

ridiculously successful as a human

and everyone before you was perfectly successful

and everyone before you Johnny

was perfectly successful so

we're sitting in a room now with a bunch of people

grappling with new opportunities and new problems

and we will be perfectly successful

agreed

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