About Jason Masciarelli

I started my career the way a lot of people do — making cold calls and learning to sell. In my case it was enterprise network hardware in the early 90s, at a time when convincing a company to invest in high-speed networking required serious market education. I didn't know it then, but those years laid the foundation for everything that followed: how to earn someone's trust, how to listen before you pitch, and how to be genuinely useful to the person across the table.

Before any of that, I tried to build a startup during the dot-com boom. It failed. I had to shut it down, absorb the lessons, and figure out what came next. What came next was Theikos.

In 2000, I co-founded Theikos — one of the first Salesforce-focused consulting firms in the country. Building it was not a straight line. We were self-funded from day one, and there were moments where the obstacles felt genuinely overwhelming — the kind that test whether you actually believe in what you're building. We pushed through. What made Theikos different wasn't just scale — it was the model. We built one of the first Salesforce partner operations in India, creating a global CRM delivery approach that was genuinely novel at the time. It worked: we were regularly getting customers live and delivering real business impact in under 60 days. Over eight years we grew entirely organically, from two consultants to 100+, completing more than 1,000 client implementations. When it was time to scale beyond what organic growth could support, I orchestrated a capital raise from Salesforce Ventures and a VC firm to fund a merger with Astadia — creating a 500-person global Salesforce firm.

I moved to Singapore to help the combined company leverage the India center of excellence we'd built and expand further across Asia — helping companies throughout the region get more from Salesforce and the emerging wave of SaaS platforms. Still based in Singapore, I then joined BigMachines to lead sales across Asia Pacific and Japan, working with enterprise clients on CPQ and lead-to-order transformation, and left just ahead of their acquisition by Oracle.

Back in Singapore, I co-founded one of the early Force.com OEM partners — a B2B mobile and commerce software company that gave me my first real experience building a product from the ground up. We operated across the US and Asia-Pacific before I eventually returned home.

2015 was a turning point — the kind that strips things down to what actually matters. I had to rebuild from the ground up, personally and professionally.

What got me back wasn't a resume or a plan. It was a relationship. A close friend with deep ties to the founder of Pegasystems went to bat for me — and because of the trust they'd built over years, a door opened that I never could have knocked on alone. In 2017 I joined Pega to build a corporate venture fund from scratch. It was a dream role, and I didn't take for granted how I got it. That experience is part of why I believe so deeply in relationship capital — not as a networking tactic, but as the thing that actually carries you through when everything else falls apart.

Since then I've spent the past several years at Pega leading partner ecosystem strategy, building and running Pega Ventures, and most recently leading Go-to-Market for Launchpad.io — helping software companies build new revenue streams on Pega's workflow platform.

Outside of work, the thing I'm most proud of is my relationship with my two sons. They're young adults now, and some of my favorite time is spent with them — whether that's on a snowboard, a motorcycle track, deep in the backcountry on an adventure ride, or grinding up a mountain bike trail. We also spend a lot of time just talking — about philosophy, life, business, tech, where the world is going. They push my thinking more than most people I meet professionally. Watching them find their paths has been one of the great privileges of my life.

The best part of where I've landed is who I get to share it with. My wife is my ride or die — adventure partner, sounding board, and the person who somehow makes me want to be better while making me feel completely free to be myself.

My journey has not been up and to the right. I've failed, lost things that mattered, and had to start over more than once. What I've learned — sometimes the hard way — is that the relationships you invest in before you need them are the ones that carry you through when you do. That's not just a business principle. It's the thread that runs through everything I've built, and everything I'm building now.

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