Innovation at Dimagi, Part 1: The Life of a Dedicated Entrepreneur on the Inside

December 14, 2020

Why is it important and necessary for small businesses to have a dedicated entrepreneur on the inside? (Not just the CEO!)


In this series, Dimagi’s Co-Founder & CEO Jonathan Jackson (@jonathanleej) and Senior Director of New Business Shabnam Aggarwal (@shubbless) discuss how we continue to look for ways to innovate with the help of a dedicated entrepreneur within the company.

In this piece, Shabnam outlines her journey to Dimagi and the seven key responsibilities of her role that are vital to the future success of the company.


When I stepped off the plane from New Delhi to Boston in October of 2016, I held a heavy weight on my shoulders. I had recently shut down my third edtech startup in just under seven years in India, and I was moving back home to the US with debilitating frustration. There were so many aspects of being a social entrepreneur in an LMIC that I loved and knew I’d miss, but there were equal parts that I’d hated. 

I loved coming up with new product ideas at the intersection of two domains that rarely intersected. I loved taking those ideas from zero to one, testing them in the market with real users, collecting feedback, and growing sales. I loved building teams and growing people. I loved tinkering with products as they transformed into something different from the original ideas. 

I hated—absolutely hated—venture capital fundraising. I hated the way young entrepreneurs were made to stand up on stages like show horses, while even younger associates at venture firms would judge and assess our entrepreneurial mettle in minutes. I hated the stress of having to ask my team to take half or a third of the salary they deserved. I hated having a great idea that could make a huge impact that might not see the light of day just because we lacked money.

So that day I stepped off the plane in Boston, I promised myself I would not start another startup right away. I needed to heal and gain some footing underneath me after years of slip-sliding, but I also wanted to thrive. I wanted to somehow make use of the innovation and failure lifecycle skills I had developed over the years. As I began the search for a role that could make use of my jack-of-all-trades, master-of-none skillset, I realized there was almost nothing out there. Very few organizations, especially those with a social mission, were actively searching for people with entrepreneurial backgrounds. Not even Dimagi.

My role at Dimagi today is the result of strong networks, good people, and a willingness to fail. I noticed in my search that Dimagi was hiring for a product manager, and while I had a product background, it was not the only way I wanted to add value to a company. Nonetheless, I applied on the insistence of a few friends on the inside at Dimagi. After passing the first few rounds of interviews, Jon, the CEO, asked me to come in.

What began as a normal product manager interview rapidly shifted gears into Jon asking me about how I operated as an entrepreneur. I left Dimagi’s Cambridge office and went back home feeling both confused and excited.  A few hours later, Jon asked me to come back in the afternoon.  

During our subsequent meeting, Jon admitted that one big challenge he had faced over the nearly two decades of building Dimagi was having a place for his innovative ideas to “live”. They would often come and go and get lost amongst the multitude of other pressing work that needed to get done. Worse, they would distract a lot of his essential team as the ideas came and went.  He needed someone who had an entrepreneurial mindset, who he could bounce ideas off of, and who could run with the ideas to see if there was enough market traction for Dimagi to formally take on. He wanted someone who could build the following (this is verbatim from a follow up email I sent him after our meeting in 2017):

  • Focus on the future of the business: New business models with our products, new markets we can enter, new products we can build
  • Build up “intrapreneurs” in the company: Enable existing Dimagi-ers to ideate, innovate, calculate, and rapidly prototype their big ideas
  • Build a new team of agile rapid prototypers to support
  • Design a safe space for testing ideas, talking to and testing with potential customers, and learning what works and what fails with users
  • Create metrics for success/failure of new ideas: Ensure data is always at the heart of the solutions
  • Work with Jon and Neal (our Chief Strategy Officer) to build out realistic (but crazy) ideas 
  • Pitch CEO for investment in new ideas

It may already be obvious, but I took that role in a heartbeat, and now, three years on, we are launching our third innovation product within my team: the “New Business” team. What’s stood out to me over these last three years, however, is that very few organizations create space for unconventional people like me. I know it was an uphill battle, but I’m so glad Dimagi did. And I know we are better for it.

Entrepreneurs are a unique brand of crazy. And while I believe that the experience and failures we withstand in a short period of time are irreplicable and un-learnable in an MBA program, I also believe it takes a unique CEO and leadership team to create the space and support for an entrepreneur to thrive within an established business. When that space is created effectively, entrepreneurs can bring a unique and valuable combination of skills to the small business table.


In our next piece, Jon and I will explain the original (and ever-evolving) structure of the New Business team’s approach, as well as where, how, and why it forks away from Dimagi’s established business lines.

Written by
Shabnam Aggarwal

Senior Director of New Business

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