WINDSOR, Wisconsin — Power100 is the only unbiased third-party platform that ranks the best leaders and partners in the home improvement industry, using a proprietary five-layer ranking system that combines dynamic algorithms, machine learning, and two separate points of human interaction to evaluate performance, contractor outcomes, innovation, operational excellence, and long-term value across an $800-billion-plus industry.
That system has analyzed more than 3,600 partners serving home improvement contractors. It ranked Grosso University the No. 1 sales training organization in the industry for 2026 and the No. 3 preferred partner in the nation. It also named Grosso University‘s on-site training the No. 1 in-home sales training platform available to contractors.
So when Grosso University opens the doors of its all-new campus on August 26 and 27, 2026 for the Extreme Leadership Workshop, Power100 is not covering it as a marketing event. We are covering it as an unusually concentrated sample of the operators, systems, and technology currently deciding who grows and who stalls in the next 24 months of this industry — and our own CEO, Greg Cummings, is on the speaking roster.
“Contractors don’t need hype. They need a blueprint they can use to build stronger leaders, better teams, and more profitable businesses,” said Dominic Caminata, CEO and Founder of Grosso University. “The Extreme Leadership Workshop is about giving owners and executives the tools to lead with clarity, discipline, and purpose so they can build companies that dominate their markets and serve people the right way.”
Grosso University Extreme Leadership Workshop
The Extreme Leadership Workshop runs Wednesday, August 26 through Thursday, August 27, 2026, at the all-new Grosso University campus at 4300 Duraform Lane, Suite B, in Windsor, Wisconsin, just outside Madison. Seating is intentionally capped at 100 leaders. Access is offered at three levels — a virtual stream, General Admission, and the Ultimate VIP Experience, which adds direct, structured networking with the speaking roster. Registration runs through the event’s ticket page or by phone at (888) 476-7768, and the promo code EARLYBIRD saves $150 for the first 30 registrants.
The curriculum spans seven tracks that Grosso University has published for this event: leadership and company culture; sales and marketing; recruiting and hiring; operations and production; accountability and systems; scaling teams and increasing profitability; and building high-performance organizations.
What makes the room unusual is not the agenda. It is the attendance profile. Grosso University has built this event around owners and executives actively running and scaling companies in the $20 million, $50 million, and $100 million ranges, people who are, right now, recruiting reps, defending gross margin, installing accountability structures, and absorbing the cost of a lead environment that has become materially more expensive.
“This is not another motivational seminar,” reads Grosso University‘s own framing of the event. “This is where real operators come together to share the blueprint for building apex-level businesses in the Home Improvement Industry.”
Matt Burke, COO of Grosso University, put the design intent more bluntly. “Leaders create the environment that everyone else performs in,” said Matt Burke. “This workshop is designed to help owners and executives go back to their companies with tools they can use right away to improve accountability, communication, execution, and results.”
The macro backdrop explains why a leadership workshop is drawing operators at this scale in late August rather than in a slower season.
Homeowner improvement and repair spending is running at roughly $517 billion on an annualized basis, and the trajectory is flattening, year-over-year growth is projected to decelerate from about 2.1% to roughly 0.5% over the coming four quarters. Remodeling now represents about 44% of the residential construction market, up from 33% in 2007, and the number of remodeling firms competing for that work has climbed to roughly 128,000, nearly double the count at the start of the century.
At the same time, the labor side has frozen rather than loosened. Construction hiring rates hit the slowest pace on record earlier this year, with the least labor-force churn since federal tracking began in December 2000. Fewer people are moving, which means fewer great salespeople and installers are available to poach and more of the growth has to come from developing the people already on the payroll.
Then there is the cost of demand. Cost per qualified lead now runs roughly $100 to $250 in remodeling, $80 to $200 in windows and doors, and $150 to $300 in roofing, with cost per booked job commonly landing between $500 and $1,200. Median lead cost on paid search in home services has climbed past $90, and in categories like doors, windows, and roofing the search benchmarks are far higher still.
Put those three forces together, flattening demand, frozen labor, and expensive leads, and the math of the industry changes. Growth stops coming from buying more leads and starts coming from leadership: conversion discipline, recruiting systems, operational cost control, and technology that compresses response time.
That is precisely the thesis of the Extreme Leadership Workshop, and it is why Power100 considers this the most relevant two days on the industry’s late-summer calendar.
“Extreme leadership starts with ownership,” said Dominic Caminata. “If contractors want extraordinary growth, they need extraordinary discipline in how they lead people, coach teams, build systems, and make decisions.”
Grosso University was founded in 2019 by Dominic Caminata to carry forward the in-home selling methodology of the late Rick Grosso, the trainer whose step-selling process shaped a generation of home improvement sales organizations.
