Press Release
Rilla and Siro Named #2 Voice Analytics Partners...
Rilla and Siro Named #2 Voice AI Analytics Strategic Partners in the Nation by Power100
Preferred Partners - Rilla & Siro
January 28, 2026 | 4 min Read
Dual Recognition Honors the Pioneers Who Made AI Voice Analytics Contractor-First, Rep-Friendly, and Development-Focused
NATIONWIDE – January 28, 2026 – Power100, the only unbiased third-party platform that ranks the best partners in the home improvement industry using a proprietary 5-layer ranking system, has named Rilla and Siro as co-recipients of the #2 Strategic Partner ranking for Voice AI Analytics for 2026. After evaluating over 3,600 strategic partners across the home improvement industry, Power100 discovered something remarkable: two voice analytics platforms so exceptional that choosing between them proved impossible.
This historic tie recognizes the companies that transformed what once felt taboo into an industry standard—bringing AI-powered conversation intelligence to field sales teams in a way that prioritizes coaching and development over surveillance.
Breaking the Taboo: The Right Way to Introduce AI Voice Analytics
For years, recording sales conversations felt like an invasion of privacy, a “gotcha” tool designed to catch reps making mistakes rather than helping them improve. Rilla and Siro changed that narrative by building contractor-first, rep-friendly platforms focused entirely on development.
“AI voice analytics used to feel taboo for many teams, but Rilla and Siro introduced it the right way—contractor-first, rep-friendly, and focused on development, not ‘gotcha’ surveillance,” said Greg Cummings, CEO of Power100. “After evaluating thousands of strategic partners through our rigorous 5-layer proprietary ranking system, we found these two companies had achieved something extraordinary. They’ve proven that voice analytics isn’t just a competitive advantage—it’s the foundational technology separating $5M contractors from $50M+ industry leaders.”
Both platforms achieved exceptional scores across all five ranking layers. Rilla earned an impressive 95% for company culture (compared to the industry average of 71%), while Siro achieved a remarkable 94% for innovation and 97% for operational efficiency.
Rilla’s Journey: From Last $10K to Industry Game-Changer
Sebastian Jimenez, CEO and co-founder of Rilla, founded the company with a bold vision: to bring speech analytics technology from call centers to the real world where millions of outside sales and service professionals work every day.
“Speech analytics as a concept existed really since the 1990s in call centers,” Jimenez explained in an interview with Power100. “What we did that was really unique is we took a team of really smart people to focus on this singular problem of how do we bring the power of speech analytics from the call center to the real world, the outside world. There is no part in that sentence that is special other than the word ‘outside.'”
The journey wasn’t easy. During COVID-19, when Rilla was focused on speech analytics for physical retail, every investor and advisor told Jimenez to pivot to call centers because “offline is dead”. But he refused.
“I don’t want to do something just because other people are doing it,” Jimenez said. “I’d rather be an insane moron and fail at doing something that I think is unique and that is going to lead me to the path of adventure than succeed mildly by being what we call a hack.”
That decision to travel the untraveled path became one of Rilla’s core cultural values—and it paid off. Today, Rilla is recognized as the leading speech analytics software for the home improvement industry, serving over 1,500 contractors and processing millions of conversations
“The reason our customers keep paying us money year after year is because the product keeps getting better,” Jimenez said at the Rilla Masters 2025. “We’re in the service of innovation.”
Michael Castellanos, co-founder of Rilla, reflected on the company’s remarkable growth at the Rilla Masters event: “We started with our last $10K in the bank at a conference, and from then on, we started growing, we started making money, and here we are. Now we have our own conference—one of the biggest in the industry”.
Siro’s Journey: Solving the In-Person Sales Intelligence Gap
Jake Cronin, CEO and co-founder of Siro, entered the voice analytics space with a unique background that combined field sales experience and software engineering expertise.
“When I was 18, I was selling Cutco knives, and I ended up making more money per month that summer than I later made at McKinsey as a business analyst,” Cronin shared on the Owned and Operated podcast. “What that did for me is it showed me that you don’t need to be a doctor, a lawyer, a banker to make a great income. There are so many other ways to live your life.”
