Bringing the Enterprise Wisdom of Oracle and IBM to Wade & Wendy: Spotlight on Sumit Gupta, W&W’s CTO

By: Wade & Wendy Team

Sep 18, 2019

What’s the secret to getting really, really good at computing? We think we know the answer: spending the eighties obsessed with your Sinclair, Commodore, and IBM XT — and learning to write code as a teenager, so that you can make a game rather than merely play one. This was the path taken by Wade and Wendy’s CTO, Sumit Gupta.

After working at a number of startups, Sumit’s talent for computing eventually landed him at software behemoth Oracle. He was there for four years, in the early days of web services. What Sumit learnt at Oracle sets him up perfectly for his CTO position at W&W: “I learnt a tonne about what it means to build software for enterprises, work on standards with other organisations, and deploy and manage web services,” he says.

At Oracle, Sumit became very comfortable with the nuts and bolts of enterprise software: integrations, workflow, privacy, stability and so on. All experience he brings to the W&W software.

After Oracle, Sumit moved on to Princeton Softech, a startup working on data privacy, masking, and archiving. Princeton Softech was acquired by IBM in 2007. It was a big shift, going from a company environment that was small and nimble to one that was large and regimented. But Sumit learnt even more about the demands of building software for enterprises:

“At IBM, they have a process for everything. This has its pros and cons, but it did really teach me how rigorous you have to be when you are at scale, and how excellence can only be made repeatable if you have strict, clear systems. At IBM, I learned the formality and the art of building out teams.”

I also learned what it meant to sell a vision and an idea for a technology within an organisation, rather than just to buyers. This has been really valuable as I’ve moved on to organisations like Wade and Wendy. Because here we have to stay nimble and continue to innovate, whilst also growing the organisation and delivering enterprise grade software.”

After IBM, Sumit moved on to Voxware, a company that manufactures voice recognition technology for the warehousing industry. The focus on voice recognition also set him up nicely for W&W: “I began to think hard about understanding conversation, intention. All super important for what we’re doing at W&W.”

It was at Voxware that Sumit took his first position as CTO.

“Like most engineers, I started out saying that I just want to be a technologist; I don’t want to deal with people; I don’t want to manage people. But then, sort of to my surprise, I began to discover a knack for managing people and time. And I ran with it. Over time, this aspect of what I did wound up becoming the most gratifying, as you see how you can help people progress through their career paths.”

All of this previous experience meant that, earlier this year, taking a position at Wade and Wendy was an easy decision for Sumit:

“Wade and Wendy aced my decision matrix for evaluating a startup. One, it was clearly a fantastic team, all passionate and intelligent people, people I wanted to work with. Two, it was a business problem that I could really get my head around. I understood that recruiting was backward and broken; I’d experienced this myself. Drew’s vision struck a chord with me.

And finally, three: I’m a technologist at heart. I have to have interesting and hard problems to solve. That’s my fuel. The technology challenges and goals of Wade and Wendy are top level, and super engaging.”

As CTO, this is what Sumit sees as the most fascinating, boldest part of W&W’s mission:

“At the highest level, within the AI realm, this is about understanding conversation, evaluating conversation, and improving conversation. These are unsolved problems, even for a human being. To get machines to understand a human conversation is a fascinating challenge. I mean really understand; not just parse out text, but actually comprehend. That is a big and bold challenge for any engineer.

And it’s not just tech for tech’s sake. We truly want to remove this bottleneck in the world of recruiting, and allow for frictionless ways for companies to find the right talent. At Wade and Wendy, we have a big problem, but we’ve set limits, so we can know what success looks like. And that success will truly benefit millions of people. That is thrilling.

So we are delving into some interesting areas that are at the nexus of philosophy and technology. At the same time, we are creating this super practical tool for a specific industry. That really excites me.”

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