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Paving the way for the next generation of women in technology

Dipali Trivedi, CTO Everyday Life Insurance

Leader Speak with Dipali Trivedi

Team Meytier was so inspired by our interview with Dipali Trivedi, CTO and Co-Founder of Everyday Life. Dipali’s passion for helping more women and girls thrive in technology is infectious. We loved hearing Dipali’s incredible journey to becoming an executive and co-founder, and we know you will as well.

Dipali Trivedi, CTO Everyday Life Insurance

Leader Speak with Dipali Trivedi

Team Meytier was so inspired by our interview with Dipali Trivedi, CTO and Co-Founder of Everyday Life. Dipali’s passion for helping more women and girls thrive in technology is infectious. We loved hearing Dipali’s incredible journey to becoming an executive and co-founder, and we know you will as well.

"How are we going to inspire girls to be CEOs and leaders if they constantly think they should be liked by others? Damn likability to get a seat at the table."

I’d love to start broad, tell us a little bit about who you are and how you came to be where you are now.

I am a technologist and an entrepreneur. I’m currently a co-founder and the Chief Technology & Product Officer for Everyday Life. How I reached here is not a straightforward path. I was born and brought up in a small village in India. I did my undergraduate and masters there. My background is in technology and engineering. I started my career at small product companies, I worked in Germany and London and then I moved to Boston for work. I’ve always wanted to do something on my own, to build something from scratch. I started my first company, Cloudfountain Inc, providing Salesforce, Big data, CRM, AI and Machine learning implementation services. My second company, Everyday Life, brings innovation to the insurance domain via technology. 

When/where did your passion for technology start?

I wasn't lucky enough to have exposure to technology growing up. We didn’t have a telephone or a TV, I saw a computer for the first time when I was in undergrad. But in hindsight, my technology mindset began when I was young and has grown and evolved ever since. I see it as three main interests, optimization, automation and intelligence. When I was a kid, I was very interested in how things worked and I saw that you can optimize any process that you see. It fascinated me that things can always be done better and more efficiently. During my undergrad, I saw the power of automation. Using programming, I learned that any task can be done faster. When I got my masters in AI and machine learning, I learned the potential of technology to have intelligence of its own. At that time, language processing, parallel programming, and machine learning were still theories. I was really interested in how a machine can have intelligence to make its own decisions and help humans make better decisions. When a human makes a decision, the mind uses so many parameters, everything you’ve ever done, learned, all the interactions you’ve had are factored into a decision. How can you replicate that in a machine? That really reignited my passion for technology. At each stage of my life, I’ve seen the possibilities of technology.

You’ve worked at all kinds of companies, from large corporations to startups, how has your big-business experience informed your startup work and vice-versa? What can they learn from each other? 

My big-business experience has really helped me in the startup world. In startups, you partner with those big companies either to use their product on your platform or to sell your product to them. I’ve been there, I know how they think. Having that knowledge is super valuable. My experience in smaller companies has shown me that big companies can learn to cut out the bureaucracy. There is so much waste in terms of money, resources, and time. A big ship can’t go fast. Big companies can learn from startups to have flex structure and have bottom up decision making so they can innovate and compete.

When I worked for a big company, I was managing a huge project. I had over a hundred and fifty people under me and that gave me exposure to a lot of personalities. That exposure to different people made me a better leader. In large scale management roles, you have to manage the expectations of the executive team while also inspiring, mentoring, and motivating the team that will achieve the goals you’re working towards. It helped me build empathy and learn how to work with different kinds of people.

"I wanted to be able to say, 'I’m happy that I tried' instead of 'I wish I tried'."

You’re a startup co-founder, what led you to make the jump to start your own business? What have you learned?

