What I Wish I Knew Before I Took My First Director-Level Agency Role

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Galen Low: Hey folks, thanks for tuning in. My name is Galen Low with The Digital Project Manager. We are a community of digital professionals on a mission to help each other get skilled, get confident, and get connected, so that we can amplify the value of project management in a digital world. If you want to hear more about that, head on over to thedigitalprojectmanager.com/membership.

Okay, today we are talking about making that leap up to a director-level role at an agency, and doing a bit of a "things I wish I knew before taking on a leadership role." With me today to share her own journey into multiple director level agency roles is Jessica D'Amato Crosby — Director of Digital Marketing at Vye, seasoned agency operations specialist, and unabashed dog lover.

Jess, thanks for joining me here today. 

Jessica D'Amato Crosby: Thanks for having me, Galen. Totally unabashed, and they might make an appearance. Who knows? They might just make themselves known. 

Galen Low: Yes. And in the green room, I was telling Jess, I'm like, Oh, we got to find a way. Google podcast is no longer a thing. They're syndicating it over to YouTube and it's making these YouTube videos of just a still image.

And we're like, okay, I guess now's our opportunity to do video podcasts. And then it would be starring adorable dogs on your side. 

Someday. Dog cast. So let's dive in. 

You have been working in the marketing and marketing agency world for a bulk of your career and you've held a lot of different roles along the way. I was wondering, could you just take us through a quick journey of some of those roles and how they built a path to the next ones? 

Jessica D'Amato Crosby: Yeah, absolutely. Like you said, I worked with a couple of agencies in my career, and I started out as an individual contributor. I was in the weeds of paid media and all the things, and then eventually moved into more of a generalist marketing role at the next agency I went to.

And from there, just again, grew in my role into a director level role. And then moved on to a little bit of an in-house role. And then I apparently can't get away from agency life and went back to agency life and found myself in the role that I am now. I think a lot of what's driven me is just this passion I've had for business, for ops functions, marketing, and opportunities.

They arose at my last agency to take on more of that leadership level role and really I took advantage of that opportunity, obviously, and was excited about what it meant, the different types of projects I could work on and how I functioned in the agency. And I think from there, it really built my career thus far is just strengthening my network.

I made really great connections. I met a lot of really incredible people and I've had been able to build a lot of great relationships that have helped me get to where I am today. 

Galen Low: In the last podcast episode that you and I recorded together, we were talking about curiosity. And it strikes me that yeah, that's woven into your story as well, where, you could have been in these roles, with your blinders on, just doing your job. But you couldn't help yourself, you're curious, you wanted to find out about what all these teams are doing, you were, passionate about the operations, like how it actually all worked together, and like the business itself. 

And clearly, interested in agency sort of operations as well. Yes, I know. It's that claw that keeps pulling you back in, right? You try and get out of agency and then suddenly you find yourself back in. John Wick all over again. I love that sort of notion that yeah, it is sort of like looking around and being curious and taking in the bigger picture.

I think in many agencies, yeah, there is desire from folks to climb the ladder. And definitely there's need for folks to take on leadership roles. And then there's this gap in between of like, how do we make this individual contributor into a leader? And I think a lot of it stems from that sort of, curiosity.

Jessica D'Amato Crosby: Yeah. And sometimes the opportunity doesn't always present itself either. Like sometimes you either accidentally find yourself in it, or like you say, Hey, there's this thing that I think would be really incredible for our agency. I'd love to pursue it. I'd love to do a pilot. I'd love to just learn a little bit more about it and figure out how it can, slot into what we do as an agency or continue to expand our agency.

Galen Low: What was your first director-level role? Did you chase it? Was it just handed to you? Something else? 

Jessica D'Amato Crosby: I probably inserted myself more than anything. And whoo, I just blessed my team for being as patient as they were with me back then because they were like, okay, you can do this thing. And yeah, anyway, I'm sure I annoyed the heck out of everybody, but I had a really incredibly supportive team.

