Start Planning Customer Holiday Gifts TODAY!

Start Planning Customer Holiday Gifts TODAY!

We try not to be alarmist here on the O’Daily. Startup life has enough fire drills without adding to it.

But here’s the reality.

If you haven’t started planning holiday gifts for customers, you’re behind.

But it’s the first week in November??? How could I be behind???

Yep, it snuck up on me too. It always does.

What I like to do is make an abbreviated plan for this year and then implement the “ideal” plan next year when I’ll have more time and be better prepared.


I really always think that though.

Luckily, it’s not too late to get a great customer gift plan in place!

Today, we’ll cover timelines, questions to consider, and how-tos of customer gift giving.

Next week, we’ll share suggestions on the type of gifts to give with specific recommendations and unexpected lessons learned from real customer gifts.

Let’s get to it. These gifts aren’t going to plan themselves!

Customer Gift Timeline (Starting Now!)

Let’s work backwards.

Dec 12 - Dec 16: Gifts arrive!

You want gifts to arrive before everyone is out for holiday break. Out of town, out of the office, out of touch. You don’t want your $50 cookie box getting moldy during the 2 week ghost town between Christmas and New Year’s.

Nov 28 - Dec 2: Gifts ship.

Some items take 5-10 days to arrive. Especially for the standard (read: most affordable), non-rush shipping option.

If you’re delivering to an office, there can also be a lag between mailroom arrival and when it gets into the hands of your customer.

Nov 14 - Nov 25: Gift prep. Collect addresses.

Getting branded swag made takes time. So does putting together gift boxes, signing cards, coordinating a team photo, or whatever other prep items you do.

If you’re mailing a physical item, you’ll also need to confirm addresses which is extra fun in this work-from-anywhere world. 😁

Note: Businesses (including yours!) may be closed for 2-3 days over Thanksgiving.

Nov 7 - Nov 11: Finalize gift strategy, budget, and plan.

Things to do next week: gift ideation, research, rough draft customer list, budget, get quotes (total cost + timeline), get final approval, place order.

No big deal though. Just another Tuesday in the fast paced world of startups! 😉

Your Gifting Strategy: Questions To Ask

1. Why?

Take a few moments to identify the purpose of your holiday gift. It will help clarify your target audience, budget, and gift item.

Holiday gifts are an opportunity to:

  • Stay top of mind
  • Show appreciation for customers
  • Highlight your thought leadership
  • Further solidify a contract renewal or upgrade
  • Help close a new deal
  • “Wow” your most loyal, vocal, and effective champions
  • Reinforce your brand promise

2. Who?

Which users or customers should receive a gift? This can get complicated…

Gift recipient considerations:

  • All customers?
  • Largest customers?
  • Reference customers? (Customers who love you and talk you up to others.)
  • Case study customers?
  • One gift for the whole company or gifts for individual users?
  • All users, power users, or the executive sponsors? (Decision makers may not be the main users.)
  • Non-customers to include?
  • Employees
  • Investors
  • Advisors
  • Friends of the company
  • Prospects


Once you have a “who” plan, circulate a tentative spreadsheet of gift recipients. Other teammates, especially in sales or leadership, may have specific customers to add. Do it upfront to prevent leaving off someone important or not having enough gift supplies!

3. How Much?

What’s your budget for this project?

Take into account:

  • Cost per gift
  • Shipping costs
  • Packaging, gift wrap, notecards, stickers
  • Your “why” and the total number for “who” – are you doing many, smaller gifts or fewer but nicer ones?
  • What your company can afford (duh.)


Order a few extra of everything. Typos, water spills, last minute additions, package malfunctions, internal requests – wiggle room comes in handy.

4. What?

What kind of gift should it be?

Gift brainstorming:

  • What do your users like and use?
  • Any gift ideas that align to your product or problem you solve?
  • What have you received that you liked, kept, or used frequently?
  • Food? Swag? Both? Neither?
  • Do you have company values or mission to uphold through your gift?
  • Are you including a card?
  • Holiday specific or neutral (to be used again)?
  • Handwritten note? Hand signed?
  • Printed message inside?
  • Company logo/branded or generic?
  • Branded with your logo or company colors?
  • Include company logo stickers? (Tech startup requirement. 😂)


DIY is less expensive but takes (significantly) more time. There’s no right or wrong but be aware and intentional about the tradeoffs.

5. Where?

Where should this project live? Who handles the execution?

It’s 100% dependent on your company size and structure.

I’ve seen customer gifts handled by:

  • Founder/CEO
  • Virtual assistant
  • Executive/in-person assistant
  • Customer Success
  • Marketing
  • Chief of Staff

Feeling overwhelmed?

Corporate gifting is a $258 billion market for a reason.

A few easy options to get you started:

  • Outsource to a gift company.
  • Do something fully digital like a gift card. No shipping or addresses to collect!
  • Send a fun email.
  • Make it a New Year’s gift.

(^^I have done all of these before. 🤪)

We’ll have specific gift suggestions next week including some surprising learnings on what customers love. Spoiler Alert: it’s NOT the most expensive gift we sent.

Holiday gifts are a great way to stay in touch with customers and spread goodwill.

Start planning now so you can be thoughtful, thorough, and creative!

Other advice for customer holiday gifts? Any gifts or strategies that worked well?