Episode 9: Jen Perry on Building Empathy for Stakeholders [Full Transcript]

This is the full transcript of episode 9 of Creative Ops Compass, “What Going In-House Taught Me About Stakeholders, with Jen Perry.” Jen is the Executive Creative Director at Vagrants, a creative agency in Boston. She started her career at big network agencies, went in-house to build a creative team from the ground up, and then, unlike most people who make that move, went back to the agency side. In this conversation, we talk about the empathy gap between creatives and stakeholders, what living on both sides taught her about the pressures each group faces, and practical ways creative leaders can build genuine empathy into how they work.

You can listen to the full episode here.

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Intro

Jesse Krinsky: Welcome to Creative Ops Compass, your navigation system for turning creative chaos into strategic impact. My name is Jesse Krinsky. I'm a creative operations consultant and the founder of In Focus Consulting. I help in-house creative teams streamline workflows, improve stakeholder relations, and elevate their role as strategic partners.

Jen Perry: That's your job as a leader: to make sure that the business objectives and the things going on that you're involved with get down to the team in a way they can understand and take action on.

Jesse Krinsky: That's Jen Perry. She's the Executive Creative Director at Vagrants, a creative agency in Boston. Jen had an unusual career trajectory. She started at big network agencies, then went in-house, where she built a powerhouse creative team. And then, unlike most people who go in-house, she went back agency side.

That experience of living on both sides gave her something rare: genuine empathy for the pressures and constraints that both creatives and stakeholders face. And in my work with in-house creative teams, I constantly see the risks of that empathy gap. Creatives think stakeholders just don't get it. Stakeholders think creatives are precious artists who can't handle feedback. And that core misunderstanding undermines the work, damages relationships, and keeps teams stuck in a reactive, order taking mode.

Jen and I talked about why empathy matters, what it takes to build it, and how it transforms not just your relationships but the quality of the work itself. If you've ever felt frustrated by stakeholders who seem to dismiss good creative, or if you lead a team that struggles to communicate its value to the business, this conversation will challenge some assumptions and give you practical ways to bridge that gap.

From Agency to In-House and Back Again

Jesse Krinsky: Jen, thanks so much for joining me today. You have a very unusual career trajectory. You started in the agency world, went in-house, and now you're back on the agency side again. Walk me through that journey.

Jen Perry: Yeah, it's funny because I remember over the years hearing, once you go brand side, you're never going to go back. But when this opportunity came up to become part of a tech company, I was very curious about the other side and getting more context. You get a brief on the agency side, but you don't see what really goes on in the inner workings of a company and a marketing org.

Jesse Krinsky: And what made you decide to go back to the agency world?

Jen Perry: The tech company I had been working for had just been bought by a venture capital firm. There were leadership shuffles, reorgs, all kinds of tumultuous changes. At the same time, this small agency reached out to me. If it hadn't been the type of agency that it was, I probably wouldn't have gone for it. But it was all purpose driven, mission driven work, work for good causes. That's something I had always said I wanted to do. And it was an opportunity to build and grow the creative department. As a person who's kind of a builder, that was really appealing to me.

Jesse Krinsky: That's interesting, because one of the unfortunate truths of agency life is you often just have to do the work that arrives, whatever client is willing to hire your agency. I struggled with that, doing work for clients I felt icky about. So it's amazing you found an agency where you could work for clients you felt good about.

But I want to dive into something else. I often say that the major value proposition of an agency is breadth, whereas on the in-house side it's depth. When you're in-house, you get to know the brands, the people, the mission. When you're on the agency side, you get exposed to many more styles, many more types of people. So what are some of the things you learned in-house that you couldn't have learned on the agency side?

What Agency Life Never Shows You

Jen Perry: It was hugely eye opening. Coming into a tech company in the suburbs, everything was a culture shock. I remember telling my agency friends, it's like when you go visit the client for a client meeting? It's like that, except I work there all the time.

Jesse Krinsky: You're there every day.

Jen Perry: Once I was there, it was like a veil had been lifted. There are so many things that are kept away from creative people at those bigger, traditional shops. You're kept under the stairs like Harry Potter. You can't interact with the client, you can't interact too much with the account team even.

