Ben Leone and the team at Contractor Appointments aren’t just helping contractors find work—they’re reinventing how it happens. The Minnesota-based company serves as an inbound appointment generator, connecting homeowners with vetted contractors and ensuring both sides have a streamlined, transparent experience.
"We help homeowners schedule estimates and help contractors fill their calendars," said Ben, Chief Technology Officer. "It's a win-win model that thrives on efficiency."
But with lead volumes growing to be in the hundreds per day, efficiency started to break down. That meant building scalable, always-on workflows powered by automation and AI.
"Over the past seven years, we’ve built most of our business automation on Zapier. It’s critical to how we operate," said Ben.
Contractor Appointments' results, by the numbers:
$134M in reported revenue from clients attributed to Zapier-powered lead flows.
80–90% of top-of-funnel lead replies handled automatically via Zapier and OpenAI.
20–50 additional appointments booked per day with after-hours auto-scheduling.
$300K in incremental annual revenue from long-term nurturing automations.
Booking appointments from after-hours texts
Many homeowners reply to estimate offers via SMS late at night, well outside normal business hours. Contractor Appointments was losing potential business simply because no one saw those replies in time.
To fix it, Ben built an AI-powered scheduler using Zapier. When a homeowner responds via text through Front, a Zap kicks off an AI workflow that:
Parses the message with OpenAI to extract a date and time.
Checks contractor availability by matching the zip code and service type against an internal calendar database.
If there's a match, it books the appointment automatically via API.
The impact? 20 to 50 additional appointments are booked daily without any human input.
"It helped us stop losing those late-night replies. We now automatically book appointments that would’ve fallen through the cracks," said Ben.
Turning texts into human conversations
Text nurturing used to be rigid and transactional. The team asked closed-ended questions like, "Do you need a roof repair?" If a homeowner responded with a sentence instead of a keyword, the system stalled.
Now, with Zapier and OpenAI, Contractor Appointments uses open-ended prompts and natural-language responses to guide homeowners more thoughtfully down the funnel. When a homeowner replies, a Zap:
Sends the message to ChatGPT to extract pain points.
Crafts a personalized response based on those issues.
By making automation more human, the company significantly improved appointment set rates.
"We wanted the ethos of the company to be relational. With AI, our messages feel like they’re coming from a person, not a robot," said Ben.
Nurturing long-tail leads into additional revenue
Most lead gen companies treat unready leads as dead. Not Contractor Appointments. Ben built a flexible follow-up system using Zapier to keep these conversations alive.
With a simple comment like "CB 30 ET" (meaning callback in 30 days, Eastern Time), a Zap:
Extracts the delay and timezone.
Schedules a future follow-up in their marketing system.
This system means a lead who isn’t ready today might still turn into revenue next quarter—or even next year.
"We’ve seen 5 to 10% of monthly revenue come from leads we nurtured from previous years. That added up to $300,000 in additional revenue over one year," said Ben.
Building smarter, faster, leaner
With over 300 to 600 new leads daily and a small team of two handling text nurturing, Zapier enables Ben to do more with less. Even complex workflows that involve AI, API calls, and custom logic are manageable without a full-time dev team.
“When we talk about Zapier internally, we always compare it to hiring a full-time developer. With Zapier, we’ve avoided that cost entirely. Zapier lets us build quickly and scale fast. I can test and implement ideas in a day, not months," said Ben.
Contractor Appointments isn’t just helping people fix roofs and replace windows—they’re proving how AI and automation can build stronger customer relationships. With Zapier as their backbone, they’re setting a new standard for how service businesses connect with customers.
About Contractor Appointments
Company Size: 11-50
Industry: Professional Services
Location: Minnesota
