ClickUp vs Smartsheet pricing

The two pages

Tier by tier

Rows are lined up by position on each page, not by tier name, because the names never match across two vendors. Row 1 is the top tier on each page, row 2 the one under it. Where one page has fewer tiers than the other, the row is left blank rather than paired with something it is not.

1. Row 1
   ClickUp

   Free$0/user/mo

   SmartsheetNo tier at this position.
2. Row 2
   ClickUp

   Core$9/user/mo

   SmartsheetNo tier at this position.
3. Row 3
   ClickUp

   Business$17/user/mo

   SmartsheetNo tier at this position.
4. Row 4
   ClickUp

   EnterpriseCustom

   SmartsheetNo tier at this position.
5. Row 5
   ClickUp

   Max$100/user/mo

   SmartsheetNo tier at this position.

The entry tier

Changes we recorded

Every change we have written up for either page, newest first.

• ClickUp removes Audio Generation from AI features, rebrands Unlimited Plan to Core Plan, and adds Creative Studio and AI Workflows product links.

  ClickUp·12 Nov 2026

  ClickUp removes Audio Generation from AI features, rebrands Unlimited Plan to Core Plan, and adds Creative Studio and AI Workflows product links. Why it matters: • Plan naming change from Unlimited to Core signals potential tier restructuring; competitors should monitor whether this reflects broader plan architecture changes or pricing tier repositioning. • Addition of Creative Studio and AI Workflows links indicates ClickUp is expanding AI-native capabilities and feature discoverability, suggesting intensifying focus on AI-powered work tools. • Removal of Audio Generation and reframing of AI governance from 'Coming soon' to 'Feature trial' suggests product roadmap recalibration away from audio toward video and governance maturity. Features: - Video & Audio Generation removed; Video generation added (audio capability discontinued or de-emphasized). - AI governance status changed from 'Coming soon' to 'Feature trial' across trial and paid tiers. - New product links surfaced: Talk to Brain (URL changed from /talk-to-text to /voice), Creative Studio, AI Workflows, and Sheets. Plans: - Unlimited Plan renamed to Core Plan (guest seat allocation policy unchanged: 5 seats for 1 paid user, 2 seats per additional paid user). What to do: • Audit ClickUp's full plan naming and tier structure to assess whether Core Plan rename signals rebranding of the entire tier ladder; update positioning if ClickUp is consolidating or repositioning entry/mid-market segments. • Evaluate your own AI feature roadmap against Creative Studio and AI Workflows; if ClickUp is bundling generative content and workflow automation natively, consider feature parity or differentiated AI positioning. • Track ClickUp Brain product messaging; increased link density suggests ecosystem expansion and suggests monitoring for new pricing models or upsell paths tied to AI modules.

• Unable to assess pricing page changes due to content blocker interference-diff contains only extension error messages, not actual page content.

  Smartsheet·11 Nov 2026

  Unable to assess pricing page changes due to content blocker interference-diff contains only extension error messages, not actual page content. Why it matters: • No competitive intelligence can be extracted from this diff as it captures a browser extension block (ERR_BLOCKED_BY_CLIENT) rather than Smartsheet's actual pricing page content. • The Optimizely CDN block suggests either ad/script blocking or privacy extension interference, preventing visibility into any real pricing, plan, or positioning changes. Content Capture: - Diff contains only error pages and extension block messages, not Smartsheet pricing page HTML or copy What to do: • Recapture the pricing page with extensions disabled or using a clean browser session to obtain actionable competitive data. • Retry the page scrape to determine if any material pricing, plan, or feature changes have actually occurred.

• ClickUp rebrand from Free/Unlimited/Business/Enterprise to Free Forever/Core/Business/Enterprise with AI credits model and 33% yearly discount (up from 30%)

