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A successful CMO has many roles, including leading an organization's marketing department, establishing marketing strategies, and tracking successes and failures. How can a CMO create a highly successful career? What tools, strategies, and approaches can a CMO use to be successful? As part of this series, we had the pleasure of interviewing Kathy Bryan.

Kathy Bryan

Kathy Bryan

With more than 25 years of marketing and advertising experience, Kathy Bryan is a trusted and effective strategic marketing communications leader who is currently leading the marketing team for Electives, an enterprise live learning platform. Kathy is an expert at identifying innovative marketing strategies that engage audiences and get them to take action. With a career spanning global and boutique advertising agencies plus in-house marketing teams across a number of leading sectors, Kathy now specializes in building and scaling full-funnel organic and earned marketing initiatives.

Thank you so much for doing this with us! To start, can you share a bit of your 'backstory' and how you got started in your career?

I’ve been a marketer my entire life, and I don’t just mean my entire professional life. I remember a moment, as a young kid, when my dad pointed to a package of crackers and told me that someone had designed it. That tiny lesson was life changing. After that, when I walked around stores, I would evaluate packaging and in-store signage, optimizing it all in my mind to enhance performance.

My first job was at an advertising agency, working on the Amtrak campaign. I was an assistant account executive back during the years when you had to put in your time. At least three nights a week, I was at the office late, waiting for color printouts that could be folded into an envelope and raced to the FedEx office at Dulles Airport. The cutoff for next-day shipping was 10pm, and I often cut it close. 

In those early years, I was truly an “advertiser,” paying for space and impressions. Over the years, I transitioned to more of a “marketer.” And now I specialize in brand building along with earned and organic media. It turns out I enjoy the win more when it’s not guaranteed.

I’ve led marketing teams and initiatives for a long list of great brands and had the privilege of being the CMO when Digital Media Solutions (NYSE: DMS) went public. Now I’m building the customer acquisition machine for Electives, an enterprise live learning platform.

Throughout my career, I’ve worked with a long list of people doing what I love to do and having a lot of fun along the way.

What do you think was a pivotal moment that led you on your path to becoming a CMO?

I’ve always considered myself to be a “generalist” in the marketing world. However, in 2011, I realized I had only limited experience in a growing marketing category: lead generation. I made a bold transition, taking a job managing lead generation campaigns for an education agency. I learned a lot… including that it was not for me.

I transitioned from that role into corporate marketing for the same agency and progressed from director to VP to CMO for a public martech company. Along the way, I discovered that it’s important to know what you enjoy and what you’re good at, and then stack your bench with people who are good at the other things.

Can you share an interesting story that has happened since you began leading your company?

In 2020, I had the great privilege of launching Women of Martech along with our co-founder Melissa Ledesma. Women of Martech is a nonprofit professional organization designed to amplify the voices of women in the marketing and technology industries. With less than $5,000 spent, we grew to be more than 1,000 members working together to lift each other up. I stepped down from my role as president in 2022, and I look forward to seeing more women grow in their careers.

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

It’s impossible to name only one person who has helped me get where I am today, so I’ll name three:

West Herford was one of the most amazing bosses I’ve ever had. He was hard on us, but in the best way possible. He let us know that he expected our best… and he helped us deliver it. West’s leadership style greatly impacted my current leadership style.

Melissa Ledesma and Charlene Sterphone. I put these two together because the three of us created a triad for about four years. All three of us are generalists, but with different specialities. Melissa is amazing at communications and events, and Charlene is the marketing operations person you want always at your side. Together, the three of us could conquer the world. They were by my side when I became a CMO. And, though all three of us are at different companies now, we all know that we’ll always—always!—have each other’s backs.

Can you please share your favorite 'Life Lesson Quote' and how it has been relevant to you in your life?

This story requires me to mention a fourth person I’m grateful for: Jeff Costantino. Jeff was one of my first bosses. Early on in our working relationship, Jeff asked me, “You can hire one of two people. The first gets the job done in 40 hours. The second gets the job done in 60 hours. Who will you hire?” I answered the one who gets the job done in 40 hours, of course… and then realized what Jeff teaching me. Go home on time! There will be days (and sometimes weeks) when you need to work late. But never work late just to work late. This is a lesson I have lived by and that I have passed on to many.

Can you share with us three strengths, skills, or characteristics that helped you to reach this place in your career? How can others actively build these areas within themselves? 

Getting to where I am in my career took:

1. Desire. I’ve always wanted to be a marketing leader, because I enjoy the business of marketing. I knew that I didn’t always want to be executing other people’s ideas throughout my entire career, and that meant I had to have a breadth of knowledge and experiences in my portfolio that I could tap into at any time. I’ve intentionally sought opportunities that would build that portfolio—even when that took me outside my comfort zone.

2. A collaborative spirit. I often say that marketing is a team sport. My favorite career moments—and the times when I believe I produce the best work—are when I’m white boarding with a group of people, and I have no idea whose idea was the winning idea because we all got there together.

