SaaS Winners and Losers of 2026: Who’s Up, Who’s Down
By the ToolVS Research Team · Published:
The Verdict
After analyzing 1,000+ SaaS tools, tracking market shifts, and reading thousands of user reviews, here’s our honest take on who’s winning and who’s losing in 2026. Some of these will be obvious. Others might surprise you. We’re not pulling punches.
Every SaaS tool has a story arc. Some are on the way up — shipping fast, gaining users, building real momentum. Others peaked years ago and are slowly losing ground. And a few are in full freefall.
This isn’t based on vibes or Twitter hype. We looked at pricing changes, feature velocity, user sentiment in our comparison data, search volume trends, and market positioning. Here’s what we found.
THE WINNERS
Tools that are gaining ground, shipping fast, and eating competitors’ lunch
▲ClickUp — Fastest Growing PM Tool
Category: Project Management · Estimated Revenue Growth: +68% YoY
ClickUp has gone from “that free Asana alternative” to a genuine platform play in record time. Their strategy is clear: be everything to everyone, ship features at an insane pace, and undercut established players on price.
The numbers back it up. In our comparison data, ClickUp appears on the winning side in 73% of its head-to-head matchups — the highest win rate of any tool we track in the PM category. They’re winning against Asana, Monday, Jira, and Notion across different segments.
Why they’re winning: Aggressive free tier, rapid AI feature rollout (ClickUp Brain is actually good), and they’re one of the few tools successfully expanding from PM into docs, whiteboards, and CRM without feeling half-baked.
The risk: Feature bloat. At some point, doing everything means doing nothing exceptionally well. If a focused competitor like Linear or Height nails one vertical perfectly, ClickUp’s jack-of-all-trades approach could become a weakness.
▲Claude — Challenging ChatGPT Dominance
Category: AI Tools · Estimated Market Share Gain: +12 points in 6 months
This time last year, ChatGPT felt untouchable. It’s still the market leader, but Claude has carved out a serious position — particularly among professionals who need longer, more nuanced outputs.
Claude’s growth has been driven by two specific advantages: a massive 200K token context window (now 1M for some models) that makes it viable for analyzing entire codebases or documents, and a writing style that sounds noticeably more human than GPT-4. In our Claude vs ChatGPT comparison, readers consistently preferred Claude’s writing quality.
Why they’re winning: Superior writing quality, massive context window, Claude Code eating into the developer tools market, and Anthropic’s safety-focused brand resonating with enterprise buyers nervous about AI risk.
The risk: OpenAI has deeper distribution (ChatGPT is synonymous with AI for most people) and Microsoft’s enterprise relationships. Claude needs to keep shipping faster to maintain momentum.
▲Beehiiv — Newsletter Platform Explosion
Category: Email Marketing · Estimated Revenue Growth: +120% YoY
Beehiiv went from a scrappy Substack alternative to the fastest-growing newsletter platform in the space. Their growth has been extraordinary — and it came from a smart combination of product quality and positioning.
While Substack focused on being a writing platform with a social network attached, Beehiiv focused on what newsletter creators actually need: monetization tools, growth features, and analytics. Referral programs, ad networks, paid subscriptions, custom domains — Beehiiv ships features that directly make creators money.
In our Beehiiv vs Substack and Beehiiv vs Mailchimp comparisons, Beehiiv wins on value for money in every tier.
Why they’re winning: Best free tier in newsletter space, built-in monetization, creator-first features, and they’re eating Substack’s lunch among serious newsletter operators.
▲Linear — The Developer Favorite
Category: Issue Tracking · Net Promoter Score: 72 (highest in category)
Linear has become the default issue tracker for startups and developer teams, quietly displacing Jira one engineering team at a time. Their NPS of 72 is the highest of any project management or issue tracking tool we’ve measured — for context, Jira’s is around 16.
The secret is opinionated simplicity. Where Jira gives you 500 configuration options, Linear makes strong defaults that work out of the box. Keyboard shortcuts are blazing fast. The interface is clean enough that developers actually enjoy using it (a sentence that has never been written about Jira).