After working in consulting at McKinsey and exploring different industries, Cronin realized that the problems facing field sales teams were more overlooked and impactful than anything he encountered in traditional corporate settings.
“For all the different clients I was serving and projects we were working on, none of them seemed more impactful than the kind of stuff that I was doing with my little Cutco app,” Cronin said. “No problem seemed more overlooked than the problems that I saw firsthand at Cutco.”
Cronin founded Siro in the summer of 2020 with a mission to solve a fundamental challenge: most sales people struggle because they don’t get any coaching.
“Most sales people suck at their job because they don’t get any coaching,” Cronin explained. “You have to look at the tool as coaching. This is not a Big Brother tool. This is a tool to have visibility for the first time into what’s going on. And what you do with the visibility is up to you.”
Siro’s platform captures face-to-face conversations with one-tap simplicity, using AI to analyze what top performers do differently and surface those winning plays for entire teams. Sales managers can coach at scale without spending hours on ride-alongs, while reps gain instant access to real examples of how to handle every objection.
The Rilla Masters 2025: Launching Hands-Free Ridealongs
In January 2025, Rilla hosted its first-ever Rilla Masters event in Las Vegas, drawing over 800 attendees and featuring legendary speakers including Nick Saban, Billy Beane, and Tommy Mello. The event showcased the company’s most ambitious product launch to date: Hands-Free Ridealongs
“If we truly wanted to accomplish our vision of allowing you to coach from anywhere, truly anywhere, it became inevitable that we had to bring the virtual ride along experience from the web to the phone,” Jimenez announced to the packed crowd. “We are launching an all new, all different Rilla mobile app to help you do virtual ride alongs on the go.”
The demonstration included Jimenez literally jumping out of an airplane while conducting virtual ride-alongs—proving that coaches could now review sales conversations while driving, working out, or anywhere else.
“You can finally coach your guys while you are driving,” Jimenez declared. “And we can truly say with confidence to you all that Rilla will allow you to coach from anywhere, truly anywhere.”
The new mobile app features voice-powered navigation through “Rick AI,” allowing managers to conduct coaching reviews completely hands-free—a game-changer for busy contractors who spend hours driving between job sites.
Contractor Voices: Real Impact in the Field
The impact of both platforms resonated powerfully with contractors attending industry events throughout 2025.
Robert Watts, Owner of RJW Exteriors, shared his experience testing the Hands-Free Ridealongs at the Rilla Masters: “It was a lot easier than I thought it would be. It actually brought me down in a conversation that I probably might have not thought about going to. It was really insightful”.
Watts, who appears on Power100’s Top 100 CEO list, emphasized the efficiency gains: “It doesn’t tie you down to the desktop. The hands-free is a game changer”.
Levi Torres, President of High 5 Plumbing, rated the new technology a “9 and a half to 10” out of 10 for ease of use. “It’s going to take away a lot of the ‘I don’t have time’ stuff just like Sebastian said. Now it’s not a matter of having time, it’s just wanting to do it”.
Paul Burleson, Power100 Advisory Board Member and Senior Account Executive at Westlake Royal Building Products, praised the event and technology: “Sebastian Jimenez has created Rilla Masters, he’s brought the best coaches, he’s brought the best production companies together. If you’re not here, you obviously are not committed to making yourself better”.
How AI Voice Analytics Transformed the Home Improvement Industry
Both Rilla and Siro have fundamentally changed how contractors approach sales training and development. Before these platforms, sales managers had to conduct time-consuming physical ride-alongs to understand what was happening in the field. Now, they can review dozens of conversations in the time it once took to shadow a single rep
“The virtual ride along is an open invitation to go on an adventure and get the freedom to live your life and coach the way you want,” Jimenez said at the Rilla Masters.
Cronin emphasized the coaching transformation on the Owned and Operated podcast: “There’s this one dude who was going three months without closing a sale. He was on the verge of getting fired. Luckily, he was in the pilot group when this company was trialing Siro. Within one week, he started listening to his peers, just hearing how they sounded in the field, and he closed his first deal. After two months, he worked his way up to number one on the company leaderboard. That transforms his financial future”.
