I Was the Loudest Voice for Linear on Our Team. Then We Had to Switch Back.

Six months ago, I was the loudest voice on our infrastructure team advocating for Linear. I'd watched enough Twitter discourse and read enough glowing reviews to believe we'd found the answer to our project management problems. Jira was bloated, slow, and everyone complained about it. Linear was sleek, fast, and built by engineers for engineers.

So we made the switch. And then, six months later, we switched back. Sort of.

Here's the thing about the Linear vs. Jira debate for software development teams: most of it is noise. People love dunking on Jira. It's become a meme at this point. But the honest reality of daily engineering workflows is messier than any hot take can capture. What I want to share isn't another "Linear good, Jira bad" piece or vice versa. It's what actually happened when a mid-sized engineering org tried to modernize their tooling and learned some expensive lessons.

Our Setup: Why We Thought Linear Was the Answer

Let me paint the picture. We're a cloud infrastructure company, so our tech stack is heavy on Go, Kubernetes, and Terraform. Three squads make up the engineering team: platform, reliability, and developer experience. We'd been on Jira for several years when I started pushing for Linear.

Complaints about Jira were the usual suspects:

• Everything took too many clicks
• Parts of the UI felt like they were designed in 2008 (because, well, they were)
• Sprint planning sessions turned into "how do I configure this" sessions
• ICs avoided updating tickets because the experience was painful
• Mobile was basically unusable

I remember showing our engineering manager a 30-second video of Linear's keyboard navigation. He was sold. Within two weeks, we'd started our migration.

A faster tool means a faster team, right? Less friction means more documentation. Better UX means happier engineers.

Some of that turned out to be true. Some of it really didn't.

What Linear Actually Does Better

Let me be clear: Linear is a genuinely excellent product. Is it worth it for engineers? For many teams, absolutely yes. Here's where it legitimately outperformed Jira for us.

Speed is real. Linear loads in under a second, noticeably quicker than most project management tools. I can't overstate how much this changes your day. Jira's loading spinners had become so normalized that we forgot software could be fast. When you're checking a ticket 40 times a day, those three-second delays compound into genuine productivity loss.

Keyboard-first design changes behavior. Within two weeks, even our most keyboard-averse engineers were navigating without touching their mouse. Cmd+K to open the command menu, C to create issues, number keys to set status. Sounds small, but it meant people actually used the tool instead of avoiding it.

Opinionated design, in good ways. You can't have 47 custom fields and 12 issue types like Jira projects tend to accumulate over time. This constraint helped us clean up years of workflow cruft. [Link: project management best practices for engineering teams]

Developer adoption was instant. This one surprised me most. Engineers who had to be nagged to update Jira tickets started updating Linear issues proactively. GitHub integration felt native. The whole experience felt like it was made by people who understood how we work.

So why did we partially switch back? Because speed and UX aren't the whole story.

The Hidden Costs Nobody Warned Us About

Around month three, cracks started appearing. Not in Linear itself, but in how Linear fit into our actual organization.

Integration gaps were bigger than expected. We use Datadog for monitoring, PagerDuty for incidents, Confluence for documentation, and Salesforce for customer data. Jira connects to all of these natively or through mature plugins. Linear's integrations exist, but they're thinner. Take our incident management workflow, which automatically created Jira tickets from PagerDuty alerts with full context. Rebuilding it from scratch with Zapier and custom webhooks took three weeks. It never worked as smoothly.

Reporting became a problem. Engineering managers could pull sprint velocity reports, cycle time analysis, and cross-team capacity views from Jira in minutes. Linear's reporting is improving, but getting equivalent data required exporting to spreadsheets or building custom dashboards. When leadership asked for quarterly metrics, someone had to spend half a day assembling them manually.

Stakeholder friction was real. Product managers and support teams had learned Jira's quirks over years. They knew where to find things, how to search, how to create filtered views for their needs. Linear's different paradigm meant retraining everyone outside engineering. And honestly? Some of them never fully adapted. We started hearing "can you just put this in the old system" more than I'd like to admit.

Customization ceiling appeared fast. Linear's simplicity is a feature until it isn't. We have compliance requirements that need specific approval workflows. QA needed certain fields for test coverage tracking. Linear's answer was often "that's not how Linear works." Jira's answer was "here are 17 ways to configure that."

