James is a Senior Account Executive at Prodigal, bringing deep experience in sales and business development. He joined Prodigal in 2021 as an Account Executive after working at another YC-backed startup, where he played a key role in scaling sales efforts.

Where did you grow up, and where are you based now?

I grew up in the Bay Area, California, in San Carlos—a small town that, 20 years ago, was a quiet, slow-paced community. It was mostly families and retirees, and life felt a lot simpler. But with the explosion of tech—Meta, Google, Apple, and other giants taking over the Bay—the area has become crowded and fast-paced. It’s a completely different world from the one I grew up in.

I’ve lived all around the Bay, from the wine country of Santa Rosa and Petaluma to the East Bay in Walnut Creek, which has beautiful hills and great hiking spots. I loved the diversity of these areas—each with its own unique feel. A couple of years ago, I moved out to Rocklin, near Sacramento. It’s quieter, more suburban, and a bit of a change of pace from the constant buzz of the Bay. It’s also just an hour from Tahoe, which makes it perfect for skiing and getting outdoors.

What’s your educational background, and what were your previous work experiences before joining Prodigal?

I started my college education at community colleges—Cañada College and College of San Mateo—before transferring to UC Berkeley, where I graduated with a degree in Environmental Economics and Policy. After graduating, I had no clear direction, so I applied for a variety of roles, from business analyst to marketing and sales. My family had a strong sales background, so I leaned in that direction and landed an SDR role at a young startup called Pulse Q&A. I was the first sales hire and had to figure everything out from scratch. It took me about ten months to get the hang of it, but then I started performing at 250-300% of my targets, got promoted to AE, and helped scale the business until we were acquired by Gartner.

After that, I knew I wanted to stay in startups, so my former CEO posted my profile on the YC job board. That’s when Shantanu and the team at Prodigal reached out, and here I am.

What attracted you to join Prodigal, and how has your role evolved since you started?

I was initially drawn to Prodigal because of the company’s stage and mission. When I spoke to Scott Hamilton and Vijayan, they described Prodigal as a disruptor in a stagnant industry, which immediately intrigued me. I liked that it was a young company where I could have a real impact—not just in sales but also by contributing to marketing and product discussions. I tend to stick my nose in areas beyond my role, but that flexibility was something I really valued.

I started as an Account Executive, and it took time to learn the industry—collections is highly nuanced, and relationships matter a lot. Once I found my footing, things took off. In 2022, when we launched ProNotes GA, we saw massive demand. It was an exciting time since we were the first to market with that solution.

Now, I’m the lead salesperson at Prodigal, handling partnerships, channel conversations, and the core AE responsibilities of engaging buyers and closing deals. My role hasn’t drastically changed—it’s more about deepening relationships and keeping Prodigal top of mind in the industry.

Can you share a significant project or achievement you’re proud of during your time here?

Two deals stand out.

The first was with Consumer Portfolio Services (CPS), one of our biggest auto finance wins. I met the VP of Originations at a conference in San Diego, bought her a beer, and started a conversation. That led to an introduction with their VP of Servicing, and we ran a highly detailed ROI analysis that helped us close a $404,000 deal for ProNotes across their 400+ agent team. It was a huge milestone for us in auto finance and showed how strategic relationship-building drives success.

The second was Crown Asset Management. It was a complex, multi-threaded deal that took time to build trust. Closing partnerships like these, along with Track America, has been instrumental in strengthening Prodigal’s reputation in the space.

What are your favorite hobbies or activities outside of work?

I have too many hobbies. I race cars—I built and drive a turbocharged 1994 Mazda Miata. I also golf, fish, and ski. This past weekend, I went fishing and skiing back-to-back. I play PC games like Escape from Tarkov and recently got back into Fortnite (which is embarrassing to admit). I also garden—I grow a little bit of everything!

Which of Prodigal’s values resonates with you the most, and why?

I’d say Pursue Excellence and Radical Candor. I tend to be a perfectionist, which sometimes slows me down, but I strive to deliver high-quality work. Radical Candor is also key at a company of our size—we need to be direct and honest to operate effectively. I also have an asterisk on Curious Optimism—I’m naturally more of a realist, but I always remain curious and questioning.

Is there an interesting fact about yourself that your colleagues might not know?

I was an amateur sponsored skateboarder in high school and early college. I was even sponsored by a local skate shop. If you look up 'JR Vitale Skate' on YouTube, you’ll find my old skate videos.

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