UpSmith is introducing a new tool that brings generative AI into a sector that’s long been underserved by modern software. The Dallas-based company recently launched JennyAI, a product designed to support skilled trades businesses—HVAC, plumbing, electrical, and beyond—by automating customer outreach and helping convert inbound interest into booked jobs.
UpSmith closed a $5 million seed round last year from TechNexus Venture Collaborative, Hannah Grey Ventures, a16z, GSV, Asymmetric Capital Partners, Cubit Capital, Crow Holdings, Kimbel Mechanical, Crescent Ridge, Karman Ventures and others.
At its core, JennyAI is an AI agent that maximizes customer engagement by identifying potential leads and automatically reaching out to these existing customers with context-aware messages. Better yet, it books proposed appointments in real-time. For owners and technicians often juggling fieldwork and operations, JennyAI becomes a quiet layer of support, handling the repetitive tasks that otherwise fall through the cracks.
JennyAI is built specifically for trades businesses. That distinction matters. Major operational changes are especially difficult to implement for companies in the trades, but JennyAI is designed to meet businesses where they are. It seamlessly integrates into systems like ServiceTitan, where it scans existing customer data and schedules follow-ups and appointments. For many small and mid-sized service providers, this means fewer missed leads and less time spent playing phone tag.
"We have thousands upon thousands of contacts in our database, but we've never had the capacity to fully engage them," Chris Harrison, GM of Roland Black Heating & Cooling, said in a statement. "We spun up JennyAI in a matter of hours to leverage that data for the first time, automating personalized outbound messages to customers and truly generating opportunities out of thin air."
The opportunity is significant. The U.S. home services industry is valued at over $500 billion, and much of it still runs on phone calls, spreadsheets, and word-of-mouth. Bringing generative AI into this space means introducing scalable tools to a workforce that has long lacked them. From efficient lead conversion to more consistent customer experiences, the upside for businesses that adopt these tools is substantial—and largely untapped.
The launch aligns with UpSmith’s broader mission of addressing the skilled labor shortage by improving workforce productivity. Alongside tools like Compete, which gamifies job performance to improve employee retention and revenue, JennyAI represents a move toward more thoughtful digital infrastructure for the industry.
As AI continues to reshape how businesses operate, the company is betting that the next wave of innovation won’t be confined to offices—it’ll show up in workshops, vans, and job sites, too.