SafeSend Gather AI / Organizer rollout — how are you handling bulk intro emails + opt-outs?

We’re preparing to roll out SafeSend Gather AI and Organizer and are trying to learn from firms that have already done this successfully.

We have too many clients to send emails one-by-one, so bulk delivery is required — but we’ve never emailed our client base in bulk before, which makes us cautious.

I’d really appreciate insight on:

• What method do you use to send the initial introduction emails (SafeSend-triggered, Outlook mail merge, CRM, email platform, etc.)?
• If not Outlook, what tools have worked well without causing deliverability or spam issues?
• How are you handling opt-outs / unsubscribe requests in a clean, compliant way?
• Did you segment clients (individuals vs businesses, prior-year e-file clients, etc.) or send one announcement to everyone?
• Any lessons learned or things you wish you had done differently?

We want this to be professional, compliant, and easy for clients — including a clear opt-out option — while avoiding deliverability problems.

Thanks in advance for sharing your experiences.