Courtney Riley of Proximo Marketing Strategies

    We Spoke to Courtney Riley of Proximo Marketing Strategies

    As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Courtney Riley.

    Courtney Riley is the CEO and visionary behind Proximo Marketing Strategies, an international marketing firm based out of Hampton Roads, Virginia. Driven by passion and a calling to serve, Courtney leverages her talent for innovative thinking with a genuine enthusiasm for seeing others succeed, to help her clients find and pursue their true purpose while also providing them with the necessary tools to successfully position their brands in the marketplace. A published author and recent recipient of the 40 Under 40 and Woman of Excellence award, Courtney Riley is one to watch in the marketing world.

    Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

    I was raised by “serial entrepreneurs” who owned building, construction, and real estate companies. It did not inspire me to be a business owner. In fact, I was adamantly against the idea of owning my own business, simply because of the ups and downs I witnessed growing up. I wanted security and stability, and I didn’t think it would be possible to achieve that as an entrepreneur. So, I pursued an education in criminal justice with the intent of joining the legal field. I worked in a medical office during my time in college to pay the bills — it was just supposed to be a temporary thing. But, of course, life happened, and I ended up staying there for 5 years and running their marketing department because I showed a natural talent for it. I know it’s cliche, but it’s absolutely true that I didn’t choose it, it chose me! And thank God it did because it was definitely the right path for me. Ten years later, I’m happily positioned as the CEO of my own marketing firm with a team of talented individuals working alongside me. Together we help alleviate some of the stress of business ownership by allowing our clients to unburden themselves of the tasks they just don’t have time or energy for. Our approach is focused on freeing up the mental space and energy that’s been taken up by tasks they’re not meant to be doing, so they can focus on exactly what they ARE meant for. For us, it’s not just about marketing. It’s about providing a service that allows our clients to step out of chaos and into their God-given purposes.

    Can you share the most interesting story that happened to you since you began leading your company?

    I’m not sure “interesting” is the right word, considering how everyone has been feeling over the past year and a half but, for me, the pandemic has definitely been an interesting experience not only to navigate through as a business owner but to watch other business owners learn to adjust. Seeing everyone learn from each other and shift their business models to stay viable during a worldwide quarantine — from the way they sold their products, to the way they communicated, to the way they managed their teams. It really shook up the idea of “business as usual” and I think that can only be good for the marketplace. It forced us all to get innovative and reevaluate our position, and I think some really positive growth came from that for a lot of businesses.

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

    I’ll be honest, I tend to cringe more than laugh when I think back on some of the mistakes I made as a rookie! I really can’t think of a mistake I made that was funny, but what I can tell you is that I’ve learned to laugh at myself and not take myself so seriously a lot more now which I think is a healthier way to go through life and business!

    None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

    While I’ve worked with and learned from so many different people throughout my career, I’d have to say the person who has made the greatest impact on my life and business is my COO, Katy Calabrese. I’ve known her throughout several different seasons of my life — as a speaker at events, as a friend and in other capacities — but over the course of the past year, she has breathed so much life and love into our company. I have such a passion to lead with love in my business, but I really didn’t know how to put it into practice on a bigger scale. I started working with Katy as a consultant for process management and that blossomed into her current role with us at Proximo Marketing Strategies. She has added structure and process into my vision that we desperately needed, and it has allowed me to step back from the areas of my business that were distracting me from living out my purpose as a CEO. Couple that with the astronomical growth we’ve seen as a result of her process management expertise — a 400% increase in our sales and a tripling of our internal team (in the middle of a pandemic!) — and it’s impossible to deny the mark she’s left on our company in such a short period of time. It has truly been life changing and I am so glad to have her as a part of the team so that we can share her talents with our clients, allowing them to step out of chaos and into their callings.

    As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

    I think in any industry, welcoming and making room for the inclusion of diverse opinions, backgrounds, cultures, etc. is important and necessary in order to ensure that we’re reflecting the world we serve. And, speaking specifically to the industry I work within, I think diversity of thought and experience are important to the creative process because when our worlds get bigger through inclusion, our minds open to all the possibilities we might have otherwise overlooked.

    As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

    I think that creating a more inclusive, representative and equitable society starts with changing the ways we do business — we must do better which is why I am so passionate about leading with love. It encompasses everything — from the way we speak to each other, to the goals we set, to the ways we show up in the marketplace. Love-centric businesses see the value of each human being (whether an internal member of their company or a consumer) and allow love to inform their words and actions.

    As a marketing agency, one of our primary objectives is to give our clients a voice and that voice must be truly, authentically theirs. It’s our duty to amplify their unique stories because it’s important within the complex fabric of our society that every voice is heard and every story is told, valued and respected. Everyone deserves to see themselves represented and reflected in the world around them.

    Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

    I am fortunate to have a team full of leaders. Each member of our team at Proximo has a specialty and strength that they graciously share with our team and our clients, and I love seeing them each take the lead on the things that they are most passionate about. At any given time, you could see any member of my team operating in a leadership role — motivating their teammates, sharing their expertise and unique perspectives and jumping in to help wherever they can. They are the driving force behind the work we do for our amazing clients, and I am so blessed by their willingness to serve.

    From my perspective, an executive leader does not exist to steer a ship full of stagnant subordinates who never rise above their current roles. A great executive leader grows other leaders through mentorship, encouragement, and education. I don’t want a team full of people who aren’t hungry to learn and grow. Give me people who have a passion and a vision for their future, and I will do everything in my power to help them walk that out.

