Authority Magazine – Holly Wasson of We Are Rosie: 5 Non-intuitive Ways To Grow Your Marketing Career

Marketing is equal parts art and science. If you are burned out and constantly spinning your wheels, there is simply no way to focus on either part well.

As part of my Marketing Strategy Series, I’m talking with fellow marketing pros at the top of their game to give entrepreneurs and marketers an inside look at proven strategies you might also be able to leverage to grow your business or career. Today I had the pleasure of talking with Holly Wasson.

Holly Wasson is the Chief Marketing Officer and Chief Community Office at We Are Rosie, a flexible career platform that matches independent marketing professionals with flexible roles at companies like IBM, Meta, IHG, and Bumble.

Thank you so much for doing this with us! Before we dig in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Growing up, I wanted to be a journalist. I have always loved writing and telling stories. I was also influenced by my mom and her side of the family — all who love the written word and are made up of journalists, writers, and English teachers (my dad’s side are all amazing sales leaders).

I studied Broadcast Journalism at The University of Georgia while writing for the Red & Black, reporting for WUOG 90.5 FM, and interning at WTOC in Savannah, Georgia. After college, I was incredibly lucky to land a job at CNN as an assistant in the Audience & Marketing Research department. My goal was to eventually shift over to the editorial side within the news giant.

Little did I know that I was learning the backbone of marketing. I was gaining an understanding of how to analyze quantitative and qualitative research to uncover consumer trends. I was truly enjoying my work and interactions with the marketing department at CNN. It opened my eyes to another way of storytelling. I viewed marketing as storytelling on a larger scale. And it allowed me to tap into both my mom’s and dad’s gifts — selling through storytelling.

After two years at CNN, I was able to take my consumer research knowledge and move into a Marketing Manager role at TNT. And the rest is history. I fell in love with understanding audiences and finding a way to effectively and persuasively communicate with them. The fact that the mediums we use to market are constantly evolving, made the industry even more exciting and challenging to me.

Can you share a story about the funniest marketing mistake you made when you were first starting and what lesson you learned from that?

At TNT, we were launching a Steven Spielberg series titled Nightmares & Dreamscapes. Each episode was a scary story. One episode, starring William Hurt, involved a dream where the tiny green army men he collected came to life and took him hostage.

To celebrate our launch of the series among our colleagues at Turner, we had a group of interns dress up as the little green army men in the series and greet teammates as they entered the room for our all-hands meeting of the entertainment networks.

Unfortunately, teammates from other networks across the building were a little shocked and concerned to see what they assumed to be military troops walking through our headquarters with 9/11 still fresh on everyone’s brains. The scene caused a bit of shock, concern, and a little panic among employees.

Lesson learned! Don’t get so wrapped up into what you think is a fun or engaging stunt without thinking of everyone who will encounter that action. Remember that consumers are not close to the campaign and will not relate it to your brand automatically. It’s easy for what you think is a great idea to backfire if you aren’t thinking about your broad audience.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

My tipping point was driven by the moment I began to get out of the tactical weeds and the “how” of marketing and shift to the “why” of marketing. It is so easy for marketers to get distracted by new, shiny objects. We want to be the first to market as new mediums and tactics are introduced. But, it’s easy to forget the audience and stay grounded in the best way to reach them in their daily lives. We need to stay focused on “who” we are targeting and showing them “why” our product, service, or content is relevant to them.

This came to light during a campaign launch that was targeting women. Excited about our product and shiny new marketing mediums, we bought all of the sexy marketing tactics we could find. These new mediums targeted younger, fashion-forward, tech-savvy, pop-culture-aware women in large markets while our true audience was women in their 40s and 50s, whose children had mostly left home, who were later adopters of new tech and who shopped with a price-conscious mindset and lived in mid-sized markets. Needless to say, our original campaign didn’t hit the mark.

As soon as we shifted our thinking and developed a true profile of our target, we were able to develop compelling messaging and uncover the right tactics to reach her. We had tremendous success after that re-do in our strategy.

What do you think makes your company stand out?

We Are Rosie is on a mission to change the way work gets done in the advertising industry. Stephanie Nadi Olson built this company to ensure that marketing work is inclusive for all. We’re dedicated to creating opportunities and access for independent marketers, especially those who’ve historically been marginalized by the industry.

