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“If people aren’t giving you opportunities, create them for yourself” with Penny Bauder & Asha Visweswaran

If people aren’t giving you opportunities, create them for yourself. Quitting Deloitte and embarking on a job search was an incredibly humbling experience. I had no real network to enter the startup world, and no prior startup experience. By deciding to go down the entrepreneur path, I ended up creating a space for myself to learn […]

If people aren’t giving you opportunities, create them for yourself. Quitting Deloitte and embarking on a job search was an incredibly humbling experience. I had no real network to enter the startup world, and no prior startup experience. By deciding to go down the entrepreneur path, I ended up creating a space for myself to learn and realize I had a lot of strong skill sets to bring to bear. I recognize that not everyone will have the luxury to be able to quit their job, but as much as possible if you can find ways to create spaces for yourself to do #3 above, you’ll build your own self confidence and realize how much you have to offer.


As a part of my series featuring accomplished women in STEM, I had the pleasure of interviewing Asha Visweswaran.

Asha is the co-founder and COO of Swing Education, an on-demand marketplace for substitute teachers. Founded in 2015, the company addresses the nationwide substitute teacher shortage by helping schools connect with qualified educators via an easy-to-use, web-based marketplace.

Asha’s earliest STEM memory was when her dad worked at IBM and brought home a PS/2 with the revolutionary DOS operating system. This ignited her interest in technology and showed her the magic of computers and ASCII-based games. In high school she interned at Lockheed Martin, which provided an early indoctrination into the coding world, as well as being the only female in a male-dominated environment. This was something that would persist during her time at Cal where she studied electrical engineering and computer science. She recalls being able to look around 200-person lectures and counting the number of women on both hands.

It wasn’t until later in her career that she fully absorbed what the value of a STEM background brought to her life and the unique experience of being in a male-dominated field. She believes this background gives her confidence in her ability to tackle the hard and put structure around the unknown. This has been invaluable in both her consulting past-life and her current startup life at Swing Education.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

Tosay I stumbled into starting a company may sound ridiculous, but it’s not far from the truth. It might sound crazy today, but once upon a time it was a very tough job market for job seekers. When I graduated from Cal in 2003, it was during the post dot-com-bust, and finding a stable, big company job was the name of the game. I was lucky to get a job as a consultant at Deloitte, and from there built a steady career.

After 12 years, I had the itch to do something different. I didn’t know what, but I also knew I wouldn’t be motivated to find it until I quit. So that’s what I did. I had lunch with a high school friend, Mike, and he mentioned he was working on creating a faster, easier way for schools to find substitute teachers. I thought it sounded fun and interesting so I offered to help as a side project while I looked for something “real.” After a few months, we realized this was a bigger pain point than we realized, so we applied and got into a startup accelerator program. And just like that, I stumbled into starting what’s now a 65-person company that’s filled over 220,000 teacher absence days.

Can you share the most interesting story that happened to you since you began at your company?

Fun fact about quitting my job — on the day I gave my two-week notice, I found out I was pregnant. “Well, [expletive],” I thought. I wasn’t sure what was going to happen, but I’ve realized there’s never a perfect time for anything (and that life has an interesting sense of humor).

Around November 2015, I took a break from Slack-ing to lie down, and the next day I had a beautiful baby girl, Kira. From there on out I embarked on two things I felt uniquely unqualified to do: 1) be responsible for the well-being of a small human, 2) run a successful company. The dual challenges have been good parallels to each other: amazingly rewarding, challenging, full of laughs, and “count to 10 to calm down” moments (sometimes all in the same day).

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When we were raising our seed round of funding, I remember one of our investors asked us if we had a “data room.” Being newbies to the startup and fundraising world, our immediate thought was “we don’t even have an office!”, but we wisely answered “oh, uh…not yet” then furiously Googled after.

What do you think makes your company stand out? Can you share a story?

I’m thankful that diversity and inclusion have become more and more of a focus in Silicon Valley, though we obviously have a long way to go to see that realized in practice in the startup space.

That’s why I’m so proud of Swing — we’ve made D&I a focus point since we first started the company. Today our company is 2/3 people of color, we’re 2/3 female and 1/4 under-represented minorities, and 60% of our board is female. Our strength is in our diversity — we strive to reflect the schools, substitute teachers, and communities we serve.

That reflects in how we engage with each other, and how we have fun at work — think a ton of great travel recommendations, delicious potlucks that spread the breadth of our employee backgrounds, and spirited debates about the right way to cut a mango.

Are you working on any exciting new projects now? How do you think that will help people?

Yes, I’m especially excited about our TEACH (Teacher Engagement and Certification Help) program. There’s a nationwide teacher shortage, and similarly a nationwide substitute teacher shortage. But, it’s not that easy to become a substitute teacher — and it’s often cost prohibitive for the educator. Swing’s TEACH program directly tackles the substitute teacher shortage by helping individuals quickly become certified to substitute teach and by providing candidates with monetary, personal, and professional support in becoming working substitute teachers.

The reason I’m so excited is by doing this right, we’ll be creating new substitute teachers, creating a pipeline of full-time teachers, helping our schools run smoother, and making a big impact on our students.