  ClickUp·8 Nov 2026

  ClickUp rebrand from Free/Unlimited/Business/Enterprise to Free Forever/Core/Business/Enterprise with AI credits model and 33% yearly discount (up from 30%) Why it matters: • ClickUp is repositioning AI as a tiered, credit-based consumable (500-3K credits/user/mo) rather than unlimited access, creating new upsell motion and revenue per seat • Plan rename from 'Unlimited' to 'Core' signals shift in positioning-Core now emphasizes AI/Brain² integration as central product differentiator across all tiers • Automation value messaging increased significantly ($20→$100→$1000 per tier), reframing automation as premium feature to justify price increases Pricing & Plans: - Plan restructured: Free Forever → Core → Business → Enterprise (previously Free Forever → Unlimited → Business → Enterprise) - Yearly discount increased: 30% → 33% - 'Unlimited' plan renamed to 'Core' with new positioning around AI accessibility AI/Brain Integration: - ClickUp Brain² now prominently featured across all paid tiers with credit-based consumption model - Free Forever: 500 credits/workspace - Core: 1K credits/user/mo (pooled) - Business: 1.5K credits/user/mo (pooled) - Enterprise: 3K credits/user/mo (pooled) - Free tier now includes 'Trial Premium Model Usage' and 'ClickUp Brain² Trial' - Business tier adds 'ClickUp Brain² Scaled' with 'Unlimited AI Notetaker' Features: - Free tier gains: Time Tracking, SyncUps Video Calls (previously Unlimited plan features) - Free tier removes: 'Basic Custom Field Manager' (now 'Custom Fields & Task Types' in Core) - Core tier now includes: '1K Automations/mo' (valued at $20) vs previous tier's baseline - Business tier raises: '10K Automations/mo' (valued at $100) vs previous '5K Automations/mo' - Enterprise tier adds: '1M Automations/mo' (valued at $1,000), white labeling, advanced governance/SSO/SCIM/SAML, audit logs, HIPAA+BAA, connected search across Google Drive/OneDrive/Gmail/Teams/Slack Positioning: - Shift from feature-count parity to AI-credit gating as primary differentiation - New 'MAX' plan introduced: described as 'ONE PLAN. EVERYTHING MAXED' with 'full Max AI engine plus every Enterprise-grade control' - AI/Brain now core to positioning-removed generic '25+ products' messaging, emphasizing Brain², Super Agents, and AI Notetaker as tier drivers What to do: • Audit whether your AI features/pricing strategy can compete with credit-based consumption model; ClickUp is monetizing AI more aggressively and making it table-stakes across all tiers • Benchmark your automation/workflow limits vs ClickUp's new tiers ($20/$100/$1K value messaging) and assess if your positioning on automation is defensible • Review whether free tier feature parity (Time Tracking, video calls now in free) pressures your freemium strategy; prepare counter-narrative on what justifies paid conversion in your product

• Smartsheet removes 'New' tags from AI and portfolio features, repositions Advanced Portfolios as enterprise differentiator.

  Smartsheet·8 Nov 2026

  Smartsheet removes 'New' tags from AI and portfolio features, repositions Advanced Portfolios as enterprise differentiator. Why it matters: • AI capabilities (Smart Assist, formula generation, data analysis) are now standard positioning rather than new-signals Smartsheet considers AI table stakes and is normalizing it across tiers • Control Center rebranded to 'Advanced Portfolios' with governance language, no longer highlighted as premium add-on for Business/Enterprise, suggesting shift in go-to-market around portfolio-level execution • Feature gating remains aggressive: Pro tier still excludes Portfolios, Scenario Planning, and all AI features, indicating Smartsheet is doubling down on upsell motion to Business and above Positioning: - AI features (Conversational AI, formula generation, data analysis, text summarization) removed from 'NEW' callouts-repositioned as core platform capabilities rather than differentiators - Control Center renamed to 'Advanced Portfolios' with updated value prop: 'Govern execution across projects and processes at scale' (vs. previous 'Deliver consistent, visible projects...') - 'Connect to external AI tools' (MCP integrations) now positioned as standard feature, not new innovation Features: - Portfolios, Scenario Planning, and AI-powered features continue to be gated behind Enterprise and Advanced Work Management tiers for existing plans - No new capabilities added-consolidation of existing feature set messaging - Control Center educational content and use cases removed from pricing page (video/description removed) Plans: - No plan additions or removals - Pro tier continues to exclude Portfolios, Scenario Planning, and all AI features-still positioned as 'Not included' - Business tier: Portfolios remain 'Not included', Control Center remains add-on (no change in gating) - Enterprise tier: Portfolios and Control Center now fully included (no change) What to do: • Audit your AI narrative: if Smartsheet is normalizing AI as table stakes, ensure your messaging either matches that commoditization or clearly articulates a differentiated AI value prop (e.g., faster time-to-value, lower hallucination, better domain specificity) • Pressure-test your portfolio/governance features: Smartsheet's 'Advanced Portfolios' rebrand suggests they're making a harder pitch to large orgs on execution governance-map competitive win/loss to understand if this repositioning is working and if you need to elevate your portfolio story • Monitor tier gating: Smartsheet's continued Pro exclusion of these features is aggressive; validate whether your price-to-value narrative for mid-market (Business tier equivalent) creates an opening if their upsell motion is leaving money on the table.