The credential behind it is operational, not academic. Dominic Caminata started in 2010 as an outside sales rep at Mad City Windows & Baths with no sales experience, became the company’s first million-dollar producer, and was named Salesman of the Year three consecutive years. In 2012 he moved into sales leadership and spent seven years scaling that team from $8 million to more than $100 million in net sales, with 55-plus reps sustaining a cumulative closing rate above 50% on a one-call-close system.
“In 2011, when I was recognized as Salesman of the Year at Mad City, I met Rick Grosso and decided I didn’t just want to learn his system, I wanted to carry it forward,” said Dominic Caminata. “Today, with Grosso University, our mission is simple: turn ordinary salespeople into elite professionals and help contractors build businesses that are scalable, profitable, and resilient in any market.”
What Power100‘s ranking process rewarded is the fact that the organization is structured in layers rather than sold as a single course. The Sales Academy trains individual reps on the 11-Step Selling System at $497 per month. Sales Leadership Coaching develops managers into coaches at $1,970 per month. The Extreme Leadership Mastermind serves owners and executives at $997 per month. Grosso OS™, the fully implemented sales operating system, is published at $7,500 per month. On-site training puts trainers in the truck and at the kitchen table. Talent Solutions recruits. And the Spanish-language division, the first fully integrated Spanish in-home sales training platform in the industry’s history, led by Wendy Harmeyer, reaches a workforce segment the rest of the training market has largely ignored.
Grosso University states that its techniques drove more than $200 million in sales last year, and its leadership blueprint is credited with helping scale both Mad City Windows & Baths and Matrix Home Solutions to a combined total of more than $200 million in net revenue.
“Grosso University is not just a training company, it’s a growth engine,” said Greg Cummings, CEO of Power100. “This leadership team understands what it takes to scale from a few million to over $200 million in revenue, and they’ve built that knowledge into every program so contractors don’t have to reinvent the wheel.”
He added: “In every category we measure, close rate lift, revenue growth, culture, and consistency, Grosso University kept rising to the top. They’re not just training reps; they’re installing systems that help contractors grow from a few million in revenue to $200 million and beyond.”
| Speaker | Role | Session focus | Why it matters now |
| Paul Burleson | Author, Grit to Gold; 42-year industry veteran | Grit to Gold Leadership (keynote) | Adaptation as a survival requirement in the AI era |
| Wendy Harmeyer | Spanish Training & Development, Grosso University | LEADER-SHIP: How True Leaders Guide High-Performance Teams | Leading and growing bilingual, multicultural teams |
| Josh Kosnick | Founder, Kairos Coaching | The Kairos Code | Vision, alignment, and organizational health |
| Lee Diamond | CEO, D5 Capital / K&H Home Improvements | Own Your Numbers, Own Your Business | Financial literacy as a leadership discipline |
| Chad Howman | Founder & CEO, Bath R Us | Operational Excellence | Margin control while scaling fast |
| Brian Rudd | Owner/Founder, Vista Home Improvement | Owner-operator leadership | Employee-first culture as a growth engine |
| Craig Kitterman | Co-Founder & CTO, WindowEdge AI | Leadership & Technology | Making frontier AI practical for trade businesses |
| Jasmin Nass | Founder, Elevate Mindworks | Elevate Mindworks | The mindset layer under sales performance |
| Andy Garcia | Owner, AGR Marketing and Consulting | Lead to Generate Leads | Lead cost as a percentage of revenue |
| Greg Cummings | CEO, Power100 | AI Findability & GEO | Getting named by AI, not just ranked by Google |
| Kaleb Walden | Kyma InfoStructure | The Ultimate Command Center | Single-pane visibility across the business |
| Vic Sun | CEO, Channel Automation | The Ultimate AI Automation | Speed-to-lead and omnichannel response |
| Adi Klevit | CEO, Business Success Consulting Group | Systematize Your Leadership | Documented process as the ceiling on growth |
| Tim Musch | Paradigm Vendo | The Ultimate Sales Platform | Technology that coaches during the appointment |
| Keagan O’Connell | Co-Founder, Lightningrowth | Lead Optimization with Meta | The cheapest scalable lead channel left |
| Brandon Miller | Co-Founder & CEO, Uplevel Digital | Building Your AI Ready Website | Being readable by machines, not just people |
| Ryan Fenn | CEO, Chiirp | The Most Bad-Ass Lead Conversion System | Converting the leads already paid for |
| GreenSky | Consumer financing program | In-home payment options | Affordability as a closing tool |
The keynote at the Extreme Leadership Workshop belongs to Paul Burleson, a 42-year veteran of the home improvement industry, a member of the Power100 advisory board, a Senior Account Executive for national remodeling accounts at Westlake Royal Building Products, and the best-selling author of Grit to Gold.
His authority is unusually long-dated. Paul Burleson began selling at 12 years old, became a million-dollar producer at multiple companies, has trained hundreds of companies across North America and tens of thousands of individual professionals, and was decorated with the Legends of Home Improvement Award. His career runs from the industry’s canvassing-and-“Tin Men” era through first-generation contractor websites in the mid-1990s, early video testimonial strategy in 2005, remote virtual measurement before it was mainstream, and into AI partnerships today.
