In 2015, Karri Saarinen joined Airbnb as a principal designer and had to use Jira for the first time. His reaction, as recounted in Build Orbit’s account of Linear’s founding, was blunt: “What is this thing? It’s so messy and so complicated.” He refused to use it for a while, then built a Chrome extension, a CSS stylesheet that loaded a cleaner interface on top of Airbnb’s internal Jira. About a hundred colleagues installed it. Four years later, that frustration became Linear. The story is the whole story of project-management tools in miniature: the people who open the tool every morning rarely choose it, so for fifteen years nobody built for them. Now, finally, they are choosing, and the choices have settled into a pattern that is sharper than most software categories ever get.
The fifteen-year churn
The category has been a graveyard of defaults. Trac and Bugzilla gave way to Jira, which Atlassian rode to dominance and never relinquished among engineers. Trello made Kanban boards mainstream and got acquired by Atlassian. Asana arrived from Facebook’s cofounder Dustin Moskovitz with a cleaner take on task management. ClickUp launched in 2017 promising to be “one app to replace them all,” per Monday’s own comparison writeup. Monday.com rebuilt itself around a “Work OS” pitch. Notion turned a note-taking app into a database engine. Each wave promised to end the switching, and each wave produced more switching.
Jira’s grip never actually broke. In the 2024 Stack Overflow Developer Survey, which drew over 65,000 respondents, Jira topped the most-used asynchronous tools for the third year running, and its share rose from 52.37 percent in 2023 to 57.5 percent in 2024. Confluence, its sibling, climbed from 34.16 to 35.3 percent. So the headline is not that Jira lost. It is that a clear second pattern formed alongside it, and the second pattern is where the interesting decisions live.
The 2026 convergence
Strip away the marketing and three landing spots account for most of what working teams settle on. Engineering teams converge on Linear. Cross-functional work, where engineers, designers, marketers, and operators all need the same page, lands in Notion. Operations-heavy teams that run on process and reporting keep ClickUp, Monday, or Asana. The boundaries blur at the edges, but the centers are distinct, and which center a team gravitates toward is mostly a statement about how that team likes to work.
The tell is that the convergence does not track company size or stage. It tracks temperament. A team that values a single opinionated way of doing things picks differently from a team that wants to model its own process in software. Both can be right. They are answering different questions.
Why engineering teams pick Linear
Linear’s pitch is the opposite of flexibility, and that is the point. Saarinen describes his belief plainly in a framework summary of his Lenny’s Podcast appearance: “productivity software should be opinionated… flexible software creates friction because people spend time figuring it out.” Rather than offering ten ways to view tasks, Linear forces work into Cycles, its fixed-length iteration model, and ships strong defaults instead of a settings panel. Cofounder Jori Lallo put the philosophy directly in Build Orbit’s account: “We design it so that there’s one really good way of doing things.”
The company practices what it sells. Per a summary of Saarinen’s Lenny’s Podcast interview, Linear runs with almost no product managers, uses no A/B tests, and sets no metric-based goals, relying on taste and a cyclical review process instead. Three Finnish founders, Saarinen, Lallo, and Tuomas Artman, started it after meeting for beers in early 2018, raised a $4.2M seed from Sequoia in 2019, and ran a deliberate year-long private beta before opening up. By the time of Build Orbit’s reporting, Linear was a $1.25B product, with customers including Block, Vercel, Ramp, Retool, and Mercury per the podcast summary.
Engineers self-select into Linear because the opinionated design removes the configuration tax. The tradeoff is real and worth naming: a team that wants to model a bespoke approval chain or a non-standard workflow will fight Linear, because Linear was built to refuse exactly that. For most software teams, that refusal is the feature. For some, it is the dealbreaker.
The Notion-as-PM argument
Notion wins a different problem. Engineering trackers are built for engineers, which means everyone else, the marketer waiting on a launch, the operator chasing a contract, the founder writing a spec, ends up locked out of the context. Notion’s cross-functional pitch names the symptom precisely: information scattered across “buried decisions in Slack, floating specs in Google Docs, and disappearing projects in Jira tickets.” Its answer is a block-based workspace where a product requirements doc can link directly to the task that implements it.
The adoption curve backs the pitch. Per a practical guide citing TapTwiceDigital figures, Notion’s user base grew from 20 million in 2022 to over 100 million by 2024, with 80 percent of users outside the United States and more than half of Fortune 500 companies using it. That fivefold jump is not coming from engineering teams abandoning Linear. It is coming from cross-functional teams that need one source of truth and are willing to trade dedicated tooling for a shared surface.
Which center a team gravitates toward is mostly a statement about how that team likes to work.
The honest limit is the inverse of Linear’s. Notion’s flexibility is also its failure mode. A workspace nobody designs with intention becomes the same mess of scattered pages it was meant to replace, just inside one app instead of five. Notion gives you the blocks. It does not give you the discipline, and teams that lack the discipline rebuild the chaos.
What ClickUp, Monday, and Asana still own
The long tail is not a leftover. It is a real category: operations-heavy teams whose work is process, handoffs, and reporting across departments rather than shipping code. Here the customization that engineers reject is the entire value proposition.
The 2026 comparisons sort these three cleanly. Per a head-to-head from TrackingTime, the verdict by team type is that agencies favor ClickUp, product teams favor Asana, and operations teams favor Monday, with startups split between Asana early and ClickUp as they scale. The same writeup lists entry paid pricing on annual billing at $10.99 per user per month for Asana, $9 for Monday, and $7 for ClickUp. ClickUp’s differentiator is depth and customization, with a moderate-to-high learning curve; Monday’s is visual workflows and cross-team dashboards; Asana’s is structured task hierarchy with a gentler ramp.
Monday’s own enterprise comparison makes the operations case explicitly: basic project management “falls apart after 100 employees,” right when teams need to coordinate across departments, and the hidden costs are integration complexity and data silos rather than the sticker price. That is a different buyer than the one Linear courts. The operations buyer wants to encode a workflow that spans finance, legal, and delivery. The engineering buyer wants the workflow decided for them so they can close tickets.
The choice is about culture
The reason the convergence is this sharp is that the tools have stopped competing on features and started competing on philosophy. Linear sells one correct way and refuses configuration. Notion sells infinite configuration and refuses to impose structure. ClickUp, Monday, and Asana sell structured configuration tuned to operational handoffs. A team picking among them is really answering a question about itself: do we want the tool to decide, do we want to decide everything, or do we want to model a process we already run?
Jira is still on top of the engineering survey because plenty of teams never had to make that decision, and inertia is cheaper than migration. The teams that did make it landed where their culture pointed. Saarinen’s hundred Airbnb colleagues who installed a Chrome extension to make Jira bearable were the early version of that sorting, choosing a cleaner surface years before anyone gave them a real option to switch.
