Hey from NYC,
Happy Sunday and happy November!!! It's officially gifting season, which means the branded tumblers are about to start shipping. Not on my watch!!
Forgot about holiday marketing? No problem, you still have time. Just promise me you won’t send cheap gifts that go right in the trash.
As I said, if your CMO is ordering branded tumblers this year, put them on a PIP.
Your brand needs to be chic. Why?
Because you want that ARR, baby.
So use the time you have left to spoil your customers, stakeholders, employees, board members, etc.
Giving incredible gifts = how people fall more in love with your brand. Plus, it gets you happy moments worth posting so you can flood dopamine on and offline.
P.S. Almost everything on this list works for your own team too if you need to spread internal love :)
Here's how to make your software brand the cool this season:
1. Trendy treats only (no sad snack boxes)
Nobody is excited about a bag of trail mix, even if they are branded as “lux cashews”.
Send whatever your city is lining up for right now.
In New York, that's Mimi's froyo (ceremonial-grade matcha, olive oil, pistachio sauce, and IMO the best cookie dough toppings) and Dotcakes from Butterfield Market, the $11 cups of cake with rainbow sprinkles people line up for hours before the Wednesday and Saturday restocks.
If you have AI $$, are consumer software, and want to splurge on a fun IRL activation - do a custom flavor or mixture at Mimi’s.
Don't want to have one of your employees wait to pick treats up? Hire a line sitter (Same Ole Line Dudes starts at $50 for two hours) and send it with a note: "Someone stood outside for six hours for you. You're worth it." Then, send via Doordash.
Not in New York? Find your city's version and splurge on overnight shipping.
2. We'll cover your subscriptions for a year (aka, retention cheat code)
Ask what they're paying for every month: Netflix, Spotify, NYT Cooking, Peloton, the Max account they still share with their ex. Pick one (or three) and pay for it for 12 months.
Every time they open it, they think of you. And now you get 12 months of brand impressions for the price of a nice dinner, and you'll be very hard to churn.
People don’t cancel the company sponsoring their Netflix. Put it on a marketing credit card.
3. What’s truly fabulous (your logo is not a gift)
Nobody wants another Nike hoodie, and they definitely don't want one with your logo on it. Also - skip the ceramics, tumblers, pens. You're just going to fill homes with clutter, and I'd rather you send nothing.
Buy things they'll use every day and think of you every time.
Start with what they wear. People want Kith, Arc'teryx, or a brand they already love. Find out their style, get their size, and buy something good. A tiny matching sweater for their dog? Obviously.
Then the bathroom. You know that moment at a nice hotel when you get out of the shower and wrap yourself in a towel the size of a duvet? Give them that every morning. Send an XL bath sheet from Parachute or Brooklinen's Super-Plush line, wrapped with a ribbon and a note: "for the long showers you deserve." Nobody ever throws out a great towel, and I say this as someone who still has a beach towel from when I was 4 with my name stitched into it.
Then the airport. Everyone's flying home this month. Send them off with the Away Everywhere Bag, a Satechi passport holder with Find My tracking, an Aesop Ginger Flight Therapy roll-on, a Summer Fridays Jet Lag mask, and a FarmHouse Fresh lip mask (insaneeee) for the dry plane air. Monogram their initials on the bag.
4. Hotter than hot chocolate
Roll a custom hot chocolate cart into a customer's office or — even better — outside of your competitor’s holiday event!
Great drinks, an irresponsible amount of toppings (calories don’t count if it’s work), delicious pastries (hello, L’Apartment 4F), cute cups with a sassy saying.
For remote customers, send a delivery or pick up the tab at their favorite local café. Give them an afternoon treat worth disconnecting for and feeling warm and cozy.
5. Book them an out-of-office (no basic mixers, I'm begging)
Find out what the majority of your top customers are into (maybe 15 total), then send a small menu: massage, golf lesson, pickleball lesson, movie tickets. They pick, you handle the the bill.
No pottery classes or anything basic! Those read as boring and unoriginal.
Pro tip: Ask your VCs what their portfolio companies are offering for holiday discounts and see if you can extend it to your customers. You typically can get access or preferred pricing!
6. The insider's guide to [your city, or company HQ — should likely be SF or NYC]
Make a guide to everything worth doing in your city over the next two months, then put your touch on it. If you have a Head of Community, this is something they should do for your customers!
In New York: skating at different parks around the city, hot chocolate at Jacques Torres or Ralphs, the Dyker Heights or UES brownstone lights, the Union Square Holiday Market, a cozy martini at a dimly lit bar, the NYC Ballet.
Then make it more than a list.
Prepay the skate rentals, hold a table somewhere hard to book weekly and offer it to different customers (hello, 4 Charles), put a gift card at the café you recommended.
Send it as a fabulous, sophisticated guide, and let customers forward it to their teams!
7. Rent out your engineers for a day
Ask customers for the most annoying part of their week, whether it's the spreadsheet they rebuild every Monday or the report they copy and paste by hand. Then, have your engineers help fix it. Build a Claude automation, Slack bot, or a tiny app for their hobby.
It’s fun, encourages communication between eng and customers (rare) and will make people’s lives easier. The downside is that they might hit you up for bug bashing on this random thing built, but that’s an after problem.
8. Team up with your software friends & bundle
Team up with a few adjacent startups and make one holiday discount guide people in your vertical want. Each company contributes something excellent, and every participating company helps distribute it.
Longer list of gifts + a much bigger audience through each other's customers, newsletters, and social channels.
Send something worth opening!
9. Pick up the phone and call
Emails are so…..everyday? Call a few of your fav customers. Tell them something specific you appreciate about them, ask how their year's been, and chat it up.
If you know someone they'd love to meet, make the intro. A new friend, collaborator, or customer could be the best thing you give them all year.
10. Hold a table for 4 every week in December, at a trendy spot and let your customers go!
Bookings get crazy this time of year. So, take it off their hands. You can have a standing reservation somewhere that you “need to know someone” to get into - like Polo Bar, for example. Maybe you even work with the restaurant to curate a special drink for the season, samples for all dining reservations on the house.
Bonus if you pick up the tab!
Bonus, but basic: Their year, Wrapped
Everyone's doing it, so it won't win you any originality points. There’s no reason not to do it anyway. Hours saved, deals closed, their busiest day, the weirdest thing they used your product for. Make it look cool and easy to forward on Slack with a “send on Slack” button. Never a bad time to remind customers how much they'd lose if they left!
Non-negotiable: Pics or it didn’t happen
Your customers enjoying their luxe pajamas, munching on trendy froyo, or sharing your expertly-curated holiday guide on socials. Show everyone how cool, fun and thoughtful your company is.
Well, How'd I Do?
Software brands that act like thoughtful, boutique luxury brands are going to win this season. The bar is on the floor (hello, basic happy hours), so stepping over it should be easy.
Give people happy moments to look at on socials and smile, and give your customers a reason to feel happy in the first place.
Enjoy, enjoy, enjoy!
I hope you have an incredible week ahead.
Julia
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