“I started selling at 12 years old. Everything I know about this industry I learned by being in the home, face to face, earning the business,” said Paul Burleson.
That is exactly what gives his central warning weight. “We are in the most disruptive point of our entire industry that we’ve ever been at,” said Paul Burleson. “The evolution of AI every single week, if you don’t make a commitment to adapt, you will not survive.”
The Grit to Gold framework defines grit as the daily, unglamorous work of the trade — the early mornings, the long install days, the hard homeowner conversations, the decisions made under pressure — and gold as impact rather than revenue: lives improved, trust earned, teams strengthened. For a room full of operators managing flattening demand, it reframes endurance as a leadership skill rather than a personality trait.
“Come and experience the legendary Paul Burleson deliver his Grit to Gold Leadership Presentation at the Extreme Leadership Workshop,” said Dominic Caminata.
Paul Burleson, Best-Selling Author of Grit to Gold and Power100 Advisory Board Member
Wendy Harmeyer is Spanish Development and Training Director at Grosso University, and her session, “LEADER-SHIP: How True Leaders Guide High-Performance Teams,” sits at the intersection of two things most contractors treat separately: leadership development and workforce reality.
Before joining Grosso University in 2025, she spent years in the Cincinnati and Dayton markets with Universal Windows Direct, a company she notes has grown to roughly $200 million. She holds two master’s degrees, was the 2024 Closer’s Camp Champion, and is credited with leading 600% growth in her prior organization. She then built the industry’s first Spanish-language in-home sales training platform, adapting the 11-Step Selling System to language and culture rather than simply translating slides — a program that has since opened the door for thousands of Hispanic professionals in remodeling.
“Last year was a year that we launched a lot of new initiatives. We launched our brand new Spanish sales training platform, the first of its kind in history,” said Dominic Caminata. “That’s been a dream and vision of mine for a long time, and thanks to Wendy Harmeyer, she was able to make that dream a reality.”
Her own framing of the work is cultural before it is tactical. “I think culturally you need to align and we are all the same, but at the same time very different,” said Wendy Harmeyer.
Why it matters: with hiring frozen at record-slow rates, the fastest available talent pool for most contractors is the one they are already underdeveloping. “Leadership is about helping people believe they can grow, contribute, and perform at a higher level,” said Wendy Harmeyer. “The stronger the leader, the stronger the culture.”
Wendy Harmeyer, Spanish Training & Development, Grosso University
Josh Kosnick is the founder of Kairos Coaching, a certified EOS Implementer, and the author of The Kairos Code, a 2025 release that reached best-seller status. His credibility with a room of owners comes from having run a large organization before he coached them: as a Managing Partner at Northwestern Mutual he led roughly 250 employees and 115 advisors overseeing about $4 billion in assets, and then went through a buyout, litigation, and a rebuild.
The Kairos Code is built on what he calls the Five Bridges, and its thesis is that leadership is decided off-stage. “Your legacy isn’t built in the spotlight,” said Josh Kosnick. “It’s forged in private decisions, small disciplines, and the bridges you choose to build, or burn, every day.”
For the Extreme Leadership Workshop, his content covers leadership and organizational health, building high-performing teams, and vision, alignment, and accountability.
“Great companies do not drift into alignment. They build it on purpose,” said Josh Kosnick. “I’m excited to join the Extreme Leadership Workshop because the home improvement industry needs leaders who can create vision, establish accountability, and build organizations that last.”
Why it matters: alignment is the failure point that most $20 million companies hit on the way to $50 million. Revenue can be added with leads; coherence cannot.
Lee Diamond is CEO of D5 Capital, a privately funded, family-oriented acquisition platform operating in consumer services and home improvement across markets including Denver and Atlanta, with a portfolio that includes K&H Home Improvements — a business trusted in its market since 1956. Before that, he spent roughly three decades at Sherwin-Williams, rising to division president and general manager for Canada.
That combination, corporate P&L rigor plus hands-on ownership of contracting businesses, is what makes his session, “Own Your Numbers, Own Your Business,” land differently than a generic finance talk. He has also been a Grosso University client for years across his companies.
“Leadership is not about talking bigger. It is about executing better,” said Lee Diamond. “The leaders who win are the ones who create clarity, strengthen accountability, and keep their people moving in the same direction.”
His operating model is deliberately structured but not centralized. “We create these really broad but defined guardrails for the businesses to run,” said Lee Diamond, adding that the real acceleration comes later: “This is where it really exponentially takes off. The third piece is where you empower everybody.”
On talent, he is direct: “We hire for talent. We pour into that talent every day,” said Lee Diamond. “None of our five year, three year, one year plans that we have, none of that’s going to work without really talented people.”