So I think what I saw is just opportunities and conversations. And just working day to day where it's like, Hey, we could do this better, or we could do this in a different way. Or we could think about it this way that, maybe saves us X amount of time or X amount of dollars spent.

And so I would, like I said, be a sponge and observe and ask if I could maybe take on that opportunity or if I could just watch somebody doing something. So I was really proactive about how I could grow and how I could understand more and eventually led me to my first director level role. And I think at the time I was pretty passionate about systems and processes for better business function and it's continued to lead me down like this pseudo ops marketing path.

Galen Low: I like the sort of like pragmatic nature of that story because sometimes we talk about doing your next job before you get the promotion or whatever. And sometimes that's very vague and unhelpful advice for a lot of folks. They're like, how do I know if I'm doing that job if I haven't done that job?

And then I think there's the other side of it where folks are like, I've got ideas, but I'm going to wait until I get that promotion to tell anybody. And like you said, sometimes those opportunities aren't handed around. Sometimes those opportunities, are not available. And meantime, you're just like waiting, like bottling up all this watershed of ideas.

That you will then, deliver once you get that promotion or, are you someone who actually just believes that, there are better ways that we can optimize the way we run and work together and run our business and, be seen doing that. And yes, inserting yourself but like, actually just delivering more value or, like sticking your neck out a little bit actually. 

And yeah, I mean, I know that not everyone's going to be overly excited about ambitious colleagues, right? We'll get there, but you know, I love that, there is this sort of notion as well yeah. Who would be a good candidate for this role, and, someone sticking their neck out, then let's support them, or at least tolerate them. 

Jessica D'Amato Crosby: Yeah. Yeah, just smile and nod and say, okay, who do you think? No, and I think the other thing too, is one of the things that, I don't know if it was necessarily like that I was passionate about it. But I think, when I was at the agency that I was at and being a director of operations, I was like, the only way that we're going to grow is if we can take things off the CEO so they can focus on, sales or whatever they need to focus on. And, we take that work and distribute it throughout the rest of the team members.

And so I think I had just like pretty strong, maybe it's just an opinion of how we were going to grow and Hey, if we're going to do this thing, we need to do X, Y, and Z. And take like client management off the CEO, we need to take HR off the CEO, we need to, do these things. And then that allows us to sell more, to get more revenue, to build a team and then be able to bring on team members who can fill those gaps or fill those roles that we absolutely need to fill.

So I think that also again, maybe it was a little bit more annoying than anything, but I just pushed to say Hey, if we're going to do this, we need to do this, Hey, just keep thinking about this. Or, Hey, have you considered this? And that's, I think, again, somehow how I ended up in the director role that I was in at that time.

Galen Low: It's actually like a lens that I find is different, maybe unorthodox for people, right? Because like, when you look down the sort of org chart, as a good leader, you'd be like, okay, identify strengths and weaknesses and sort of, make accommodations for that and provide support where needed.

But when you look up the org chart, it doesn't always occur to people that like, yes, your leaders also have strengths and weaknesses. Your CEO has strengths and weaknesses. Yes, they are, whatever, at the top of the org chart. But if where they make the biggest difference is whatever, going and on tour and doing like talking at conferences and, building those relationships and like doing the sales, then yeah, don't make them do all the other stuff that maybe they don't like, aren't good at.

Like, how can we make this all sort of work? And I think that is a really interesting lens, an important lens of sort of getting to that, fundamentally, even like at a director level role, it's upper middle management, depending on the org chart. And you still need the perspective to look at it both ways, folks who report to you and the folks that you report to.

Jessica D'Amato Crosby: Absolutely. I fully agree. 

Galen Low: Talk to me about what happened when you did take that big job. You took on a director-level role. What was part of that role that was a surprise to you or that you felt underprepared to take on? What was your main source of imposter syndrome? 

Jessica D'Amato Crosby: Oh gosh, I have to say that my main source of imposter syndrome was probably everything.

