Meet Ushashi Chakraborty, Wisely's VP of Engineering (& Former Comic)

Nov 9, 2020
min read
Written by

isely is thrilled to welcome Ushashi Chakraborty as our new VP of Engineering. Ushashi is a restaurant technology leader with a Masters degree in Computer Science and 10+ years of experience with companies like Microsoft, Groupon, and Mode Analytics. Wisely caught up with Ushashi to hear about her career, her passion for mentoring engineers, and how comedy shaped her as a tech leader.

What are some highlights from your career prior to joining Wisely?

At my time in Groupon, I was an engineer in an extremely fast growth state organization. Everyone was doing more than what their job parameters demanded. I started learning to look at the larger picture. I began learning how engineering execution works, how to build relationships with various stakeholders, and how to plan an entire engineering cycle (and keep to it). That was a key moment in my career as I grew into a leadership role.

Another highlight was when Groupon acquired Living Social. Myself and a principal engineer led the engineering side of the project, which relied on multiple engineering teams who were not directly reporting to us. I had to learn how to lead with influence. I also had to make decisions about engineering pieces that my team hadn’t built, or in some cases that I didn’t know properly. This led me to develop an engineering instinct that ultimately shaped my trajectory.

Finally, I moved to San Francisco a couple years back and started at Mode Analytics as Director of Engineering. When I started, I had a very small team, and when I left, I had five teams with engineering managers on each of them. It was a very good experience joining at an early stage and helping to grow and scale the team.

What advice would you give people thinking about a career in engineering?

Starting out in engineering can be overwhelming. With the sheer number of things to learn, it’s easy to wonder “when will I ever learn enough?” To anyone feeling that way, I would say that feeling still rings true when you are 10 or 20 years into your career—technology evolves every single day. My advice would be to start enjoying the process now. Understand that you will never learn everything—you will always be iterating on the knowledge you’ve built.

For anyone looking to transition into engineering management, it requires a shift in perspective. As an engineer, we focus on building, quality, design, architecture, and ensuring we build in an optimized way. In engineering management, what used to be a singular focus becomes one part of your job. The more you grow, the less and less you get time to do that part individually, and the more and more you need to ensure that your team is accomplishing that work with your help.

Also, no matter how much you focus on executing on the engineering aspects of the job, a question to remember is, who is building? The people. If your team doesn't feel motivated, or invested in the vision, they will not stay, or do the work the way you want them to. It is critical to ensure that you are building strong relationships, understanding each person’s motivations, and working with them accordingly.

Finally, you must build your stakeholder relationships. As an engineering leader, your stakeholders become product, design, and data science partners—and in a more senior role, marketing, sales, and other execs. Having a great product isn’t enough if no one buys it. You need to ask questions to understand why you are building what you’re building.

Again, I don’t want to make it sound overwhelming. If you can enjoy the process and think “this is just a new thing to learn,” it will really be fun.

You studied comedy at The Second City Training Center—how has that shaped you as a leader?

Yes, I did a bunch of improv for a few years, and a little bit of stand-up. I studied both. Comedy definitely shaped me as a leader, just like being a technical leader has shaped me as a human being. Everything we do shapes us. I try to be aware of what those things are, and if they’re helping me, I try to magnify them.

With stand-up, I was impacted by how much you iterate on what you write. So many times I tried a line with a group of fellow improvisers and comics, and what I thought was very funny wasn’t actually funny. I learned so much through the process of taking one sentence, saying it in 10 different ways, and seeing which way makes the most impact—where to pause, where not to pause, whether you get a laugh.

You learn so much through that process, but then you go up on stage, and it’s completely different. In that moment all you can rely on is audience feedback. You are so cognizant of where you are—how do I switch it up, this is working, this isn’t working, I can’t freak out...

That practice helped me develop a lot of skills.

1. Being comfortable in uncomfortable situations.

2. Thinking on my feet, and really connecting with what is being demanded or required of me.

3. And finally, no matter how much work has been put in at the end of the day, the audience is going to give the verdict.

Translating this to product and engineering, it means your customers are key. The hard work is extremely necessary—it gets you closer to the end goal—but you still have to take feedback, iterate, and come back to the audience. You can never say “I got it, and I don’t have to work on it anymore.”

Wisely Engineering - Ushashi Chakraborty

With improv, you don’t have a script—all you have are your fellow actors on stage and you’re relying on each other to build a relatable scene so the audience can laugh with you. This practice helped me develop nuance in how I pay attention to others. Certain people are quieter in meetings, but bring insights later on. Others are more forthcoming. 

Managing those differences, while keeping the team on track, is just like building a scene on stage to tell a story in real time.

In 5 years, what do you want to be true about the restaurant and tech industries?

For the restaurant industry, I want restaurants to have a more data-driven, customized approach to people. I want them to know what I like because I mostly order the same thing, or that I like sitting on the patio, I would love it if they were aware of those things. Sometimes it happens because a particular person remembers you, but to have that knowledge in their toolkit so that service isn’t dependent on one person—I think that would be very exciting for the restaurant industry.

In tech, but really across all industries, I want to see equitable pay for underrepresented minorities.

Let’s wrap-up with 3 fast facts—ready, set, go.

  1. I was raised in Kolkata, India
  2. I went to grad school in Fargo, North Dakota
  3. I live in San Francisco CA, with my husband, Richard

Finally, why restaurant technology and why Wisely?

Restaurant technology is a space that excites me. My loves in life are food, travel, and technology. Wisely brings together two of those loves in one domain (and I can always travel for food, right?).

I also think there is great potential for a more data-driven approach in this space. I believe that the work we do at Wisely will have a huge impact on the whole restaurant industry.

Connect with Ushashi on Linkedin, Twitter, and Instagram

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