When I arrived in that environment, it was a huge culture shock. I had to do things like write marketing emails. I had never written a marketing email in my life. And when I started that job, I had already had 15 years of experience in the industry. I just hadn't done that type of work because I wasn't exposed to it.

Jesse Krinsky: The roles are far more bifurcated in a big agency. When you're in-house, especially if you're starting a team, it's all hands on deck. You're doing everything.

Jen Perry: It's just like parenting, where you can know something in theory and then you're in it and it's completely different. I always knew philosophically what I did at the agency meant for what the clients were dealing with day to day. But once I was embedded in it, it was so eye opening.

I realized how busy they are. That was a big one. Because I think on the agency side, sometimes you think the campaign you're working on is the center of the universe. You think it's a bigger deal than it actually is to the client, because they're juggling so many different initiatives and politics and bosses and boards and CEOs and different people to answer to, all with competing agendas.

The other thing that was very eye opening is just how small the agency's part is of the whole. I knew it in theory, but seeing it close up was really eye opening. And just getting to know all of the different parts of marketing. I didn't have a good grasp on marketing holistically until I understood all of the different types of roles that go into a more sophisticated marketing org.

Connecting Creative Work to Business Value

Jesse Krinsky: One of the biggest challenges I see in-house creative teams face is communicating their value in business terms, terms that matter and are relevant to their stakeholders, to leadership. And often it's because creatives don't have an understanding of it. They don't have the background, the education, in not just how to communicate, but in understanding why what they're doing matters to the larger enterprise. They're great at delivering beautiful creative, but they often struggle to connect that to things like revenue, conversion rates, or whatever KPIs are relevant to leadership. So when you went in-house, how much visibility did you have into business performance and metrics, and connecting the work you were doing to the larger goals of the company?

Jen Perry: So much more than I ever had on the agency side. So much more. Exponentially more understanding.

Jesse Krinsky: How did you do that? Because that's a challenge so many teams have. The stakeholders either keep it to themselves or they don't even know to share it. And a lot of creatives don't even know what questions to ask. So how did you get that insight?

Jen Perry: I think I was in a bit of a unique position, because I wasn't an individual contributor. I was coming in to run a team and build a team. So I was in a more senior role, and I was more involved in the leadership meetings with the CEO or the CMO and things like that. So I could then take that information and translate it down to my direct reports.

And I have to give credit to my boss at the time, Tim Weldon, who had come from the agency side but had been brand side for a very long time. I think he really helped teach me how to think and speak like a business person. And he helped me understand exactly what you're talking about: that you need to take all of your wild creativity, and the team's creativity, and translate it into language that folks care about.

The VP of marketing isn't as excited as you are about a particular film technique. They want to know how it's going to impact the bottom line. How it's going to make them look good to their higher ups. Everybody has somebody to answer to.

And I think a lot of the time, and I'm only speaking for my own experience, at traditional shops there's almost a culture where understanding the client as a human being, and their very real challenges, isn't something that's prioritized for the creatives. It's almost like, let the account team worry about that, or the strategy team, or the leadership team, because that's the structure. The idea is to protect creative from all of the other stuff so they can focus on the creative, which in theory I understand. But in practice, what it does is actually stunt creative growth, because you're not understanding all the different aspects of the business. The fact that I entered brand side with 15 years of experience and there was still so much I didn't know, I think is a testament to the fact that I was kept under the stairs like Harry Potter in a lot of instances. That's just the structure and the setup.

Naming the Empathy Gap Between Creatives and Stakeholders

Jesse Krinsky: There's also a game of telephone that happens. The account director gets to talk to the client in the agency setup, and communicates the needs or the brief to the producer, who then maybe communicates that to the editor. And oftentimes the editor for the video never gets to speak to the account director, let alone hear from the client. So you get translations, or mistranslations, along the way that end up ballooning budgets and taking more time, which ideally you wouldn't have in-house.

I wanted to dive into something else you mentioned. You were very fortunate that your manager at the time brought you in, gave you access to leadership. You were able to, if not ask questions, at least hear what was going on. That's not the case a lot of the time in in-house environments. So I'm curious, how did having that greater amount of context about the business side change the way you approached creative projects and ran your team?

Jen Perry: Oh my gosh, it completely changed the way I ran my team, thought about creative projects, thought about how to talk about creative to marketers and other folks outside of marketing.