    What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

    I would love to dispel the belief that the hustle and grind mentality is a requirement of entrepreneurship or of leadership, that self-sacrifice is the way to be a good leader. I don’t believe it has to be that way and when we live out that non-stop, success at any cost mindset, we have to remember who’s watching us do that. Do we really want to encourage our employees to burnout because the job is just too important? Do we want their personal lives and relationships to suffer because they can’t relax, and their work is bleeding into off-the-clock time? I really don’t think that’s what we want for our employees, not if we care about them as we should. Being an executive leader is a stewardship of more than just a business. Our employees are trusting us with their lives. They trust us to compensate them fairly, to respect their time, to provide opportunities to better their lives. We need to lead by example and show that success comes in all different forms, and you can achieve it in a way that doesn’t sacrifice everything that matters most to you.

    What is the most striking difference between your actual job and how you thought the job would be?

    When I got started, I was young, and I had no grasp on loving people or really even loving myself. I was so self-centered — like many twenty somethings — and thought being an executive would be flashy and sexy. It was all about controlling how I was seen by others. I thought I knew what success had to look like — the fancy car, the high heels and power suits, the country club — all of it. And, of course, there is absolutely nothing wrong with having any of those things. I’ve just realized that my motivation for attaining them was more about looking the part and chasing after someone else’s idea of success than it was about finding my own happiness. Now, after over a decade in executive leadership, I realize that it’s so much more about doing things for the benefit of others than it is about me getting mine. Executive leadership is about developing other leaders and serving your team more than you serve your own interests. Authentic love-centric leadership isn’t self-sacrificing in the sense of giving up my own needs, but it is definitely not self-serving.

    Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

    I think it really all comes down to self-discipline and the ability to keep your cool. Executives are required to deal with a tremendous amount of pressure and anxiety, so it is absolutely vital to success to have the ability to stay calm — especially in the midst of a crisis when your team looks to you for guidance. And self-discipline is important because when you’re a CEO, you don’t have anyone telling you what to do and when. Your discipline will play out in your time management, work ethic and will also help with setting boundaries (which is unavoidable as a CEO). I think those skills may come naturally to some, but I also believe they can be learned, developed and honed over time. I don’t think any of us are ready to be an executive right out of the gate — much of the skills we put into practice as executive leadership are ones we learned with years of experience in subordinate positions.

    What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?

    It always comes back to love — you have to love on the people you’ve hired and get to know them on a deeper level so that you can make meaningful impacts on their lives and in their careers. I’ve seen this play out in my own company, as we’ve recently started implementing love languages and enneagram personality tests into our hiring process in addition to having each existing team member take the assessments. The information we’ve gathered from those simple activities has allowed me to get to know my team better and to provide support, encouragement and opportunities in the ways that are most meaningful to each of them. Prioritizing our company culture has resulted in exponential company growth — we’ve tripled the size of our team in less than a year (and during a pandemic!).

    How have you used your success to make the world a better place?

    It is my deepest desire to leave a positive mark on the world and I do believe that the ripples we create within our own team and with our clients are powerful. I’m so excited to share my message of a love-centric business model with other entrepreneurs and CEOS so that they can create ripples of their own.

    Fantastic. Here is the primary question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

    1. Ditch the hustle mentality. I wish I had my current mindset when I was in my twenties — I think I would have been much kinder to myself! I wish I had known what all the hustling leads to (burnout) so that I could have avoided it, but of course I would have missed out on such an important lesson.
    2. The investment in your team has the biggest ROI. Worry less about the metrics and more about ensuring that your team feels valued and loved. Obviously, we can’t ditch the metrics all together because we can’t grow if we don’t know where we came from or what needs attention. But I wish someone had told me to invest in others from the start.Stay missionfocused. Know your people. Know your purpose. Know your mission. Know your values. And keep them at the forefront of everything you do. Have the flexibility to understand that those things may evolve over time and be willing to adjust, but don’t lose sight of who you are and who you serve.
    3. Picture the end goal. When we start a business, we’re so excited about the start and we don’t really want to think about the end. But if you don’t articulate the end goal, you could find yourself heading towards something you don’t really want. Ask yourself, “Why am I doing this?”, “What is the end game here?”, “What is the legacy I want to leave?”
    4. Stay agile. You’ve got to picture that end goal as you develop your business, but you also have to be okay with it not turning out the way you planned. The end often doesn’t look like what you thought it would, but that is totally okay. Know that it will likely change and be ready to adapt.


    You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

    100%, without a doubt, my answer is lead with love. Let every decision you make, every word that comes out of your mouth, come from a place of love. Too often in business, we lead with metrics or expectations and results. And, while I know there is a place for that, I’ve always believed there needs to be room for love in business. Treat your employees with love and understanding. Take the time to get to know them and appreciate their unique personalities, talents, and offerings to the company. Treat them with respect and dignity, build up their confidence and support their dreams. Give them room to thrive both professionally and personally. If we could, as leaders and employers, make it more common to pour into our people and less common to focus on the money or the metrics, I think we’d see growth in all areas. Because people who feel loved, fulfilled, and empowered will always work at their highest level which can only benefit your business.

    Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

    I have always dreamed of making an impact on the world and being a crusader for change — I don’t know if it’s the millennial in me or just who I was born to be, but I just want to make a difference. So, the quote that has always resonated with me is one by Paul Shane Spear. He said,

    “As one person I cannot change the world, but I can change the world of one person.” And that’s what it’s all about — doing what you can, whenever you can to make the lives of everyone you meet just a little brighter. If we all commit to doing that, together we can change the world.

    We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

    I would absolutely love to connect with Gary Chapman, author of 5 Love Languages. It has been such a game changer for me in life and in business. We use the Love Language test as a tool in our hiring/onboarding process and it really helps me to meet the needs of each member of my team. It’s something that factors heavily into my leadership and is mentioned in my upcoming book, The Love-Centric Business Model. So, if you’re reading this, Gary, let’s team up for a Business-based love languages test!