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HEY vs Microsoft 365

HEY
7.0/ 10
Higher score
Microsoft 365
7.4/ 10
Across 4 measured dimensions: HEY wins 0, Microsoft 365 wins 2 (2 tie / n/a)
[01]

Side by side.

8 dimensions
MetricHEYMicrosoft 365
Score
Winner: right
7.07.4
Δ 90 days
— flat— flat
Parent & badge
37signals
Microsoft Corp.
Founded
20202011
Best for
People who agree with 37signals' philosophy of email as a workflowBusinesses that need Exchange features and desktop Office
Price per mo
Winner: right
$8.25/ mo$6.00/ mo
Renewal multiplier
——
Tagline
Opinionated workflow, $99/yr, no IMAPOutlook + Exchange + Office, billed by the seat forever
[02]

What works, what doesn't.

Per provider
HEY4 pros · 4 cons
+ Pros
  • ✓Screener kills cold/marketing email at the door
  • ✓Imbox/Feed/Paper Trail workflow is genuinely novel
  • ✓Built by 37signals — long-term commitment to product
  • ✓Flat $99/year, no per-mailbox seat math
– Cons
  • ✗No IMAP, ever — you can't use your own client
  • ✗Annual billing only, no monthly option
  • ✗Custom domain requires separate $99 plan
  • ✗Migrating out is intentionally difficult
Microsoft 3654 pros · 4 cons
+ Pros
  • ✓Exchange features still unmatched for corporate mail
  • ✓Desktop Office included on Standard
  • ✓Strong compliance/eDiscovery features
  • ✓Wide IT support ecosystem
– Cons
  • ✗Admin center sprawl is genuinely terrible
  • ✗Pricing/SKU structure changes constantly
  • ✗2024 price hikes plus Copilot bundling
  • ✗New Outlook regressed long-standing workflows
Make the call

Pick one and go.

Both links are affiliate. Score doesn't move because of it.

VisitHEY ↗Score 7.0VisitMicrosoft 365 ↗Score 7.4
← Read full HEY review·Read full Microsoft 365 review →
[03]

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