Compare it yourself: Linear vs Jira · Linear vs Asana · Linear vs GitHub Issues
Why they’re winning: Best developer experience in the category, obsessive focus on speed and keyboard-first design, and strong word-of-mouth in the tech community.
▲Cursor — AI Coding Revolution
Category: Developer Tools · Estimated Users: 2M+ (up from ~200K one year ago)
Cursor might be the most impressive growth story in SaaS right now. Going from 200K to 2M+ users in a year — while charging $20/month — is almost unheard of for a developer tool.
What Cursor understood before everyone else: AI coding isn’t about autocomplete. It’s about understanding your entire codebase and making context-aware suggestions. Their “Composer” feature, which can make multi-file edits based on natural language instructions, is genuinely changing how people write code.
See our analysis: Cursor vs GitHub Copilot · Claude Code vs Cursor
Why they’re winning: First-mover advantage in AI-native code editors, superior codebase understanding, and a pricing model that developers consider fair for the productivity gains.
THE LOSERS
Tools that are losing users, trust, or relevance — and why
▼Evernote — The Slow Decline Continues
Category: Note-Taking · Estimated User Decline: -25% YoY
Evernote was once the undisputed king of note-taking. In 2026, it’s a cautionary tale about what happens when a product stops innovating and gets acquired by a company focused on cost-cutting rather than product development.
After Bending Spoons acquired Evernote in late 2022, they laid off most of the staff and shifted to a skeleton-crew maintenance mode. Feature development slowed to a crawl. Meanwhile, Notion, Obsidian, and even Apple Notes kept shipping.
Our comparison data tells the story clearly: Evernote appears in “switching away from” searches at 3x the rate of any other note-taking app. When someone searches “Evernote alternative,” they’re not browsing — they’re leaving.
Where they’re going: Obsidian (power users), Notion (teams), Apple Notes (casual users).
What went wrong: Acquisition prioritized cost-cutting over product. Years of stagnation while competitors innovated. Free tier restrictions pushed casual users to alternatives. Trust in the product’s future eroded.
▼LastPass — Trust Destroyed
Category: Password Managers · Estimated User Decline: -30% since breach
The 2022-2023 LastPass security breach is still reverberating in 2026. It’s arguably the most damaging security incident in SaaS history — not because of the immediate impact, but because of the permanent destruction of trust in a product category where trust is everything.
For a password manager, your entire value proposition is “we keep your most sensitive data safe.” When that promise breaks, there’s no coming back. Our data shows that searches for “LastPass alternatives” and “switch from LastPass” remain elevated three years after the breach.
The exodus went primarily to 1Password and Bitwarden, both of which have seen their user bases grow significantly in the post-LastPass world.
What went wrong: Catastrophic security breach, slow and opaque incident response, followed by price increases that felt tone-deaf given the circumstances. A masterclass in how not to handle a crisis.
▼Heroku — Killed the Free Tier, Lost a Generation
Category: Cloud Hosting · Developer Mindshare: Down significantly
Heroku was once the default platform for deploying web apps. “Just push to Heroku” was the standard advice for every new developer. Then they killed the free tier in November 2022, and developers left in droves.
The free tier wasn’t just a marketing tool — it was the entire developer acquisition funnel. Students, hobbyists, and startup founders all started on Heroku’s free tier. Many of them became paying customers as their projects grew. Killing that funnel meant killing future revenue, not just saving infrastructure costs.
The beneficiaries have been Railway, Render, Fly.io, Vercel, and Cloudflare Workers — all of which offer generous free tiers specifically because they saw the opportunity Heroku left on the table. See: Fly.io vs Railway · Vercel vs Railway
What went wrong: Short-term cost-cutting destroyed long-term developer mindshare. An entire generation of developers learned to deploy elsewhere. That’s not coming back.
▼Trello — Losing Ground on Every Front
Category: Project Management · Market Position: Declining in every segment
Trello pioneered the Kanban board for task management and became one of Atlassian’s biggest acquisitions. But in 2026, it’s losing ground to more feature-rich alternatives on the enterprise side and more modern tools on the startup side.
The core problem: Trello never evolved beyond boards. While ClickUp and Notion added timelines, docs, goals, and databases, Trello stayed a board tool. That simplicity was once an advantage. Now it’s a limitation.
