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Calendars · head to head

Assistant.to vs HEY

Assistant.to logo

Assistant.to

Calendars

The easiest way to schedule meetings

From
Free
Rated
-
Full reviewWebsite
HEY logo

HEY

Productivity

Flat annual subscription email service from 37signals, with its own hey.com domain and a distinctive Screener

From
$99/year
Rated
-
Full reviewWebsite

The short version

  • Only Assistant.to has a free tier, so it costs nothing to try first.
  • Each has a real cost: Assistant.to no publicly published pricing rates on website; HEY there is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.
  • They diverge on capability: Assistant.to covers In-email scheduling, HEY covers The Screener.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

Only the attributes on which Assistant.to and HEY actually diverge.

Attributes where Assistant.to and HEY differ
AttributeAssistant.toHEY
Starting priceFree$99/year
Pricing modelfreemiumPer user per month
Free tierYesNo
PlatformsChrome-extensionMac, Windows, Web, iOS, Android
CategoryCalendarsProductivity
Founded2014Unknown

Identical on both: user rating (Not yet rated).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Assistant.to

  • In-email scheduling
  • One-click booking
  • Google Calendar sync
  • Time zone handling
  • Simple interface
  • Gmail
  • Google Calendar
  • Chrome-extension support

Only in HEY

  • The Screener
  • Imbox, Feed and Paper Trail
  • Reply Later stack
  • Focus and Reply mode
  • Screen sharing style clips
  • No tracking pixels

What people use each for

The jobs each tool is most often brought in to do.

Assistant.to

  • Schedulingnot HEY
  • Appointment bookingnot HEY
  • Time trackingnot HEY
  • Resource managementnot HEY
  • Team coordinationnot HEY

HEY

  • Someone who wants to replace Gmail or iCloud Mail entirely with an email service built around approving senders before they reach the inboxnot Assistant.to
  • A user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversationnot Assistant.to
  • A family that wants shared but individually addressed email under one annual plannot Assistant.to
  • A small company wanting HEY for Work on its own domain with the Screener model for the whole teamnot Assistant.to

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Assistant.to

  • No publicly published pricing rates on website
  • Requires scheduling demo or contacting sales to obtain pricing information
  • Free trial available but no specific trial duration mentioned

HEY

  • There is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.
  • Adopting HEY means changing your actual email address, not just installing a new client, which is a bigger migration than switching apps on an existing address.
  • The Screener and categorisation model is a real departure from a standard inbox, and some users take time to adjust or find it gets in the way for high volume mail.
  • Short vanity addresses carry steep additional annual fees, up to 999 US dollars a year for a two character address.
  • It does not connect to or manage existing Gmail, Outlook or iCloud accounts, so it cannot be used as a general client the way Mimestream or Apple Mail can.

Pricing, plan by plan

Assistant.to

Free
  • FreeFree
    • In-email scheduling
    • Basic features
  • Pro$5/month
    • Team features
    • Custom branding
    • Priority support

HEY

$99/year
  • HEY for You$99/year
    • One hey.com email address
    • Screener, Imbox, Feed and Paper Trail
    • Billed annually only, no monthly option
  • HEY for Families$179/year
    • Covers up to five family members
    • Same features as HEY for You per member
  • HEY for Work$12/month
    • Per user, for organisations on a company domain
    • Admin controls for a team

Which should you pick?

Choose Assistant.to if

  • You need in-email scheduling.
  • You want to start without paying.
  • You work on Chrome-extension.
  • You also want one-click booking.
Assistant.to review

Choose HEY if

  • You need the screener.
  • You work on Mac, Windows, Web, iOS, Android.
  • You also want imbox, feed and paper trail.
HEY review

Questions people ask

Is Assistant.to or HEY better?
Neither clearly leads. Assistant.to starts at Free and HEY at $99/year, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Assistant.to or HEY?
Assistant.to has a free tier; the other does not. Paid plans start at Free for Assistant.to and $99/year for HEY.
Does Assistant.to or HEY run on more platforms?
Assistant.to runs on Chrome-extension. HEY runs on Mac, Windows, Web, iOS, Android.
Can I use Assistant.to for free?
Yes. Assistant.to has a free tier, so you can try it without paying. HEY starts at $99/year.
What is Assistant.to best used for?
Assistant.to is most often used for scheduling, appointment booking, time tracking, resource management. Of those, scheduling and appointment booking are not what HEY is typically brought in for.
What can Assistant.to do that HEY cannot?
Assistant.to covers In-email scheduling, One-click booking, Google Calendar sync, Time zone handling. HEY covers The Screener, Imbox, Feed and Paper Trail, Reply Later stack, Focus and Reply mode.

Answered from the vendors’ own pages

Assistant.to: How much does Cirrus Insight (Assistant-to) cost?

Cirrus Insight does not publish specific pricing on its website. Pricing is customized based on your organization's needs. The platform offers a free trial and allows you to build a custom quote in the self-service hub or schedule a demo with the sales team.

Source
HEY: Can I use HEY with my existing Gmail address?

No. HEY provides its own hey.com email address; it is not a client layered over an existing Gmail or other account.

Assistant.to: How does Cirrus Insight pricing work with seat selection?

Cirrus Insight allows you to have full control over seat selection, meaning you can purchase different quantities of users for different features. For example, you could license 10 users for Email Sync and 5 users for Calendar Scheduling in the same account.

Source
HEY: Is there a free plan?

No. HEY offers a trial but bills annually only, with no free tier and no month to month option for individuals.

HEY: What is the Screener?

A feature that holds mail from any new sender until the user explicitly approves them, before it appears in the inbox at all.

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