We’re thrilled to welcome Proby Shandilya to the Work-Bench team as our first-ever Researcher!

At Work-Bench, we’ve always been a thesis-driven firm. We pride ourselves on going (really) deep into the enterprise software stack, which shapes how we invest, support founders, and stay ahead of the curve. The Researcher role is a cornerstone of this philosophy, and we spent a long time searching for someone who wasn’t just smart, but relentlessly curious. Someone who could spot the signals before they become trends and distill technical complexity into clear, actionable insights.

Proby is exactly that someone.

He brings with him a sharp analytical mindset, prior experience at venture firms, and most importantly, a genuine love for learning. Whether he's writing deep dives, hosting his podcast, or studying the rise of enterprise legends, he brings a rigor and passion that’s infectious. (Yes, he’s the kind of person who casually analyzes the history and architecture of enterprise giants for fun.)

At Work-Bench, Proby will be diving headfirst into our core investment themes – AI/ML, Infra and Dev Tools, Cybersecurity, and Enterprise Applications. We’re at an inflection point in enterprise software: agentic software, accelerated GTM motions, and a wave of technical innovation are rewriting the playbook. It’s a wild and exciting time to be building and backing companies in this space and Proby’s research will play a role in how we navigate it.

Beyond his research chops, Proby fits right in with our team of proud enterprise nerds. His journey from analyzing basketball dynasties to breaking down SaaS business models is very on-brand for us. (Fun fact: he even wrote a book about it!) He’s already joined us for Olive Garden breadsticks, the real rite of passage at Work-Bench, and we’re looking forward to seeing what song he picks first at karaoke. No pressure.

If you’re a fellow enterprise enthusiast, founder, or just love diving into the history and future of software, reach out to Proby at proby@work-bench.com. We couldn’t be more excited for what’s ahead.

Let’s go!! Onwards 🚀

Obligatory Olive Garden pic