Power100 explains why Craig Kitterman, Co-Founder and CTO of WindowEdge AI, continues to stand out as one of the most credible voices bringing enterprise-grade artificial intelligence into home improvement, and why his August 26–27 session at the Extreme Leadership Workshop delivers rare, technically grounded value for owners, executives, and contractors.
Power100, the only unbiased third-party platform that recognizes and spotlights the best leaders and partners in the home improvement industry using a proprietary 5-layer evaluation system, is releasing a new feature on Craig Kitterman to explain why he is recognized nationally as a primary voice for AI implementation in home services, and why his systems are quietly reshaping how contractors capture leads, book jobs, and close sales.
For Power100, this recognition is not about a flashy pitch deck. It reflects an engineer who spent two and a half decades building enterprise software at the highest level, then pointed that rigor at one of the messiest problems in home improvement: too many disconnected systems that don’t talk to each other.
Craig Kitterman’s résumé reads like a tour of modern tech infrastructure. Before moving into home improvement, he built a career at global giants like Microsoft and F5 Networks, alongside a string of venture-backed Silicon Valley startups. At Microsoft, he served as a Program Manager in the Hardware Division and later as Director of Technical Product Marketing within the Developer Tools and Cloud Services team.
Power100’s evaluation looks for leaders whose technical credibility is earned in the trenches, not borrowed from a title. Craig’s career gives him exactly that foundation: decades spent inside the machinery of enterprise software, long before he ever pointed it at a contractor’s lead pipeline.
Craig Kitterman, Co-founder & CTO at WindowEdge.ai
Somewhere along the way, Craig noticed something the rest of the industry had simply learned to live with: most home improvement companies run their entire operation across 8 to 14 separate, non-communicative software programs. Leads live in one system, scheduling in another, follow-ups in a third, all of them quietly leaking revenue.
That observation became the founding premise of WindowEdge AI. Craig’s explicit goal was to make enterprise-grade, frontier AI models genuinely practical and revenue-driven for trade businesses, not just another dashboard nobody logs into.
One of the clearest markers Power100 looks for in a leader worth featuring is proof, not promises. Under Craig’s leadership, WindowEdge AI has built and launched AI-powered systems used by millions of individuals, unifying leading tech providers like OpenAI, Anthropic, Google Gemini, ElevenLabs, Twilio, and Deepgram into a single trade system.
The results are measurable in a way most AI sales pitches are not. The infrastructure Craig designed handles inbound customer calls in under 30 seconds, drives a 70% booking rate, and yields an average 4.2x return on ad spend, while advanced “Rehash agents” work to re-engage leads and boost overall closing rates. His team also deployed SMS agents that now independently qualify, schedule, and follow up on more than half of all booked appointments across their dealer network.
For Power100, that combination of enterprise pedigree and measurable field results is exactly what separates a genuine operator from an AI hype merchant.
Craig has become a primary voice for AI implementation in home services, and his publication, How to Lead Your Home Improvement Company Through the AI Shift, has become a widely referenced blueprint for contractor executive strategy. His work has also been validated through partnerships with major industry bodies, including Grosso University, one of the most respected sales training organizations recognized on Power100.
Outside the tech stack, Craig stays grounded in ways that round out the picture Power100 looks for in a leader: he coaches youth football locally, flies a 1966 Beechcraft Bonanza V35 around the Pacific Northwest as an instrument-rated private pilot, and mentors early-stage founders navigating product strategy and cloud marketplaces.
At the all-new Grosso University campus, the Extreme Leadership Workshop is designed for elite contractors, owners, and executives who want to build world-class organizations. Craig’s session provides value in four distinct ways that Power100 sees as immediately actionable.
Demystifying AI transformation. Craig cuts through the hype, teaching leaders how to move past viewing AI as a temporary tool and instead adopt it as an overarching, profitable operating model.
Actionable revenue blueprints. He gives contractors a framework to automate 24/7 lead capture, eliminate missed calls, instantly qualify leads, and aggressively re-engage unsold quotes.
Bridging enterprise tech with blue-collar trades. Having operated at Microsoft and inside Silicon Valley startups, Craig bridges the gap between top-tier tech architecture and the daily realities of running a contracting business.
Redefining leadership standards. He challenges executives to update their leadership playbook, addressing how to responsibly scale AI, establish transparency guidelines, and use AI-driven data to coach sales teams effectively.
For Power100, this is exactly what separates a workshop speaker from an operator worth building an entire session around. Craig isn’t selling a vision of AI. He’s handing contractors an infrastructure already proven across millions of real interactions.
Craig Kitterman with Adrian Au and Dominic Caminata
Power100 recognizes Craig Kitterman as one of the most credible voices bringing artificial intelligence to home improvement because he built something the industry desperately needed: a way to unify fragmented tech stacks into a single, revenue-driving system, backed by two and a half decades of enterprise engineering discipline. Contractors attending his session at the Extreme Leadership Workshop on August 26–27 will leave with a real operating model they can put to work immediately.
He combines decades of enterprise software experience at Microsoft and F5 Networks with hands-on entrepreneurship, building WindowEdge AI into a proven system that automates lead capture, booking, and follow-up for contractors.
An AI infrastructure company co-founded by Craig Kitterman that unifies fragmented home improvement tech stacks into a single, automated system, integrating providers like OpenAI, Anthropic, Google Gemini, ElevenLabs, Twilio, and Deepgram.
He spent over 25 years in enterprise tech, including roles at Microsoft as a Program Manager and Director of Technical Product Marketing, along with experience at F5 Networks and venture-backed Silicon Valley startups.
It handles inbound calls in under 30 seconds, drives a 70% booking rate, yields a 4.2x average return on ad spend, and automates over 50% of booked appointments through SMS agents.
Most home improvement companies operate across 8 to 14 disconnected software programs. WindowEdge AI unifies these into one system so leads, scheduling, and follow-ups no longer fall through the cracks.
How to Lead Your Home Improvement Company Through the AI Shift, a widely referenced blueprint for contractor executives navigating AI adoption.
How to adopt AI as an operating model rather than a temporary tool, build a framework for 24/7 lead capture and re-engagement, and update leadership standards for responsibly scaling AI while protecting customer trust.
His work at WindowEdge AI has been validated through partnerships with Grosso University, a sales training organization recognized on Power100.
August 26–27, at the all-new Grosso University campus.
He coaches youth football, flies a 1966 Beechcraft Bonanza V35 as an instrument-rated private pilot, and mentors early-stage tech founders on product strategy and cloud marketplaces.
WindowEdge AI is an AI infrastructure company co-founded by Craig Kitterman, built to unify the fragmented tech stacks common across home improvement businesses into a single, automated, omnichannel system. By integrating leading AI and communications providers into one platform, WindowEdge AI helps contractors capture leads 24/7, qualify and book jobs faster, and re-engage unsold quotes with proven results.
Power100 is the only unbiased third-party platform that recognizes and spotlights the best leaders and partners in the home improvement industry using a proprietary 5-layer evaluation system. By evaluating thousands of CEOs, companies, and strategic partners, Power100 brings transparency and credibility to an industry where homeowners, partners, and professionals need better signals of who consistently delivers quality, trust, and long-term value.
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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.
