THE BLOG
02/26/2014 07:54 am ET | Updated Apr 28, 2014

Women in Business Q&A with Kyla Brennan, Founder & CEO of HelloSociety

Kyla Brennan is the Founder & CEO of HelloSociety, a Pinterest marketing and technology firm, focused on developing a natural bridge for marketers using Pinterest. Kyla's first foray into social media came during her tenure at MySpace where she quickly became a believer in the power of marketing through social influencers. She developed a structure around those beliefs and launched HelloSociety in April of 2012 to tap into Pinterest's rapid rise to a leading social network. As the Founder & CEO, Kyla sets the Company's vision and goals, leads business development strategies to achieve them and effectively manages the Company's financial resources all while continually promoting a positive company culture. Kyla earned her Bachelor's Degree in Advertising from the University of Nebraska-Lincoln and although she's never baked a thing, her most popular Pinterest board is "Beautimous Desserts."

How has your life experience made you the leader you are today?
A lot of people are surprised to learn that prior to starting HelloSociety, my work history was comprised entirely of jobs as an executive assistant. Being an assistant had a huge impact on my development as a leader - working in what was often the lowest position on the company totem pole made me realize what's important to employees at all levels, and I still haven't forgotten the things my superiors (direct bosses and otherwise) did that either drove me crazy, or made me feel more valued and ultimately more loyal. I think it's this ability to put myself in other people's shoes that most strongly guides my everyday decisions as a manager.

How has your previous employment experience aided your position as the founder of HelloSociety?
While some might consider my pre-HelloSociety résumé a detriment to starting a company, I think it's the best beginning I could have had. Coming in with basically no knowledge about starting a company meant that I wasn't hindered by pre-conceived notions of what I "should" be doing, or what running a business was "supposed" to look like. I felt freer to just follow my instincts, stay focused on my vision, and do what worked best for the company at that time.

How do you maintain a work/life balance?
To be honest, this is something I could improve on. I spend most of time and energy on HelloSociety - which I don't think is necessarily a bad thing, since it's still a young company that is continuing to grow pretty rapidly. The challenge is keeping myself present when I do make time for friends and family - being able to unplug and focus on them in that moment. Sometimes that can be as basic as making a point of not checking my phone, or mentally packing away all my work thoughts and "locking the door", as my mom likes to say.

What have the highlights and challenges been during your tenure at HelloSociety?
There have been more of both than I can count! I can sum them up in the broadest way possible, at the risk of sounding eye-rollingly obvious: Starting a new business - especially for the first time - is the biggest challenge, filled with hundreds of smaller ones. And the highlight has been watching it grow, thrive and become something that isn't just very successful, but something I'm proud to have built.

What advice can you offer individuals who are seeking a career in the social media industry?
It's easy for people to label themselves as "gurus" in social media, so I think it's important to have a lot of focus and learn all you can about a specific area, then build out from there - back up your claims of expertise with actual knowledge. Also, focus on real results - many social media companies rely on fluff and buzzwords; if you give your clients measurable results and data, you're already one step ahead of much of the competition.

What do you think is the biggest issue for women in the workplace?
I think that women can sometimes be their own worst enemies in the workplace. Women tend to be more timid than men when it comes to saying no, negotiating, or making sure that they're sufficiently recognized for what they bring to that table, whether that recognition be in the form of compensation or otherwise. I think that once women feel more comfortable acknowledging their worth (which often requires letting go of the fear of being perceived as "bitchy", "bossy", "difficult", or any of the other labels that are often unfairly assigned to assertive women), they can change their own professional experience for the better.

What are your thoughts on Sheryl Sandberg's Lean In book and movement?
For me, Lean In was a great read, mainly because it provided a lot of much-needed affirmation. Sometimes just knowing you aren't alone in your insecurities is enough to get you past them, and that's exactly what this book did for me. For instance, hearing Sheryl admit that there are still some days she feels like a "fraud" made me realize two things at the same time: that I often found myself thinking that exact same thing, and that even some of the world's most successful people feel that way. It helped me become more self-aware and start to shift my way of thinking.

How has mentorship made a difference in your professional and personal life?
Mike Jones, CEO of Science, has been a great mentor since the inception of HelloSociety. Aside from being incredibly patient while helping me understand basic business concepts like equity and cap tables, he's been by far the biggest help when it comes to thinking bigger. When I first started HelloSociety, I was overly focused on the details - probably because that was my job as an assistant. Mike taught me that being a good CEO meant learning to delegate the small stuff and concentrate on big ideas - it took me a while to get used to, but it was one of the most helpful lessons I've learned. He's been an invaluable sounding board and source of sound advice the past two years. I strongly believe that every new entrepreneur should have a mentor they like and trust!

Which other female leaders do you admire and why?
There aren't really any public figures who I've held as real role models in my life - I was always more inspired by people I actually know. When it comes to women I look up to, my mom will always be that person for me -- she achieved a lot professionally while still being an amazing mother and wife. I've always admired how she manages to have such a ballsy, assertive personality while still being one of the most well-liked people I know."

What are your hopes for the future of HelloSociety?
We're working on some specific new initiatives within HelloSociety that I'm really excited about and will be announced next year. More generally speaking, I want to continue to perfect everyone's experience with HelloSociety - deliver even better offerings for our brand partners, develop a stronger community for our amazing pinners, and build out our awesome team here in Santa Monica. I'm proud of what we've all accomplished over the past two years, but I'm even more excited to see what we can do in 2014!