As in other industries, the overwhelming majority of CEOs in tech still resemble the mugs found in the infamous Real Businessmen blog — lots and lots of men. The times are changing, but even in this period of renewed consciousness around gender inequality, the corporate world still poses formidable — you might say unfair — challenges for ambitious women.
This persistent adversity means that the women who have successfully founded or taken the reins of a technology company are an especially valuable resource. What helped them succeed? How did they break through? And what lessons can they pass on to the next generation? We had the privilege of speaking with four Los Angeles tech CEOs about their career journeys so far and the lessons they’ve picked up along the way.
If you want to know how to build a global tech company or career in fintech, Shivani Siroya is the person to ask. Siroya is the founder and CEO of Tala, which has provided over $4 billion worth of loans to more than four million people around the world since launching in 2011. Tala employs almost 600 people around the world and has raised over $200 million in funding, including a recently announced $110M Series D.
What inspired you to launch Tala?
The inspiration for Tala came while I was working as an analyst with the UN Population Fund after graduate school. I conducted microfinance research across West and Sub-Saharan Africa and spent time with thousands of small business owners. I was quickly struck by the lack of financial options they had to improve their livelihoods. I was so frustrated that I started personally lending to some of them.
While banks couldn’t underwrite this population and development organizations struggled to make micro-loans profitable, I realized I was sitting on troves of non-traditional data that told a story of these people’s lives and could be used to make lending decisions. As much of this same data sits on phones, we decided to build an app that could capture data customers shared with us and turn it into a credit score. We then started issuing unsecured loans to people in Kenya we’d never met. The results proved their creditworthiness in the way that matters most: They paid back their loans.
...I really think it’s important for women to trust themselves and take calculated risks as we build our businesses.”
What are the most valuable lessons you've learned along the way, and how might other women apply these lessons in their own careers or businesses?
The most valuable lessons I’ve learned are to trust your instincts and prioritize learning. I was lucky to have had a lot of guidance from advisors and mentors, but I really think it’s important for women to trust themselves and take calculated risks as we build our businesses. You can have all the mentorship and advice in the world, but no one knows the problem and your customers better than you. So know your unit economics, understand your data and spend time with your customers to continue learning from them — and never stop focusing on solving the problem you set out to solve. I also think it’s important to surround yourself with a diverse team who shares your values. Do this early!
What do you do when the school semester starts, or when your kid wants to take on extracurricular activities — but public transport isn’t an option and you just don’t have the time? This was the problem that plagued HopSkipDrive Co-Founder and CEO Joanna McFarland, to the point where she felt compelled to have a crack at solving it for her and every other working parent out there.
What inspired you to launch HopSkipDrive?
For me, it started with guilt. I felt very guilty that I had to tell my son Jackson he couldn’t do karate because it was on Thursday at 3 p.m. and I had no way of getting him there. I was a full-time working mom, my husband worked, our kids were school age. Every parent I talked to felt this challenge of needing to be in multiple places at once, and not trusting just anybody to drive their kids. At first, I had no intention of creating a company. I had a good, steady job that paid the mortgage and preschool. But as I talked to more families, I became more and more obsessed with the idea of solving this problem. It consumed me. It got to the point where I simply had no choice but to start this company.
For me to start a company, I had to be super passionate about what we were doing, and it had to be mission-driven. It is such hard work starting something and building it and scaling it. I couldn’t do it for just any product. As our company has grown and evolved to serve school districts, our mission has evolved as well — to transport all kids to their highest potential. It’s something we rally around as a team and that inspires us every day.
Write your company values down early, talk about them often and make sure you hire a team that lives those values.”
What are the most valuable lessons you’ve learned along the way?
You will hear 10,000 “no’s” in starting a business, every which way you turn. Potential customers, potential employees, potential investors, potential suppliers will all tell you “no.” It’s up to you to have a super thick skin, get back up, brush yourself off and keep going. You have to be a super-creative problem solver and figure out the non-obvious ways to get to “yes.” It takes grit and hustle and learning not to take rejection personally. They’re not rejecting you — they’re rejecting the proposal, job or investment.
Find someone you can talk to: a coach, a CEO group, somebody. There are things you can’t talk about with employees or investors or even co-founders, and your significant others get tired of hearing it. You need someone you can share your highest highs and your lowest lows with, who you can open up to about your fears and celebrate your wins with.