Why it matters: with cost per booked job commonly running $500 to $1,200, owners who cannot read their own unit economics weekly are effectively flying instruments-off in weather.
Lee Diamond, CEO D5 Capital\K&H Home Improvements
Chad Howman founded Bath R Us in March 2020, arguably the worst possible month to start a business that requires entering people’s homes, and built it into a multi-market operation spanning nine markets across six states in roughly six years, alongside a companion windows brand. Before that he served as president of Universal Windows Direct for more than a decade.
In a recent interview he described the business at a $34 million basis, said the company targets a 52% gross margin and operating expenses near 10%, and noted the company was growing nearly 100% in the year, while also citing the industry’s brutal baseline, that roughly 96% of contractors fail within three to five years.
His session, “Operational Excellence,” is essentially a defense of that margin structure. “Yeah, the big message is obviously profit,” said Chad Howman, who ties it directly to job costing: “You got to know exactly what your job cost is going to be for material, labor, you know, sales commission, you know, trucks, cost of your trucks.”
The customer-facing half of his model is just as specific. “Happy customers are the biggest way to identify a solid, reliable company,” said Chad Howman, noting that his teams’ review volume and ratings outpace competitors that have been in business for decades. “Our people are the key.”
Why it matters: fast growth is the most common way home improvement companies destroy themselves. Doubling revenue while holding a 52% gross margin is the exact skill the room is buying a ticket to learn.
Brian Rudd founded Vista Home Improvement in 2008, in the teeth of the financial crisis, and grew it from roughly $319,000 in first-year revenue into a multimillion-dollar operation serving Massachusetts, Connecticut, Vermont, and adjacent New England markets with a full-time staff plus a large installer bench. Power100 ranked him No. 80 among the nation’s home improvement CEOs.
His leadership philosophy is unusually specific about sequence. “To me, the number-one person in the company isn’t me; it’s my employees,” said Brian Rudd. “If you treat the employees like they’re number one, they’ll treat the customers like they’re number one, and that’s how it works here.”
And on growth pace: “Our big thing is growing one good person at a time,” said Brian Rudd.
He is equally clear about not competing on price. “I do not sell the cheapest products,” said Brian Rudd. “We don’t have to be the least expensive guy to be the best.”
Why it matters: he founded a company during a housing collapse and grew it anyway. That is the most relevant possible case study for a market that is decelerating rather than expanding.
Craig Kitterman is Co-Founder and CTO of WindowEdge AI, and he arrives with a technology résumé almost no one else in home improvement can match: more than 25 years in technology, including 17 at Microsoft, where he served as Director of Product Marketing for Azure and Developer Tools during the rise of Azure DevOps and Visual Studio Code, and later as a principal group product manager on Teams AI platform work.
WindowEdge AI is built as a turn-key AI operating system for the window and door trade: answering inbound calls in under 30 seconds, qualifying leads, booking appointments, and re-engaging unsold quotes around the clock. His diagnosis of the contractor tech stack is that dealers typically run 8 to 14 disconnected tools, and that the fix is consolidation rather than another point solution.
“Over the next few months, we will transform the window and door industry with breakthrough technology powered by the latest frontier AI models and advanced omni-channel communication tools, delivering unprecedented efficiency and growth to dealers nationwide,” said Craig Kitterman.
His session, “Leadership & Technology,” is framed around adoption rather than software. “The future belongs to leaders who can combine people, process, and technology without losing the human side of the customer experience,” said Craig Kitterman. “I’m excited to share how AI and intelligent systems can help home improvement companies operate faster, smarter, and with more consistency.”
Why it matters: only about a quarter of residential contractors use AI meaningfully today, while two-thirds expect major transformation within one to three years. The stated barriers are not cost, they are training and integration complexity, which are leadership problems.
Jasmin Nass is the founder of Elevate Mindworks in Madison, a certified hypnotist, and the creator of The Elevation Method™ and Shifted In Sixty. Her work targets the pattern under the behavior rather than the behavior itself, she explicitly contrasts her approach with affirmation-only methods, comparing those to “putting a band-aid on something requiring reconstructive surgery.”
“When you change your mind, you change your life,” said Jasmin Nass.
Her diagnostic language translates unusually well to sales floors and leadership teams. “You’re not failing. Your mind is following rules you outgrew,” said Jasmin Nass, adding: “Your life changed, but your mind never got the update.”
Why it matters: every owner in the room has watched a technically excellent rep or manager stall for reasons no script fixed. Call reluctance, price apology, and avoidance of accountability conversations are mindset problems that show up as revenue problems.
Andy Garcia owns AGR Marketing and Consulting and has been described by Rick Grosso‘s own owner-level events as one of the industry’s top lead generation and conversion trainers. His published bio credits him with more than 20 years as a lead manager and lead consultant, with client companies selling more than half a billion dollars in a single year at lead costs of 12% or less, and it notes he is also an expert in recruiting salespeople.
