How AI Automation Helped HomeHop Scale to 108 Properties, No New Hires

TL;DR

• Grew portfolio from 40 to 108 listings without hiring additional guest support staff
• Achieved 70 percent automation with a clear path to 24/7 autopilot
• Replaced an unreliable VoIP system and a failed AI vendor with a single unified platform
• Zero staff reductions—VA team shifting from reactive messaging to escalation management

The Challenge

HomeHop nearly tripled its portfolio in two years, from roughly 40 short-term rental listings to 108 across the Cleveland and Akron markets. Messaging volume grew with it, and with it operational challenges.

HomeHop had been burned before. An earlier AI vendor promised to automate guest messaging, but the product never worked as advertised, and support was slow to help.

"It was just issue after issue after issue," Dan said. "It didn't do what they said it was supposed to do. Very, very underwhelming."

Dan lost confidence in AI chatbots and automatic guest messaging. Virtual assistants spent their shifts jumping between Google Drive and communication tools, hunting for the right piece of information before they could reply to a guest.

The phone system compounded the problem. HomeHop relied on Google Voice until the day the team got locked out—no password reset, no support line. They had to rebuild from nothing.

HomeHop had the ambition to scale, but the operations couldn't support it. Every new property meant more messages, more calls, and more pressure on a team already stretched thin. The infrastructure to sustain growth was not there.

The Solution

Dan's business partner Nate pushed to try Conduit despite the previous AI failure.

"I was a little leery, just to be completely honest, just because the whole AI thing didn't work for us before," Dan said. "So why would it now?"

They gave it a chance. Confidence built as the AI responses made sense and the team could control when to approve messages and when to run on autopilot.

HomeHop deployed Conduit across every channel—email, SMS, OTA messaging—so guest inquiries flowed through one system and could be managed by AI. They added voice AI for overnight phone coverage between 1 AM and 7 AM, it replaced the night shift entirely.

The team wired Conduit into the tools they already used. Notion and Slack picked up operational knowledge. SuiteOP handled property operations, linking guest verification and door codes into automated workflows. The team stopped toggling between tabs.

"The way that those two things integrate has just been awesome," Dan said of SuiteOP. "The ability to use AI in workflows with SuiteOP is going to be an absolute game changer."

The Transformation

The AI demanded better inputs. To respond accurately, it needed documented policies, up-to-date property details, and clear procedures. Most of that lived in people's heads, in scattered places, or buried in communication threads. HomeHop focused on formalizing what it knew, and fill in what it didn't.

"By improving the AI, it's forcing us to improve ourselves and improve our processes and improve the quality of the information that we want to give," Abraham said. "You're training someone and then you're like, well, but I don't even have that information. So how am I going to train this one?"

The accuracy work paid off in a second way: it freed the VA team from repetitive messaging. Questions about door codes, parking, check-in instructions, and cancellation policies stopped reaching a human. The team shifted to work that still required judgment—refund requests, emergencies.

The third shift was growth. With guest messaging handled, the team had capacity to onboard new properties properly instead of scrambling to keep up. HomeHop is migrating vendor contacts from Google Sheets into Conduit's maintenance inbox, building a system it can replicate as it enters new markets beyond Cleveland and Akron.

"Whether we're at a hundred units or two hundred units, I don't see us needing to hire additional employees to handle guest messaging," Dan said.

Results

• Nearly three times portfolio growth—from 40 to 108 properties in two years without adding guest support headcount
• After-hours AI coverage from 1 AM to 7 AM across messaging and voice
• Replaced Google Voice with reliable phone and SMS through Conduit
• Unified communications—guest messaging, vendor coordination, and phone in one system
• Zero staff reductions—VA team moved from reactive messaging to escalation management

Looking Ahead

Abraham is working with his team through the knowledge base and escalation center, clearing gaps to push automation toward 24/7 autopilot. The team is migrating vendor contacts into Conduit to extend their Cleveland playbook into new markets.

HomeHop operates 108 short-term rental listings across the Cleveland and Akron markets. The company has been a Conduit customer for approximately two years and is currently expanding into additional markets.

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