Write your company values down early, talk about them often and make sure you hire a team that lives those values. When making hard decisions, there is often no black or white but many shades of gray. If your team lives those values, the decisions become a lot less grey, and therefore easier to make the right call.
MatchCraft creates marketing software for companies around the world, helping them sell, manage and scale search, social and display ads. The Santa Monica company serves clients around the world and, before she stepped up into the chief executive role, CEO Sandy Lohr was one of them. Lohr’s advice to women coming up in the tech industry today? Ignore that infamous glass ceiling and smash through it like it’s not there at all.
What inspired you to lead MatchCraft?
MatchCraft has been a key player in the digital marketing technology industry since being founded in 1998. Since then, MatchCraft has grown from being a smaller U.S.-based operation in an apartment in Santa Monica to a global adtech provider, with resources in the U.S., Europe, Brazil, Mexico and India. MatchCraft has a client base in 44 countries with technology that supports over 23 unique languages and dialects.
I made the change from being a client of MatchCraft to leading the MatchCraft team nearly four years ago. My eight years as a MatchCraft client helped ease the transition. I knew the team, the culture, the platform and their unwavering commitment to client value. A big part of what MatchCraft strives to bring to our clients is an understanding of the pain points our reseller partners and ad agencies are facing. A lot of my time is spent having strategic discussions with our clients all over the world, sharing use cases of similar clients that we have helped strategize to grow their digital advertising business.
Ignore that there is a glass ceiling so you can shatter it as you advance.”
What are the most valuable lessons you’ve learned along the way? How might other women apply these lessons in their own careers or businesses?
My best mentors have been those who believe in rolling up their sleeves and leading by example. I strive to humbly lean in and continuously learn from the talented team I am privileged to lead. Early in my career, I was typically the only female sitting in a board room or high-powered meeting. As the only woman in these meetings, it would have been easy to think my role was to be silent as the “token female.” Learning to trust my instincts and voice my opinion was not only welcomed but, more importantly, expected. I was guarded in those early years and had to learn to not be afraid of asking questions — others were usually wondering the same thing.
My advice to my mentees is this: listen first and always speak with meaning and contribution. Ignore that there is a glass ceiling so you can shatter it as you advance. March forward with your goals, and don’t believe anyone that says you can’t do something. Use those who might put up roadblocks as the motivation to obtain your goals. Don’t set limits on yourself and, above all, love what you do. Life is too short to not be doing something you are passionate about. In my case, growing people is my passion and my purpose.
Milana Rabkin Lewis knows that making music can be a hard way to earn a living. She’s worked in the industry and comes from a family of musicians, all of whom gave up their passions to earn a more sustainable living. Her personal and professional experiences led her to found Stem Disintermedia, whose technology gives artists more visibility into their finances. Rabkin Lewis shared what she’s learned in her four years as Stem’s CEO.
What inspired you to launch Stem?
When I told my very Russian immigrant parents that I wanted to go to film school, they told me that it sounded like a good hobby — but not a viable career option. My father and both my grandfathers are musicians, and in their lifetimes, being an artist was not sustainable so they had to sacrifice their passion. This really upsets me, and the need to change it is at the core of my being.
Creators can’t build sustainable businesses or careers if they don’t have visibility into their finances. With the proliferation of data, there’s a movement toward transparency but transparency can be a data dump. Our goal with Stem is to simplify and clarify the way money flows down to creators and provide them with a digestible and actionable financial picture of their business.
Integrate your values into the way you hire, praise and promote.”
What are the most valuable lessons you’ve learned along the way, and how might other women apply these lessons in their own careers or businesses?
Do everything you can to optimize your decision-making speed. First, get the data you need so you can digest information quickly and syndicate it to key people. Next, have a diversity of perspectives around the table. Hire for the skill set of driving alignment rather than consensus. Surround yourself with people who are aligned with the mission, aren’t afraid to ask tough questions, think differently than you do and have a different risk tolerance. Then when it comes time to make a hard decision, put a line in the sand for when you need to come together and make a call.
People need to hear things 10 times before they resonate, so don’t underestimate the value of repetition when it comes to your mission, vision and values. Integrate your values into the way you hire, praise and promote. Keep a gratitude journal and write down three things you are grateful for every day. It helps add perspective when things get difficult. Finally, create a personal board of advisors. Think of yourself as a business and have a handful of people who are invested in your growth and are willing to hold you accountable for it.
