Chiefy Pricing 2026
Complete pricing guide for Chiefy — plans, costs, and free options.
💰 Chiefy Pricing Overview
Chiefy uses a paid pricing model. Requires a paid subscription or one-time purchase. Current pricing: 14-day free trial, cancel anytime, no contract. Pro is listed at $19.99/month billed yearly against a $29.99/month regular rate, covering smart-inbox sorting, drafting in your voice, calendar awareness and memory. The team tier, positioned for teams of 50+, is listed at $49.99/month/user billed yearly against $69.99, adding dedicated support and custom workflows.. Chiefy is a popular productivity tool known for ai chief of staff for gmail and outlook: automatic triage, calendar-aware drafts in your voice, and a conversational agent over your mailbox. You can get started with Chiefy for free and upgrade to a paid plan as your needs grow.
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🔍 Compare Before You Buy
See all 5 alternatives →Comparing Chiefy to similar tools helps you make the best choice for your budget and needs:
Agentys
FreemiumAI email assistant that learns your voice from sent mail and drafts replies in Gmail or Outlook — you review and send
Free: USD 0 forever with no credit card — smart inbox sorting, custom automation tools and 1 inbox (Gmail or Outlook). Starter is USD 16.99 per month billed annually (USD 23.99 month-to-month): 1 inbox, 500 AI draft replies per month and smart inbox sorting. Professional is USD 24.99 per month billed annually (USD 29.99 month-to-month) and is marked most popular: 1 inbox plus calendar, 2,000 AI draft replies per month, voice dictation, automatic follow-ups, automated workflows and priority support. A seven-day trial applies to the paid tiers.
Compare with Chiefy →Superhuman
PaidPremium AI email client for reaching inbox zero daily
Starting at $25/month
Compare with Chiefy →Inbox Zero
PaidOpen-source AI email assistant that labels your inbox, pre-drafts replies in your voice, and bulk-unsubscribes
Starting at $18/user/month
Compare with Chiefy →Complete Your Productivity Stack
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Chiefy Plans & Pricing
Pro is listed at
billed yearly against a $29.99/month regular rate, covering smart-inbox sorting, drafting in your voice, calendar awareness and memory
The team tier, positioned for teams of 50+, is listed at
/user billed yearly against $69.99, adding dedicated support and custom workflows.
* Pricing information is based on publicly available data and may not reflect current promotions, annual discounts, or regional pricing. Visit the official Chiefy website for the latest pricing.
Is Chiefy Free?
Chiefy offers a free tier that lets you try the platform without any payment. The free plan typically includes core features with usage limits. For power users, paid plans unlock additional features, higher limits, and priority support.
Chiefy Feature Comparison
Here's how Chiefy's key features are typically distributed across pricing tiers. Feature availability is estimated based on common SaaS patterns — check the official site for exact tier details.
| Feature | Pro is listed at | The team tier, positioned for teams of 50+, is listed at |
|---|---|---|
| Automatic categorisation into action-shaped buckets, not folders | ✓ | ✓ |
| Drafts written in your learned tone with calendar availability built in | ✓ | ✓ |
| Persistent memory of people and projects across threads | ◐ | ✓ |
| Conversational agent that searches the mailbox and answers directly | — | ✓ |
| Works with both Gmail and Outlook | — | ✓ |
✓ = Full access · ◐ = Limited · — = Not available. Feature availability is estimated and may vary.
Is Chiefy Worth It?
Chiefy is a premium productivity tool that offers 5 key features including Automatic categorisation into action-shaped buckets, not folders, Drafts written in your learned tone with calendar availability built in, Persistent memory of people and projects across threads. Chiefy is an AI chief of staff that sits on top of Gmail and Outlook and does three jobs: sorting, drafting and answering. Sorting is automatic categorisation into buckets that map to what you would do next rather than to folders — To Respond, Action Needed, Meeting, FYI, Promotions — so the inbox surfaces the two threads that need you and pushes the newsletter digest out of the way. Drafting learns your writing voice and produces replies that match your tone, with calendar awareness built in, so a request for a call comes back as a draft that already proposes real windows from your availability rather than a placeholder. It carries memory across threads, so context about a person or project persists and the drafts improve over time. The third surface is a conversational agent over the mailbox itself: ask it to find the Stripe invoice Accounting sent, check your calendar, or summarise a long thread, and it searches and answers rather than handing back a result list. Setup is per-provider — you connect Gmail or Outlook and start — with a 14-day free trial and no contract. The product is aimed at individual professionals first, with a per-user team tier for organisations of roughly fifty people upward.
✅ Chiefy is a good choice if you need:
- •Automatic categorisation into action-shaped buckets, not folders
- •Drafts written in your learned tone with calendar availability built in
- •Persistent memory of people and projects across threads
- •Conversational agent that searches the mailbox and answers directly
- •Works with both Gmail and Outlook
💡 Value Assessment
With a free tier available, Chiefy is an easy recommendation for anyone looking to try productivity tools without financial commitment. The paid plans offer good value for power users who need the additional features and higher usage limits.