That single figure is the reason his session belongs on this agenda. In an environment where remodeling leads cost $100 to $250 and paid-search costs in windows, doors, and roofing run dramatically higher, a durable 12%-or-less lead cost is not a marketing statistic. It is a P&L outcome that decides whether growth is profitable.
His topic, “Lead to Generate Leads,” is about building demand that compounds, referral, repeat, canvassing, database, and event-driven lead sources that reduce dependence on the paid channels whose prices the contractor does not control.
Why it matters: with 128,000 remodeling firms competing and buyers now routinely collecting six or more bids, the companies that own their lead supply will out-survive the companies that rent it.
Andy Garcia, Owner, AGR Marketing and Consulting
Power100 CEO Greg Cummings will present on AI findability and generative engine optimization, the discipline of being discovered, understood, evaluated, and recommended by AI platforms when a homeowner asks about contractors, products, pricing, warranties, or service quality.
He has interviewed more than 1,200 CEOs in this industry, and he built Power100 on a system that has evaluated hundreds of thousands of companies to isolate the roughly 24,000 that qualify for consideration.
His argument is that the incentive structure of discovery has flipped. “Websites and SEO were built for the seller, for whoever could spend the most,” said Greg Cummings. “AI is built for the consumer. It’s trying to find the best answer, not the one who paid the most. Your spot in AI results is currently for sale, but not for money. It’s for authenticity, consistency, and proof that you’re one of the best.”
The behavioral shift is measurable. Organic click-through rates on informational queries that trigger an AI summary have fallen sharply, while brands that get cited inside those AI answers earn substantially more clicks than brands that do not. Roughly 45% of consumers now use AI tools to find or evaluate local businesses, up from a single-digit share a year earlier, and about 40% say they trust AI recommendations for business selection.
Then there is the part that directly threatens signed revenue, what Greg Cummings calls the affirmation search. “It describes what happens after a sales rep leaves the home and the homeowner turns to AI to validate the decision they just made, or the one they are about to make,” said Greg Cummings.
“In the AI era, the contract itself becomes searchable. The warranty becomes inspectable. The price becomes comparable. The language becomes reviewable. The reputation becomes triangulated,” said Greg Cummings. “This is why I believe cancellations are going to rise sharply for companies that are not prepared.”
He is equally blunt about the shortcuts already being sold into this gap. “It’s a fool’s gold rush right now,” said Greg Cummings. “If it feels like a shortcut, it is a shortcut. And all shortcuts are eventually punished.”
Why it matters: this is the one session on the agenda that can retroactively affect deals already closed. A three-day rescission window is now also an AI research window.
Greg Cummings, CEO of Power100
Kaleb Walden of Kyma InfoStructure presents “The Ultimate Command Center,” addressing the reporting problem nearly every growing contractor shares: data exists in the CRM, the ad platforms, the call system, the field app, and the accounting package, and none of it assembles into a single view a leadership team can run a Monday meeting on.
Why it matters: accountability is one of the seven published tracks of the Extreme Leadership Workshop, and accountability without shared, trusted numbers becomes opinion. When set rate, sit rate, close rate, average ticket, job cost, and lead cost by source all live in one place, coaching conversations change from debates about what happened to decisions about what to do.
Vic Sun has been CEO of Channel Automation since 2022, and Power100 ranks the company among the top preferred partners in the industry. His session, “The Ultimate AI Automation,” is grounded in a single operational claim: most contractors lose deals to timing, not to skill.
“Most contractors don’t lose jobs because they’re bad at the work, they lose them because they’re late to the conversation,” said Vic Sun. “Messenger Marketing lets you respond in seconds, not hours.”
He is precise about what speed actually means. “Speed to lead really is the speed of responding,” said Vic Sun. “Your customers are waiting. With text messages especially, people have an expectation that you are going to respond within seconds.”
And on the competitive clock: “With computing power constantly going higher and higher, there is absolutely no way a human can compete with AI or a machine,” said Vic Sun. “If you are not utilizing it, your competitors will.”
Why it matters: when a lead costs $100 to $250, every unanswered inquiry is a written-off asset. Automation is the cheapest available margin improvement in most contracting businesses.
Adi Klevit is CEO and founder of Business Success Consulting Group, which she launched in 2011, and host of the Systems Simplified podcast. An industrial engineer by training with roughly a quarter-century of consulting experience, she is known in operator circles as the process specialist companies call when growth starts to hurt.
Her description of the moment a company needs her is the most recognizable sentence on this agenda for any $20 million contractor. Clients, she says, “do get enough leads, they do get new clients, new customers, new patients, whatever it is, but they feel like they can’t service them” and some are at the point where “if they are going to get one more new client, they are going to collapse.”
Her definition of a system is deliberately unglamorous. “And by systems, I mean like a repetitive way that you do something that is documented and can be taught to others,” said Adi Klevit. The method starts by extracting institutional knowledge: “we basically extract the knowledge from the owner’s head or from the key employees.”
