The Marketing B-Sides

The Marketing B-Sides

Track #24: Heidi Henderson – How Mentorship and Critical Thinking Support Job Security in a Quickly Evolving AI Era

Jul 7, 2026 · 33 min · 8 segments

It is easy to scroll through LinkedIn and convince yourself that every executive has it completely figured out. But according to Heidi Henderson, Chief Marketing Officer at Engineered Tax Services and…

It is easy to scroll through LinkedIn and convince yourself that every executive has it completely figured out. But according to Heidi Henderson, Chief Marketing Officer at Engineered Tax Services and host of the Slash Tax podcast, real professional stability does not come from pretending to know everything. Instead, Heidi joins Tom to explain how mentorship and critical thinking give you true security in a quickly evolving AI era, sharing her own non-traditional journey from a windowless accounting office to commanding the room as a creative marketing leader. Heidi pulls back the curtain on what it takes to build authentic trust in a highly competitive, heavily commoditized industry. We discuss why raising your hand to help, attaching yourself to seasoned experts, and showing up completely vulnerable is a career superpower. We also dive into the relentless nature of modern media, what Tom calls the infinite mail delivery route where there is no permanent finish line, and why True ROI is built on long term human relationships rather than automated quick fixes. We take a pragmatic look at the current state of AI platforms, with Heidi sharing how using multiple tools can act like an organizer on steroids for drafting video scripts, while simultaneously forcing our own critical thinking skills to be on steroids to catch and validate blatant errors like mismatched calendar dates. This episode is a call to action for leaders to keep their analytical filters sharp, embrace their wrinkles over robot facades, and focus entirely on the real human being behind the work.

It is easy to scroll through LinkedIn and convince yourself that every executive has it completely figured out. But according to Heidi Henderson, Chief Marketing Officer at Engineered Tax Services and…

Speakers: Heidi HendersonGuestTom HoopmanHost

Show Opening & Guest Teaser0:05 – 2:17

Tom HoopmanHost

0:05

Howdy, partners.

Tom HoopmanHost

0:05

How cowboy of me just now.

Tom HoopmanHost

0:07

Giddy up.

Tom HoopmanHost

0:08

My name's Tom Hoopman.

Tom HoopmanHost

0:09

Welcome to the Marketing B-Sides.

Tom HoopmanHost

0:11

This is a podcast that's not just about marketing, but is always about marketing, if that makes any sense whatsoever.

Tom HoopmanHost

0:16

We firmly believe here that every single one of you is a marketer, and none of us even remotely have begun to have any of this figured out as well.

Tom HoopmanHost

0:23

So I am the CEO and founder of Mixtape Digital.

Tom HoopmanHost

0:26

This is where I talk to people from within the marketing, executive, business, entertainment stratosphere, and just get to know their stories.

Tom HoopmanHost

0:35

And today is a fun one.

Tom HoopmanHost

0:36

I'm reminded of a quote by the amazing Roger Sterling of Mad Men, who said, this is the greatest job in the world if it weren't for the clients.

Tom HoopmanHost

0:45

I'm joking, of course.

Tom HoopmanHost

0:46

Kind of.

Tom HoopmanHost

0:47

Not really.

Tom HoopmanHost

0:48

I am joking.

Tom HoopmanHost

0:48

And full disclosure, today's guest has been a Mixtape Digital client.

Tom HoopmanHost

0:53

Now, I first met Heidi Henderson, goodness gracious.

Tom HoopmanHost

0:57

about a year ago now, a little less, maybe a year ago or so.

Tom HoopmanHost

1:00

And she came on board as a client and we immediately hit it off.

Tom HoopmanHost

1:03

She's a great listener.

Tom HoopmanHost

1:04

She can command presence in a room, executive presence.

Tom HoopmanHost

1:07

She's honest.

Tom HoopmanHost

1:08

She's invested.

Tom HoopmanHost

1:09

She actively listens.

Tom HoopmanHost

1:11

She takes feedback to heart and provides honest feedback without being a jerk about it.

Tom HoopmanHost

1:15

Thank you, Heidi.

Tom HoopmanHost

1:16

And I was intrigued from day one by her story.

Tom HoopmanHost

1:19

Like yours truly, she has been in her business for a little while now and has bridged the gap a bit between real estate and now a accounting tax services.

Tom HoopmanHost

1:28

And she's the host of Slash Tax, the popular podcast that I, full disclosure, have been fortunate enough to be on.

Tom HoopmanHost

1:36

What do I know about taxes, let alone slashing taxes? Nothing.

Tom HoopmanHost

1:39

But that's what was fun about it, is a different perspective.

Tom HoopmanHost

1:42

See, sometimes it's about the friends we make along the way.

Tom HoopmanHost

1:46

A wonderful conversation with an amazing individual who I cannot speak more highly of.

Tom HoopmanHost

1:51

Thank you, Heidi, for making time to be on the podcast.

Tom HoopmanHost

1:54

Fascinating conversation.

Tom HoopmanHost

1:55

I hope you get a lot out of it.

