WoW Woman in Wearable Tech | Sky Gillespie, Director of Digital Communications at Ripple

Interview by Marija Butkovic (@MarijaButkovic)


Sky Gillespie was born and raised in Boca Raton, FL. In 2016, she graduated Magna Cum Laude from the Jim Moran School of Entrepreneurship at Florida State University where she earned a degree in Entrepreneurship, as well as a degree in Real Estate. Upon graduating, she joined Ripple, and resides in her current role as Director of Digital Communications.

What is the idea behind Ripple?

The idea behind Ripple is quite simple: How confidently could you live if you knew someone always had your back? Ripple is a first-of-its-kind personal safety service that gives you 24/7 access to a professional monitoring team of safety specialists from anywhere you are in the country for just $10/month. Click your penny-sized Ripple wearable and get all the help you need right from your team.

When did all start and do you have other members in your team?

Ripple’s founder Rees Gillespie got the idea for Ripple in November of 2014. He came up with the idea after his mom, a real estate agent, would ask him to check in on her when she showed property to unknown clients. Rees started to think, what if she could communicate her need for help just by clicking a tiny button. Rees ran into a friend that he had grown up with, Jaime Gomez, and they co-founded the company in February of 2015. Upon graduating in 2016, I joined Ripple as Director of Digital Communications. So far, we’ve had over 40 people contribute to getting Ripple where it is today.

What was the biggest obstacle?

For our team, the obstacles changed as the journey progressed, but a couple stand out. Early on, it was identifying what the ideal business model looked like: who was our target audience, what do we offer them, how do we make it work. We experimented a lot with different offerings, and really came full-circle back to focusing solely on personal safety. Midway through, the biggest challenge was managing so many moving parts. Creating Ripple has been this constantly evolving process that has taken consistent refinement and attention to detail. Making sure everybody is moving in unison requires 24/7 attention.

What are the challenges of being an entrepreneur in the niche you are in? How about being a female founder / entrepreneur?

My biggest challenge has been introducing something that hasn’t existed before to the market. The idea of Ripple is completely new - for ten dollars a month you’re connected to a team of safety specialists anytime you need them, anywhere in the United States. My job is to demonstrate to consumers just how powerful that is. Being an entrepreneur means making major sacrifices and commitment to proving yourself. Being a woman just gives me a little more motivation to go out there and make people take notice.

What are your biggest achievements to date?

For me, it was helping to tailor Ripple’s positioning and messaging for a female audience. The team needed to see our product and service through a female lens.

What are projects you are currently working on within your company?

I am constantly evaluating everything we do with the female perspective in mind. Whether that is our digital assets, our app UX, or even our social ads, I’m mindful of our female audience every step of the way.

What will be the key trends in the wearable tech and fashion tech industry in the next 5 years and where do you see it heading?

On the smaller scale I’d say Smartwatches. As soon as you no longer need to tether your smartwatch to your smartphone, opportunities are really going to open up. On a larger scale, it’s got to be VR. The ability to actually build your ‘reality’ means possibilities will be endless. I have my eyes on a couple things I want to see take shape in fashion tech. I’m a runner, so any technology integrated apparel that can help me learn about and improve my performance, I’m all for it.

Is #WomenInTech movement important to you and if yes, why?

Of course it is! It’s our responsibility to pave the way for other women that want to follow this path, and the way we do that is by proving ourselves as effective leaders and successfully guiding our organizations. If we do it, the industry takes notice and opens more doors to ladies with the same passion and ability as us.

What is the most important piece of advice you can give to all female founders and female entrepreneurs out there?

It takes courage and commitment to do what you’re doing. You have to believe in it every single day. There’s plenty of people out there who will tell you that you can’t do it, never let yourself be one of them.

Who are your 3 inspirational women in wearable tech and / or fashion tech?

Advances in technology are forcing designers to rethink the way they make and design clothing and accessories. Jeanne Jackson, Rebecca Minkoff, and Tory Burch are three women in the wearable and fashion tech industry who have inspired me. I love what Tory Burch did with FitBit, that was one of the first times I felt somebody seamlessly navigated the intersection of high-fashion and wearable technology.

Website: Ripple

Twitter: Ripple

Facebook: Ripple

Instagram: Ripple

This interview was conducted by Marija Butkovic, Digital Marketing and PR strategist, co-founder of Women of Wearables and Kisha Smart Umbrella. She regularly writes and speaks on topics of wearable tech, fashion tech, IoT, entrepreneurship and diversity. Visit or follow Marija on Twitter @MarijaButkovic @Women_Wearables @GetKisha.