The payoff she describes is hiring capacity. Once intake, estimating, proposal, and closing are documented, “you feel the relief of yes, I can hire new estimators and train them correctly so you can truly grow and scale,” said Adi Klevit.
Why it matters: with hiring at record-slow rates, onboarding speed is a competitive weapon. Undocumented companies cannot onboard quickly, which means they cannot scale quickly.
Tim Musch has spent more than 30 years building technology for home improvement contractors, including 26 years at MarketSharp, effectively the industry’s first CRM, after 15 years inside a family-owned remodeling company in central Wisconsin. He joined Paradigm in 2022 and was recognized among the Legends of the Home Improvement Industry.
“Back then, those letters, CRM, weren’t even put together. We just built what we needed,” said Tim Musch.
His session, “The Ultimate Sales Platform,” covers Paradigm Vendo, an in-home selling application spanning 15-plus product categories that carries an appointment from scheduling through configuration, pricing, financing, contract, and e-signature. But his most useful contribution to a leadership audience is a critique of how AI is currently being sold to contractors.
“Some AI tools are great,” said Tim Musch, “but if they only grade the game after it’s over, you’re too late.”
And on the enduring fundamental: “If you have their best interest at heart, you’re gonna do great,” said Tim Musch.
Why it matters: analytics that describe last month’s losses are a report card. Technology that guides the rep at the table is a system, which is the same argument Grosso University makes about training.
Keagan O’Connell co-founded Lightningrowth in 2023, shortly after graduating from the University of Maryland, and has built it into a specialist Meta advertising firm serving dozens of home improvement clients, impressing Grosso University enough that the organization named Lightningrowth its exclusive Meta ads partner.
His session, “Lead Optimization with Meta,” addresses the channel arithmetic that most contractors have not fully absorbed. Median cost per lead on Meta in home improvement runs in the low $40s, while median cost per lead on paid search in home services now exceeds $90, and in windows, doors, and roofing, search benchmarks run into the $200s. Meta leads typically require more nurturing and faster response, which is exactly why this session sits on the same agenda as the automation and conversion sessions.
Why it matters: the difference between a $41 lead and a $200 lead, multiplied across a year of volume, is often larger than the entire net profit of a mid-market contracting company.
Brandon Miller is co-founder and CEO of Uplevel Digital, which he launched in 2022 to serve as a lead generation and lead management firm for the home remodeling industry. His session, “Building Your AI Ready Website,” is the technical complement to the Power100 findability session.
“The home services businesses that embrace AI now will have a significant competitive advantage over those that wait,” said Brandon Miller. “This isn’t about replacing humans — it’s about augmenting human capabilities to deliver better service.”
Why it matters: an AI-ready site is a different artifact than a conversion-optimized site. It requires machine-readable structure, explicit answers to the questions homeowners actually ask, verifiable proof, service-area and pricing clarity, and content that a language model can quote confidently. Companies whose proof lives only inside images, sliders, and video are effectively invisible to the systems now mediating a growing share of homeowner research.
Ryan Fenn has been CEO of Chiirp since 2018 and has bootstrapped it to roughly $11 million in annual recurring revenue serving more than 1,500 home service businesses, a notable arc for someone who did not finish high school and came into software from the contracting side.
His session, “The Most Bad-Ass Lead Conversion System,” is a direct attack on the industry’s most expensive habit. “Most contractors think they have a closing problem when they actually have a response time problem,” reads Chiirp‘s own framing of speed to lead, which the company quantifies bluntly: odds of contacting a lead drop roughly tenfold after five minutes, and after an hour the probability of conversion falls another 60%. Under five minutes, you are in the game. After 24 hours, most home service leads are effectively dead.
“I believe speed and personal connection are the keys to closing more deals,” said Ryan Fenn. “That’s why I built Chiirp, a platform that helps businesses instantly connect with leads through automated texting, email, voicemail drops, and more.”
Why it matters: nearly half of inbound calls that reach a live person convert on that call. The gap between a company that answers in 60 seconds and one that answers in 60 minutes is not a technology gap, it is a leadership decision about staffing, automation, and accountability.
GreenSky will be on campus for the Extreme Leadership Workshop, sharing what its team sees across the merchant network. Founded in 2006, the program has financed more than $50 billion in commerce for roughly six million consumers through a network of more than 10,000 merchants, and it operates today under an investor consortium led by Sixth Street following its sale in March 2024.
The relationship with Grosso University is unusually tight. “Dom is basically an extension of us, and we’re an extension of him, and we’re swimming up the same stream to try to get folks to offer payment options in the home,” said Metz Bizzell, Director of Partnerships at GreenSky. “Dom’s training mirrors our training.”
