Heather Stephenson is a rare breed: both a wildly successful digital entrepreneur and an award-winning corporate executive. She's just been brought on to create strategy at a new company that is poised to take service to another level.

Stephenson oversees all brand direction at Super, a new online subscription-based service that reinvents the homeownership experience by providing premium access to maintenance for homes. The task will definitely be challenging, but Stephenson's background has primed her for success. Recently she offered some insights that all female career-climbers should have in their arsenal. Stephenson's path is also very inspirational and a great way to reinforce any career goals you've made for yourself this new year. Let's get started.

How did you get your start in marketing, Heather? You've done so much from working at Microsoft to NBC to the BBC. What initiated your career?

It was a complete fluke. I studied government and English at Georgetown. I finished up my master's in English and decided to delay going on to get my PhD for a year or two. I assumed I'd be a college professor or a politician. But at the time, I just needed a break from school, and it's a break I'm apparently still on. Through Georgetown connections, I found myself interviewing in advertising, and I got my first job at Anderson & Lembke, an early pioneer in internet advertising that was later acquired by McCann-Erickson.

As they say, the best-laid plans. But it's worked wonderfully. What were the most valuable lessons you learned early in your career that you believe are instrumental to your current success?

My main two early career lessons might seem somewhat contradictory: 1) If you're smart and willing to work hard, it's not difficult to please people and do well at your job; and 2) fake it until you make it. In the early days of internet media, we were all making everything up as we went along. I always felt sort of like a fake, until I realized that everyone else was doing the exact same thing. An entrepreneur is always attempting to create something that hasn't been created (or created well) before, so you have to have a heady tolerance for feeling like you are stretching beyond your comfort zones, and you have to be willing to try something, throw your entire self into it. Not a day has gone by since then that this "dive in and try it" attitude hasn't informed my work day.

Strong advice. You've worked at major corporations, but also founded three digital media companies. At what stage did you begin to be an entrepreneur and why?

In 2000, I was working for an online advertising sales and technology company, and I had the opportunity to move to London to open up our European headquarters. I was 27. It was an amazing opportunity, since it allowed me to sort of "start up" a business, with the backing of a company that had IPO'ed. It was all part of the experience of starting something, with little personal risk. After that, I was bit by the startup bug. There was no turning back after that.

Tell us a little more about some of the companies you have worked at and your overall experiences, because we hear so much about Wild-West early digital adventures from a man's perspective, but rarely from a woman's.

The two companies I mentioned earlier -- Anderson & Lembke and L90 -- were sort of classic dot-com 1.0 experiences. A&L was just phenomenal. They took their obligation to teach and train their teams seriously, and the brilliant kids I worked with and learned from while there have gone on to do amazing things.  L90 was scrappier -- I was the eighth employee, and we rode that dot-com wave from dodgy startup out by the airport, through an IPO, and then down through the crash and closing that followed. I had to do a lot of self-teaching at L90, but the lessons I learned there (both good and bad) gave me a grounding in how I wanted to build out my own businesses in the future. But my most formative experience was really in co-founding and running Ideal Bite. It was a daily email on how to be "light green." We were the classic story of "right place, right time, right idea."  We started it in 2005, before the green movement really took hold and took off in 2007. We were speaking to and for "soccer moms who drive their SUVs to Whole Foods," and we hit a much-needed nerve and grew like gangbusters. We went from an email list of 300 friends and family to more than 550,000 daily readers in just over three years. (And this predated social media.)

Amazing. What are some the key differences between working at large Fortune 500 corporations versus entrepreneurial ventures?

Well, I have enormous respect for the people I encountered at Disney -- they are some of the best and brightest minds in media. But I also learned that I love the pace of a startup. I didn't really know what to do with myself in the 270,000-person ship that is the Walt Disney Company. In large-scale organizations like that, you do have to "have meetings about having meetings." It all felt terribly inefficient to me. I was used to seeing a problem in the morning, making a decision to try to solve it by mid-afternoon, and implementing that solution by evening. Clearly, you can't turn on a dime like that in a giant company like Disney. There's an entirely different approach that is required to manage a larger enterprise and staff successfully.

Do you think there are any particular differences between the two when it comes to gender?

For 10 years, I worked on teams that were almost exclusively female, because I built those teams myself, and I guess I tend to like working with women. That said, the startup world in the Bay Area is horrifically gender imbalanced -- even more so than it was in the mid-'90s. And while many large companies see their gender imbalance and are trying to address systemic issues of inequality and struggling with trying to affect change in a system that is already in place, I see so many startups that just don't address the issue at all. They see it as something that they can afford to care about later -- once they are more established. But the fact is, you have to bake these things into the business from the beginning -- once you've established a culture of inequality, it's often too late.

Let's move now to the selling of your company to Disney. What was the process like?

