Rilla Masters 2026 Brings Elite Leaders Together in Miami to Build the Future of In‑Person Sales and AI

Rilla Masters Brings Leaders Together to Learn, Grow, and Build the Future of Home Improvement

MIAMI, FL, 2026 – Rilla, the AI platform built for real field work, is bringing its flagship Rilla Masters conference to The Diplomat Beach Resort in Miami for three days of high‑performance learning, coaching, and connection focused on the future of in‑person sales. Building on the momentum and impact of the inaugural Rilla Masters 2025 event, the 2026 edition is designed to help contractors, home service leaders, and sales teams turn AI‑powered insights into daily habits, stronger cultures, and scalable growth.

Last year, Rilla Masters brought together contractors, coaches, and leaders from across the country for a people‑first experience that combined real‑world learning, live product demos, and hands‑on exposure to Rilla’s newest AI tools such as Hands Free Ridealongs. The event proved that when technology, leadership, and community share the same room, teams can learn faster, execute better, and move the entire industry forward together.​

“Great technology becomes a habit. It becomes part of your day. It becomes hard to stop using,” said Sebastian Jimenez, CEO of Rilla. “Our goal is to give leaders their time back. We want technology to work for them, not against them.”​

From Las Vegas 2025 to Miami 2026

The first Rilla Masters event in Las Vegas marked a turning point for the industry. Rilla hosted one of the largest gatherings focused on AI and in‑person sales, showcasing its most ambitious product launch to date and demonstrating how AI can support, not replace, human performance. Co‑founder Michael Castellanos reflected on how far the company had come, recalling a time when Rilla had only ten thousand dollars left in the bank at an industry conference—well before hosting a premier national event of its own.

“It’s surreal. We started with almost nothing, and now we are here with our own conference, one of the biggest in the industry,” said Michael Castellanos, Co‑Founder of Rilla. “Everything we build is for our customers. Without our customers, we are nothing.”​

Rilla Masters 2026 takes that same DNA—real voices, real stories, real tools—and scales it in Miami. Hosted at The Diplomat Beach Resort, the event is built like a high‑performance training camp for sales teams, combining leadership insights, AI‑driven coaching strategies, and an environment that encourages deep connection and collaboration.

A People‑First Approach to AI and Sales

Rilla’s philosophy is simple: the future of sales is not about replacing people with technology; it is about empowering leaders and teams with tools that feel human, intuitive, and natural to use. Rilla builds AI products by going into the field, watching how contractors and reps actually work, and then designing tools that fit into their day instead of adding friction.

Hands Free Ridealongs, launched around Rilla Masters 2025, exemplifies this approach. Instead of requiring managers to sit at a desk and manually review calls, Hands Free Ridealongs allows them to use voice commands to review conversations and coach reps while driving, moving between jobs, or managing their day.

“We are not asking leaders for more time. We are giving them time back,” Sebastian Jimenez said. Customer feedback at the event reinforced that message. “It was under promised and over delivered. It was easy. It was simple. It just worked,” said Coach Aaron, a Rilla customer who tested the feature live. Another customer, Rick, shared, “This takes away the ‘I don’t have time’ problem. Now it’s not about time. It’s about wanting to do it.”​

Speaker Lineup: Building High‑Performance Cultures

Rilla Masters 2026 brings together a lineup of leaders from elite sports, technology, and home services—each selected for their proven track record in building high‑performing teams and cultures. Rather than focusing only on theory, the conference emphasizes practical systems, frameworks, and habits that attendees can immediately apply to their own organizations.​​

Featured speakers include:

