I Spent 3 Years Defending Jira. Here's Why We Finally Left.

It was a Tuesday morning, and I was watching one of my engineers spend 45 minutes trying to figure out why a ticket had disappeared from our sprint board. Again.

The culprit? Someone had accidentally changed a custom field that triggered an automation that moved the issue to a different project. Classic Jira.

I'd been defending our Jira setup for three years. "It's the industry standard," I told myself. "We just need to configure it better." But sitting there, doing the math on how much time my 12-person platform engineering team spent fighting our project management tool instead of building things, I finally admitted what I'd been avoiding. The roughly $98 per month we paid for Jira was the cheapest part of the equation.

What was the real cost? Lost context. Meeting overhead to sync what should've been obvious. And the slow erosion of developer productivity that's hard to quantify but impossible to ignore.

This is the story of how we evaluated Jira alternatives for small engineering teams, what we learned from running four different tools in production, and why we ultimately landed where we did. Leading a team under 20 people and wondering whether there's something better out there? This is for you.

Why Enterprise Tools Backfire for Smaller Engineering Teams

Jira is built for enterprises that need to track work across hundreds of teams with different methodologies, compliance requirements, and reporting needs. And it does that well.

But when you're a small dev team, all that flexibility becomes weight you have to carry.

In my 15 years of platform engineering, I've seen this pattern repeatedly. A startup picks Jira because it's what everyone knows. Those first few months are fine. Then someone adds a custom field. Then another. Then an automation. Before you know it, you've got a Frankensteined system that requires tribal knowledge to navigate.

Our specific pain points:

• Configuration complexity that only I understood, making me a bottleneck
• Slow performance that made opening a ticket feel like loading a desktop app from 2005
• Context switching between Jira, Confluence, and our actual development tools
• Onboarding friction where new engineers needed a full day just to understand our workflow

That $8/seat/month pricing looked cheap on paper. But when I calculated the productivity tax (factoring in time spent on tool maintenance, confusion, and workarounds) we were paying closer to $50/engineer/month in lost productivity.

With lightweight project management tools for developers, this overhead is unacceptable. Your tool should disappear into the background, not demand constant attention.

Our 30-Day Experiment: Testing Linear, Notion, GitHub Projects, and Shortcut in Production

I didn't want to make a decision based on demos and marketing pages. So we ran an actual experiment.

We split our team into pairs, and each pair used a different tool for their work while maintaining a shadow copy in Jira (just in case). After 30 days, we compared notes.

What did we test?

Linear

The developer darling. Everyone on Twitter seems to love it, and I wanted to see if the hype was real.

What worked: Speed is genuinely impressive. Everything feels instant. Keyboard shortcuts make sense. And the opinionated workflow means less configuration.

What didn't: That same rigidity limits customization. Our platform team has some non-standard workflows for infrastructure work, and Linear pushed back against them.

Notion

We were already using Notion for documentation, so this seemed like a natural fit.

What worked: Flexibility is incredible. You can build literally any workflow. Database views are powerful, and having docs and tasks in one place reduced context switching.

What didn't: Notion is a blank canvas, which means you have to build everything yourself. My team spent more time designing our project management system than doing project management. Also, the lack of proper sprint planning features meant we were hacking workarounds constantly.

GitHub Projects

A free Jira alternative for software teams that lives where your code already does.

What worked: Zero context switching. Issues link directly to PRs and commits. And the new Projects experience (not the old one, the 2022+ version) is actually pretty good. Plus it's free with our GitHub plan.

What didn't: Reporting is basic. Need velocity charts, burndown reports, or anything beyond "here's a board"? You'll be disappointed. Non-engineering stakeholders found it confusing too.

Shortcut (Formerly Clubhouse)

This middle-ground option promised Jira's power without the complexity.

What worked: Good balance of features and simplicity. Milestones helped us think about bigger-picture goals. Integrations were solid.

What didn't: It felt like Jira-lite rather than something genuinely different. Better, yes. But not transformatively so.

Feature-by-Feature Breakdown for Teams Under 20 People

After our experiment, I sat down and created a comparison matrix. Evaluating what are the best Jira alternatives for small engineering teams? This is what actually matters:

Speed and Performance

Tool	Rating	Notes
Linear	⭐⭐⭐⭐⭐	Blazing fast, feels native
GitHub Projects	⭐⭐⭐⭐	Good, occasional lag on large boards
Shortcut	⭐⭐⭐⭐	Solid, no complaints
Notion	⭐⭐⭐	Can get slow with complex databases
Jira	⭐⭐	You know the pain

Learning Curve

Tool	Time to Productivity	Notes
GitHub Projects	30 minutes	Assuming you know GitHub
Linear	2 hours	Opinionated but learnable
Shortcut	4 hours	Similar enough to Jira
Notion	1–2 days	Building the system takes time

Best Agile Tools for Teams Under 20 People

Sprint-based teams specifically should consider:

Linear wins when you're running two-week sprints with a standard Scrum-ish process. Cycles are clean, and automatic rollover of incomplete work is thoughtful.

