Sitting Down with True Fit's CTO, Raj Chandrasekaran

An interview with our new CTO, takes us inside the vision of True Fit's tech-driven future, his favorite fits and driving get what you love solutions.

March 31, 2022

Welcome to True Fit’s exclusive interview series, where we sit down with various members within our dynamic organization across three continents, to get their inside view of the industry and True Fit in 2022.

We are thrilled to kick things off with Raj Chandrasekaran, True Fit’s new CTO. With extensive experience in the engineering and technology industries, working in leadership roles with revolutionary companies like eBay and OpenTable, Raj joined True Fit in January of 2022 and immediately made an impact, with the support of his great tech team. 

We sat down with Raj to discuss his first impressions of True Fit, what lies ahead in retail tech space, and of course, some of his favorite fits!


You've been at True Fit for two months now, what has your experience been like so far?

To say it has been amazing is an understatement. Everyone is passionate about one simple thing - how do we get better at fit guidance and fit confidence? It’s a unified theme all throughout the ecosystem. 

True Fit is already a frontrunner in the field of personalized fit recommendations, it has been incredible to observe people unified in this vision continuously raising the bar on personalization, fit guidance, and how we can help both shoppers, retailers and brands alike to make excellent win-win relationships.

What is something that has surprised you so far as True Fit's CTO?

What I noticed in my on-boarding experience as well as in several of our processes was that this is a well oiled machine. There are a lot of best practices that are part of our business life cycle. Be it the onboarding, or rollouts, or some of the guiding principles we have across the board, it all gives you a picture of what a well-oiled machine True Fit is. 

With your engineering background, and your technology leadership experience at places like eBay and OpenTable, what drew you to the mission of True Fit?

I first spoke with CEO Bill Adler and Founder Jessica Murphy  in Q4 of 2021. The first key element that appealed to me was that they explained their vision of growing 10x. At the surface it may sound like a very difficult target to accomplish, but the secret is to find the mechanisms for 2x. The learnings and the way we adapt can get us to 10x. True Fit is in the right spot to help make curated experiences for our shoppers and partners. There is so much untapped potential in the space we operate, we are not just set at the right spot to have a larger share of the pie, we have the potential to increase the pie itself. 

I had similar experiences at eBay and OpenTable, working with large merchants in the B2B space and B2C. You aim to partner with both sides and make sure it's a win-win. That’s what leads to growth.

What is the biggest challenge you look forward to tackling with your team at True Fit?

To get to 10x it is important to focus on automation at different levels. How do you go after processes that are slowing us down? How do you revisit technology that can speed up what and how we run the ecosystem. If we can think like a startup, but scale like an enterprise, we would have unlocked the means to get to 10x.

In my conversations with many members across the board, there is an innate desire to move faster, set us up for scale, innovate further, and also be the first in many different areas. I, as well as the leadership within the tech team, are fully committed to enabling this to happen. How we achieve this 10x is always top of our minds. 

In terms of online retail technology, are there any trends you see going on now or around the corner that will be growing over the next five years?

I’m learning more and more about "Experiential retailing" - Personalized shopping experience for our customers based on their shopping habits and favorite brands. 

Many retailers are interested in what their shoppers are doing. This space of better personalization is something I think we will be growing over the next five years. The expertise we have built in this space has very few parallels. With this expertise as our base, we can bring out a lot more innovation on the personalization front, normalization front.

"Try before you buy" - is very normal in offline shopping. Of late, we see more adoption towards trying before you buy even in online shopping. We’ve seen more and more adoption coming through. I think it will allow many retailers to offer this feature. 

“Virtual Try-ons” (aka mimicking real life experiences, virtually) is another pattern I see in the digital ecosystem. Lastly, I am very intrigued by how we can innovate solutions in an effort to share resources together within the digital landscape.

Our new user experience (v7) serving fit guidance to 100% of traffic is a big and exciting initiative for True Fit in 2022, what can you say about that?

It’s been an awesome cross-functional effort to get v7 live. There are three aspects of it that is going to be significant game changer:

  1. High-Performance widget, we know slimmer websites/apps perform very well in terms of conversions and adoption and we see it already with the performance uplift v7 brings about. The new widget is performing a lot better in terms of load time and overall performance. 
  2. Modern UX - Very new UX patterns are being introduced and we believe these will be a trendsetter. We are setting a new trend on how fit recommendations show up. 
  3. Ease of Integration: We are about halfway into this journey. We are going to focus on further making the integration as smooth and intuitive as possible. 

What excites you most about what lies ahead for you and your True Fit team?

Potential for scale with retailers. We can make their experience as blissful as possible. Getting 200 millions shoppers in our system is not an easy task, but can it get to 400 million, Billion+ ? There’s a huge potential. 

With partnerships (Aggregators, Brands) can we integrate them with Google, or eBay for example.? Can we become the platform that establishes a relationship between all these parties?

We center everything around the customer. Many tech focuses on tech first, value later. We put the customer first in everything. 



Fun Facts, Getting To Know Raj:

When was the first time you used True Fit?


What is your favorite technology product from the past five years?

It is hard to pick one favorite when you come across amazing product suites. Each is great in its own right. 

My recent favorite is our own product of course. Before this, I was working on a voice assistant for teachers that helped them a lot in classrooms. I thought that was a fascinating product. 

What clothing brand do you wear the most? 

Van Heusen.

What is your favorite footwear?


What was the last clothing item you purchased online? Did it fit you?

Levi's shorts, it sure did fit because I used True Fit, which recommended my accurate size! 

How would you characterize your personal style in one word?


How would you characterize your personal brand in one word or phrase?

Transformational/Servant leadership. Challenging the status quo constantly. If we do something in one hour, can we do it in one minute? We have an amazing team. I always strive to make sure we don’t have any roadblocks so that the team can do what they are good at. 

Favorite Season of Clothing?

Winter. I live in the bay area and we hardly get to see snow. You have to drive 300 miles. Those are the best moments with my family. I grew up in the southern part of India. We had three seasons - hot, hotter and hottest. Winter wins any day.