3. Balanced confidence and ego. Although marketing performance is regularly calculated, there’s a lot of subjectivity applied to marketing evaluations. If you’re not confident in your abilities, it’s easy to get pulled down as someone critiques your strategy or copy or design. Likewise, if your ego isn’t in check, you may not learn and grow from the critique coming your way.

For marketers currently growing their careers, I encourage them to be honest with themselves about who they are and what they want. Figure out what you’re good and and what you enjoy, and look for opportunities that align.

Which skills are you still trying to grow now?

In my last position, I was marketing to marketers and had to read marketing news as part of my job. Currently, I’m heading up the marketing for an enterprise live learning company and relying on my historical marketing expertise, but not enjoying as much time to read about current marketing innovations and changes. For that reason, creating a habit of reading marketing news is a priority for me right now, so I stay current even as the pace of marketing innovation accelerates.

Having reached this space, what do you believe are the five things you need to be a highly successful CMO?

1. Curiosity. Marketing is always evolving, which means marketing leaders must continually be researching, studying and learning. The strategies and tactics that worked last year may or may not be the ones that will work best for you this year. It’s on you to know what you need to know—from new channels, to algorithm changes, to new tools (like AI)—to efficiently and effectively build relevant strategies and campaigns for today’s audiences and platforms.

2. Be an active listener. I’ve often called myself a “crumb collector” because I’m regularly collecting crumbs of knowledge as I hear things. It’s a marketer’s job to be proactive, but not all of the information we need is given to us proactively. Therefore, it’s on us to listen and to ask questions so we can be prepared for what lies ahead.

3. Maintain your drive. There is always room to be better in marketing. Even when you beat your best-ever performance, there’s still better. And you’d better be planning to get there. Marketing leaders need to have that drive to seek more and to seek better and to plan paths to get there. 

4. Be okay with failing. In marketing, we’re always experimenting. Often, experiments goes well. Sometimes they do not. That’s why I always tell people that the only time you fail in marketing is when you fail to recognize that you’ve failed. All those other times, when an experiment doesn’t work out… you didn’t fail, you learned.

5. Seek out the fun. I am a fun seeker, because (1) fun is fun and (2) when you’re having fun, you’re usually doing good things. Across the teams I lead, I seek to match passions to work, because I find that this leads to happier team members and better performance. Work can be fun… in fact it should be.

Are there any underrated skills or qualities that you encourage others not to overlook?

Being a successful marketing leader requires you to be a great leader. This seems pretty obvious, but this is worth being stated: not all great marketers are great leaders.

In addition to being great marketers, great marketing leaders:

  • Listen to the people on their team
  • Empower the people on their team
  • Help grow the people on their team
  • Advocate for the people on their team

What are some of the issues that other CMOs commonly struggle with, and what can be done to address those challenges?

The job of a CMO can be tricky, because you’re the bridge between the executive leadership team and the rest of your marketing team. When I see CMOs struggling, it’s usually because of one of these reasons:

  1. They’re trying to execute an old playbook. It’s easy to assume that an old playbook will succeed again. But usually, too much has changed—including the players, the field and sometimes even the game itself.
  2. They’re waiting for priorities to be shared with them. When CMOs wait for priorities to be defined for them, they often end up reactive. CMOs need to listen to what the team is prioritizing, and ensure they’re one step ahead.
  3. Not creating alignment with the CEO. No matter how good of a marketer or leader you are, if your vision is not aligned with the CEO’s vision, you will fail as a CMO. 

What do you believe is the most effective way to stand out and make an impact as a CMO?

The best way to make an impact as a CMO is to build the people that work for you into leaders. As a CMO, it’s your job to coach the team. You’re not the captain, and you’re not a player on the field. It’s your job as a CMO to make sure your team is ready and prepared to win every day.

If you could inspire a movement that would bring a great amount of good to the greatest number of people, what would that be?

This year, my kids and I vowed to put less plastic in the trash. We’re doing that by thinking about what we buy and asking ourselves if the purchase is worth our waste spending 1,000 years in a landfill. (It’s amazing how that question can change your purchase decisions!) Unfortunately, it’s become very hard to avoid plastic. From groceries to toys, plastic wrappers are ubiquitous. 

I’d like to create a movement of consumers asking themselves that very question, “Is this purchase worth littering the Earth for 1,000 years?” Likewise, I want to encourage the top CPG and toy brands to offer alternatives to plastic packaging. 

Lastly, is there a person with whom you would love to have a private breakfast or lunch, and why? They might just see this!

I would like to have a private lunch with Marc Pritchard, Chief Brand Officer at P&G. Marc believes brands can be a force for good, and I’d like to learn about the challenges and opportunities he’s studied and experienced, and how he believes we can collectively solve environmental and societal challenges.

Stephanie Hood
By Stephanie Hood

Stephanie Hood is an experienced marketing professional and Editor of The CMO. With nearly a decade spent as Marketing Manager at Discover Holidays and Executive Editor at VIVA Lifestyle & Travel, she built her career leading editorial and marketing teams and strategies that turn six-figure budgets into seven-figure profits. She now enjoys connecting with the world's top executives to learn their secrets to business success, and shares those insights right here with her community of like-minded professionals. Curious what she’s uncovered? Be sure to sign up for The CMO newsletter.