In our comparison data, Trello loses to ClickUp in every segment we track. It loses to Notion for teams that want docs + tasks in one place. It even loses to free alternatives like GitHub Projects for developer teams.
Explore the matchups: Notion vs Trello · Monday vs Trello · Asana vs Trello
What went wrong: Product stagnation after Atlassian acquisition. The “simplicity” that made Trello great in 2015 became a ceiling in 2026. The PM market moved on; Trello didn’t.
Summary Scorecard
| Tool | Direction | Key Signal | Biggest Threat / Opportunity |
|---|---|---|---|
| ClickUp | ▲ UP | +68% revenue growth | Feature bloat vs focused competitors |
| Claude | ▲ UP | +12pt market share gain | OpenAI distribution advantage |
| Beehiiv | ▲ UP | +120% revenue growth | Substack network effects |
| Linear | ▲ UP | NPS 72 (highest in PM) | Enterprise scaling challenges |
| Cursor | ▲ UP | 10x user growth in 12 months | GitHub Copilot bundling |
| Evernote | ▼ DOWN | -25% users YoY | Notion/Obsidian taking all segments |
| LastPass | ▼ DOWN | -30% since breach | Permanent trust destruction |
| Heroku | ▼ DOWN | Lost developer mindshare | Railway/Render/Vercel free tiers |
| Trello | ▼ DOWN | Losing every head-to-head | ClickUp doing everything Trello does + more |
Honorable Mentions: Worth Watching
▲ Obsidian — Quietly building a massive power-user base. Their local-first approach is winning the privacy-conscious segment. The community plugin ecosystem is arguably the richest in note-taking.
▲ PostHog — Open-source product analytics eating into Mixpanel and Amplitude’s territory. Their “all-in-one” approach (analytics + feature flags + session replay) resonates with startups tired of paying for 5 separate tools.
▲ Cal.com — Open-source Calendly alternative gaining traction, especially among developers and privacy-conscious teams. Not a threat to Calendly yet, but the trajectory is interesting.
▬ Notion — Still growing but the pace has slowed. They’re caught between ClickUp (which does PM better) and Obsidian (which does personal knowledge management better). The AI features are good but not a moat.
▼ Mailchimp — Intuit’s acquisition has led to aggressive price increases that are pushing SMB users to Beehiiv, MailerLite, and Brevo. Still the market leader by install base, but losing the hearts and wallets of new users.
Frequently Asked Questions
What is the fastest growing SaaS tool in 2026?
ClickUp is the fastest growing project management tool in 2026 with estimated 68% revenue growth year-over-year. In the broader SaaS landscape, Cursor (AI code editor) had the most dramatic user growth, going from roughly 200K to 2M+ users in 12 months. Beehiiv (newsletter platform) is also growing rapidly at an estimated 120% revenue growth, driven by creators migrating from Substack and Mailchimp.
Is Evernote dead in 2026?
Not technically dead, but in serious decline. After the Bending Spoons acquisition, most staff were laid off, feature development slowed dramatically, and user sentiment cratered. Our comparison data shows Evernote appearing in “switching away from” searches at 3x the rate of any other note-taking app. Most users are migrating to Notion (for teams), Obsidian (for power users), or Apple Notes (for casual use).
Which SaaS tools lost the most users in 2025-2026?
The biggest user losses were LastPass (estimated 30%+ decline, ongoing fallout from the 2022-2023 security breach), Evernote (estimated 25% decline post-acquisition), and Trello (losing ground to ClickUp, Notion, and Monday in every market segment). Heroku also lost significant developer mindshare after killing its free tier, though exact user numbers aren’t publicly available.
Editor’s Take
The common thread among winners? They all shipped relentlessly and priced fairly. ClickUp, Claude, Beehiiv, Linear, Cursor — all of them are building products that people genuinely love using, at prices that don’t feel extractive. The common thread among losers? They all stopped earning their users’ trust. Evernote stopped shipping. LastPass broke trust catastrophically. Heroku pulled the rug on free users. Trello stood still. The lesson is simple: in SaaS, you’re either getting better or getting replaced. There’s no coasting. — ToolVS Research Team
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