• Pat Riley, President of the Miami Heat, who will share the leadership principles, discipline, and standards that built NBA dynasties with the Lakers and the Heat, and how those same frameworks can help companies build dynasty‑level sales cultures.​
• Sebastian Jimenez, CEO of Rilla, who will deliver a State of the Union on the teams winning with Rilla, the product breakthroughs driving the biggest gains, and the shifts defining the next era of in‑person sales and coaching.​
• Alan Rush, CEO of Rush Profits, known for designing sales systems and training programs that help contractors turn front‑line reps into consistent producers.
• Allan Langer, best‑selling author and body‑language sales coach, who has studied FBI interrogation and nonverbal communication frameworks to help thousands of reps read buyers’ signals and close more effectively.
• Joe Adams, CEO of Adams Automotive, who scaled his business into a $100M nationwide organization by building a culture of customer obsession and hospitality‑centric service.
• Boris Valkov, Founder of Lace AI, who partners with top brands to prioritize AI investments, measure what actually works, and turn AI into daily operational impact.
• Sarah Sharfstein, VP of Commercialization at Aspen Dental, who led the effort to scale Rilla from 0 to 1,200 salespeople in 30 days using structured training, real‑time coaching, and clear KPIs to drive adoption.
• Tyson Chen, Founder of Avoca, who focuses on the future of hybrid workforces and how companies can design sales and service organizations that are flexible, data‑driven, and resilient.
• John Thompson, Owner of Thompson Family Plumbing, a frontline operator who uses Rilla Live and real‑time coaching to drive revenue lift, protect margins, and scale performance across his team.
• AJ Jain, CEO of Broccoli, who brings a product and growth perspective on modern customer journeys and profitable scaling.
• Kathryn Howard, Founder of KP Performance, whose story—from “the clank to the bank,” scaling company sales from $3M to $30M and transforming a life behind bars into a multimillion‑dollar exit—was one of the most powerful keynote moments at Rilla Masters 2025.​
• Rob Parker, Managing Director at Piper Sandler, who offers a capital markets and strategic view on building companies that investors trust and value.
• Chris Masterson, Sales Manager at Cardinal Heating & Air Conditioning, representing the on‑the‑ground sales leadership that turns systems and tools into consistent results.

“And many more” top operators, coaches, and innovators will join them on stage and in breakout rooms, creating a cross‑section of perspectives that combines blue‑collar experience, elite coaching, and cutting‑edge technology.

Real Voices. Real Stories. Real Impact.

A defining feature of Rilla Masters is how many real voices come through—owners, reps, coaches, and leaders sharing honest reflections about performance, mindset, and leadership. With Power100 on site capturing interviews and conversations, the 2025 event documented the culture of an industry that is hardworking, people‑driven, and increasingly data‑driven.​

Attendees spoke about the importance of managing by numbers instead of emotions, the mental strength required to lead under pressure, and the conviction it takes to stand on data even when it is uncomfortable. Many returned home not only with new tools, but with new habits, new beliefs about what is possible, and new relationships that continue well beyond the event.​

Rilla Masters 2026 will amplify those voices. By placing operators like John Thompson, innovators like Boris Valkov, and culture‑builders like Kathryn Howard alongside figures such as Pat Riley and Sebastian Jimenez, the event creates a bridge between different worlds united by a shared focus on performance.​​

“Growth comes from people. Leadership comes from people. Impact comes from people,” Kathryn Howard shared from the stage at Rilla Masters 2025. Her message captured the heart of the conference and continues to shape how Rilla designs both its products and its events.​

AI, Coaching, and the Future of Sales

Rilla Masters 2025 showed that AI is not replacing salespeople; it is helping them perform better by making coaching easier, more consistent, and more data‑driven. Rilla’s AI tools are built to support leaders, coaches, and teams in real ways—from call reviews and objection analysis to hands‑free coaching experiences that fit into busy schedules.​

With tools like Hands Free Ridealongs, AI becomes part of daily life, not extra work. Leaders can coach while driving. Teams can learn while working. Growth becomes part of the day, not another task on the list. Rilla Masters 2026 will continue to spotlight how AI and real‑time conversational intelligence can be integrated into onboarding, performance management, and everyday operations across large teams.

Culture, Community, and Shared Growth

Above all, Rilla Masters is about people. The conference creates space where leaders support leaders, teams support teams, and growth feels shared—not isolated. Rilla, Power100, and the leaders in the room have shown that the future of the home improvement and in‑person sales industries is not just about tools; it is about trust, culture, learning, and community.​

Rilla Masters 2026 will again bring together leaders, builders, thinkers, and doers who care about the future of their teams and their industries. It will highlight that:

• Leadership matters.
• People matter.
• Culture matters.
• Innovation matters.
• Community matters.

Rilla Masters is not just a place to hear about the future; it is a place where the future is actively being built.