Flexible housing platform

Orca

A membership platform for remote workers to live anywhere in the world

Overview

I co-founded Orca and owned all product, design, and engineering. Devan ran marketing, sales, and operations. We both shaped product strategy together.

The Problem

How do you make it effortless for a remote worker to land in a new city — fully set up — in under 3 days?

Mid-term housing (1–6 months) sits in an awkward gap. Too long for Airbnb pricing, too short for traditional leases. Remote workers were stitching together solutions manually across a dozen platforms with no consistency, no local support, and no trusted curation.

What We Built

Orca was a membership platform bundling:

• Furnished mid-term rentals at discounted rates
• Travel insurance
• City guides
• On-the-ground local experts per destination

The single KPI we optimized for: member up and running in a new city within 3 days.

Stack

• Gatsby — static site generation for fast, SEO-friendly pages
• Contentful — CMS for managing destination and listing content without deploys
• React + TypeScript — frontend
• Microsoft Clarity — session recording and telemetry

How We Sourced Supply

Most platforms list everything. We did the opposite.

1. Scraped Airbnb and other platforms to map supply in each city — pricing, occupancy, operator patterns
2. Filtered down to the top 10% worth approaching
3. Manually qualified and onboarded the top 1% — reliable operators with units remote workers actually wanted for a month-plus stay

For many of those conversations, we showed up in person. Walking properties and sitting face-to-face with managers changed the dynamic entirely compared to cold outreach.

Rapid Iteration

The biggest iterations weren’t features — they were the business model itself.

We cycled through multiple versions of what Orca was:

• Pure subscription
• Flat membership
• Different bundle configurations
• Different ways of packaging discounts and services

Each version was a hypothesis. We’d ship, watch behavior in Clarity, talk to members, and revise.

Pivots That Mattered

Membership-optional

Early on, Orca was membership-only. Users who found value in individual bookings but didn’t want a recurring commitment churned or didn’t convert. We moved to membership-optional — keeping the bundle for users who wanted it, removing the barrier for everyone else. It widened the top of funnel meaningfully.

Bundle evolution

We started with housing. We learned users needed more: insurance, local guidance, someone to call when the WiFi was down. The bundle grew from what users told us was blocking them from actually booking a new destination.

Growth

After experimenting with many channels — online communities, content, paid — what consistently worked was:

• Word of mouth from members who had a great experience
• In-person outreach to both property managers and remote work communities
• Referrals from happy members who recommended Orca to colleagues planning their next destination

Orca Score was our most creative growth hack: a Chrome extension that overlaid a personalized compatibility score on any Airbnb listing as you browsed. It analyzed the listing against your preferences — location, amenities, price — and gave you a score in real time. No signup required to install it. It put Orca in front of anyone actively searching for a place, exactly at the moment they needed it most.

The insight behind Orca Score — that people were already searching Airbnb for mid-term stays but getting a poor experience — planted the seed for what came next.

What Came Next

Orca Score surfaced a bigger opportunity: Airbnb had trained millions of travelers to search for stays, but the best hosts were paying 15–20% commission on every booking. We started exploring whether those hosts could own their guest relationships directly.

That question became OpenBnB — a platform for direct bookings between guests and top-rated hosts, cutting out the middleman entirely.

Impact

• Scaled to 35+ destinations globally
• $100k+ MRR
• Hundreds of members across 35+ destinations

Takeaways

• Owning design and engineering end-to-end compresses iteration cycles significantly
• The most important pivots were business model, not product features
• Showing up in person — to users and suppliers — surfaced things no dashboard could
• Curation beats volume: fewer, better listings built more trust than a long tail of mediocre ones