We work directly with our clients to set — and often exceed — talent diversity goals. Our inclusive community comprises 18,000+ marketing entrepreneurs, and 40% of all “Rosies” booked on projects in 2021 identify as BIPOC.

Our mission is supported by a highly diverse core team: 52% of our full-time employees identify as BIPOC and 87% are women. We’re also proud to be a woman-founded and women-led organization, with 5 of 6 C-Suite positions held by female executives.

We Are Rosie has connected marketers looking for a better, more human way to work to thousands of meaningful, challenging advertising projects. I am so proud of how we are helping both the marketing talent, but also our clients understand that a little flexibility in how work gets done can lead to amazing, innovative marketing.

None of us are able to achieve success without some help along the way. Is there a particular person you are grateful for who helped get you to where you are?

I have been incredibly lucky to have so many champions throughout my career. My mentors across Turner stand out the most as I spent 17 years of my career with the organization.

Throughout my tenure at Turner, I had such amazing mentors who I have to thank for their advice, leadership, for believing in me, and for giving me opportunities throughout my career. Sandy Padula, Laura Dames, Scot Safon, Steve Koonin, Kellie Appel, and Molly Battin stand out the most. Of all of them, I think I lean on learnings from Steve Koonin most often.

Steve Koonin, one of the most brilliant marketers and leaders I’ve ever met, taught me so many lessons in my early-to-mid career. It was Steve who pushed the TNT team to really dig into the “who” and the “why” of the strategy-building process. I remember meetings in which he would challenge my marketing strategy and ask me tough questions to ensure that I learned to think deeper and bigger. Steve was a huge supporter of working smarter, not necessarily longer hours.

Steve was ahead of his time when it came to working mothers building successful careers and raising our families. He was open to flexible hours and even working from home when needed in the early 2000s — well before policies supporting caregivers were ever even thought of. Steve was also a very open and honest leader who was willing to share the good, the bad and the ugly with his team. I like to think that I have modeled some of my own leadership communication style to him.

Is there someone you consider to be your hero?

My father (who I still refer to as Daddy) is my hero. He came from an extremely humble background and experienced a lot of tragedy at a very young age, losing his brother, father, and cousin in short succession and then having the home he and his mother lived in destroyed by a fire.

Despite losing so many people in his young life and overcoming so many obstacles, my Daddy was the kindest, most empathetic, and caring human being who always had a smile, a kind word, or a hilarious story or joke for anyone. He was the first in his family to attend college and was the hardest-working person I’ve ever met. He spent a 42-year career as a salesman in the commercial building industry, climbing to VP of Sales in an Atlanta-based company and later founding his own company in the industry.

My Daddy was not only the life of every party and the center of attention of any gathering — large or small — but a magnetic personality with a huge heart. He had a smile, a kind word or a helping hand to make someone’s day. He had such a soft heart and he hated gossip. He used to tell my sister and me that a simple smile could make a person’s day because we never know what they might be going through.

There are so many small acts of kindness that we witnessed my Daddy perform over the years. From acting as a surrogate Daddy to so many of our friends, to slipping a crying young mother gas money on Christmas Eve because the bank was closed and she couldn’t cash her paycheck, to spending an entire evening picking up stranded teachers and motorists in his Jeep during a snowstorm. My Daddy never wanted recognition for these small kindnesses, but my sister and I saw these beautiful, selfless acts and they made a deep impression.

He was always my sister’s and my biggest champion, showing up to softball and basketball games (even though I rode the bench), swim meets, football games (even though my sister and I only performed at halftime), and all of the amazing musicals my talented sister performed in. He and my mother encouraged us to follow our own passions and celebrated our differences.

My Daddy found ways to connect with my sister and me as individuals. Daddy raised two girls in the 70s and 80s who were confident that we could be anything or achieve anything as long as we worked hard. As my sister and I grew up and left the house, Daddy remained our steadfast champion and protector. He sent me cards and letters at least once a month when I was in college. Even as I got my first job at CNN, we met for lunch every single Friday just to catch up. He gave me so much career and life advice during those amazing afternoons.