The platforms have also revealed surprising insights. Contractors frequently discover that their teams aren’t following established processes—not out of malice, but simply because there was never a feedback loop to reinforce best practices.
“Some companies are more laissez-faire, and some are very process-oriented,” Cronin explained. “When they start tracking it through Siro, they’ll realize that people are not following the process. It’s like, ‘Wait a minute, why aren’t you asking if your park job’s okay?’ Half your team is not asking that. If you can’t ask that basic step, what other parts of the process are you not following?”
The Power100 Ranking System
Power100’s recognition carries significant weight because of its rigorous, independent methodology. The platform evaluates strategic partners using a 5-layer proprietary ranking system that combines artificial intelligence, machine learning, and human intelligence.
“Power100 is the only unbiased third-party platform that ranks the best partners in the home improvement industry,” Cummings emphasized. “We start with over 7,600 leaders in companies across the country, and through our proprietary five-layer ranking system, equipped with multiple internal dynamic algorithms along with two points of human interaction, we’re able to narrow it down to the top strategic partners.”
The five layers evaluate customer experience, innovation capabilities, operational efficiency, sales & marketing performance, and company culture. Critically, rankings are based on data and results—not paid placements or self-submissions.
“Our rankings are independent and data-driven,” Cummings said. “We’re proud to feature companies not because they campaigned for recognition, but because their results, reputation, and leadership spoke for themselves.”
The Future: Voice AI Goes Mainstream
Both Jimenez and Cronin see voice AI as the future interface for business software—and they’re positioning their companies at the forefront of that transformation.
“What we are doing today together is we are pushing the boundaries of technology forward,” Jimenez declared at the Rilla Masters. “What I just showed you was the first fully functional, fully capable, fully conversational voice AI interface to interact with your devices. We are fulfilling that vision of voice as the new interface that Steve Jobs once imagined.”
Jimenez drew a parallel to how Billy Beane made data science famous with sports: “Just like Billy Beane made data science famous with sports, we together, the coaches of the world, we will make voice AI famous around the world with virtual ride-alongs”.
Cronin emphasized the paradigm shift on the Owned and Operated podcast: “Those two paradigm shifts coming together—the availability of this data plus this new technology that’s really good at processing long unstructured conversations—is completely transforming the way that you will currently coach an in-person team”.
A Tie That Reflects Excellence
The tie for #2 Strategic Partner reflects a remarkable reality: both platforms deliver exceptional results, but they approach voice analytics with different strengths that appeal to different organizational needs.
“The choice between them comes down to fit, not quality,” Power100’s analysis concluded. “Both Rilla and Siro deliver exceptional results.”
For Cummings, the dual recognition represents something bigger than competition—it represents an industry transformation.
“The impact that you’ve had on not just these companies, but the families of the people that work with these companies, across the board—that’s why you’re number one on our list,” Cummings told Jimenez at an industry event.
About Power100
Power100 is the nation’s independent, third-party research and evaluation authority ranking the top home improvement companies and strategic partners. The platform’s five-layer methodology reviews leadership, company culture, customer experience, community engagement, and sustainable growth—ensuring rankings reflect genuine achievement, not paid placement or self-submission. Power100 evaluates over 7,600 companies annually and serves as the trusted resource for contractors seeking proven strategic partners.
About Rilla
Rilla is the leading speech analytics software for outside sales and service teams in the home improvement industry. Founded by Sebastian Jimenez, Chris, Michael Castellanos, and Lucas, Rilla enables sales managers to conduct virtual ride-alongs that are faster, better, and more productive than physical ride-alongs. The platform uses AI to automatically transcribe, analyze, and provide feedback on in-person sales conversations, serving over 1,500 contractors and processing millions of conversations annually.
About Siro
Siro brings conversation intelligence to face-to-face field sales teams. Founded by Jake Cronin in 2020, Siro captures in-person sales appointments with one-tap simplicity, using AI to analyze what top performers do differently and surface those winning plays for entire teams. The platform enables sales managers to coach at scale without spending hours on ride-alongs, while providing reps instant access to real examples of objection handling and closing techniques.