Chiefy Key Features
Chiefy comes packed with features that make it a strong contender in the productivity space. Here's what you get:
Available in the free plan with limits — Automatic categorisation into action-shaped buckets, not folders helps you work more efficiently with Chiefy.
Powered by advanced AI models, Chiefy delivers intelligent content generation capabilities.
Available in the free plan with limits — Persistent memory of people and projects across threads helps you work more efficiently with Chiefy.
Powered by advanced AI models, Chiefy delivers intelligent content generation capabilities.
Powered by advanced AI models, Chiefy delivers intelligent content generation capabilities.
Chiefy Alternatives & Their Pricing
Considering alternatives to Chiefy? Here's how competing tools compare on pricing:
Agentys
FreemiumAI email assistant that learns your voice from sent mail and drafts replies in Gmail or Outlook — you review and send
Pricing: Free: USD 0 forever with no credit card — smart inbox sorting, custom automation tools and 1 inbox (Gmail or Outlook). Starter is USD 16.99 per month billed annually (USD 23.99 month-to-month): 1 inbox, 500 AI draft replies per month and smart inbox sorting. Professional is USD 24.99 per month billed annually (USD 29.99 month-to-month) and is marked most popular: 1 inbox plus calendar, 2,000 AI draft replies per month, voice dictation, automatic follow-ups, automated workflows and priority support. A seven-day trial applies to the paid tiers.
Superhuman
PaidPremium AI email client for reaching inbox zero daily
Pricing: Starter $25/mo, Business $30/user/mo. No free tier.
Inbox Zero
PaidOpen-source AI email assistant that labels your inbox, pre-drafts replies in your voice, and bulk-unsubscribes
Pricing: 7-day free trial on all plans, billed annually: Starter $18/user/month (labeling, drafted replies, cold-email blocking, bulk unsubscribe and archive, analytics, pre-meeting briefings), Plus $28/user/month (adds 2 email accounts per user, Slack integration, digests, auto-filed attachments, unlimited knowledge base), Professional $42/user/month (adds team-wide analytics, priority support, dedicated onboarding). Monthly billing is higher — $20/$35/$50. Enterprise with SSO, SCIM, and on-premise is quoted by sales. The code is open source and self-hostable.
NewMail AI
FreemiumAI inbox agent for Gmail, Outlook and Apple Mail — drafts in your voice, prioritises, schedules, stores nothing
Pricing: A free trial gives full access for two weeks with no credit card, no download and no payment details, including the personalised AI agent and a two-minute setup. Professional is $25 per month and includes AI drafts written in your voice with your FAQs and links, a priority inbox, custom categories, task extraction and scheduling, zero data retention under GDPR, and support for Gmail, Outlook and Apple Mail. Annual billing is advertised at 20% off. Enterprise is contact-priced and built for teams of roughly 20 to 200-plus, adding team context alongside personal voice, a KPI dashboard covering adoption, response time and ROI, volume pricing, SSO, a DPA and enterprise security, a dedicated account manager, and onboarding and training.
Replai
FreemiumAI email assistant that learns and writes in your own reply style
Pricing: The reply generator is free forever — $0/month, no card and no inbox access required. Pro is $6/month billed $72/year and covers unlimited replies, AI style learning, full inbox automation, drafts and draft-reply settings, Outlook Calendar integration, unlimited meeting recordings with speaker diarization and priority support. Team is custom-priced for teams that want shared reply identities, admin controls and volume terms.
Is Chiefy your tool?
Claim this listing to get a Featured badge, correct the pricing on this page yourself, and stand out from the 5 alternatives listed above. All plans include a permanent dofollow backlink to your site.
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Visit the official website for the latest pricing and to get started.
Frequently Asked Questions
Is Chiefy free to use?
Yes, Chiefy offers a free tier that you can use without paying. Paid plans starting at $19.99/month unlock additional features and higher usage limits.
How much does Chiefy cost in 2026?
As of 2026, Chiefy pricing is: 14-day free trial, cancel anytime, no contract. Pro is listed at $19.99/month billed yearly against a $29.99/month regular rate, covering smart-inbox sorting, drafting in your voice, calendar awareness and memory. The team tier, positioned for teams of 50+, is listed at $49.99/month/user billed yearly against $69.99, adding dedicated support and custom workflows.. Pricing may vary based on billing cycle (monthly vs annual) and region. Visit the official Chiefy website for the most current pricing.
What is the cheapest Chiefy plan?
The cheapest option is the free tier. If you need premium features, the most affordable paid plan is Pro is listed at at $19.99/month.
What are the best alternatives to Chiefy?
Popular alternatives to Chiefy include Agentys, Superhuman, Inbox Zero. Each offers different features and pricing structures. Compare them on AISO Tools to find the best fit for your needs and budget.
Is Chiefy worth the price?
Chiefy is well-regarded in the productivity space, offering features like Automatic categorisation into action-shaped buckets, not folders, Drafts written in your learned tone with calendar availability built in, Persistent memory of people and projects across threads. Whether it's worth the investment depends on your specific needs, usage volume, and budget. The free tier lets you try it before committing to a paid plan.
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