Looking for a free way to automate post-booking emails? Discover the best Gmail extensions and simple CRM tools to send thank-you messages, review requests, and rebooking reminders effortlessly.

As a performing artist, staying in touch with clients after a show is crucial for building relationships, getting reviews, and securing repeat bookings. Manually sending emails can be time-consuming, but there are free and simple tools to help automate the process.
If you're looking to send a sequence of emails — a thank-you message, a review request, and future booking reminders — without investing in a complex CRM, here are the best solutions. Just note that the "free tier" landscape has shifted considerably in 2026.
YAMM remains one of the strongest Gmail-based tools for sending personalized bulk emails directly from Google Sheets. With a 4.8/5 rating and over 17 million installs in the Google Workspace Marketplace, it's trusted by organizations worldwide. It delivers emails to the primary inbox with open rates up to 20x higher than traditional bulk-email solutions, and lets you track opens, clicks, bounces, and responses in real-time from a Google Sheet. However, be aware that YAMM has gradually been reducing the effectiveness of its free service — the free tier now covers only a limited number of sends per day. Best for: review requests and personalized follow-up campaigns.
Still a reliable zero-cost option for drafting emails in advance and scheduling them. Not automated in the true sense, but works for simple, low-volume sequences.
HubSpot's free plan remains one of the most feature-rich in the market for contact and pipeline management. You get unlimited users, up to 1,000,000 contacts, one deal pipeline, email tracking, meeting scheduling, live chat, and forms — with no credit card required. That said, email sequences to nurture your leads require an upgrade to the $90 per user/month plan. The free plan works best for testing HubSpot or running very low-volume operations — not for long-term automated sequences. Best for: organizing your client list and basic follow-up tracking.
Streak remains a compelling Gmail-native CRM, and it has been actively adding features. In early 2026, Streak introduced AI Autofill, which pulls information from your email timeline or performs web research and writes values directly into your pipeline to keep records up to date. However, Streak no longer offers a completely free plan — its entry-level plan includes core CRM features like pipelines and basic tracking, but you'll need to upgrade to higher tiers to unlock advanced tools such as automations, reporting, and team collaboration. Best for: artists willing to pay a modest monthly fee for a seamless Gmail workflow.
Still a solid option for automated email workflows with date-based triggers. Good for setting up a post-show sequence tied to booking dates, though free plan limits apply as your list grows.
Mailchimp was previously listed as a free option, but its free plan has been significantly downgraded. The free plan is now capped at 250 contacts and 500 sends per month, and automation was fully stripped from the free tier by mid-2025. Mailchimp has raised prices or reduced free plan limits almost every year since the Intuit acquisition. On the upside, Intuit has announced new Mailchimp product innovations in February 2026 aimed at ecommerce businesses, including more ways for merchants to connect data and activate omnichannel campaigns. But for a solo performing artist on a budget, Mailchimp's free tier is no longer a practical fit.
If you need emails to go out over 18+ months, Zoho Campaigns or a paid tier of HubSpot or Streak is your most reliable path. For free options, YAMM + Gmail Scheduled Send remains the most practical combination — just be mindful of YAMM's daily send limits on the free plan.
For quick & free: YAMM + Gmail Scheduled Send
For structured client management: HubSpot CRM (Free) for organizing contacts, paired with Gmail for sending
For a true inbox-based workflow (paid): Streak CRM
Skip for now: Mailchimp free tier — too limited in 2026 for meaningful automation








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