Zillow Onboarded an Entire Sales Floor to Chili Piper in Under 20 Minutes Per Rep

An API-gated onboarding app, a smarter implementation router, and a cross-business-line reporting hub, all built by one person.

Zillow connects home shoppers with real estate professionals through its network of partner agents and brokerages.

Location: Seattle, WA

Size: 7,000+ employees

Industry: Real Estate Technology

Products: Chili Piper API & MCP, Orchestrator

Win: Nearly 100% of a 300+ rep floor onboarded in the 2 week timeline, most in 15 to 20 minutes each

Alex needed a tool with a flexible API

Alex Coventry, Senior GTM Systems Manager at Zillow, runs go-to-market engineering for the agent software and advertising business, serving real estate agents, teams, offices, and brokerages, with 300 to 350 sellers spread across three business lines.

When Zillow evaluated scheduling tools, one thing mattered to him more than any other feature: an API he could actually work with. As a builder, he needed something that could be molded to fit the way he and his team work. Working with a vendor that didn't have a flexible API was a non-starter. Enter: Chili Piper.

Today, the Chili Piper and Gong MCPs run in his agents every day.

"It's become a backbone for me."
— Alex Coventry, Senior GTM Systems Manager at Zillow

A scattered scheduling stack made it impossible to track a rep's day

Before consolidating, reps were spread across Calendly, SalesLoft's scheduler, and plain Outlook invites, each team doing its own thing.

"It was a little bit of a mess all over the place."
— Alex Coventry

That fragmentation made it nearly impossible to trace a customer's journey before or after a sale, or even do basic reporting like searching meetings by title.

When Zillow moved to consolidate onto Chili Piper, Alex was given two weeks to migrate his entire floor of over 300 reps.

An API-gated onboarding app got the floor live in 15 to 20 minutes each

Instead of running multiple massive live trainings, Alex built an onboarding app on Replit that walks each rep through onboarding setup: log in to Chili Piper via Okta, connect Google Calendar, connect Zoom, set availability, install the Chrome extension.

The app polls Chili Piper's API roughly every 15 seconds to confirm, in real time, that each step is genuinely done, not just clicked through. Seven of its nine onboarding modules are gated this way. At the end, every rep completes a real test booking, scheduled, rescheduled, and canceled, to prove the whole flow actually works for them.

He layered in a semi-agentic assistant on top: it messages reps in Slack if they stall on a step or never start, answers questions, and runs some of its own validation checks. There are even training modules for key concepts and an AI chatbot reps can query if they get stuck.

Nearly the entire floor got through it in the short timeframe.

"We had a darn near 100% of our floor... getting through this in 15 to 20 minutes."
— Alex Coventry

Compared to multiple live training sessions for the same headcount, that's not a small win. It's the difference between a rollout and a bottleneck. The results were strong enough that Alex is now expanding the same pattern to other tools, starting with Gong.

He didn't stop at onboarding

Two more builds came out of the same API-first instinct.

From round robin to book-time assignment. As Zillow shifted from a transactional sales model toward a traditional SaaS motion, Alex needed a smarter way to route closed-won deals: full implementation, a CSM, or self-serve. The old approach assigned in round robin at the time of sale, which ignored who actually had availability.

Now, a closed-won booking feeds a decision engine (running on Claude) that classifies the deal, and Chili Piper assigns the real scheduling link at the time of booking instead of the time of sale. An onboarding assistant agent posts that link to Slack automatically, and for implementation consultants, the system writes the account-team assignment straight into Salesforce.

Multi-dashboard app tracking meeting booking. Alex needed a cross-business-line view of pipeline and funnel health that didn't belong inside the tool itself. So he built it. An app that tracks booking volume, unique accounts, and cancellation rates, cross-referencing Gong to confirm a booked meeting actually happened before auto-summarizing it.

"There's data that I wouldn't expect or want or need in Chili Piper that I do want to overlay on some of these meetings."
— Alex Coventry

The onboarding app was so well-received that he's now exploring ways he can replicate a similar experience for other tools.

"This [onboarding app] was meant to be a one-time... And the feedback was really, really positive. So I have now just expanded, and we're including our other systems in there. But Chili Piper is at the forefront so far on what we can pull from."
— Alex Coventry

The Toolbox

• Chili Piper API: connection-status checks for calendar and Zoom, availability and booking endpoints, scheduling links (both ownership-based and round-robin), and the meeting object as the system of record across all three builds
• Chili Piper MCP: lets his coding agents build and validate directly against Chili Piper, "a backbone" for his day-to-day work
• Chili Piper Orchestrator: writes account-team assignments into Salesforce and automates re-engagement outreach for unbooked implementations
• Gong: confirms meetings actually happened and feeds outcomes into the reporting hub
• Claude Code, Replit, and Codex: designs and tests in Claude Code, deploys to Replit via SSH, and runs adversarial code review in Codex

What he'd tell the next builder

Alex describes his role less as a solo builder and more as running a small team, just one made of agents.

"In doing all of it, I find that my biggest role is orchestrating the team of agents."
— Alex Coventry

He also believes it's not API vs. MCP, but rather both of them working together. The MCP provides the ability to brainstorm and plan with the help of an agent, then surfaces the right API endpoints to actually create the build.

"The MCP has been a really great partner, because I will send Claude or Codex deep down the rabbit hole and go through iterations and testing, and then ultimately find my [API] endpoints and set this up in a more scalable way. The two of them together have really, really strong power."
— Alex Coventry

The Results

• Nearly 100% of the floor onboarded, most in 15 to 20 minutes each.
• Onboarding pattern now expanding to other tools, starting with Gong.
• Implementation routing moved from round-robin-at-close to availability-based assignment at time of booking.
• Full visibility into the implementation pipeline and at-risk deals that didn't exist before.

Want the full walkthrough of Alex's build? Watch it below.

From one rep's workaround to a whole GTM stack

Alex started with an API he could actually work with. See what you can build with the same one.

In the meantime, stay spicy! 🔥