Making It Video

Whitney Headen on Strategy

From the early steps of a career path, to the final stages of client deliverables, strategic thinking is a critical skill for entrepreneurial success. For Whitney Headen, CEO of a creative execution agency and founder of mentorship platform, The Life Currency, understanding and employing strategy has been a powerful tool.

Watch the video above for Whitney’s insights about making a business plan, as part of the CCNYC’s 2020 Creative Curriculum, launched in partnership with Squarespace. She also talked with us about all the wrong career fits that eventually led to the right roles, how she consistently works to deliver against client needs, and why integrating her work and personal life has been key to her happiness and career goals.

SQUARESPACE: You’ve built a successful career in digital marketing and brand strategy. What originally inspired you to pursue this career path?

Whitney Headen: Honestly, I had no idea that my current career path even existed. I grew up in Virginia and went to college at a state university. Even though I majored in Marketing, I don't think schools do a great job of telling you what the possibilities are from what you develop an expertise in. I knew I wanted to work with brands or in entertainment, but I didn't realize there was a job that combined the two. My first job out of college was in fashion public relations and I hated it. I then went into production, which I also didn't like, and from there I landed my first integrated marketing job. A series of strategic wrong fits would eventually lead me to my dream career.

SQSP: Your work is a mix of creativity and strategy. How do you translate inspiration into action for your clients?

WH: 3 letters: KPIs (key performance indicators). Setting clear expectations and goals to reach from creative ideations is the key. Marketing is a sales function and a creative extension — you have to always keep in mind what end result you're trying to achieve and what pathway you are encouraging consumers to take on their road to purchase, awareness, or brand loyalty. If your idea only makes sense to you, how are you going to inspire people to make a decision off of what you create? I make sure that when I'm working with a brand directly I always keep the objective in mind and make sure to give them enough information to understand all the touch points we may hit along the journey to achieve their goal, as well as get a feel for the creative and how we’ll bring it to life. Depending on the opportunity, that can be a mood board, renders, mocks, video treatments, whatever makes the most sense to get the point across best.

SQSP: How does your lived experience influence your work, if at all?

WH: I've lived a lot of life. I've traveled all over the world, I've worked in multiple different settings from corporate to start-ups, I have friends and especially family from different cultures, I have experienced deep love and painful losses — and because of that, my lived experience influences my work every single day. I'm an information and media junky. I really thrive off of immersing myself into new things and experiences. It's very difficult for people to speak to things or to audiences they've never experienced and you can almost always tell when there isn't an authentic connection. That's why the push for inclusive marketing is so important. Having varied experiences at the table will almost always create a better body of work, and that goes for everything: race, gender, ethnicity, socio economic status, sexuality. You name it, and someone has a different perspective or experience that they should be allowed to bring to the table versus constantly seeing someone's interpretation of what they believe from the outside looking in. 

SQSP: As an entrepreneur and CEO, how do you balance your professional responsibilities with making time for yourself?

WH: I've never believed in the concept of work-life balance, so I created a life that made me not have to choose between life and my career. They're all the same. I like to say I strive to live an integrated life. I started a company with my friend, and we hire people that are amazing at their jobs but also happen to be or eventually become friends. I intentionally seek out relationships with people that not only support my goals but want to do whatever they can to help me make them a reality.  I believe in creating families and ecosystems we don't need an escape from. 

SQSP: What role has your online presence played in your career success?

WH: It's two fold. My career success began at a time where people weren't looking to the internet to quantify and validate professionals as much as they are today. I got

my first job based on a binder of papers I put together and called it a portfolio. So in hindsight, I'd like to say my online presence helped very little. I'm still considered fairly young to be where I'm at in my career, but we didn't have professional networking websites, some social platforms still required a college email, and some were spaces we were using as online diaries that we'd eventually learn jobs would use to evaluate our character traits. 

So for me personally, my online presence hasn't played too deeply into my early career success. However, my early success as an entrepreneur, positive press, digital channels and client testimonials have been everything. Having even just a small digital presence allows for an understanding of who you are and what you do without you even having to say anything. Both of my businesses have been built off of positive customer experiences and discovery, and that would have been impossible without an online presence. 

Discover more expert advice and inspiration from Black entrepreneurs and creatives.

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