So things like quantifying how many jobs your team did in a year. Most in-house teams use something like Workfront or Asana. So reporting from those tools and translating that into: here's the amount of jobs we did, here's the type of work it was, here's the team we did it for. Just this idea of managing up, and of sharing information in a way that folks can understand.

I think in the past there were a lot of assumptions I was making about what people knew and didn't know, or what people understood and didn't understand. And I think it goes the other way too. Marketers make a lot of assumptions about what the creative team knows or understands. So I learned a lot more about taking the time to really translate information and help people understand what's going on, from creative to marketers and outside of marketing. And in the same way, I made an effort to get out of my comfort zone, out of the creative team, and start trying to understand people's roles in different parts of the organization, proactively.

Jesse Krinsky: So when you did that, when you started understanding, or trying to understand, people's roles, I have to imagine that also helps you understand their motivations and their interests and their needs, their fears, their concerns, professionally but also personally, because it all gets wrapped up together. That's so important for anybody to understand when they're working with another person, but it's next to impossible to do when you're outside, when you're on the agency side. When you're in-house, in an ideal situation, you have the opportunity to go deep, to understand the people you're working with.

In my experience, there's a fundamental misunderstanding on both sides. Creatives think stakeholders just don't get it, or don't care about good work. Stakeholders think creatives are precious artists who can't handle feedback. How would you describe the typical attitudes that creatives and stakeholders have toward each other?

Jen Perry: Yeah, I think this actually applies outside of an in-house org as well. I think creatives assume that outside of creative, nobody cares about creative, or gets excited about creative, or could even possibly understand our thought process, what's cool and what's not, what's interesting and what's not. There's an assumption of, we're the only people who really get it.

And then there's an assumption, I think, from the other side. It's kind of the same assumption: we're the only people who really get the business. These people just want to make things that are cute and cool because they want to have fun and make cute little things. There's an assumption that creative is trying to trick people into making something for their own personal gain, their own agenda.

Jesse Krinsky: So when you went in-house, did your view of stakeholders change? And what did you learn about the pressures and constraints they're dealing with, that a lot of creatives don't know about or don't think to worry about?

Jen Perry: Honestly, that completely changed the entire trajectory of my career. It's changed the entire way I look at doing creative. It's changed the way I look at clients. I think one of the things that really stood out is that they're just like us. They're actually just like us. It's like People Magazine, or Us Weekly: stars, they're just like us.

Jesse Krinsky: Celebrities, yeah. So I joke that clients are just like us. They have fears, they have deadlines, they have anxieties, they have bosses who are mad at them about this or that. They have people they have to impress, a promotion they're trying to get, mortgages to pay, kids, pressures, all of it.

So from there, I take that insight and try to educate people on my teams. One of the things I feel like is a refrain I say a lot is, guys, I understand, I value creativity too. I'm a creative. I love getting weird as much as the next person, but you have to understand, this isn't your personal creative playground. This is a business. And it's hard for me as a creative to say that, because I get where people are coming from, but it really isn't. It's not our little creative playground. It's a business.

We are solving business problems with creativity. That's what I have to remind people all the time. So I like to bring it back to the business reality and to the brief. I want people to take it to the weirdest place they can, and I'll rein them in. I don't want to stunt anyone's creativity at all, but people do need to remember there are real business realities we're trying to solve with this work. It's not just about winning an award.

How to Build Empathy for Stakeholders in Practice

Jesse Krinsky: So on a practical basis, how can creative leaders develop empathy toward their stakeholders? What are some of the daily habits or approaches that actually make a difference in fostering that empathy?

Jen Perry: It sounds so simplistic, but talking more to people that maybe you wouldn't normally talk to, spending time trying to understand people who are outside of your comfort zone. Product marketing, for example. That's very technical. At a tech company, they know all the ins and outs of the product. Or even the sales team. People you haven't spent a lot of time with, because coming from the traditional agency side, you don't really spend time with product marketers. You spend time with the brand marketers or the CMO, a little bit higher up, or a different part of the business.

You don't get a lot of time with product marketing or the UX team. Spending time with people who have a completely different understanding of the business, a completely different agenda than you do, a different set of expectations placed on them, you learn so much. So it's the product marketing team, but also the sales team, which sounds very uncool to most creatives.

