Kristi Ross is the co-CEO and President of dough, Inc, a newly formed company which includes tastytrade, the fastest growing online financial network and dough, a financial technology content aggregator. Previously, Ms. Ross was the CFO of thinkorswim where she led numerous mergers, acquisitions and integration. thinkorswim sold to TD Ameritrade for $750M in 2009. Prior to thinkorswim, Ms. Ross was CFO of Automated Trading Desk Specialists, a stock specialist on the Chicago Stock Exchange (CHX). Ms. Ross started her career in public accounting, specializing in financial services industry clientele including individual traders, proprietary, market makers, specialists, discount brokerage and advisory firms. She is also a certified public accountant and has been in and around the trading business for more than 20 years.
How has your life experience made you the leader you are today?
I learned early in life, when I was 16 and my mom was dying of cancer, that I needed to take control of my world. No one else was going to do it for me. I learned that I was 100 percent accountable for the decisions I made for myself. When there was someone to help guide me, I was always appreciative of the time they gave me. Drive, accountability and an appreciation for mentoring others have all made me a better leader.
How has your previous employment experience aided your position at dough?
A majority of my career I held the CFO seat at financial trading firms. I have often held a strategic role within the companies because I was not afraid to share my opinion. Two things in my career gave me a unique perspective that I bring to dough.
First, I was involved in multiple mergers and acquisitions throughout my career and with each one, I learned something new, particularly on integration. Integration allowed me to truly test whether our strategic assumptions were correct or not. The M&A work taught me to never underestimate how important "culture" is when combining two companies. I have been focused on culture ever since with everything we do at dough, including rolling out new initiatives internally.
The second thing was being involved in marketing and sales initiatives earlier in my career. Although it was unfamiliar, I tried it thinking, "When will I ever get a chance like this to try something new?" It taught me how to see the company from the outside inward. My viewpoint is now far more focused on customer experience, and it helps me now as I run the day-to-day at dough. I believe two of the most important things at a company are your employees (culture) and your customers (customer experience).
What have the highlights and challenges been during your tenure at dough?
My day is filled with challenges and many highlights already, even after three years. When the company's mission is to change an industry, you can bet there are going to be challenges. To start, any time you launch a brand new product with no direct competition, it can add additional unforeseen challenges during testing. You need to be willing and able to move quickly to adjust your direction.
We started out with a different approach to getting our message out. Initially, we planned to be an Internet radio show with the mission to make finance fun and engaging, all while empowering the do-it-yourself investor. The mission is the same today, but we've shifted to eight hours of live programming every day on tastytrade and doughTV. We also now provide financial education on investing through our trading technology app, dough, which launched in January 2014. Using dough, customers can have a 360 experience while watching our shows or using the trading app as a standalone.
Our challenges were in finding the right business model. We changed it a couple times early on, but settled on providing all of our content for free to our customers, which is a win-win all around. The highlights include two private capital raises and a third successful funding round with a venture capital firm; acquiring two companies to catapult our infrastructure; launching our newest innovation dough in January 2014; our company being named a Chicago Innovation Award winner, Best in Biz winner, Moxie winner, Ernst & Young Entrepreneur of the Year and Top Tech 100.
What advice can you offer women who are seeking a career in financial services?
Although the financial services industry tends to be fairly male dominated, don't let that discourage you from jumping in. Be bold, confident, have an opinion and be ready to share it. Focus on your strengths, and be sure to communicate your accomplishments so you receive the credit and respect you deserve.
Tell us more about EveryHandCounts, the non profit that you founded.
Every Hand Counts is an organization I started with a mission to provide fun, educational childrens' books and stories about how easy getting involved in philanthropy can be. It is intended to help build more confidence, compassion and community-minded character in elementary age children. I have three wonderful children and as a busy mom, I have always wanted my kids to participate in community service and recognize how impactful they could be even as children. I finished publishing my first book and am working on a second. I have been doing this in my "spare time" (which is almost non-existent), but my progress is wonderfully rewarding.
