Shaili Gupta, Senior Strategy Manager @ xFact

Shaili Gupta is a strategy leader who has multiple perspectives from sitting all around the startup table as an investor, operator & stand-in CEO, and product consulting expert. Today she is a Senior Strategy Manager at xFact, helping the public sector better plan for the future.

Growing up in India alongside her two younger sisters, Shaili’s dad was a banker who moved cities & roles throughout his career. Her mom was a homemaker and artist who demonstrated you could jump into just about anything as she reinvented herself continuously. 

Initially it was painful to start over after a move every few years. But moving around really shaped who Shaili is and how she works. In retrospect, it gave her the resilience and ability to deeply connect with people in any situation. Relationships are important to her as are understanding different perspectives. Being transported across India to experience different cultures, joining new communities, and making friends was hard work.

She had the most fun time in Bangalore, where she worked after graduating from university. It was the longest she’d lived anywhere until Boston. She thinks there are more parallels and similarities than differences between the two cities, even though they’re separated by a couple continents.

As an undergrad, Shaili studied Engineering and worked with data in SEO & SEM to begin her career in ad tech. She witnessed the potential of data in the growing digital world. After attending an MBA fair, she met the admissions director from Ohio State, feeling a connection for how they took care of their international students. So off she went.

What was it like to come to America for the first time as an MBA student? Well, the exchange rate was a bit of a shock. 70 rupees was…$1. Shaili spent her first week in NYC running around the center of capitalism surviving on KIND bars. 

Ohio State’s Fisher School of Business was a small, fantastic program. Almost immediately she began working at Columbus based venture capital firm Ikove Capital. They focused on early stage, deep tech investing helping to commercialize emerging technologies. This role opened her eyes to the startup ecosystem for the first time. She was hooked! 

From her childhood she knew how to jump into new things and move quickly, drawing energy from these early stage teams and the impact these growing companies could have on society. While at Ikove, she began working more closely with the NeuroPlay team as the founders were looking for some strategic help. They were developing brain-training technology solutions for seniors and autistic children.

NeuroPlay ended up bringing 27 year old Shaili on as their CEO. Quite the promotion! For some roles, outside perspective is very helpful and she was able to bring the power of questioning into this early stage company. She also..didn’t sleep for a couple of years while working as a CEO and full time investor!

Shaili learned to solve problems that customers actually care about. It’s easy to lose the link between “does this really matter?”, but building great products by staying close to your customers was an important early lesson. And to strive to be different, building a value proposition that far exceeds the incumbency. 

When NeuroPlay needed to pivot, Shaili looked for another challenge and moved to Boston. Committed to building her network (like she has done many times!), she started advising and working as a mentor with MIT Bootcamps.

In Boston she has served as a Senior Strategy Manager at xFact, a public sector consulting firm where she is focused on technology products & digital transformation, modernizing legacy systems. 

Shaili goes deep with her customers on technology & product evaluation to improve their organizations. She is in charge of leading their product based consulting practice, helping to de-risk businesses that are grappling with AI, quantum computing, and other frontier technology evaluation. She helps customers understand how to manage and evaluate tools based on their existing offerings. Shaili even helped develop a customer engagement program which has really helped customer satisfaction (CSAT) increase and drive a positive impact on their reputation.

She has done work for the Commonwealth of Massachusetts technology office to come up with a Generative AI evaluation matrix of different product offerings in the space too. Now, the local government can take a cautiously innovatie posture to evaluating and adapting these new technologies so as not to be left behind. Government is designed to be slow, but still innovative, due its large impact on the population. It can’t exactly move fast and break things.

In her spare time she enjoys salsa dancing, even attending an International Salsa Congress, where she got to dance with the world’s #2 salsa dancer. Shaili teaches us that if you put your mind to anything with the proper speed, persistence, and confidence you can learn lots of new things. It just takes a little bit of confidence.

Being Adaptable & Pivoting
Adaptability and nimbleness are key traits that have driven Shaili throughout her career. The one thing she learned early in life? The only constant is change. It’s inevitable. 

Shaili has found it critically important to embrace that change and be ready to pivot when the signs are shown to you.

When she took on the CEO role at NeuroPlay, they had a great product but the problem they were trying to solve was (in retrospect) a niche market. There were signs. When they wanted to test their solution they had difficulties recruiting for clinical trials. They struggled to get the sample size they wanted to further their research. It was a sign. Even though they had done a thorough academic market analysis, in practicality there was a limited potential customer population and therefore limited momentum they were able to create.

If they had pivoted faster to leverage their solution for a larger problem space they might have been able to find more traction. Therefore, Shaili learned that finding PMF is a structure problem. First, you need to identify what you’re solving, for whom, and how will that vector of change make their lives better? When commercializing new technology it’s critical to pause and ask yourself “is this path scalable?”

If that flywheel doesn’t spin faster, and more continuously, it might be a signal to change your approach. That point was driven home when a similar startup aimed at a larger segment of the market raised a large round of fundraising by a tier one VC soon after Shaili’s departure.

3 Career Insights / Learnings

Be Generally Curious – “Ask questions and don’t listen to answer. Truly be curious. Say yes to things, figure out what’s happening. Challenge yourself by being curious about everyday life and then carry those learnings with you to try new things”

Build Strong Relationships – “Build true relationships with people. Whether that’s people who can be your mentors, your peers, or even people you might mentor experiment with meeting new people to better impact your career and life”

Focus on Impact – “Make a meaningful difference in whatever you’re trying to do at work, at home, or even in society. Go and volunteer, get involved with something you’re passionate about. The growth that you get from these experiences will take you far and broaden your perspective”

Shaili wants to continue leveraging groundbreaking technology in her career to drive growth through product development and build products that are scalable. She is focused on driving positive social impact and solving problems for customers that also face the world at large.

She’s even starting a podcast with a friend of hers, where imagination meets innovation, called Boundless. Their first episode is on Space tech. Keep an eye out!

For more about Shaili you can find her mentoring early stage startups, salsa dancing or recording new episodes of her podcast by night, continuing to experience the city of Boston, or on LinkedIn. Thanks for sharing. We’re excited to see the teams, technologies & impactful work you continue to do in the years ahead!