I’ve always wanted to start my own business. I come from a humble background, so I wanted to make a living first. Life happened, I had a child, I bought a house, I had things to take care of. But it was always in the back of my mind that I wanted to do something of my own. One day, I was watching an interview of residents in senior living homes on TV. The interviewers asked everyone if they had any regrets. Almost 80% of them said they had something they had always wanted to do, learn dancing, travel somewhere, start something, and that they wished they’d just done it. Something clicked for me, I didn’t want to have that regret. I wanted to be able to say, “I’m happy that I tried” instead of “I wish I tried”. That made me really do it instead of keep thinking about it.

What advice do you have for others who want to make it to technology leadership like yourself?

First, be authentic. You should speak your mind. You might not please people, but you can achieve results and you will inspire people in the long term if you are authentic. Second, take risks. There is no other alternative to success other than taking risks. Your success lies outside of your comfort zone. I see it every day, really smart people not using their full potential because they’re afraid to take risks.

What needs to happen to help more women and other underrepresented groups get into tech and stay in tech?

I’m passionate about helping more women get into not just tech, but entrepreneurship as well. There are two categories I see myself in, Asian and Women of Color. The change has to start from the bottom up. It has to start with parenting. I have two kids of my own and I can see how things really add up, mindset is built early on. If you raise your kids to be efficient instead of innovative and creative, they will be great employees, but they will not be risk takers. Let them explore, let them take risks, and have the kind of environment that celebrates failure. In my own experience, Asian parenting is more about having the best outcomes. The problem is that kids raised like that don’t take failure well. They’re too scared to take risks. It’s so important to celebrate failure.

For women in particular, there is so much social conditioning, by the media, our environments, by simple things we say. If you go to a toy store, there'll be an aisle where all the toys are pink, strollers, kitchen toys, and dolls, and on the other side, the creative toys like legos and blocks have boys on the front of the boxes. We are telling girls that their job is to please men, raise families, cook and clean. There's nothing wrong with any of those things, but how are we going to inspire girls to be CEOs and be leaders if they think they need to constantly be in service of others? Women have to break the mindset that they need to be likable. Why do women have to be in supporting roles? Why do women always have to be supporting a male lead? Why can't they take center stage?

"Behind every successful woman, there is another woman who supported her."

Who helped you rise to this role and how do you pay it forward?

I have an incredible support system. My family, my husband, my mother, my kids. But I really have to give a big shoutout to my mother-in-law. It’s almost impossible to manage work, kids, school- I did my MBA a few years back when my kids were pretty young. Anytime I’m overwhelmed she will say “I’ve got this. Don’t worry about it.” She has been such a big support. She is an incredibly smart woman who never got the opportunity to fulfill her dreams and she has really enabled mine. Behind every successful woman, there is another woman who supported her and that’s what she is for me.

For my first company, CloudFountain, we started a training program to bring women back into the workforce after taking maternity breaks. It’s so difficult for women to return after a break, especially in STEM because everything changes so fast. If they don’t have recent experience, companies overlook them. When I was working at a big company, I started a project to help middle management take the next step, the next leadership role. Many times they are skeptical and worried about the pressure or stress. I provided mentorship to encourage people to pursue the next step in their careers. Since getting my MBA at MIT, I have a big network of women entrepreneurs and I try to support them in any way possible. 

How do you hire? What do you look for in people?

First and foremost, I want an A+ team. I want to hire the best talent. There are four things I look for in team members. The first is curiosity. If they are not curious, they can’t be in tech. The second is problem solving. There are no straightforward answers to most questions in this industry. Technology changes constantly, if you are not a problem solver you’ll fall behind. The third is passion. Startups are difficult, there will be tough times. If you’re passionate about what you do then you’ll stick with it. The fourth is great team players. You can be an excellent individual contributor but if you can't work as part of a team then you're not the right employee for me.

Meytier interviews leaders of all backgrounds about their journeys, their work, and their outlook for the future. Know someone who we should interview? Reach out to us here.

Read recent leader speak interviews:

How GenAI will change the tech services model, an interview with Saurabh Gupta

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