It's I'm down at everything immediately. I think you just, a lot of it, I think your first year in that role, you're finding the confidence just to be in that role and say okay, somebody put me in this role for a reason. I need to believe in that reason and believe in the vision that they have for me.

So I think that was obviously a part of getting over the imposter syndrome, and I would say everybody, I think, listening or in a room would raise their hand and say, I am forever, dealing with imposter syndrome. 

Galen Low: Yep. It's always in the passenger seat, isn't it? 

Jessica D'Amato Crosby: Yes. Definitely is. I think it was more so what I didn't realize was that I took on this new role, but I'm still doing my other job.

I think that's like a misconception. I think a lot of us see people keep these like promotions or they get new titles and they're like, Oh, this person is doing something completely different. And they're no longer doing that other job. And it's actually no. You're more than likely still juggling your previous role on top of this new role in addition to other projects or in addition to other tasks. 

So I think it's switching my mind frame and trying to figure out how can I potentially start to delegate work that, maybe other team members could do or other projects that team members are excited to take on that I could help be there as a guide and help get them from point A to point B. But they fully own it and is almost an opportunity for them to dip their feet in the water of what it looks like to maybe step up into leadership or to take on more responsibility.

So I think that part of being unprepared was just figuring out how to shift my mindset. And then I think, again, working a little bit more autonomously versus being directed. Sometimes, especially in a smaller agency, the role might be entirely new. And so there is no do nor for what you should and shouldn't do.

So you're figuring it out as you go. And so I think having that comfortability to work autonomously and be comfortable there and probably fail sometimes and feel like you aren't doing the right thing and you do need to pull on other people and say Hey, help me figure out what we should prioritize because I want to make sure I'm on the right track.

So, there's a lot that comes with stepping into the role and realizing, oh, there's so much more to this that I didn't realize or that I needed to consideration, mind shifts that need to happen. I think you and I had talked about letting go of your babies being comfortable with just saying, hey, like I can't do this anymore. How can we help bring somebody into this process? 

So if my list to respond to this question, if we could take like the next 45 minutes, I would do that, but I'll stop myself.

Galen Low: By Jess's book. 

Jessica D'Amato Crosby: Yeah. 

Galen Low: No, but honestly, you just dispelled so many myths about, getting the big job, right, that promotion. First of all, a promotion is not like this single, one dimensional point in time. It's a gradient, right? Like you're doing the next job before you get into the new job, and you're doing your old job as you get into that new job. Like it's never going to be that thing that, is just, okay, today you were doing this and tomorrow you're doing this and you don't have to worry about anything, in your past job.

And then there's that attachment to the work because, you're not like, yay, I'm a director now. I get to leave all those projects behind. You're like, I love those projects, actually, I love doing that job. I'm going to miss that job and I have to let go. And then that whole idea that like things are going to be crystal clear.

Now it's going to be ambiguity. There's more and more ambiguity as you get up the chain. And to your point, it might be a new role. There's no playbook, right? The expectations aren't even clear. Your scorecard for your role is not even clear. And then the last one is just like that, like you don't have to be able to do it alone, like you can ask for help. 

And some of the best sort of, management teams, leadership teams, they support one another and they do ask for help and they do build those relationships so they can ask each other for help, because it's not easy, because it's not always clear, because there's so much ambiguity.

Jessica D'Amato Crosby: Yes, because we're all flying by the seat of our pants at the end of the day. 

Galen Low: Yeah. You're solving more complex challenges together and then you have to be accountable for all the work that, your team is doing that you used to do yourself. 

Jessica D'Amato Crosby: Exactly. 

Galen Low: That's a wild shift. 

I wanted to circle back around to that, the colleague question, right? And this notion of sort of being promoted and one day you're a peer and the next day you're their boss or you're senior to them. How did you navigate your promotion with colleagues? Who, were on your team was there any friction? Was there any conflict? And was there any guilt even, right, of just being like I got this thing. There was not that many seats at the top. 