• ClickUp emphasizes "25+ products" access across all plans and adds annual billing discount messaging to pricing page.

  ClickUp·3 Sept 2026

  ClickUp emphasizes "25+ products" access across all plans and adds annual billing discount messaging to pricing page. Why it matters: • ClickUp is repositioning as a bundled all-in-one platform rather than itemizing features by tier, making it harder for competitors to claim feature differentiation • The prominent "SAVE 30%" annual discount messaging signals aggressive retention focus and may pressure competitors to match or communicate similar discounts more visibly • By listing AI/Brain and Super Agents at plan-level rather than as paid add-ons in the forefront, ClickUp is normalizing these capabilities as table stakes across their entire product line Positioning: - Shifted messaging from individual feature lists to unified "25+ products" bundling language - Elevated AI/Brain and Super Agents to headline tier visibility, signaling these are no longer premium/optional but core platform features - Added prominent annual billing discount callout ("SAVE 30%") above pricing tiers Features: - Explicitly highlighted AI/Brain, Super Agents, Tasks & Projects, Forms, Gantt, Sprints, and Clips as representative of 25+ bundled products - Created '12 more' expandable link to obscure full feature depth (likely reducing comparison friction for lower tiers) What to do: • Audit competitor pricing pages for similar bundling/all-in-one positioning and test messaging that either emphasizes specialized depth vs. breadth or transparent feature-per-tier clarity • Model out impact of ClickUp's 30% annual discount on your own churn/retention benchmarks; prepare customer comms around your own billing incentives if not already competitive • Review whether AI capabilities are positioned as core (free) or premium in your own pricing; align positioning strategy to either match ClickUp's inclusivity or deliberately differentiate on modular pricing.

• ClickUp pricing page changed

  ClickUp·31 Aug 2026

• ClickUp pricing page changed

  ClickUp·30 Aug 2026

• ClickUp pricing page changed

  ClickUp·26 Aug 2026

• ClickUp pricing page changed

  ClickUp·21 Aug 2026

• ClickUp removes its 'all plans include 25+ products' messaging and simplifies feature visibility on pricing page

  ClickUp·18 Aug 2026

  ClickUp removes its 'all plans include 25+ products' messaging and simplifies feature visibility on pricing page Why it matters: • Signals potential shift in how ClickUp is positioning its all-in-one value prop-may indicate they're segmenting features more aggressively by tier • Removal of 'SAVE 30%' annual discount messaging reduces pricing page friction and could indicate testing different monetization incentives • Simplified feature list removes cognitive burden but may confuse buyers about which products/features come with each plan tier Positioning: - Removed messaging that 'All plans give access to 25+ products' as headline differentiator - Removed explicit feature callouts for Super Agents, AI/Brain, Chat, Tasks & Projects, Docs & Wikis, Forms, Calendar, Whiteboards, Gantt, Time Tracking, Dashboards, Sprints, and Clips from pricing page view - Removed '12 more' feature indication suggesting hidden features across all tiers Pricing Display: - Removed 'SAVE 30%' annual discount messaging from billing toggle - Removed 'Monthly/Yearly' toggle language emphasis What to do: • Audit which features ClickUp is now gatekeeping by plan tier-identify gaps in competitor's base offering your team can exploit • Test messaging emphasizing feature availability across your own pricing tiers to capture buyers confused by ClickUp's reduced transparency • Monitor whether ClickUp re-introduces this messaging or doubles down on tier-based feature segmentation in next 30 days

• ClickUp removes Templates link from pricing page navigation

  ClickUp·15 Aug 2026

  ClickUp removes Templates link from pricing page navigation Why it matters: • Templates section deprioritized in pricing page UX-suggests either lower usage or repositioning as secondary feature • Simplified navigation may indicate internal focus shift away from template-first onboarding Navigation/Positioning: - Templates link removed from pricing page header/menu navigation - No corresponding plan changes or pricing adjustments What to do: • Monitor whether templates remain available in product or if this signals deprecation of that feature • Check if ClickUp is shifting template strategy toward in-product discovery vs. external marketing