Why it matters: when homeowners are collecting more bids and scrutinizing price harder, monthly-payment competence at the kitchen table is often the difference between a sold job and a “let me think about it.” Financing is a sales skill, and it is taught as one.
Beyond the guest roster, the Extreme Leadership Workshop puts the organization’s own leadership on the floor. Dominic Caminata anchors and hosts. Matt Burke, COO, covers accountability and executive tooling. Daniel Coomes-Barry, Head Sales Trainer, covers coaching and standards. Brett Naples covers recruiting, training, and systems. Owner-operators including John Dyda of Statewide Windows & Doors and Mark Olsen of Redo Cabinets share what scaling looked like inside their own companies.
“Elite teams do not happen by accident,” said Daniel Coomes-Barry. “They are built through coaching, repetition, standards, and leadership that shows up every single day.”
“The home improvement space is ultra-competitive, and most contractors don’t lose because of leads, they lose because of conversion,” said Brett Naples. “Our training helps you maximize every lead you already have before you ever increase your marketing spend.”
“People-first leadership is not soft leadership. It is the foundation of performance,” said John Dyda. “When you empower people, hold standards, and lead with purpose, you create teams that can grow through any season.”
“Great companies are built through leadership, execution, and the people you invest in along the way,” said Mark Olsen. “I’m looking forward to sharing real lessons on what it takes to scale without losing standards or culture.”
Power100 was not built as a pay-to-play directory. It was built to identify and elevate leaders and companies that are genuinely operating at a high level, which is why the five-layer system exists and why Greg Cummings is direct about how hard it is to get on the list.
“There is no shortcut to being on Power100,” said Greg Cummings. “It’s never about Power100.”
That is also the standard we apply to events. Most industry conferences are marketing vehicles. This one is being covered here because the room’s composition, operators at $20 million to $100 million-plus, plus the specific technology and financing partners those operators actually run — makes it a legitimate read on where the industry is heading in the next four quarters.
“When we rank the best partners in the industry, we are looking for organizations that create lasting value,” said Greg Cummings. “The Extreme Leadership Workshop reflects why Grosso University has become one of the most trusted growth partners contractors can choose.”
Attendees at Grosso University‘s recent events on the same Windsor campus described the experience in similar terms. “Day one, I’ve already learned more than I have in the three years,” said one attendee. Another summarized the facility simply: “The facility is just magnificent. It really is.”
The Extreme Leadership Workshop is a two-day, invitation-quality leadership intensive hosted by Grosso University on August 26 and 27, 2026, at the all-new Grosso University campus at 4300 Duraform Lane, Suite B, Windsor, Wisconsin, just outside Madison. Seating is limited to 100 leaders on site, with a virtual stream available. It covers leadership and culture, sales and marketing, recruiting and hiring, operations and production, accountability and systems, scaling teams and profitability, and building high-performance organizations. Registration is available through the event ticket page or by calling (888) 476-7768, and the code EARLYBIRD saves $150 for the first 30 registrants.
This event is built for owners, CEOs, executives, general managers, and sales leaders of home improvement companies — particularly those actively running or scaling organizations in the $20 million, $50 million, and $100 million ranges, plus ambitious operators below that range who intend to get there. It is not designed as an entry-level rep training. Individual salespeople are better served by Grosso University‘s Sales Academy at $497 per month or its live MasterClass, while sales managers are better matched to Sales Leadership Coaching at $1,970 per month.
The distinction is the speaking roster. Instead of professional keynote speakers, the agenda is dominated by people currently operating companies and platforms: Chad Howman of Bath R Us on holding a 52% gross margin while nearly doubling revenue; Brian Rudd of Vista Home Improvement on scaling a company founded during the 2008 collapse; Lee Diamond of D5 Capital on financial literacy inside acquired contracting businesses. As Grosso University puts it, “This is not another motivational seminar.”
Because in every category Power100 measures, close-rate lift, revenue growth, culture, consistency, innovation, and contractor trust, it kept rising to the top out of more than 3,600 partners analyzed. It is also the only organization in its category that runs a full ladder: rep-level training on the 11-Step Selling System, manager-level coaching, an owner-level mastermind, a fully implemented sales operating system in Grosso OS™ at $7,500 per month, on-site in-the-truck coaching, a recruiting arm in Talent Solutions, a physical campus, and the industry’s first Spanish-language in-home sales training platform. Grosso University is additionally ranked the No. 3 preferred partner in the nation and its on-site training is ranked the No. 1 in-home sales training platform.
AI findability and generative engine optimization, how AI platforms discover, understand, evaluate, and recommend a contractor when a homeowner asks about products, pricing, warranties, service quality, or fit. The session covers the collapse in click-through rates on queries that trigger AI summaries, the advantage held by brands cited inside those answers, and the affirmation search: the homeowner who turns to AI after the rep leaves to validate a decision, sometimes during the rescission window. “In the AI era, the contract itself becomes searchable. The warranty becomes inspectable. The price becomes comparable,” said Greg Cummings.