And, now you've moved into one, and in some ways taken an opportunity away from someone else. Yeah, how did you navigate that? Loaded question.

Jessica D'Amato Crosby: No, it was such a great question because I've seen this play out a couple of times and seen a lot of, some go really well and some go not really well.

And I think it's always really tough when you see co-workers who step into like promotions and they're not celebrated, because there's either internal conflict or division. I honestly was really lucky at the time. I had a great team. They were all so supportive and the best way that I could approach the conversation was just honestly, vulnerability saying Hey, I know this might be weird.

I want to like, work through any questions that you have, or if there's ways that I can better support you. I think taking that approach to some of those conversations and just not really trying to like, ignore it, but just say, Hey I know this thing happened. I'm happy to talk about it. If you don't want to talk about it and you're good with it, then great.

But I think just opening up that door at the start of you jumping into this type of role will lean to better relationships going forward too, because it shows the type of leader that you are, where you're placing your importance as you think about what is, again, the most important thing in your role and how you grow in that role and how you grow with the agency.

So I think, like I said, I got really lucky with amazing co-workers and then just maintaining a level of honesty and vulnerability. They met me halfway and we were able to say Hey, maybe this thing like bugs me a little bit, but I'm cool with it. Or, Nope, super excited for you. I can't wait to see all the things that you do.

Galen Low: I love that you kinda opened the door to have the conversation, to have, the questions asked. And I agree with you in the sense that a lot of conflict comes about as a result of a lack of transparency, and even just being transparent about what the experience is for you, right?

It's new, it's scary, not all the questions have been answered. I haven't been given like this, like placard that says, here's how everything's going to be. Here's what to tell your team. It's all new. Like I'm figuring it out. We're all figuring it out. We'll figure it out together. One thing I enjoy about your story too, is that, yes, I know you had sort of framed earlier that they tolerated you and your ideas, and you inserting yourself.

Right? But also because of that, it's not like this abrupt surprise transition. And I have been in, in organizations where there is a sort of like abrupt promotion and it's not the person you'd expect and they like, it came out of nowhere and it just, that part's weird. And I'm sure it's normal, but it just feels weird.

Whereas, in this journey, it's just yeah, you know what? You could probably look at it and go, Jess was already doing that. You know what I mean? Like a sort of natural progression into a role, rather than that myth of a, I'll do this job and then one day I'll get a promotion and stop doing that job and suddenly be doing this job and I'll come to my team.

I'll be like, I'm your boss now. You gotta do what I say. And I'm perfect. And everything's figured out and have it all under control. And don't you question me. That's where it can all go wrong. 

Jessica D'Amato Crosby: And I think to your point, sometimes when larger organizations make some of those shifts.

I think there are some organizations that are really good about having the conversations with team members and saying hey, these are the changes that we're making. Here's why. And I think when they do that, they bring the rest of the team into the conversation and into, if they have concerns, it just opens up that door for them to ask the question or to raise the concerns versus.

I think I've seen other companies that they don't say anything and they just say, yep, this is what we're doing. We're rolling forward. Catch up. And that I think leads to some of those situations like you're mentioning where, is this like, why is this happening? This makes no sense. I'm very confused and I'm considering other options.

So I think there is a tact about leadership promotions that brings the employees along in that journey and then therefore leads to stronger employee company relationships and less churn.

Galen Low: I love that because so many organizations don't look at these changes as something that needs change management. And yet, this is a classic example of why change management is important.

And you can look at it both ways, right? It is sort of the responsibility of the organization, making this change, like having a promotion occur. It's on them to sort of plan the change management and the communication around that. But also, as being the individual who is being promoted or taking on a new role, it's also not the wrong question to ask, right?

Like, how are we messaging this? Have we thought about this? What can I say? What should I say? Raising your hand if you see like friction that's going to happen and making a suggestion about how to address it. Cause I've seen a lot of that being like promotions happen. People will be fine.

