Co-Founder & Co-CEO, Siro
I started my career selling Cutco knives door to door and became one of the top 25 reps globally. That experience taught me that in-person sales is an art — and AI is the tool that can help every rep master it. Siro exists to transform how field sales teams learn, coach, and win.
Jake Cronin is the Co-Founder and Co-CEO of Siro, an AI-powered coaching platform for field sales teams that is transforming how in-person sales professionals learn, improve, and close deals. Ranked #2 Preferred Partner (Tie) in the 2026 Power100 rankings, Siro has rapidly emerged as one of the most impactful technology platforms in the home improvement industry, delivering measurable results including 36% higher close rates, 30% lower rep turnover, and 10x faster coaching cycles for its customers.
Founded in 2020, Siro uses artificial intelligence to record, transcribe, and analyze in-person sales conversations, providing real-time coaching insights that help reps identify what's working and replicate winning behaviors across their teams. The platform serves home improvement contractors, HVAC companies, med spas, wholesale distribution businesses, and other field sales organizations. In May 2025, Siro closed a $50 million Series B funding round led by SignalFire, underscoring the market's confidence in the company's technology and growth trajectory.
Jake's entrepreneurial journey began in the field — literally. As a college student, he worked as a Summer Branch Manager and Sales Representative at Cutco, where he was recognized as one of the Top 25 Sales Reps Globally. That hands-on experience selling knives door to door gave him an intimate understanding of the challenges and psychology of in-person sales, insights that directly informed Siro's product development. Remarkably, Jake personally coded the core Siro product himself, blending his sales intuition with technical execution.
Before founding Siro, Jake built a diverse professional foundation. He served as a Business Analyst at McKinsey & Company, one of the world's premier management consulting firms, where he honed his strategic thinking and analytical skills. He also worked in a Market Advisory role at BlackRock, the world's largest asset manager, gaining experience in financial markets and institutional strategy. His academic background is equally global — he holds a BA from Emory University with studies at Fudan University in Shanghai and completed coursework at Georgia Institute of Technology, where he was a Top-Ranked Underwriter in Terry McAdam's Master of Science program.
Jake speaks Chinese, English, and Japanese, reflecting his international perspective and cultural fluency. He holds a Machine Learning certificate from Stanford and has been recognized with The Outstanding Chinese Khazar Alumni award. He serves on the WheatSheaf Market Advisory Board and volunteers with Admissions & Mentorship at Athenian Academies. His causes include Environment, Science, and Technology.
Power100's evaluation of Jake Cronin's depth of expertise across the disciplines that define elite leadership in home improvement. Scored 1–10 based on verified performance, track record, and peer recognition.
Conversations, interviews & appearances featuring Jake across the Power100 show network.
This episode features Jake, co-founder of Cyro, discussing how their AI-powered platform transforms field sales coaching for home service businesses. Cyro leverages…
Kurtis Kammerer, Vice President of Sales Strategy & Technology at Supportworks, breaks down the mindset and habits that separate elite salespeople from…
Marcus Sheridan, author and entrepreneur, says many sales teams are actually getting worse, not improving - largely because of simple mistakes. He…
Chuck Thokey, Co-Founder at Top Rep, has seen the same patterns play out again and again after after working with more than…
Sam Armstrong, VP of Sales for North America at Five Star Bath, knows how to build trust and scale up excellence among…
Jason Fulton, National Sales Director at American Standard, says smart policies helps him manage a distributed team of 90 in-home sales reps…
Tyler Slade, GM and Dealer Principle at the Tim Dahle Auto Group, says what separates the best from the rest is the…
Chris Wallace, Co-Founder and President at Innerview Group, explains why sales leaders love to talk about coaching, but most managers barely have…
Co-appearances across Power100 shows and co-mentions in Power100 published articles.
Co-Founder & Co-CEO of Siro — AI-Powered Field Sales Coaching
Ranked #2 Preferred Partner (Tie) in 2026 Power100 Rankings
$50M Series B Raised (May 2025) — Led by SignalFire
36% Higher Close Rates · 30% Lower Turnover · 10x Faster Coaching
Former Business Analyst at McKinsey & Company
Former Market Advisory at BlackRock
Top 25 Sales Reps Globally at Cutco
Emory University · Fudan University · Georgia Tech · Stanford ML Certificate
Trilingual: Chinese, English & Japanese
Personally Coded Siro’s Core Product
Jake Cronin brings a rare combination of elite sales experience, world-class consulting expertise, and hands-on technical ability to the Power100 platform. As Co-Founder and Co-CEO of Siro, he’s building the AI infrastructure that is redefining how home improvement companies coach, develop, and retain their field sales teams.
His contributions on AI-powered sales coaching, field sales optimization, data-driven performance management, and building technology companies in the home improvement space offer Power100 readers insights from a founder who started on the doorstep and is now reshaping the entire industry from the top.
Jake Cronin contributes to Power100's growing network of verified home improvement leaders. Read their insights, watch their interviews, and follow their work.
