Women in Business Q&A: Jenna Fernandes, CEO, CareBooker.com

Jenna Fernandes is the CEO of CareBooker.com, the "OpenTable" for booking in-home family care services such as babysitting, pet care, tutoring and more. In 2013, Jenna was named as a top 10 female tech founder by Women 2.0 and CareBooker was ranked as one of the top "tech companies to watch."

Jenna has brought together an all-star team and a strong group of advisors and investors including the Co-founder of About.com, Founding Shareholder of Expedia, Founding Head of Sales at Hotwire.com, Founder/Chairman of Tutor.com, as well as CT Innovations (CT's Venture Fund).
Prior to founding CareBooker, Jenna and her team founded the first online booking and payment platform for pet care services. Jenna first became a CEO at age 19 while at Tufts University where she ran Tufts Student Resources (TSR), one of the largest student run businesses in the U.S.
In her free time, Jenna enjoys spending time with her husband and her two dogs--a Min Pin named Scooby and Great Dane named Casper--and enjoys playing golf, tennis and chess.

How has your life experience made you the leader you are today?
I've always been an entrepreneurial spirit. As a child I would play "store" with my friends and try to convince them to buy the items I had taken from the cupboard in my house. I excelled at selling girl scout cookies and I loved it when my father would come home from work and speak with me about the latest product development and branding efforts at his company. I've always loved brainstorming about ways to solve big issues and I've never ever been scared about making things happen and trying to push the solutions forward. I've really always had the mentality that "we can make this happen" and I've almost always said "yes" to difficult requests and challenges. I've also always taken the initiative to help others when I can - good Karma is key and so are good relationships. In creating my own personal "start-up" culture from a very young age, I've been in training to create CareBooker since before I ever thought of the idea.

How has your previous employment experience aided your tenure at CareBooker?
Prior to founding CareBooker I ran a small company in college, worked at a mid-sized consulting firm and then worked at a huge, international, consulting firm. Through these experiences I not only developed confidence and honed my strategic thinking skills, I also learned a lot about the importance of setting company culture from the get-go, different theories and applications of various management styles, and how to delegate work effectively to fit employees unique skills sets and include things that they will want to do along with things they need to do.

What have the highlights and challenges been during your tenure at CareBooker?
CareBooker has been an amazing journey and it keeps getting better. It took a bit longer than we would have liked to secure our launch date. During the tech build, I learned how to be an effective manager for programmers. I also learned how to raise money from Angel Investors the right way. Even though these were challenges they were also big highlights with great results. Now we have the right investors, the right team, the right technology and I'm really excited about what's to come. It's going to be a big next 6-12 months for us.

What advice can you offer to women who want to start their own business?
Plan, but don't over think it. A big part of planning needs to be talking to others about your idea - don't be scared to share. Make sure people want to use what you want to build.

What is the most important lesson you've learned in your career to date?
I've learned that 99% of success is based on two main things 1) Productivity - get at least 3 main things done each day and before you know it, big things are happening 2) Fortitude - failure makes you stronger - when you fail at something the most important things is to try to understand why, learn, and then keep moving forward - that in itself is a victory!

How do you maintain a work/life balance?
I'm lucky because my husband and I enjoy helping each other brainstorm about work and together we are better at what we do then if we never spent time working on things together. In fact, we like to brainstorm so much that we've made an entire wall in our house into a "brainstorming" wall covered in large sticky notes. We are each other's biggest cheerleaders, but we are also very honest about what the other one could do better and we push each other to achieve more. That said, we make it a point to make weekends about "family time." We explore new and interesting places in our area, play board games (we love Chess), visit extended family, have brunch with friends and we always have a family dinner. I also like scheduling a special "event" to look forward to at least once a month.

What do you think is the biggest issue for women in the workplace?
I think balancing success in work with success with family. Learning to ask for what we want more directly/strategically and with confidence.

How has mentorship made a difference in your professional and personal life?
There have been quite a few mentors who have helped me. My first mentors were my parents, in college it was the head of the Entrepreneurial Leadership Program at Tufts University and of course the exciting group of advisors and investors we have working with us on CareBooker.

Which other female leaders do you admire and why?
That's a great question. In fact, I think we're in a really interesting stage in society where there are so many successful women that I admire that it's hard to name just a few. I'd say the women I truly admire the most if I have to put names to it are Sara Blakely, Founder of Spanks, Joanne Wilson, Angel Investor / GothamGal.com, Jane Goodall, Jane Goodall Institute, Veronika Scott, The Empowerment Plan, Angela Merkel, Chancellor of Germany, Meg Whitman, CEO of HP, and Safra Catz, CEO of Oracle. All of these women have shown extraordinary leadership skills and have excelled in what they've set out to do and are very powerful role models.

What do you want CareBooker to accomplish in the next year?
Over the next year, we plan to grow in terms of the number of care providers, number of families who will book care through the site and types of services provided (we will launch housecleaning, personal fitness, senior care and more). We will also continue to improve CareBooker so that we're always delivering what people want and making the user experience better and better.