The best example of EveryHandCounts' impact is right in my own backyard. This summer my middle daughter organized a dance camp on her own with a friend. They developed and organized everything from top to bottom themselves, including coming up with the idea to donate all the proceeds to a local charity. What a warm, wonderful thing to see happen at eleven years old.
How do you maintain a work/life balance?
The phrase "work/life balance" used to feel like an oxymoron to me. I believed that to succeed in your work life, you needed to give it 100% of your attention. To succeed in your personal life, you needed to ensure you were doing all the things that were important to you, and do them well too. That's more like insanity. There are three very important lessons I learned over the course of my life to strike the right work/life balance for me:
1 - If you truly enjoy your work, it doesn't feel like work. You spend a majority of your time working. Why not do something you love? Enjoying the work you do provides a personal satisfaction factor, which makes it feel more balanced.
2 - I learned it is hard to not be guilt-ridden for wanting a successful career and also wanting to spend all your time with your children. To overcome that, when I get home from work, I give 110% of my focus and attention to them. It's still difficult because I know I can't split myself in three (more like 10 if I include myself, husband, friends, fitness, philanthropy, housekeeping, finances, etc.). But I learned part of the balance is about quality, not quantity. When I spend time with my kids, I make sure it is quality time because I don't have the liberty of quantity.
3 - One of the most important tools for work/life balance is my smartphone. If I need to leave work early for one of my daughter's games, I can attend, while still being connected to work. I can check, respond and take care of a number of work related items right from my phone, all during appropriate times of the game. And I can take pictures of my kids at the game at the same time. Gotta love mobile. In addition, I can coordinate schedules, book appointments, pay bills, make investments/trades from anywhere, even in line at Starbucks. Mobile is an extension of me and helps me keep a better work/life balance...if there is such a thing.
What do you think is the biggest issue for women in the workplace?
I believe the biggest issue for women in the workplace is being heard and having an opinion. This often leads to a misperception of lack of value or lack of decisiveness. I believe it simply stems from the way women and men are wired. In general, men tend to voice their opinions and make decisions (sometimes without enough appropriate information). Women tend to be better listeners, are more detailed oriented, and get to the root of issues more effectively. If women are cognizant of the differences, they can overcome misperceptions early on before it becomes an issue. Women should share an educated opinion to ensure their voice is heard, which can lead to better decisions for the company.
How has mentorship made a difference in your professional and personal life?
I was lucky enough to have a mentor early on in my career. I could ask questions and get guidance. It was done through casual conversations, and I was always prodding by asking "why" or "how." I was on my own at a fairly young age, so when I had the opportunity to get answers or guidance from someone, I whole-heartedly listened and applied what I could. In return, I do all I can to give back. I make an effort to share experiences with younger women around me and encourage them to be heard, have an opinion and champion it.
Which other female leaders do you admire and why?
I particularly admire Marissa Mayer for accomplishing a lot...fast...as CEO of Yahoo. She took a stand on important issues early on at Yahoo, and made her own mark with notable hires in the technology industry. She led major acquisitions and noteworthy strategic swings. One of the most impressive things is -- on top of all that - she started her reign at Yahoo's helm approximately six months into her pregnancy. Delivering a child and accomplishing all she did AFTER delivering her child is truly admirable. Nanny or no nanny, that doesn't change the guilt a working mom manages...while doing acquisitions, running a company...and tackling the tech world!
What do you want dough to accomplish in the next year?
I want dough to touch millions of millennials, generation Y and beyond. We provide a logical, mechanical approach to investing, and we think about it differently than any other financial media or any other investing technology out there. We are looking to change the industry by changing the way people think about do-it-yourself investing. I want this generation to know they can approach finance and do-it-yourself investing with confidence. That is our mission, the foundation for what we do every day. Within this next year, we plan to expand globally and double our user base.