Dipali Trivedi: MIT Entrepreneur on a Mission to Bring More Women Executives and Founders to the Boardroom

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Dipali Trivedi
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BOSTON–Dipali Trivedi is a MIT graduate and a serial entrepreneur. She is currently working as Co-founder and Chief Technology Officer of Everyday Life, an InsurTech startup that serves middle-income families with innovative insurance products and financial planning. It is selected as one of best companies to watch in 2022.

Prior to Everyday Life, she was the founder and CEO of CloudFountain Inc., a consulting firm focused on Big data, Salesforce CRM and Machine learning. Ms. Trivedi has 10+ years of corporate leadership experience prior to entrepreneurship. She has earned her Master of Engineering degree in AI/Machine learning and Executive MBA from MIT.

She volunteers for various non-profit organizations in USA, India, and Africa, and serves as a board advisor. She is an influencer for Women in Tech and Entrepreneurship to break glass ceiling and fight gender bias. She lives in Belmont MA with her husband and kids, she loves to run, hike and travel.

Here is a Q/A with Ms. Trivedi:

INDIA New England News: Please tell our readers about your work and what you enjoy most about it?

Dipali Trivedi: Currently I lead the product and engineering for my second company I co-founded, Everyday Life, selected as one of the best companies to watch in 2022. It is an InsurTech platform powered by machine learning, democratizing expert advice via digital platform to serve middle income market that is underserved today.

I enjoy bringing innovation to a complex domain with the help of next generation technology. Seeing your idea materialized and used by thousands of people is an amazing experience, I enjoy solving challenges of launching new venture ground- up.

Besides leading, mentoring, and empowering team members, I enjoy bringing positive impact by enabling women to pursue leadership roles in the companies I’ve founded and worked for. For example, I rolled out a program to train and employ women who took time off to raise their kids at my first company I founded that increased women employees in technical roles from 17% to 43% within a year.

INE: If you’re engaged with any charity or non-profit, please tell us why this organization and what do you do for them?

DT: I generally don’t talk about the charity work I do. I believe giving is best when done anonymously. However, I am associated with multiple non-profit organizations in India, the U.S. and Africa. Specifically, three organizations are close to my heart.

The first is SETU, a non-profit theater group in the Boston area. SETU means “bridge” in several Indian languages, and its mission is to build bridges between Indian and Western cultures through the medium of theater.

The second one is Moving health, a charity that raises money via “In her shoes”, a 5K walk as it is the minimum distance a woman has to walk to the nearest hospital to give birth safely in rural Ghana. “In her shoes” raises money to provide medical and transportation services to these women.

Finally, the third organization that’s dear to me is “Taru-Shashi” (named after my grandmother and grandfather). It focuses on working at the grass-root level in Gujarat, India to help women and children by addressing underlying social issues.

INE: What are your hobbies and interests?

DT: Traveling is high on my list of hobbies and interests. Growing up in a very small town in India, I never had the chance to travel until my late 20s. The lack of opportunity limited my horizon and exposure to new ideas. So, I want to travel the world with my kids to give them a chance to see various cultures, countries, people and challenges. It offers a new perspective to better understand the big picture and encourages them to be open to new ideas and experiences.

I enjoy dancing, fashion styling and playing chess. I also like hiking, running and other physical activities because it allows me to put day-to-day tasks and stress aside and think outside the box. I especially like to go on these hikes with my children, Aashi (10) and Vihaan (14), and my husband, Ketan Benegal. It’s a great way to spend quality family time together.

INE: In what way you feel you have most positively influenced or served the local community and your company/organization and professional field?

DT: I believe social conditioning and the entertainment industry discourage girls from pursuing STEM (Science, Technology, Engineering and Math) at an early age. This underlying gender bias and “bro culture” results in fewer dollars supporting women-founded startups. The lack of a support system and role models discourages women professionals from pursuing highly technical and demanding executive positions or starting their own ventures.

That’s why I am very passionate about bringing more women executives to the boardroom of technology companies and more female founders to tech startups so that next generation will have role model.

I have rolled out various programs to solve pipeline issue to hire more women at companies I worked for, I strive to hire diverse workforce for the companies I founded, few programs have improved female executives in the company by 28 %.

I have written many articles and spoken at numerous conferences about this topic to raise awareness. I’m trying to do my part, so the next generation has a role model to pursue these career paths

INE: What is your rare talent?

DT: I don’t think I have any rare talent, but one skill that has helped me the most is working to understand another’s perspective about any topic. I almost always put myself in the other person’s shoes to empathize with them and understand their side of the story. For example, I consider questions like, why are they behaving in a certain way? What challenges are they facing? What is their motivation? And what is the middle ground that will make all sides happy in this situation?

This perspective always helps me to exercise better EQ (emotional intelligence), an ability that is essential to leadership and building strong bonds with friends, family and co-workers. For example, today, my in-laws are my biggest support system, and my husband is my life-long cheerleader. I am very thankful for the allies I have in my friends, extended family, and co-workers that I cultivated using this valuable skill.

INE: Your favorite books?

DT: I enjoy reading, and a few of my favorite fictional books are Fountainhead and Atlas Shrugged, both by Ayn Rand, Gone with the Wind, by Margaret Mitchell, and Pride and Prejudice, by Jane Austen. For motivational books, I like the book Saat Pagala AkashMa (Gujarati) by Kundanika Kapadia, The power of habit, Grit: The Power of Passion and Perseverance by Angela Duckworth and Steve Jobs: The Exclusive Biography by Walter Isaacson.

INE: Your favorite quotes?

DT: “We are all in the gutter, but some of us are looking at the stars.” – Oscar Wilde

“I have no special talent. I am only passionately curious.” – Albert Einstein

“Be the change that you wish to see in the world.” – Mahatma Gandhi

“The question isn’t who’s going to let me; it’s who is going to stop me.” — Ayn Rand

“Courage starts with showing up and letting ourselves be seen.” — Brené Brown

“You manage things; you lead people.” — Grace Murray Hopper

INE: Who inspires you the most?

DT: My mother most positively influenced me. I attribute all my achievements to her. My father was a scholar and a genius, but he suffered from acute depression that resulted in a life-long struggle, especially because mental illness was a huge social stigma during that time in India. The family’s financial health was not strong, but my mother often sacrificed her happiness and desires to raise my brother and me and give us both a good life.

One experience really stands out in my mind. When I was 16, I was upset about social acceptance while sharing my radical ideas about feminism. My mom told me something that stayed with me all my life, “Don’t be afraid to stand out! I know it’s difficult and daunting, but you will find your true authentic self only if you find the courage to speak your mind.”

Your core value you try to live by?

DT: I strongly believe in being authentic. I was timid and introverted as a kid, but I was always rebellious and had my own mind. Still, it took me years to find the courage to stand out instead of fitting in.

During my professional life, I saw many leaders who were very effective in getting things done by being diplomatic and tactical. But they failed to motivate me if they weren’t being authentic or unable to accept their responsibility when a project or company was unsuccessful. So, I truly strived to build a culture of authenticity for the companies I founded. Even though speaking your mind is challenging and daunting, and you might upset others or open yourself up to judgment, I believe your success lies outside of your comfort zone. And you can only get there if you are ready to be authentic.

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