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Meet a Member: Payal Agrawal Divakaran

Jun 5, 2020·4 min read

Continuing with our feature series on the members of TiE Boston, we spoke with TiE Boston Charter Member, Payal Agrawal Divakaran, Partner at .406 Ventures, about her journey and what led her to TiE.


How did you get Involved in TiE Boston?

I’m Boston born and raised. My parents came to Boston from India in the 70s, so I’ve been accustomed to the Greater Boston Indian Community since my beginnings. My journey started with MIT, where I trained in electrical engineering and was grounded in a passion for technology and solving hard problems. I realized that I loved tech but had a stronger interested in understanding how the business and finance elements help to scale tech. So, I started my career in investment banking at J.P. Morgan (at the height of the 2008 financial crisis, by the way). From there, I went to private equity investing at Spectrum Equity and then got my MBA at Harvard, thinking that I would go back into PE after business school.

HBS is where I first jumped into entrepreneurship. I co-founded a company called SpotRocket, a platform that leveraged a proprietary algorithm to help students identify which startups were high potential ones to work for. We monetized via job posts, and ultimately, it was difficult to scale the way we had hoped, so after a year and a half of running the company we wound it down, taking with us a whole host of lessons. During my time at business school, I also worked at Eventbrite in corporate development. Those two experiences, starting my own company and working at a venture backed company, helped me realize that I wanted to explore venture capital and work in early stage investing so that I could be really close to innovation and disruption. I reached out cold to .406 Ventures, 100 stars aligned over a 3-month interview process, and the rest is history.

I have been at .406 Ventures for the 5 years. I started as a generalist across our three segments (digital health, cybersecurity, and data & cloud), but after I did a couple healthcare investments I realized there was an awesome opportunity ahead in digital health. The healthcare market was poised for strong tech adoption, so I could leverage my learnings in tech and was willing to get up to speed on healthcare (it helps that my husband, Sanjay, is a cardiologist!). After several investments, I was promoted to Principal and then to Partner last year. I now co-lead our digital health practice with Liam Donohue and focus on investing in software and tech-enabled services that sell to hospitals and to payers — all of our investments are ultimately focused on improving patient outcomes and decreasing costs for the healthcare ecosystem.

Given that we focus on Series A investing, we are always trying to be far ahead of the curve. For example, we invested in a number of companies around telemedicine and virtual care which all of a sudden come to the forefront. Our population-oriented investing philosophy, leading to investments in behavioral health and cardiovascular health, for example, have also made us stand out. We love doing investments at the intersection of our segments, including at the intersection of healthcare and data.

How did you get involved in TiE Boston?

I grew up with familiarity around TiE given my parents’ network, but I didn’t have a strong understanding of what the organization stood for. It wasn’t until I joined venture capital that I was formally reintroduced to TiE. In some ways, I used to think of TiE as something that my parents’ generation engaged with, so it was interesting to change the frame and engage directly. In 2015 I caught up with Praveen Tailam to discuss how my generation fits into the ecosystem of TiE and how the next wave of technologists, innovators and investors get involved in the ecosystem. It was in August of 2016 that he nominated me to be a Charter Member after convincing me to take a fresh look at TiE Boston. He’d also introduced me at that time to Satish Tadikonda, Gaugarin Oliver and more of the other members. Given my job as a VC, I was especially drawn to ScaleUp and StartupCon (now TiECon East) and was drawn to the mentorship and helping with those initiatives. Late 2016, I was invited by Monica Chandra and Vivek Soni to be involved in the TiE Boston Board. There was an opportunity for me to further help TiE Boston think through engaging a broader part of the ecosystem and community, so I joined the board in February of 2017 and I have been a board member since.

What advice would you give to entrepreneurs who want to follow in your steps?

Since we are in the middle of a pandemic and recession, it’s helpful to think back to the start of my career during the 2008 financial crisis. What helped me most during that time was putting my head down and working hard. There is no replacement for really hard, gritty work. Often when people hear my career path, they think it was perfectly orchestrated, but at each step there was a hiccup or some level of uncertainty. The hard work led to key opportunities to advance my career and key relationships that help me navigate those bumps in the road.

For entrepreneurs, it is an interesting time right now as the availability of capital has tightened and the ability to sell to customers has tightened, depending on your segment. It is really important to be scrappy and manage cash really well to make sure you have runway to both live through this uncertainty but also seize opportunities when they come. Also, feel free to reach out to me if I can help!

Thank you to Payal for sharing her story. To learn more about TiE Boston and how to get involved, check out or reach out to

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