MarketingProfs B2B Forum 2023

Reimagining Marketing Management and Leadership with Christopher S. Penn and Katie Robbert

How do you grow a small company when a leader isn’t cut out for management?

That was Christopher S. Penn’s challenge. In 2016, he excelled at his technological role as Vice President of Marketing Technology. But not so much at the people and project management side of things.

So he brought on Katie Robbert to manage his people and projects.

Together they helped grow business from half a million in revenue to about 3 million in revenue.

Katie and Chris, now co-founders of Trust Insights, tell their story of management and leadership transformation in this video and transcript from 2022’s B2B Forum.


Don’t miss Data Insight’s CEO Katie Robbert and Chief Data Scientist Christopher S. Penn at this year’s B2B Forum in Boston, October 4-6, 2023. Tickets are limited. Click here to get yours now.


Chris Penn (00:00): One of the things that [marketers] are doing… wrong is, not understanding that management is not the profession of marketing, right?

Being a marketer, being a good individual contributor is really important. Being a manager is a separate profession.

And what happens in every single company is, you work, you work, you work, you get promoted to management, right? This is like, you work, you work, you work. And now you’re a surgeon. Like, what?

And yet we do this to people in every single company!

I can’t think of a single company where an individual contributor can rise to the same level of status and pay as another executive, without becoming a manager.

And it turns out that as a manager, I suck! I’m a terrible manager. 

Katie Robert (00:49): This is a hundred percent accurate!

But this is something that he and I have both had to come to terms with. So we can say this without any sort of disrespect or ego. Chris is a terrible manager and has no business managing people at all.

Chris Penn (01:04): Right.

Katie Robert (01:06): Or hiring them. Needless to say, I had my work cut out for me. Because at the time, in that role, technically Chris was my boss—and then I was then responsible for his entire team.

And these were things that I figured out because Chris, to his credit, really had no idea what I needed to be doing with the team to fix it.

So what I took on first was figuring out, do we even have the right people on the team?

Within about 30 days, I let Chris know, “you are no longer allowed to hire people.”

Because he was hiring all the wrong people! And these were still inherently good people, but they were the wrong people for the roles.

Because it’s not just about the hard skills, it’s about the soft skills. Which, quite honestly, I hate the term soft skills. But it’s about your ability to communicate. It’s about your ability to critically think, and problem solve, and emote, and understand your clients and where they’re coming from.

And those were not necessarily skills that Chris was looking for. Chris was looking for purely technical skills.

And from where I sit, those are things that can be taught. You can teach someone technical skills if they have the right attitude and aptitude.

We started looking for new team members, which was actually pretty interesting. As I was hiring people and I said, “this is a great candidate,” I would have Chris talk to them. Because they would need to be able to work with Chris.

And every single person that I brought onto the team, Chris’s first impression was, “I don’t like them. Yeah, nope. They don’t fit in the team.”

And I was like, “that means that they’re a perfect fit. Great.”

And some of those people I remember very specifically became some of your favorite team members. And you still keep in touch with that person today.

But your first impression of that talent was, “nope! The person’s never gonna work”—who became one of our best performers on the team. 

Chris Penn (03:06): Katie has come up with this five part framework, the five P’s: Purpose, people, process, platform, and performance. Right?

Why are you doing the thing? Who’s gonna do the thing? What is the thing you’re doing? With what do you do it? And then, did you do the thing?

And as someone who is technical, I focus a lot on the platform—to some degree the process, but mostly coding the process so I don’t have to do the process—and the outcome: can I measure the process?

The most important and difficult parts, the purpose and the people, I largely ignore.

Which is not necessarily a recipe for success when a client says, “here’s our purpose, can you help us?”

Katie Robert (03:43): But it’s a fairly common challenge with people who are technology first. And that’s not to say that it’s a bad thing. But you need to recognize that you need that counterbalance.

And that’s one of the reasons why Chris and I are so successful together, is because in, a lot of ways, we are the exact opposite and it’s very complimentary.

And so, when we were still working at the agency and I was able to recognize that Chris was very focused on the technology, the performance, the numbers, the metrics, I started working with the team to understand: do we have repeatable processes?

And so we started with the process, and then I moved on to the people.

Now… one of the reasons Chris is not allowed to hire is because when he doesn’t factor in the personalities, he doesn’t recognize if there’s going to be a personality clash. Which, in the team that I inherited, there were huge personality clashes!

Chris Penn (04:38): You didn’t spend, you know, two and a half hours listening to two people break down in tears about whether Oxford commas were a good idea or not. That never happened. 

