Question 1

What's the biggest difference between CodeTwo and WiseStamp?

Accepted Answer

Architecture and buyer. CodeTwo is enterprise-grade server-side signature injection for Microsoft 365, sold to IT. WiseStamp is a client-installed per-user signature manager for individuals and small teams, sold self-serve. They rarely end up on the same shortlist unless someone is genuinely unsure whether they need enterprise infrastructure or a lightweight tool.

Question 2

Does WiseStamp work with Microsoft 365 like CodeTwo does?

Accepted Answer

It works with Outlook and OWA the same way it works with any mail client — the teammate pastes their signature via a per-user install link. It doesn't route mail through anything. CodeTwo installs a mail-flow connector at the tenant level and injects signatures on the way out.

Question 3

Which one is cheaper for a 50-person company?

Accepted Answer

WiseStamp Pro at ~$4/user/month is roughly $200/mo for 50 people. CodeTwo Signatures 365 at ~$1.50/mailbox/month annual is ~$75/mo for the same 50 — but the IT setup cost is real. A third option, Wren, is flat $99/mo for the whole team up to 50 — cheaper than both without the connector project.