ericwoo_kr 
Why I Stopped Recommending Jira to Every Startup I Work With The breaking point was a Tuesday afternoon. I’d just joined a 6-person seed-stage startup as a fractional CTO — two backend devs, one frontend, a designer, a PM, and a founder who kept jumping in on tickets. Simple team. Clear scope. We needed to … Read more
The Problem That Made Me Test Both The breaking point wasn’t a crash or a missing feature. It was a Zapier bill. One Zap — a single lead routing workflow for one client — was burning through 400+ tasks per month. That’s a client on HubSpot sending form submissions to Google Sheets, triggering a Slack … Read more
The Real Problem: Your Support Queue Is a Dumpster Fire at 2am Tier-1 tickets will kill your team’s morale faster than any technical debt. Password resets, “how do I cancel my subscription,” “where’s the export button” — these questions have known answers, documented answers, and yet they were eating the first 3-4 hours of every … Read more
The Problem: Your E-Commerce App Refreshes Like It’s 2008 Your Django App Is Lying to Customers Right Now Here’s a scenario I’ve debugged more times than I want to admit: a sneaker drop goes live, two customers both see “1 item left in stock,” both click Add to Cart, both get a confirmation email — … Read more
The Real Problem: Asana’s Free Tier Breaks the Moment You Have Real Volunteers The 15-Member Wall Hits Faster Than You Think I ran a volunteer onboarding project for a mid-sized nonprofit and we blew past Asana’s free tier limit inside the first weekend of signups. The cap is 15 members — not 15 active users, … Read more
The Problem That Made Me Try Both The sprint planning meeting that broke me happened on a Tuesday afternoon. Four of us had the same Google Sheet open — the one we’d been using as a “temporary” backlog tracker for eight months — and we were watching each other’s cursors collide in real time. Someone’s … Read more
Why Healthcare App Development is a Different Beast Most apps you build are forgiving. You ship a bug, you push a fix, users are mildly annoyed. Healthcare is not that. The first time a client asks you to pull an audit log of every field that was touched on a patient record — and you … Read more
The Problem With Letting Netlify Own Your Build Pipeline Netlify’s Git integration is genuinely great for the first week of a project. You connect a repo, it detects your framework, and deploys happen automatically on every push. That convenience has a ceiling, and most teams hit it faster than they expect. The ceiling I hit … Read more
Why I Stopped Recommending Asana to Nonprofits The Moment I Knew Asana Wasn’t Built for This The thing that broke it for me was Gantt charts — or rather, Asana quietly locking timeline view behind a paid plan. I was helping a small animal rescue org map out their summer adoption event schedule across four … Read more
I Needed a Single Source of Truth for a Distributed Team — So I Tested Both The actual breaking point wasn’t the Slack message limit. It was when our lead designer submitted a spec update in Google Docs, the PM acknowledged it in a Slack thread that later vanished into the 90-day void, and I … Read more