Where Jira Quietly Wins

I used to think Jira defenders were suffering from Stockholm syndrome. Now I understand they were just dealing with different constraints than I was.

When evaluating these tools at scale, here's where Jira's ugliness becomes an asset:

Enterprise features exist for reasons. Audit trails, fine-grained permissions, compliance workflows, data residency options. None of this is exciting. All of it matters when your legal team asks who modified a ticket six months ago, or when you're going through SOC 2 certification.

Third-party ecosystem is unmatched. Need time tracking? There are 15 apps. Need test management? Another 20 options. Need custom automation that triggers based on arbitrary conditions? Jira Automation handles it. Linear is catching up, but the gap in 2024 remains significant.

Custom workflows handle edge cases. Every engineering org has weird processes that accumulated for reasons. Maybe your security team needs to approve certain tickets. Maybe customer-facing bugs route differently than internal tech debt. Jira lets you encode basically any workflow, however ugly. Linear asks you to adapt to its model.

Cross-functional visibility is easier. When your product managers, support team, and engineering all need different views of the same work, Jira's flexibility pays off. Different saved filters, different board configurations, different dashboards. Linear's uniformity is great for pure engineering teams but struggles with diverse stakeholders.

The Decision Framework: Which Tool Fits Which Team

After going through this, I've developed a framework for thinking about whether engineering teams should switch or stick. It's not about which tool is "better" objectively.

Linear is likely right for you if:

• Your team is under 30 engineers
• Engineering operates mostly independently from other business units
• Integration needs are basic (GitHub, Slack, Figma)
• You don't have heavy compliance or audit requirements
• Speed and developer experience are your top priorities
• You're starting fresh without years of Jira configuration to preserve

Jira probably makes more sense if:

• You're above 50 people with multiple non-engineering stakeholders
• Heavy integrations with enterprise tools are non-negotiable
• Complex approval or compliance workflows exist
• Reporting requirements come from leadership regularly
• Your organization has already invested in Jira customization that works
• Cross-team visibility across product, support, and engineering matters

The hardest zone is 30-50 engineers. That's where we sit. And that's where neither tool is obviously correct.

A Hybrid Solution: Using Both Tools Strategically

Here's what we actually landed on. It's messier than I'd like but more honest than either pure approach.

Engineering uses Linear for day-to-day work. Sprint planning, individual tickets, technical discussions, GitHub integration: all happens in Linear. Speed and UX benefits are too real to give up. ICs are happier, which matters.

However, Jira handles cross-functional workflows. Customer-reported bugs that need support team visibility, projects requiring product management involvement, anything touching compliance or security approvals. All of it lives in Jira. A Zapier automation syncs certain Linear issues to Jira when they hit specific labels.

Is it perfect? No. We're running two systems, which is its own overhead. But it's working better than either pure approach did.

Getting the sync setup stable took a couple weeks, and occasional issues still crop up where context doesn't transfer cleanly. But complaints have died down from both sides. Engineers aren't forced into Jira for everything. Stakeholders aren't locked out of visibility into engineering work.

Questions You Should Actually Ask Before Switching

If you're evaluating Linear as an alternative for your team, skip the feature matrices. Ask these questions instead:

1. Who needs to see and interact with your engineering tickets? If it's just engineers, Linear wins. If it's half your company, think harder.

2. What breaks if your integrations don't work? Make a list of every tool that touches your current issue tracker. Check Linear's actual integration depth for each one, not just whether an integration exists.

3. What does leadership ask you to report on? Can Linear generate those reports today? Not "theoretically" or "with some custom work," but actually today?

4. How much Jira configuration would you lose? Be honest about whether that config is cruft or actually serves purposes. Sometimes it's both.

5. What's your team's appetite for change management? Switching tools is work. Retraining people is work. Make sure the expected benefits justify the transition cost.

Linear is a great tool. Jira is a capable tool. Neither is the answer to engineering team dysfunction, which usually stems from people and process problems that no software can fix.

If I had to give a single recommendation: try Linear with a small team or new project first. See how it fits your actual workflow for three months before committing to an organization-wide migration. How this comparison shakes out depends entirely on your specific context.

And maybe keep your Jira instance warm. Just in case.

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What's worked for your team? I stream some of our tooling discussions on Twitch occasionally if you want to argue about this live. Always happy to hear from other folks who've gone through similar migrations.