While his life was cut too short by early onset Lewy Bodies Dementia, my Daddy lived to the fullest every single minute. He loved big, he lived big, he gave big, he worked and played big and he made big impressions on those around him.

Wonderful. Let’s now shift to the main part of our discussion. What advice would you give to other marketers to thrive and avoid burnout?

Marketing is equal parts art and science. If you are burned out and constantly spinning your wheels, there is simply no way to focus on either part well. You are unable to see the trends in the data and you definitely cannot tap your creativity and innovate.

My trick is to take a break when I’m feeling overwhelmed. I’ve learned that if I have too many things clouding my mind at one time, I’m not going to be effective no matter how many more hours I put into work. I walk away from the computer and often go outside for sunshine and fresh air.

If I can, I go for a walk or I pick up whatever novel I’m reading at the time. Walking or reading fiction allows me to simply shut down all of the competing priorities in my brain. If I feel this way in the late afternoon, I’ll shut down my computer and start up again super early in the morning. I’m an early morning person and I love to tackle a strategy or problem solve in the wee hours of the day before other priorities compete for my attention.

My other piece of advice is to use your vacation time! Travel is one of my favorite things to do. Going to new places, meeting new people, and seeing new things spark your creativity. It also gives your brain a break. I’ve learned to never feel guilty about taking well-deserved time off to recharge. I know that when I return, I’m a much more productive employee.

There are hundreds of memorable marketing campaigns that have become part of the lexicon of our culture. What is your favorite marketing or branding campaign from history?

I am a Dove superfan. The Dove Real Beauty campaign was absolutely brilliant as it targeted beauty stereotypes, ultimately challenging advertising culture. Dove knew the “who” and the “why” behind what they were doing with that campaign.

Women are exhausted from seeing unachievable standards of beauty depicted across advertising. By showcasing real women and celebrating the fact that beauty takes so many different forms, Dove didn’t just drive brand loyalty, but they drove sales from $2.5 to $4 billion in the campaign’s first 10 years. And they became the U.S.’s #1 preferred soap and Unilever’s best-selling product.

Another reason that I adore this campaign and the Dove brand is that it wasn’t a “one and done” messaging tactic. The Dove brand has stayed true to portraying real women and the many different forms of beauty while working to boost self-esteem not just among adults, but among teens as well.

If you open the cabinet in my bathroom, you’ll find Dove bar soap, shampoo, conditioner, hairspray, deodorant, and body wash. Dove is my favorite brand not just for the product, but for what it stands for. If I could choose any brand in the world for We Are Rosie to partner with in the future, it would be with Dove.

If you could break down a very successful campaign into a “blueprint”, what would that blueprint look like?

A successful campaign always starts with the same key strategic building blocks: know your audience, understand their pain points and determine how only your brand can solve their problem better than your competition. That’s all textbook: Create the strategy to drive the creative execution before even considering tactics.

However, the magic in the blueprint is probably not what you’d expect. The genius behind brilliant marketing campaigns is the team that fosters groundbreaking ideas. And the teams responsible for memorable, innovative, award-winning work have something in common: they aren’t afraid of a little friction to generate that spark of genius.

Great ideas come from a team with diversity of expertise, backgrounds, ages, demographics, experience levels, and even energy. A diverse team that has different opinions, points of view, and approaches is key to avoiding the dreaded “groupthink.”

Most importantly, these differences will likely cause some friction during the creative process. However, if the team is united by a common purpose and empowered to represent their area of expertise, this friction will result in positive heat rather than negative energy.

A diverse, passionate team will not always be harmonious, and that’s a very good thing. The best ideas are usually molded and strengthened by positive friction among passionate team members.

Some of the best campaigns I’ve worked on throughout my career were developed through hours of passionate debate, willingness to iterate, and the ability for the team to push each other to make the idea stronger, better, and more memorable!

Consumers have become more jaded and resistant to anything “salesy”. In your industry, where do you see the future of marketing going?

We see the future of marketing as freelance as part of a “layer cake” workforce of some FTEs, agency partners, and independent contractors. Independent marketers are able to provide fresh, innovative ideas and infuse new thinking into brand and agency marketing teams.