Katie Robert (04:44): You only got the two and a half hour version. I spent five hours locked in your office with them—and four boxes of tissues!

And so basically what he did to solve the problem was, he brought in someone who was a professional manager. And that’s what I am. I am a lightweight marketer. I am a lightweight technologist. But at my core, I’m a project manager and I’m a people manager. Those are the two things that I excel at. And those were the gaps that Chris had on his team. And so, as he mentioned, we were able to grow the team from about half a million in revenue to about 3 million in revenue. 

Chris Penn (05:20): As we talk about marketing structures management and leadership structures, one of the things we have to do is separate out what the public perception of a role is from what the actual duties are.

But it took a while for me—mentally—to get to that point of saying, “oh, the title does not equal the things that we can do to make a company successful.”

I suddenly was not on the road 40 weeks of the year. I was not working till 10:00 PM every night, putting out client fires because the eight hours of work were all meetings.

And the amount of progress we made in fixing code and building new things, literally was 10x, right? So just taking away all the noise during the workday, and me stepping back to become just an individual contributor again, made it possible to do stuff within months that I’ve thought about for years.

We had been talking about building customer journeys, using Google Analytics data to say, okay, here’s the channels that people take to become leads or whatever.

And in your Google Analytics data, that exists. You can know, person by person, here’s exactly how they got to us. Here are the things that nurtured them along. Here are the things that pushed them over the edge to converting.

But because I was so distracted by trains, planes, and automobiles and stuff, I never got to do that until we cleared away all the noise.

And then, once we did, it dramatically changed what we could do!

So part and parcel of effective management and leadership is knowing how to clear space for your individual contributors to say,” okay, you need time to think, you need time to build stuff, you need time to experiment.”

Katie Robert (07:01): Now, on the flip side of that, as Chris is saying, he struggled with the perception of an individual contributor.

I struggled with the perception of being the person in charge. Like if you know me, you know, I love being in charge, but I’m also—I do, I’m very bossy—, but I’m also an introvert. And so that idea of having to have some sort of a big public persona in order to be a CEO freaked me out because that’s not who I am. I don’t wanna have a big public persona. I don’t wanna be on stage all the time. Occasionally is fine. And so that was something that I struggled with, but was able to sort of move past in order to say, “you know what? There’s lots of examples where the CEO isn’t the best known person in the company. Somebody else is.”

And we were very comfortable saying, “that can be Chris. Chris can be the voice, the face, the public persona of trust, insights. I don’t need to be.”

I have enough things to do to keep things moving forward, to focus on growth, to focus on product development, to quite literally keep Chris focused.

The most common question I get asked is, “how can a non-technical manager manage a technical team?”

I’ve managed software development for, as I mentioned, about a decade. And what I have learned is: ask a lot of questions.

It’s very intimidating for a non-technical manager to walk into a situation with someone like “a Chris”—who’s a data scientist, very deep into technology—and have any idea what they’re talking about. To be quite honest. I mean, how many times a day do I literally say to you, “yep, you just said a bunch of words that I have no idea what any of them mean. “

My first question will say, “what is the practical application of this? Who would use it? Why would somebody use it?”

And so, what I’ve learned over the course of my career managing technical teams, is the approach isn’t, “I don’t understand what you’re saying. Explain it to me like I’m dumb.”

Because you’re not dumb. You just don’t have the technical aptitude that somebody else has. 

But ask different questions, like, “help me understand who would use this? Help me understand how I, as a marketer, would take this off the shelf and apply it to the job I do every day?”

That does a couple of things. One, you start to understand like, does this even have legs? Is it even really a thing? But also it starts to slow down the technical person a little bit to think through, “how would I use this? Is it just a cool piece of code that I developed to curate a birthday list for one of my friends?” Which is something that Chris did last week. And I said, “yep, there’s no application for that. You can shelf that.”

But that’s the thing. Allowing your technical team the space and time to innovate and create those things is gonna keep them happy and satisfied. So you allow them to do that.

But then your job, as the manager of those technical resources, is to reign in what they’re doing when it applies to the business, when it applies to your customers. And the way you do that—at least that I found to be the most successful—is using the five P framework.

And as Chris mentioned, it’s just answering five basic questions:

  • Purpose. What is the problem we’re trying to solve with this thing? What is the point of it?
  • People. Who’s involved? Who needs to create this thing? Who wants this thing? Who asked for this thing? Who needs to maintain this thing? Understanding that is the thing that’s most often skipped over when developing any kind of technology.
  • [Process]
  • [Platform]
  • [Performance] 

Published 3/24/23

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