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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 Channing Fleetwood.

Channing Fleetwood

Channing Fleetwood

Channing is a contemporary marketing executive with a track record of growing brands in the tech, communications and consumer products industries.


In his current role as Chief Marketing Officer at RentSpree, Channing is responsible for driving brand strategy, product marketing, public relations, demand generation and events to help position and grow the company into the leading rental proptech brand.


Channing serves as vice chair on the board of directors for The California Black Health Network and earned his Bachelor’s of Business Administration with a concentration in marketing from Clark Atlanta University.

Thank you so much for doing this with us! To start, can you share your 'backstory' and what brought you to this career path? 

I grew up in mid-city Los Angeles. For college, I moved to Atlanta, Georgia, where I subsequently started my career. I cut my teeth working at marketing agencies such as HAVAS, helping to launch many consumer products from well- known brands, such as Coca-Cola, Delta Airlines, Nintendo, Ford and MTV. Experiential marketing was all the rage then, which taught me the importance of developing a deeper connection between brands and consumers. 

Mid-career, I transitioned to B2B2C and spent 6 years at inflight Internet provider Gogo, helping to drive adoption of the initial product, then global expansion, and finally a transition to public ownership. I also served as Vice President of Marketing at Laserfiche, where I led the company's global transition to SaaS before joining RentSpree in 2021.

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

The pivotal moment for me came when I was at Laserfiche. I was given a shot at taking on a leadership role by my then-boss and mentor Tim Nichols. This allowed me to leverage my experiences in event planning, brand and product marketing as well as my natural ability to lead.

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

In 2022, we embarked on a robust brand research project to understand what drives brand affinity in our space. After surveying many buyer and user persona segments, we reached an ah-ha moment. Our messaging was off! Our research gave us a new perspective on what our targets valued. While I can’t reveal our secret sauce, I can say that it’s a fundamental change that is underpinning many projects across marketing, product and sales. 

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

My wife and four kids are my reason for being, period. That said, I have two close friends who have been pivotal in my career growth. 

I’m lucky enough to have a best friend who is also a beast of a marketer. Ashley Atkins, who has held leadership roles at top PR firms, has always pushed me to lean into discomfort and grow at each level of my career. We’ve known each other since college, and I can't think of a career move I've made without consulting her. 

Perry Fair is also a very close friend and mentor. He’s paved the way for many black leaders in advertising, having been in executive leadership roles for over a decade. Perry gives the kind of strategic leadership advice that sticks with you for a long time. Years back, he told me to “put the right people in the right places,” and I've unpacked this time and time again when making decisions on strategy, team structure and my team’s development.

When considering making the transition into a CMO role, like most I was unsure if I was ready. I consulted with my wife, Ashley and Perry, and all three gave me the “you’re ready,” which gave me the confidence boost I needed.

What's your favorite 'Life Lesson Quote' and how is it relevant to you in your life? 

I can still hear my mother saying “Take care of business, and business will take care of you.” That mantra has stuck with me my entire life and is a guide for when I may veer off track. 

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? 

1. Sharpen your leadership skills: Reaching a leadership role requires a high level of understanding of how to lead people. Even when you don't manage people directly, you must be able to effectively lead people to help them achieve their goals.

2. Talk to your Mentors: Throughout my career, I've had formal and informal mentors. I’ve even had mentors who didn't realize they were my mentors. You must seek out those who have done what you want to accomplish and soak up their expertise and knowledge... It’s a fast track to leadership. 

3. Become a forever student: I discovered audio books, and my appetite for learning increased dramatically. Whether you want to sharpen your marketing skills, learn how to present data in a more effective way, or learn how to lead teams, there are books full of expert advice and established frameworks to leverage.

Which skills are you still trying to grow now?

I’ve developed an appetite for continuous learning, so i'm always looking for new ways to learn, implement those learnings in my work and life, and teach them to others. Currently I'm working to grow my data skills. I want to have a more data-driven mindset when it comes to using data to strengthen strategies. I also want to be able to teach my teams how to be more data-driven in their workstreams. 

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

  1. Being an effective leader - A year before I was put into my first true leadership position, I read a few books on how to become an effective leader. I worked over a year to implement those skills, even when I had no direct reports. I was able to influence teams across marketing disciplines to achieve goals I had for my product. I’ve honed those skills ever since and have grown to lead many teams directly and indirectly. 
  2. Putting  the right people in the right places - Having inherited teams who were misaligned, I've had to reorganize often  to point them in the right direction. I’ve also had to build marketing teams from scratch, structuring the team to achieve growth goals of the business.
  3. Understanding how to build brands - Early in my career, I thought of brand building as creative development. Slap on a clean logo and modern color pallet and you've got a brand right? Wrong, that’s a consumer-centric view of branding. I’ve learned that true brand building starts with an understanding of your company’s vision, knowing what drives your customers’ emotional and rational decisions and infusing that into your brand story, communications, product and consumer interactions.
  4.  Being self-accountable to results - There’s nothing like the feeling of setting a goal and reaching it. I’ve also had times where goals were not reached. I’ve learned the best way to deal with this reality is being honest with the reasons why the  goals weren’t met and communicating that to teams and stakeholders, including your boss. This enabled me to learn from my mistakes and build trust within my company. As a leader, it's also important to teach team members to be self-accountable, which over the long term will speed up and improve the team’s effectiveness. 
  5.  Being data-driven - At my first agency job, I produced weekly reports on how well (or not) my experiential sampling programs were tracking toward reaching targets. I’ve learned that reporting on past performance is table stakes for marketers. We must go beyond reporting outputs and leverage data to validate assumptions and strengthen marketing strategies. Challenge yourself and your teams to provide data out- and inputs.  

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

Don’t overlook empathy. Learning how to understand what people are going through will help you be a more effective communicator, and ultimately a more effective leader. When dealing with challenges, don’t look at the challenge from your perspective. Take time to hear and understand the point of view of others involved. Over time, this skill will come naturally and be an everyday instrument in your leadership toolbelt.

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

A challenge most CMOs face is effectively allocating the right amount of resources and marketing activity to hit goals while managing the P&L. I sit on the advisory board for an early stage startup, Growegy, which created software that helps marketers accurately forecast the right amount of marketing activity needed to meet goals across channels. As marketers, we must embrace MarTech such as Growegy and others to continuously improve.

Another top challenge for CMO’s is keeping up with ever-changing business environments. Industry trends, environmental trends, changing laws and regulation, customer preferences, you name it. CMOs across industries are constantly challenged to deliver relevant value propositions and build trust with target buyer and customer segments. 

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

Deliver results - CMO’s must develop a track record of delivering results to gain trust across the C-suite and garner the resources needed to continuously grow brands.

Deliver creativity - CMOs must find creative ways to deliver brand and product messaging. Brands are constantly competing for the attention of their target audiences, and creativity will be the single biggest factor that allows your brand to stand out. Ironically, it's one of the most challenging disciplines to measure. I’d love to chat with CMOs who have figured this out. :) 

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

My four children (10, 8, 5, & 2) have been the biggest life influence and the reason why I work so hard. Everything I do is for them. I’m confident, parents across the globe agree that we just want to protect our children from a world that can be harsh. Many children don’t have anyone dedicated to protecting them. If I could inspire a movement, it would be to find a child and protect them in whichever way you can.

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

I would love to have lunch with Robert L. Johnson. He’s an inspirational black leader whose presence in the business world gives representation to many future leaders. I hear he’s also a creative marketer and father of two ;) 

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.