321 Creative Rebels | Tessa Henley, Senior Product Manager

321 Creative Rebels | Tessa Henley, Senior Product Manager

View all Insights

By: 321

July 6, 2021

Tessa Henley isn’t your typical 9-5 product manager. 

She’s a Harley-gunnin’, mountain-livin’, tatted-up creative with a propensity for breaking the mold when it counts; an ad woman who flies her fashion degree in the rearview. 

She’s got one eye on the future (“nurturing the next generation of kick-butt PMs is how I’m flexing the creative muscle these days,”) and another on changing the game right now (“Product Thinking is the new Design Thinking,” she says). 

Though she’s recently transplanted to Asheville, her Florida roots run deep—raised by Indian Rocks Beach, educated by the Art Institute of Tampa (where she actually majored in Fashion and Marketing, not just fashion) and unapologetically proud of Orlando’s trajectory.

No matter how you slice it, Tessa Henley stands out in the din of digital design, a unique tour de force in an industry built on imitation. 

We asked her a set of thoughtful questions to understand how she carved out this career, where the industry is headed and how Orlando’s advertising scene stacks up with the rest of the state. 


What stands out the most about your path to 321? How does one go from an Art Institute education to Project and Product Management?

I’ve always been a person that associates a priceless value to the culture in which I work, the people I’m surrounded by while at work, and the type of work I’m putting out into the world. 

Those values mean a lot to me. 

So when I was graduating college, I started vetting companies from that perspective. I asked myself, “Where can I have fun at work and be proud of the work I’m producing while being completely myself?” 

It wasn’t fashion, for sure; I had already spent years as a Store Manager at a major retail chain, so I knew that wasn’t it. 

Approaching the workforce from that perspective ultimately led me to choose agency life. The types of companies that struck me as fun and challenging were advertising agencies with progressive cultures and a killer client list. So I started applying for literally any position I thought I could do. Mostly, project management because I knew my Type-A-Go-Getter-Hustle-Personality would suit that. 

I was initially placed on marketing campaigns and standard production work, but then quickly received small website builds that I picked up really quickly. I thank my DevOps Dad for speaking in code around me my whole life. Eventually, I was leading huge web builds and a couple of software products which led me to understand and pursue Product Management. 

I’m convinced the nature of agency structure and value for our clients is going to take a more Product Management role in the near future. A strong Product Manager can tackle Account Management, big picture, strategic thinking but also has the tactical, driving, actionable roots of a Project Manager. Now, there’s immense value in the current agency structure with Account Management and Project Management, but I really do believe Product thinking will be ingrained in agencies more and more even if the agency’s clients or organizational structure can’t support full scrum or agile methodologies as the industry currently knows it. 

Product Thinking is the new Design Thinking. 😉 

What are three unique things about yourself? Outside and inside of work. 

Hmm…well, the obvious one is I love riding my motorcycle. 

It’s a Harley Sportster Iron 883. Learning to ride the Blue Ridge Parkway is fun and challenging. 

I genuinely feel like I’ve matured and grown in my professional life over the last two years since being at 321 more than I’ve ever felt in my professional life so far. Learning to control the temperature has been an honest and welcomed challenge that I take seriously. I’m not a hot head per se, but I definitely carry a lot of pressure on myself. 

I recently moved to Asheville, North Carolina! Born and raised in Florida, it’s interesting to be surrounded by mountains and rivers instead of beaches and palm trees. 

Okay, now, specifically speaking to work—what do you bring to the table differently than everyone else, no matter the role?

Brain, spine, and guts, baby. 

No, but for real. There’s a certain level of determination that I’m aware I approach everything with. Sheer determination, grit, and brainpower have gotten me far and continue to propel me. In order to accomplish anything, all you need to do is apply yourself and I take that to heart.

I don’t half-ass anything. It’s all or nothing. All the time. 

[321 Vice President] Cathleen [Ayala] has to actively coach me on that frequently 😉 Sometimes it’s to my detriment.

That level of showing up and applying myself is, without a doubt, the reason why I know so much about building websites and technology today. I can take this personality trait and apply it anywhere! 

What does ‘creativity’ look like in your current role? How has your perception of creativity changed over the years?

Oh gosh. I do want to acknowledge something that people don’t think of as related to Project (or Product) Management. 

We hear burnout as it relates to creatives and billable team members (to this day, I still won’t call them resources), but we never think about creative burnout for Project Management. That’s very much a real thing for PMs. 

There are infinite ways Project Managers need to be creative in their role. 

The saying, “good project management happens when it goes unseen,” is so true and strikes a chord with me. We constantly have to be thinking of several ways to approach any possible scenario 10 steps ahead of everyone else, and that takes a TON of creativity and critical thinking at the same time. 

The left and right brains need to be working together simultaneously. 

How to break out budgets and work breakdown structures, how to communicate with each individual person on each project team, how to package a piece of information to your Account Manager or client, how to react if X, Y, Z happens, etc. Those are all ways PMs need to be creative. After doing this for almost seven years, I can say firsthand, it can be exhausting. So shoutout to all my PMs out there that think they don’t have much more to give. You do and you’ve got this. 

That’s just who you are 🙂 

These days I’m staying creative in my role by adding a personal element to the day-to-day grind. Focusing on nurturing the next generation of kick-butt PMs is how I’m flexing the creative muscle these days. It’s a new art form to master mentoring, managerial, and relationship building.

What’s the biggest takeaway you’ve had working in this industry? The No. 1 piece of advice you would give someone new to agency life. 

Ironically, it’s one of our values. Take Ownership. In all capacities of your life. Go get it. Don’t be shy. Just go for it. Nobody has a better chance of figuring it out than you. Then at the end of the day, personally disassociate from the work so you can apply that same energy to yourself and your personal life. 

Agency is all about high input, high output. And to me, that means strong boundaries and self-care so I can show up as strong as possible in my role. Everything is mine to own and nothing is at the same time. 

How does Orlando’s agency scene stack up to other large cities—especially in Florida?

Orlando is where it’s at. There’s no doubt about it. I’m so proud of the agency scene in Orlando. It’s small, absolutely. Everyone knows everyone, but it’s oh-so-mighty. 

Second to Miami, Orlando boasts a growing technical space for agencies. I feel that’s because Orlando has a strong draw for families and we also have UCF here so the talent is constantly being delivered or people want to move here. I genuinely would not be anywhere else in Florida if not Orlando. 

What could other creative individuals understand about your job to enhance the working relationship?

Every single one of us has nuances to the job that is an area for joy and a pain point. We all have a lot going on personally and professionally. I think choosing to see coworkers as humans first is critical.

PMs are juggling a lot. It’s a TON of meetings, slack messages, and emails. We frequently only have the option to work after hours since business hours are dedicated to talking to and working with the team. 

It’s common we don’t have time during business hours to actually do the tasks we need to do. 

It’s often not talked about or brought to awareness. Being mindful of this and asking yourself if that meeting is necessary. Or is this communication relevant and actionable for the PM? The same considerations we have to give to our teammates, if that level of consideration could be applied towards PMs too, your PM would have a bit more breathing room. 

A friend and fellow co-worker once told another co-worker of mine (with me in the room): 

“If a PM is asking you about the status of something, you’re already behind.” 

It’s true. 

The best thing any creative person can do to strengthen the relationship with PMs is to communicate and be reliable. This will build trust and make everyone excel in their respective roles. 

Help us help you 🙂 

Next Insight

+ Gamifying Creative

Gamification can be a useful way to motivate yourself to achieve goals and consistently push your creativity.  We can take some of the same skills that many of us have learned while playing video games … Continued