Doorvest

Buying a rental property you'll never walk through is a lot to ask of someone. Most first-time investors didn't fully understand cash flow, appreciation, or reserve costs, and they had no real sense of how day-to-day tenant management worked. We were asking them to wire a large sum toward a house they'd only ever seen in photos.

Almost everything came back to confidence. Before committing, people wanted to see the renovation work, understand how a home was underwritten, and know what returns to expect. The existing funnel was built around control instead of momentum, so every manual handoff added another delay and another reason to hesitate. That hesitation showed up directly in drop-off and weak repeat activity.

Between support threads and session data, how long people stayed and where they dropped off, the frustration was hard to miss. People were missing time-sensitive email alerts, and when they did show up, they were often looking at homes that had nothing to do with what they'd asked for.

The problem wasn't one broken screen. The whole experience was held together by emails, spreadsheets, and sales calls, so people couldn't move on their own. Things stalled at exactly the moment they were starting to feel ready.

One pattern cut through everything: people weren't all using Doorvest the same way. Newer investors needed education and reassurance before they'd act. Experienced investors wanted the opposite: fast access to the numbers and sharper filters so they could move quickly.

That split changed how I approached the work. One linear funnel was never going to fit both. The product had to flex to how confident and how decisive each person was in the moment.

The original experience relied on timed email property drops. The cadence manufactured pressure while giving people almost nothing to actually look at. I moved discovery and reservation straight into the product, so investors could browse and compare homes at their own pace instead of waiting for the next email.

Each listing put everything in one place: photos, financial projections, neighborhood data, and a clear Reserve Home button. I focused the marketplace on the moments where money was on the line and cut the delays that had been quietly killing conversion.

Instead of a separate swipe app, I put Like and Dislike buttons on each property card. It borrowed the familiarity of swiping without pulling people out of the browsing flow. When someone liked a home, we recorded its attributes: location, price, home type, and so on.

I argued against a standalone swipe experience. It would have rewarded novelty over real decisions and pulled people away from the actual investment. Those signals fed Doormatch, which surfaced homes likely to fit each person's criteria. It narrowed the field for them over time, without anyone filling out a preferences form.

It personalized the marketplace and gave the sales team a read on what each person wanted, without the constant back-and-forth.

I cut the reservation flow down to a few clicks by removing unnecessary fields and reusing what we already knew from someone's profile. Instant feedback, a clear confirmation screen, and a follow-up email made committing feel quick and reassuring instead of daunting.

Reserving a home was only half the journey. Ownership itself was scattered across emails, spreadsheets, and manual back-and-forth. Investors had no single place to see what they owned or how it was performing.

I pulled the whole ownership lifecycle into one dashboard: portfolio performance, renovation status, leases, and documents. Owning through Doorvest became as self-serve as buying through it.

The platform took friction out for investors and internal teams at once. Bringing discovery, evaluation, and reservation into one place removed the manual coordination that had bottlenecked the sales team. It also gave everyone a shared view across investor demand, acquisitions, and operations.

The clearest signal was engagement. Before, plenty of people finished onboarding without ever creating an account and drifted off. Once discovery and reservation lived in the product, they had a reason to stay and keep browsing. That shift, a design and product call the Head of Product and I made together and defended to the CEO and CTO, is where the lift in engagement and retention came from.

My biggest takeaway was how emotional these decisions are. People weren't only weighing returns. They were deciding whether to hand a company a life-changing amount of money for a house they'd never set foot in.

Over four years, Doorvest grew from a fragmented, operator-heavy service into a product that carries someone through the whole arc of investing: finding a home, reserving it, managing a portfolio, and the long tail of ownership.