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Most founders start with a product. Sebastian Jimenez (CAS ‘18) started with a problem — and a relentless obsession with finding the right market and the power of salesmanship.
Back in 2018, Jimenez was a fresh NYU grad and standup comedian in Queens, searching for a way to make an impact. He and his co-founder launched Ballotbox, a voting app for political canvassing. But when the midterms ended, so did the market. “We’ll see you in four years,” their customers said. The lesson became clear: markets matter more than anything.
After Ballotbox, Jimenez noticed that a critical blind spot existed in many organizations: they had no scalable way of understanding what was happening in face-to-face sales conversations.
Unlike call centers or digital platforms, field sales teams — those who sell in-person in homes, stores, or job sites — have historically been invisible to data. Managers couldn’t track what was being said in customer interactions, which made coaching and performance improvement guesswork at best.
During his time in the NYU Summer Launchpad, Jimenez developed the early vision for what would become Rilla: a platform built to unlock the “black box” of in-person sales interactions.
Surviving Years in the Red
For years, Rilla operated at a loss. The team hustled, experimented, and burned through capital, but profitability was nowhere in sight. Instead of chasing shiny new features, Jimenez doubled down on a single product vision. The product itself barely changed from the early days — what changed, over and over, was the market they aimed to serve.
The Relentless Search for the Right Market
Sebastian’s core philosophy: the market matters more than the product. While many founders obsess over tweaking and rebuilding their product, Jimenez kept Rilla’s offering steady and focused all his energy on finding the right market fit. The team cycled through markets — political canvassing, retail pilots, field marketing — each time learning, iterating, and moving on when the fit wasn’t right.
“I wasn’t just building a product. I was chasing the right market.”
Rilla didn’t become a top B2B startup overnight. Jimenez’s early journey was a masterclass in pivots, persistence, and market obsession.
Salesmanship as a Superpower
What kept Rilla alive through the lean years was Jimenez ’s sales acumen. He wasn’t just a founder — he was a master salesman. He could pitch, persuade, make people laugh and close deals even when the product was still rough around the edges. This relentless drive to sell, to get in front of customers, no matter where it would be, and to learn from every interaction kept the lights on and the momentum going.
- Demos were structured for impact: discovery, storytelling, short product reveals, and Q&A.
- No feature dumping — Jimenez sold outcomes, not just software.
- He experimented with every channel, including trade shows, cold outreach, and old-school paper contracts.
The Pivot that Changed Everything
After years of negative cash flow and market hopping, Rilla finally landed on field sales — a market desperate for exactly what their product could do. The impact was immediate:
- Productivity Soared for Customers: 30–40x improvements.
- Revenue Spiked: $130,000 in their first month in the new vertical.
- Pricing Power: Rilla could finally charge what the product was worth, moving from $30/month to $5,000/year per license, with no free trials and annual contracts paid up front. Why? There are only 12 million salespeople in America. To win, Rilla had to deliver and prove real value.
When Takeoff Finally Came
Once Rilla found the right market, growth was explosive. Years of struggle gave way to rapid expansion, major funding rounds, and industry recognition. But the product? It was fundamentally the same as it had always been. The difference was all about market fit — and the founder’s refusal to quit searching for it.
Lessons for Founders
- Stay Market-Obsessed: The right market can make up for years of red ink.
- Don’t Chase Features: Sometimes the product is fine — what you need is a new market.
- Sales Skills Matter: Great salesmanship can keep you alive long enough to find your breakthrough.
- Persistence Pays: Rilla’s story proves that sticking with your vision and adapting your market can turn years of losses into breakout success.
Jimenez’s journey isn’t about building the perfect product, it's about finding the perfect home for it, and having the grit (and sales chops) to keep going until you do.