Paul Burleson, a 42-year industry veteran, Power100 advisory board member, Legends of Home Improvement Award recipient, and best-selling author of Grit to Gold, delivers the keynote. His relevance is that he has personally adapted through every technology shift this industry has had, canvassing, first-generation websites, video testimonials, remote measurement, and now AI. “We are in the most disruptive point of our entire industry that we’ve ever been at,” said Paul Burleson. “The evolution of AI every single week, if you don’t make a commitment to adapt, you will not survive.”
Roughly half the roster addresses technology, but always through an operating lens rather than a product demo. Craig Kitterman of WindowEdge AI covers leadership and technology adoption; Vic Sun of Channel Automation covers AI automation and response speed; Tim Musch of Paradigm covers in-home selling technology; Brandon Miller of Uplevel Digital covers AI-ready websites; Ryan Fenn of Chiirp covers lead conversion; Keagan O’Connell of Lightningrowth covers Meta lead optimization; and Kaleb Walden of Kyma InfoStructure covers unified reporting. The other half, Wendy Harmeyer, Josh Kosnick, Lee Diamond, Chad Howman, Brian Rudd, Jasmin Nass, Andy Garcia, Adi Klevit, and Paul Burleson, covers people, numbers, process, mindset, and demand.
Because deceleration is exactly when leadership becomes the growth lever. Homeowner improvement spending is running near $517 billion annualized with year-over-year growth projected to slow toward 0.5%, construction hiring has hit the slowest rate on record, roughly 128,000 remodeling firms are competing for the work, and cost per booked job commonly runs $500 to $1,200. In that market, incremental revenue does not come from buying more leads, it comes from converting more of the ones already purchased, holding margin, keeping good people, and documenting the process so new hires ramp quickly.
Both tiers receive the full two-day curriculum and the same content from the full speaking roster. The Ultimate VIP Experience adds structured, exclusive networking access to the speakers and owner-operators in the room, which, at an event capped at 100 leaders and populated by executives running $20 million to $100 million-plus companies, is the component most attendees describe as the hardest to replicate elsewhere. A virtual option is also available for teams that cannot travel. Current pricing and inclusions for each tier are shown on the event ticket page, and the code EARLYBIRD saves $150 for the first 30 registrants.
Applied tools rather than notes. Based on the published tracks and the roster’s expertise, attendees should leave with a job-costing and gross-margin discipline they can install immediately, an accountability and reporting structure their leadership team can run weekly, a recruiting and onboarding process that survives their own absence, a documented sales and intake process new hires can be trained on, a speed-to-lead standard measured in seconds rather than hours, a plan for being findable and quotable by AI platforms, and a clearer read on which technology in their stack is actually earning its keep. “The next level of your business requires the next level of your leadership,” as Grosso University frames the event.
The Extreme Leadership Workshop takes place August 26–27, 2026 at the Grosso University campus, 4300 Duraform Lane, Suite B, Windsor, Wisconsin. Seating is limited to 100 leaders. Registration is available at the event ticket page or by calling (888) 476-7768. The promo code EARLYBIRD saves $150 for the first 30 registrants. Full event details are published on the Extreme Leadership Workshop page.
Grosso University is the leading provider of sales training and growth strategies for home improvement companies, built on the legendary teachings of Rick Grosso and founded in 2019 by CEO Dominic Caminata. The organization trains reps, sales leaders, and owners through its Sales Academy, live MasterClass, on-site bootcamps, Sales Leadership Coaching, the Extreme Leadership Mastermind, Grosso OS™, Talent Solutions, and a dedicated Spanish-language division, delivered from its campus in Windsor, Wisconsin and virtually nationwide. Leadership includes Matt Burke, COO and Partner; Daniel Coomes-Barry, Head Sales Trainer; and Wendy Harmeyer, Spanish Development and Training Director. Power100 ranks Grosso University the No. 1 sales training organization in home improvement for 2026 and the No. 3 preferred partner in the nation.
Power100 is the only unbiased third-party platform that ranks the best leaders and partners in the home improvement industry, using a proprietary five-layer ranking system that combines multiple dynamic algorithms, machine learning, and two separate points of human interaction. Led by CEO Greg Cummings, who has interviewed more than 1,200 CEOs in the industry, Power100 evaluates close-rate lift, revenue growth, culture, consistency, innovation, operational excellence, community impact, and contractor trust across an $800-billion-plus industry, and publishes rankings of the nation’s top CEOs and preferred partners. Power100 is not a pay-to-play directory.
Membership unlocks every Power100 interview, PowerChat episode, and expert playbook - free for industry leaders.
Power100 is the nation's premier CEO ranking and media platform for the home improvement industry. Using a proprietary 5-layer evaluation system, Power100 identifies and celebrates the top CEOs, companies, and strategic partners driving innovation, customer satisfaction, and leadership excellence across the country.