We'll just put it in the weekly email to all employees. And if you didn't get the memo, then sorry, like, and that should be good. Done, right? 

Jessica D'Amato Crosby: Classic, it was in the email. 

Galen Low: Exactly. Excellent. Well, listen, to sum it all up, I thought I'd land out with one big question as a sort of actionable takeaway. 

But in your opinion, what makes someone a good candidate to level-up to a director level role at an agency? And what can ambitious agency folks like digital product managers do to set themselves up and move towards that next big role? 

Jessica D'Amato Crosby: Yeah. Great question. I think there are four things that come to mind. I think being comfortable with ambiguity, being comfortable with humility, and having a really clear vision, and being curious.

Think what we were just talking about where you're not always going to know what is right and what is wrong or what projects you should prioritize. You may have an idea, but if you aren't sure, or you don't know how to figure this thing out, not being okay to say, okay, well, what's a baby step I can take?

Who could I potentially reach out into the organization that, would be a great partner in accomplishing this thing? Being comfortable with that, and then being able to take the next step to move along whenever it needs to be moved along, or being also comfortable with not having an answer. And having to figure out the answer yourself and say, this is the answer.

This is what we're doing. If it changes down the road, great. If it stays the same, also great. We're here again, like pushing towards the same goal and same vision. And I think when it comes to humility, it ties into this a little bit of just, you're not always going to have the right answers and you're going to be wrong a lot.

I think, okay, and owning some of those mistakes or owning some of that change and say, yeah Oh, I thought this was a great idea, but it turns out it's not. It's awful. Let's change. I think that will go a long way with the people that you work with because it shows that you are comfortable recognizing when you're wrong, and you're not going to die on any heels on things that maybe you shouldn't be dying on the hill for. Showing some of that flexibility, being vulnerable, and to recognize some of your own mistakes and owning those.

And I think vision is just across the board, incredibly important. I think when you start to lose vision or when you don't, when you're not quite sure about where you want to take something or where you want to go with something, you start to lose, I think like trust from the employees that you're managing and from the leadership team that you're working on.

And I think if you ever get to that point where you're not sure what the vision is, it goes back to humility and having humility to say, I don't know how to create this. I don't know how to share this with the team and push it forward and working with other collaborators on how to craft that vision that you can own and drive forward.

And then I think just like theme of all of our conversations, be a sponge, ask to be involved. I would say more often than not, I see people who are okay with like this is an issue. Somebody else figure it out.

The people that I see elevate into leadership roles are the ones that are like, this is an issue. I'm going to go figure it out. I want to take a stab at this. I want to figure out how we can maybe revamp this process or figure out how to better serve the client or figure out like a new, whatever it might be, but somebody who is curious to learn, expand their understanding and figure out how to chart a path forward that everybody benefits from.

So that was my long awaited response to the things that I think are most important for if somebody is trying to level-up to a director and what I think other leaders look for in future leaders. 

Galen Low: Absolutely. No, I love it. I'd also love that notion that, you think you might screw up less as you climb onto bigger roles, but you probably screw up more.

Jessica D'Amato Crosby: Oh, gosh. Yeah. 

Galen Low: But that willingness to figure it out, even if there's no sort of, like clear solution in front of you and a willingness to yeah, actually make some mistakes to get towards that vision of like how good it could be. 

Jessica D'Amato Crosby: Exactly. 

Galen Low: Jess, thanks so much for spending some more time with me today on the podcast. I always love having you on the show. 

Jessica D'Amato Crosby: Likewise, thanks for having me on the show. Galen Low: Alright folks, there you have it. As always, if you'd like to join the conversation with over a thousand like-minded project management champions, come join our collective. Head on over to thedigitalprojectmanager.com/membership to learn more. And if you like what you heard today, please subscribe and stay in touch on thedigitalprojectmanager.com. Until next time, thanks for listening.