GitHub Projects works when sprints are loose and you care more about shipping than ceremony.

Shortcut is solid when you need story points, velocity tracking, and traditional agile metrics.

Notion struggles in this area. You can build sprint functionality, but it's work.

Simple Issue Tracking for Small Dev Teams

Just need to track bugs and features without methodology overhead?

GitHub Projects. Full stop. It's free, it's where your code lives, and it's simple enough that you won't spend time on meta-work.

How We Switched Mid-Sprint Without Chaos

We chose Linear. Why? Speed, keyboard-first design, and the fact that it felt like it was built by developers who were annoyed by the same things we were.

But switching project management tools mid-flight is scary. Making it painless required a clear process:

Step 1: Export Everything (Our Data Export Script)

Jira's export is... not great. We wrote a Python script that:

1. Pulled all issues from our Jira project via the REST API
2. Preserved relationships (epics, subtasks, links)
3. Converted custom fields to labels
4. Generated a CSV that Linear could import

# Simplified version of our export logic
import requests
import csv

def export_jira_issues(project_key, output_file):
    issues = fetch_all_issues(project_key)
    with open(output_file, 'w') as f:
        writer = csv.DictWriter(f, fieldnames=['title', 'description', 'status', 'labels', 'assignee'])
        writer.writeheader()
        for issue in issues:
            writer.writerow(normalize_issue(issue))

Full script is about 200 lines. I'm happy to share if you reach out.

Step 2: Run Parallel for One Sprint

We didn't do a hard cutover. During one sprint, we tracked everything in both systems. This let us:

• Catch any data that didn't migrate correctly
• Build muscle memory with the new tool
• Keep stakeholders comfortable during the transition

Step 3: Commit and Don't Look Back

After the parallel sprint, we archived the Jira project and went all-in. Looking back is how you end up maintaining two systems forever.

Total migration took about two weeks of calendar time, maybe 15 hours of actual work.

When to Ignore This Advice: Scenarios Where Jira Is Actually Right

Look, I'm not here to tell you Jira is always wrong. Legitimate reasons to stick with it exist:

You have regulatory compliance requirements. Jira's audit logging and permission systems are robust. Need SOC 2 evidence or operating in a regulated industry? Enterprise features matter.

You're part of a larger organization using Jira. Being on a different system than the rest of your company usually costs more than it saves. Cross-team visibility matters.

You need advanced reporting for leadership. Jira's dashboards and custom reports are powerful. VP wants specific metrics in a specific format? Jira can probably do it. Linear's reporting is improving but still basic.

Your team genuinely likes it. Some teams have mastered Jira's complexity and built workflows that work. Don't migrate just because Twitter told you to.

Regarding the Jira vs. Linear for startups debate specifically: pre-Series A with a small team, Linear almost always wins. Post-Series B with multiple engineering teams? Jira starts making more sense.

Notion vs. Jira for small engineering teams is a different question entirely. Notion is great when you want docs and tasks unified and you're willing to build your own system. It's not great when you want something that works out of the box.

My Decision Framework After Three Years of Pain

After three years with Jira and 30 days testing alternatives, I developed this framework for choosing a lightweight project management tool:

A Quick Decision Tree

1. Do you need advanced compliance and audit features? → Stay with Jira
2. Is your whole company on Jira? → Probably stay, or propose a pilot
3. Do you have budget for paid tools? → Consider Linear or Shortcut
4. Are you already on GitHub and want free? → GitHub Projects
5. Do you want docs and tasks unified? → Notion (but budget build time)

My Recommended Starting Point

Teams under 20 engineers without enterprise requirements should start with Linear.

Linear offers a free tier for small teams, which is enough to know if it fits. Import from Jira works well. And if you hate it, you've lost two weeks, not two years.

Zero budget? GitHub Projects has gotten surprisingly good. Give the new version a real shot before dismissing it.

Fifteen years of helping developers be more productive taught me this: your project management tool should be invisible infrastructure. Thinking about it constantly? Something's wrong.

We've been on Linear for eight months now. I haven't thought about our project management tool in seven of those months.

That's the goal. Pick a tool that lets you forget it exists.

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Have questions about our migration or want the full export script? Find me at our monthly Tech Latinx meetup in Miami, or drop me a message. I'm always happy to help teams escape their tooling pain.