Tom HoopmanHost

1:57

As always, you know where to find us.

Tom HoopmanHost

1:59

You know what to do.

Tom HoopmanHost

2:00

You like, subscribe.

Tom HoopmanHost

2:01

Leave a review.

Tom HoopmanHost

2:02

I don't know.

Tom HoopmanHost

2:03

Send me an email.

Tom HoopmanHost

2:04

A fucking smoke signal.

Tom HoopmanHost

2:05

A carrier pigeon.

Tom HoopmanHost

2:07

Whatever you need to do to tell me what you think.

Tom HoopmanHost

2:09

What you love.

Tom HoopmanHost

2:09

What you hate.

Tom HoopmanHost

2:10

I'll pretend to take your haterade into consideration.

Tom HoopmanHost

2:15

Enjoy the podcast.

Tom HoopmanHost

2:16

Thanks for listening.

Read the full transcript.

Create an account to read the whole episode, search across every transcript, and follow the shows you care about.

Sign up Already have an account? Log in

Show Opening & Guest Teaser0:05 – 2:17

Tom HoopmanHost

0:05

Howdy, partners.

Tom HoopmanHost

0:05

How cowboy of me just now.

Tom HoopmanHost

0:07

Giddy up.

Tom HoopmanHost

0:08

My name's Tom Hoopman.

Tom HoopmanHost

0:09

Welcome to the Marketing B-Sides.

Tom HoopmanHost

0:11

This is a podcast that's not just about marketing, but is always about marketing, if that makes any sense whatsoever.

Tom HoopmanHost

0:16

We firmly believe here that every single one of you is a marketer, and none of us even remotely have begun to have any of this figured out as well.

Tom HoopmanHost

0:23

So I am the CEO and founder of Mixtape Digital.

Tom HoopmanHost

0:26

This is where I talk to people from within the marketing, executive, business, entertainment stratosphere, and just get to know their stories.

Tom HoopmanHost

0:35

And today is a fun one.

Tom HoopmanHost

0:36

I'm reminded of a quote by the amazing Roger Sterling of Mad Men, who said, this is the greatest job in the world if it weren't for the clients.

Tom HoopmanHost

0:45

I'm joking, of course.

Tom HoopmanHost

0:46

Kind of.

Tom HoopmanHost

0:47

Not really.

Tom HoopmanHost

0:48

I am joking.

Tom HoopmanHost

0:48

And full disclosure, today's guest has been a Mixtape Digital client.

Tom HoopmanHost

0:53

Now, I first met Heidi Henderson, goodness gracious.

Tom HoopmanHost

0:57

about a year ago now, a little less, maybe a year ago or so.

Tom HoopmanHost

1:00

And she came on board as a client and we immediately hit it off.

Tom HoopmanHost

1:03

She's a great listener.

Tom HoopmanHost

1:04

She can command presence in a room, executive presence.

Tom HoopmanHost

1:07

She's honest.

Tom HoopmanHost

1:08

She's invested.

Tom HoopmanHost

1:09

She actively listens.

Tom HoopmanHost

1:11

She takes feedback to heart and provides honest feedback without being a jerk about it.

Tom HoopmanHost

1:15

Thank you, Heidi.

Tom HoopmanHost

1:16

And I was intrigued from day one by her story.

Tom HoopmanHost

1:19

Like yours truly, she has been in her business for a little while now and has bridged the gap a bit between real estate and now a accounting tax services.

Tom HoopmanHost

1:28

And she's the host of Slash Tax, the popular podcast that I, full disclosure, have been fortunate enough to be on.

Tom HoopmanHost

1:36

What do I know about taxes, let alone slashing taxes? Nothing.

Tom HoopmanHost

1:39

But that's what was fun about it, is a different perspective.

Tom HoopmanHost

1:42

See, sometimes it's about the friends we make along the way.

Tom HoopmanHost

1:46

A wonderful conversation with an amazing individual who I cannot speak more highly of.

Tom HoopmanHost

1:51

Thank you, Heidi, for making time to be on the podcast.

Tom HoopmanHost

1:54

Fascinating conversation.

Tom HoopmanHost

1:55

I hope you get a lot out of it.

Tom HoopmanHost

1:57

As always, you know where to find us.

Tom HoopmanHost

1:59

You know what to do.

Tom HoopmanHost

2:00

You like, subscribe.

Tom HoopmanHost

2:01

Leave a review.

Tom HoopmanHost

2:02

I don't know.

Tom HoopmanHost

2:03

Send me an email.

Tom HoopmanHost

2:04

A fucking smoke signal.

Tom HoopmanHost

2:05

A carrier pigeon.

Tom HoopmanHost

2:07

Whatever you need to do to tell me what you think.

Tom HoopmanHost

2:09

What you love.

Tom HoopmanHost

2:09

What you hate.

Tom HoopmanHost

2:10

I'll pretend to take your haterade into consideration.

Tom HoopmanHost

2:15

Enjoy the podcast.

Tom HoopmanHost

2:16

Thanks for listening.