Remote work is a form of inclusivity for organizations, allowing brands and agencies to tap experts from around the globe to drive marketing initiatives without requiring talent to relocate to cities they may not feel a sense of community within.

For years, we’ve been talking about the emergence of freelance, but it is no longer emerging. It is mainstream and growing steadily. By 2028,1 in 2 workers are expected to hold a freelance position.

Flex work allows marketers to prioritize their values — both professionally and personally. It’s not all about having more personal time; it’s also about stretching professionally with project-based work.

The stigma of freelancing has all but disappeared and flex work is extremely profitable, dispelling myths that talent needs a full-time job to grow wealth. Many of our Rosies feel more secure having their “fate in their own hands” as independent contractors while corporate jobs are more unstable.

For brands, it’s often more cost-effective to tap independent marketers for surge capacity, special projects, or specialty expertise rather than keep an FTE on staff. During times of economic uncertainty, brands have historically relied on freelancers to help get work done.

Independent marketers are able to work on a variety of brands and gain expertise more quickly than if they stay within one organization. This knowledge makes them more valuable to employers.

What 5 things do you wish someone told you before you started?

1. Fake it until you make it: In my early and mid-career, I assumed executives knew exactly what they were doing and that they had all of the answers. It wasn’t until moved to the executive level that I realized that often, leaders are simply winging it! This was a huge shock to me. It was as if I was learning once again that Santa didn’t exist. Once I got over the shock, I realized that it’s better to act than to stand paralyzed and be too afraid to speak up and provide a point of view or way forward. And if you do this with confidence, others will have confidence in your leadership. In other words, you are faking that you know exactly what you are doing until you actually get it right. And most importantly, you learn from your failures.
2. The best leaders surround themselves with people who are smarter than they are: When I was a young manager, I thought that I needed to have all of the answers and know how to do everything. I thought that I needed to know more than my direct reports. It made me nervous when someone on my team was smarter than me. As I grew my leadership experience and took a good look at the best leaders, I realized they all had something in common. They surrounded themselves with extremely smart people, listened to their points of view and praised them for their expertise. Once I adopted this leadership approach, it felt so much better to empower experts than to try to wear all of the hats myself.
3. Marketing is not brain surgery…no one’s life is on the line: Early in my career, it was easy for me to get so wrapped up in developing marketing campaigns, meeting deadlines, and staying on budget that I’d place an unwarranted level of importance on the work. As I matured in my role, I realized that marketing campaigns in most cases are not life or death. Marketing needs to be fun. It’s part art and part science. To be innovative, you have to keep a sense of humor and take yourself and even the work a little less seriously. When you are having fun and are passionate about the work, you create brilliance.
4. Don’t be afraid to make mistakes: With a type-A personality and the desire to succeed and please those around me, I was always extremely hard on myself and terrified of making a mistake. What I’ve learned throughout my career in marketing is that if you aren’t making mistakes, you’re not innovating enough. Marketing requires you to be willing to try and fail and learn from that mistake. This knowledge has served me well at We Are Rosie because falling forward is essential for a hyper-growth start-up.
5. It’s all about storytelling: As a marketing executive, I tell stories every day. When I’m talking to our clients, coaching my team, or developing a messaging strategy, I’m simply telling a story. If you are a good storyteller, you have amazing influence as you can grab the attention of your audience in any situation. By knowing your audience and telling a compelling story to get your idea across, you are able to be extremely persuasive. You become a salesperson, an amazing coach, and a marketer by telling a good story.

One more before we go: If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

If I think about the core of inclusivity and success, it all starts with education. My mother was a middle and high school English teacher for 31 years, so I understand what teachers give to their students and the difference they can make in their lives. If not for teachers, we would not have brilliant marketers, doctors, innovators, on and on and on. A teacher can inspire a student to pursue their natural talents and passions.

What is extremely sad and unfair is just how much influence teachers have on generation after generation while being compensated so little for their extremely hard work. We need to treat our teachers better. We need to encourage more gifted people to become teachers. We need to make sure that every child in every corner of this country and beyond has access to a top education. I truly believe that education can cure so many issues that we battle across the globe. We need to invest in our future through education.

Thank you for sharing so many valuable insights with us today!