Are you currently satisfied with the status quo regarding women in STEM? What specific changes do you think are needed to change the status quo?

Absolutely not — especially with the patterns I see persisting in the startup environment. I’m so impressed by all the work that’s being done to promote STEM at the student level (e.g., through Girls Who Code, Black Girls Code, and other initiatives) and think more of these efforts to introduce STEM early and often will help.

In the professional setting, I think even more networking and mentorship efforts to help women pursue STEM roles (including leadership roles) will help. I’m biased, but companies that are started and led by women will provide more opportunities (and examples) for other women.

What advice would you give to other female leaders to help their team to thrive?

Make sure you understand the unique strengths of your team members and how to play to those strengths. This includes figuring out what motivates your team members, what structures make them most effective, and anticipating what challenges they might have.

What advice would you give to other female leaders about the best way to manage a large team?

Hire people who will challenge your way of thinking, provide them with clarity on your vision (don’t underestimate how many times you need to repeat something before it sticks), make sure priorities are clear, provide the structures for teams to collaborate effectively, make sure you have the right mechanisms to track progress (I’m an OKR and dashboards fan), and then let people run with it. If you have the right mechanisms in place, you’ll be able to create leverage for yourself, and know when you and where you need to step in. The hardest part, especially as you see a company and your team grow, is to pull yourself out of all the day to day — especially when you see things not happening the way you would’ve done it. The more you interject here, the less room people have to learn and bring new ideas to the table.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I should probably say my mom, right? Maybe my husband. Both of them were incredibly supportive when I decided to quit so I could do I-don’t-know-what.

I’d be remiss to not mention my former boss, Kieran. I worked with Kieran starting on my very first day at Deloitte. Our project happened to be a big “prove yourself” project for him, so being paired with a fresh-from-college-grad was likely not the most ideal, stress-relieving scenario. Despite that, he was gracious with his time, and over 12 years, helped me develop my consulting skills — in particular effectively communicating with all personality types, being comfortable with ambiguity, and demonstrating leadership through stressful times. These skills have helped me embrace the constant change and pressure of the startup environment.

How have you used your success to bring goodness to the world?

The reason I love working at Swing is that the work we’re doing has a direct, measurable impact on schools running successfully. Our “north star metric” is how many absences we fill, which measures how many classrooms we’ve placed a Swing substitute teacher in. To date, we’ve filled over 220,000 absence days, and are living up to our goal of helping schools run smoothly.

What are your “5 Leadership Lessons I Learned From My Experience as a Woman in STEM” and why. (Please share a story or example for each.)

Trust your gut

Being a woman in a male-oriented field can create scenarios where you doubt yourself, especially if you don’t have all the info available. That’s OK. Most decisions when broken down are not irreversible, so don’t be afraid to try things. This was one of the biggest mental shifts I had to make when making the transition from the established world of consulting to a startup.

You don’t have to have all the answers

Your goal as a leader should be to hire super smart people, and empower them to be successful. You don’t have to be the smartest person in the room, or have all the good ideas. Your role is to make sure you’re bringing this out of people and helping shape the ideas to have maximum impact.

The fastest way to learn is by doing it

Studying and reading is great, but what I’ve found is that nothing compares to getting hands-on experience. Early on in my Swing tenure, I was our de facto product person, and I found myself making the classic mistake of underestimating how complicated features could be. So I decided to dust the cobwebs off my Computer Science degree and get into the code myself. By doing that, I was able to understand the inner workings of our platform and the dependencies that impact any decision you make. This made me much more effective in understanding tradeoffs (both from a product perspective, but also thinking about how that translates to conversations with customers).

If people aren’t giving you opportunities, create them for yourself

Quitting Deloitte and embarking on a job search was an incredibly humbling experience. I had no real network to enter the startup world, and no prior startup experience. By deciding to go down the entrepreneur path, I ended up creating a space for myself to learn and realize I had a lot of strong skill sets to bring to bear. I recognize that not everyone will have the luxury to be able to quit their job, but as much as possible if you can find ways to create spaces for yourself to do #3 above, you’ll build your own self confidence and realize how much you have to offer.

Be open to new ideas and new ways of thinking

Not everyone thinks like you, and that’s a good thing. I’ve done enough personality tests to know that I like to approach things in a structured way. As a leader you need to recognize and find personalities that bring balance and open up new ideas/innovative thinking. That means relaxing on timelines and meetings to give people space, and recognizing different ways to motivate and bring out the best in people.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Snitches get stitches.” Just kidding. It’s: “Don’t make perfect the enemy of good.” I go back to this phrase over and over. It’s a great reminder that often you don’t know enough to make something perfect, and even if you think you do, it’s probably not the best use of time. So get to good enough, call it done for now, see how it does, learn and revisit from there.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I’d love to have lunch with Mindy Kaling. I still remember seeing her pop up in The Office and thinking “weird, there’s an Indian on TV!”. And from there I was more and more impressed as I read about how she worked her way to the (male-dominated, obviously) writer’s room, and then to leading her own show. She embodies a creative spirit matched with drive, and is tackling motherhood to boot.

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