But here's something super simple. Have you ever listened to a sales call? When you're on the brand side, you have the opportunity to go talk to the sales team and listen to their calls, and understand what's going on with the consumer at that point where they're considering buying your product. That's huge. You don't have that on the agency side. You get insights about the audience, about the customer, that you just don't have when you're outside.

Jesse Krinsky: One of the things along these lines that I always recommend to clients is having more conversations that aren't project based. Not waiting until you receive a brief to talk to stakeholders, and not only talking to people who are your immediate stakeholders, like the marketing teams. As you were saying, the sales team, product teams, things like that. There are a few reasons I think that's valuable.

One is you get to understand more of the business, which has its own value, because then the creatives can come up with ideas that maybe the marketers who are coming to them with briefs haven't thought of. But also, the more people they talk to, and the more conversations they have that aren't transactional in nature, it positions the creatives as people who are committed to the enterprise as a whole, and to understanding the other person.

Not only that, but as you have these conversations, you understand them a little more. You understand the pressures they're dealing with. When you're just working on a campaign or a project together as a creative, you don't necessarily know this person is struggling with their manager, or that someone new just came in and they're worried about an audit for their team. If you're just working off the one project based on that brief, it's more of a transactional relationship, which undermines the value proposition of being in-house that a lot of teams just don't take advantage of. Sometimes that's because they don't feel like they have the time for it. But more often, it's just not something they've considered. If they've come from the agency world, where things are more transactional and not as relationship based, it's not a mindset they necessarily have. So yes, absolutely, having those conversations, especially ones not based around the give and take, is immeasurably valuable.

Leading Your Creative Team With Empathy

Jesse Krinsky: In addition to fostering empathy for stakeholders, how do you, as a leader, recommend practicing empathy for your own team members, especially when they're frustrated with the feedback they're getting or the stakeholder dynamics? Because it can be easy as a leader to get frustrated, just like we do with our children, and just say, I need you to do this. But they're also dealing with their own challenges. So how do you, as a leader, maintain that empathy for the people working for you?

Jen Perry: It's a little easier for me with the people I manage, because I'm a creative myself and I understand where they're coming from. So I can put myself in their shoes. And often it comes back to information. I have more information than they do. I'm privy to more conversations than they are. I'm in more rooms than they are. So it's my job as a leader to take that information and translate it to them in a way that makes sense and has an impact.

I think a lot of the time people hoard information, or forget to disseminate it. And that's your job as a leader. It's not a nice to have. It's not optional. That's literally your job: to make sure the business objectives and the things going on that you're involved with get down to the team in a way they can understand and take action on.

So really, my job as a leader is almost like a reconnaissance mission. I have to go out and talk to all the different people, understand what's going on in all the different teams, and where my team is able to make an impact across the business. And then I have to take all of that in and make sure it gets to my team.

Jesse Krinsky: Jen, thank you so much. This is such an important aspect of creative leadership that's too often overlooked in the day to day need to just get things done. When we take a moment to pause and think about who we're working with and how to work with them better, it only helps the process, and your perspective here has been so clear and valuable. Thank you for sharing it. I really appreciate it.

Key Takeaways

First, stakeholders are just people. They're dealing with the same pressures you are: deadlines, bosses, budgets, and fears about job security. When you approach them with that understanding, tensions ease, relationships strengthen, and the whole creative process runs more smoothly.

Second, information sharing is part of your job as a leader. You need to translate business context down to your team and creative value up to stakeholders. You're on a reconnaissance mission, gathering information from different parts of the organization and making sure it gets to the people who need it. Your team can't be strategic partners if they don't have the context to think strategically.

Third, get out of your comfort zone. Listen to sales calls. Talk to product marketing. Spend time with people outside your immediate circle. Have conversations that aren't project based. Don't wait for a brief to start building relationships with stakeholders. Those relationships, and that context, will make your creative work more impactful and help position your team as genuine partners instead of order takers.

The common thread through all of this is empathy: understanding that we're all just trying to solve business problems with creativity, and we're all dealing with our own pressures and constraints. It can be a harder skill to practice than process improvement or workflow optimization, but it's just as essential.