Nester
2026
Document Management: turning an abandoned feature into a real cloud
Redesigning Nester's rigid, flat-list document system into a real folder-based cloud — because managers were abandoning it for Dropbox and Drive instead of fighting it.
Context
Nester had a documents feature. Users just didn't use it.
The existing system was rigid: files uploaded one at a time, dumped into a flat list, no folders, no hierarchy. Property managers who needed real organization gave up and kept their files in Dropbox or Google Drive instead — outside the platform entirely. The feature wasn't broken. It just lost to the alternative every single time.
Challenge
Compete with the tool people already trust, not just ship a checkbox feature.
The bar wasn't "add folders"
A flat list with folders bolted on wouldn't be enough — managers already had a system that worked for them elsewhere. The redesign had to be genuinely faster than switching to Drive, not just technically capable of the same thing.
Two very different upload behaviors, one modal
Uploading one file and uploading twenty are not the same task. One needs a name and a description. Twenty need speed — a list, a way to drop the bad ones, and one shared description for the batch. The modal had to read the situation and adapt, not force one flow onto both.
Configuring smart blocks for owners, tenants, and properties — one system, three contexts.
Approach
Reuse the platform's own patterns before inventing new ones.
Building on what already existed
The breadcrumb navigation didn't need a new component — Bootstrap already had a pattern we could adapt directly, so the folder hierarchy could ship without inventing new interaction language.
Configuring smart blocks for owners, tenants, and properties — one system, three contexts.
Designing the failure modes first
Before designing the happy path of moving a file, I mapped out what shouldn't be allowed: a folder can't be moved into itself, and none of its own subfolders can become a valid destination either — otherwise you create an infinite loop in the hierarchy. That restriction logic came before the visual design of the tree-view, not after.
Configuring smart blocks for owners, tenants, and properties — one system, three contexts.
A migration that asks nothing of the user
Every existing file needed a home in the new structure without forcing anyone to reorganize anything manually. All current documents move automatically into the root folder — the feature just gets more capable under people's feet, with zero setup required on their end.
Reflection & what's next
The target is the redesign's real test: will people stop leaving the platform?
This is still in development, so there's no adoption data yet — the goal that matters is whether managers actually stop keeping a second, unofficial copy of their files in Drive. The rollout is phased on purpose: folder structure and navigation first, then bulk actions, then preview and global search, with the last phase replicating the whole module across Tenants and Properties once it's proven with Owners.
Centralized approval dashboard for reviewing requests, tracking statuses, and reducing delays.
Designed a streamlined approval dashboard for faster reviews and decision-making.
Improved approval management through clearer workflows and request visibility.
Key Takeaway
A feature people avoid isn't a UI problem. It's a trust problem.
The original documents section wasn't missing anything on paper — it had upload, it had storage. What it didn't have was enough respect for how people actually manage files, so they voted with their feet. Redesigning it meant competing with a tool they already trusted, not just filling a spec.
