Holiday outreach starts with good intentions. A few cards, a heartfelt message, maybe a festive email or two. Then suddenly, you’re buried in spreadsheets, your printer’s out of ink, and you're elbow-deep in half-filled contact records trying to remember if Hayley prefers “Happy Holidays” or “Merry Christmas.” What was supposed to be a thoughtful gesture turns into a full-blown headache, complete with mailing labels that refuse to align.
What if I told you that client connection during the holidays doesn’t have to be a seasonal horror story for you?
At Redtail, we’ve been working hard to give you tools that turn chaos into connection, especially during the season where relationships matter most. Whether you’re sending cards, baking-themed gift boxes, or mailing handwritten year-end letters, Redtail’s CRM and a few smart strategies can turn your outreach into a well-oiled (and surprisingly delightful) holiday machine.
It All Starts with Advanced Search
Trying to send different messages to clients, prospects, or centers of influence? Use Advanced Search to narrow your list quickly and precisely. Segment based on contact status, last interaction date, or combine it with new User Defined Fields (UDFs) for hyper-personalized outreach.
Want to send a thank-you to every client who attended your fall event and also happens to be a fan of your firm’s favorite local cookie shop? You can do that now. Just create, apply, and filter with UDFs like "Event Attended" and "Favorite Cookie". Yes, really. You know how happy people get if they receive their favorite cookie as a “cookie in a jar” gift? A LOT.
Pro Tip: Once you build your list, save it as a Quicklist to reuse it anytime.
UDFs: A Small Detail with Big Relationship Power
This month, User Defined Fields got a major upgrade: you can now search them directly inside Advanced Search. That means you can group your contacts in ways that reflect who they are, not just what they’re worth. If you missed the news, you can see it in action below!
Track favorite restaurants, seasonal hobbies, dietary preferences, or even which clients celebrate specific holidays. Want to send Hanukkah cards? Use a UDF. Want to send holiday recipe cards to every client who listed “baking” as a hobby? That’s a UDF, too.
Need help setting up or customizing your UDFs? Start here.
When you capture these personal details throughout the year, your holiday outreach becomes a moment of genuine connection, and way more than just another piece of mail.
Mail Merge Without Mayhem
Once you’ve got your list, it’s time to bring it to life. Redtail’s Mail Merge tools let you create polished letters, festive labels, personalized cards, and more.
We even have a full library of downloadable templates for cards, letter formats, and envelopes to get you started, just in case you don’t have the time to design anything from scratch.
Want to print labels that match your brand or include personal messages? Check out how to create regular mailing labels or custom ones.
You can even combine your mail merge efforts with saved Quicklists to streamline outreach for different tiers of clients or event groups. Suddenly, your mailing process feels less like a disaster and more like…well, actual holiday cheer.
Make Your Outreach Feel Personal, Not Programmed
The holidays are the perfect time to remind your clients they’re more than a number. Even the smallest personal detail, like remembering someone’s favorite holiday treat or their go-to vacation destination, can make an enormous impact.
The new searchable UDFs let you use those insights in real time. And when you combine that with thoughtful outreach, even your busiest clients will pause and say, “Wow, they really know me.”
That’s not just good CRM practice. That’s relationship-building that lasts.