It was a whirlwind. They came to us, and from the time we first spoke with them, to the closing date of the sale, only two months went by (and that was over the Christmas holidays). We were selling sooner than we wanted to -- we had raised a financing round 13 months before, and we wanted time to utilize that cash infusion to put the business in a great place before ever selling.  But the opportunity to become part of something like Disney -- to tap into their vast databases of followers and to promote ourselves across their business properties, like ABC, ESPN, the parks, etc. -- it was too compelling an opportunity to pass it up. It was a fantastic learning experience, but there are many things I'd do differently next time.

What led you to Super from that?

In a nutshell, I like to work on businesses that solve problems that I have myself, because I assume I'm not the only one who needs those solutions. When Jorey Ramer [Super's CEO] told me about his idea for Super, as a homeowner, it just resonated with me. We are so used to taking care of car maintenance and budgeting for the somewhat unexpected when it comes to things like our health, but we don't apply that same approach to our single largest financial asset -- our homes. I loved the idea that I could have a service that would let me care for and maintain my home all in one place, for a flat monthly cost. And since I love that very first part of building a business -- figuring out the audience and brand and voice and feel -- I jumped at the opportunity to be a part of the team at launch.

What is a typical day like at Super and what are your biggest challenges?

There's no such thing as a typical day for me. In the early stages of startup life, everything is changing so rapidly that the only constant is the change itself. Some days are packed with meetings, planning for the long term success of the business, and some days are incredibly tactical -- hammering out web copy, solo, in my basement.

How is gender balance handled at Super?

This sound simplistic, but is so important -- we talk about it. I don't mean that we just pay it lip-service. I mean that we speak about it out in the open. Hardly an executive team meeting goes by that we don't discuss our hiring, our staff, our advisers, our and board of directors, and explore ways to improve our diversity. We aren't there yet. We don't have the diversity that we want to see, long-term. But it's part of our conversation, and we are baking an awareness of that into the fabric of the company. And in an imperfect world, where we don't yet have gender parity in the work force, that awareness and intention is an incredibly important first step.

What role (for good or bad) do you think gender has played in the rise of your career?

I think that early on, when I was in tech sales, being a successful woman in largely male-dominated field probably let me stand out a bit. That said, I definitely have horror stories (we all have them, don't we?). I was at an executive team conference in Spain in 2001 with a company that was in the final stages of diligence to adopt the technology that I and my team were selling. Because it was such a huge deal, the president of our tech division and the SVP of engineering (both men) came out to help close it. At one point, the male CEO of the European company leaned over to me and said "Why don't you go put your bikini on and head out to the beach -- we're going to talk business now." I was speechless. I obviously didn't leave and stayed there to negotiate, but it was humiliating, shocking, and maddening that we could be in a new millennium and still deal with misogyny on that scale in the workplace. Over the past 10 years, though, I've focused my work on businesses with broad consumer appeal, and I have to say, I think that being female helps to craft a more inclusive approach, and is a distinct asset that helps our story to reach the right audience.

Which of your career achievements to date are you most proud of and why?

I can't begin to describe how amazing it feels to be "doing well by doing good." At the height of my time at Ideal Bite, we were actually changing the way people lived their lives. To this day, people still come up to me and say, "You started Ideal Bite? I completely changed the way I [feed my family, purchase products, drive my car, etc.] because of Ideal Bite. I'm still a Biter!" That feeling -- that the hard work that is getting you so much attention actually matters to the world, that's the stardust of a career.

What advice do you have for other women seeking to break into marketing?

Take every interview you can -- ask for informational interviews from the career center at your college, ask your best friend's mom to circle you up with her coworkers -- just get in there and start learning, networking, and practicing. If an internship or a volunteer opportunity is available, jump into it. I am always impressed when I see in a resume that someone took on a marketing challenge for a charity or non-profit organization -- it shows a willingness to dive in and learn by doing.

What advice do you have for other women seeking to develop and sell their own companies?

Quit your day job. This is so much easier to say than do. But the fact is, if it's not a good enough idea to entice you to put everything on the line for it, it's not a good enough idea, period. When I built my first company, I didn't have a spouse or partner supporting me. I didn't have a trust fund or a savings account. But I had a lot of access to credit card debt, a good idea, and the willingness to work 16 hours a day, and it paid off.

How do you achieve work-life balance in your own way?

Does anyone really ever feel like they have work-life balance? I have two young children -- there are just never enough hours in the day, regardless of what I'm working on. When I stopped stressing about finding balance, I think that more balance found me, because I stopped expecting to achieve some perfect mommy-executive-wife-friend blend. Some days, I'm a full-time mom, and some days, I'm a full time marketer. It ebbs and flows. At Super, we are deeply committed to fostering a culture that respects each employee as an individual -- with lives, friends, families, aspirations beyond the workplace.

Guest post by Lauren deLisa Coleman.

Published on: Feb 2, 2016