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Q4 Holiday Planning for B2B Software and Services

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As we stumble back to work after the summer, there’s one thought on every marketer’s mind: winter is coming. Or, more accurately, Halloween, Black Friday, Thanksgiving and Christmas.

The last three months of the year squeezes in more festivals and shopping moments than the other nine combined, with an equal rise in promotions and ads.

For that reason, the work for Q4 starts in September. 

This matters to you as business, even if you are not running any holiday campaigns. Your audience is bombarded with ads and their personal inbox will be overflowing with promotional emails. By the time December comes around, they are fatigued and you are fighting for a shrinking slip of attention. 

If you want to hit your revenue targets, you need to be smart, strategic and early to the party. 

Map your audience’s salience points across the quarter

No-one wants to read a sales report over Thanksgiving dinner and most teams will defer spending decisions after the 19th December. The trick is to go light when others go heavy and go personal when they are broad and generic. 

Here's your guide to the rest of the year.

September is good for…

  • Lunchtime webinars, 
  • Conferences, 
  • Whitepapers
  • Getting-to-know you content. 

This month one of the best opportunities in the year to run a re-activation campaign on old prospects and clean up your database. If you have not reviewed your welcome and win-back sequences since January, set aside time to scrutinise them, as your business has probably come out with a new feature or product offer since then.

How to boost your results

- Use personalised subject lines, industry references and relationship markers (“Dave, we haven’t heard from you since May!”) or critical milestones. Your customers are staring down the barrel at end-of-year reports like you are and they still have twelve weeks to make a difference. 

Micro-segments are your friend here, it takes a little more work to create them, but the results pay off and the sales team will find it easy to pick up the leads. Match people direct to your offer (based on who has bought, rather than who you think will buy), who have been reading your website/posts/newsletters in the past 3 months.  

How do I do this?

Select your offer + add a bonus
Look who has bought (and who was interested and didn't buy).
 - For everyone who did not buy: email with the new time-limited bonus.
 - For everyon who has bought, look at their characteristics and see who else fits. If they left feedback or a testimonial, you can see why they bought and what they got out of it. Use this in your next email.

 - Be picky; go after people who have recently read your website, email or social posts. There's no point in targeting people from 6 months ago, unless they are expecting a follow-up. 


October is good for…

  • Planning guides
  • VIP access to your solution or service
  • Online and on-demand events (play with the timings)
  • Seasonal launches  - it’s a reasonably quiet month if you want to do it.

October is when the larger corporations start their end-of-year planning as the managers think in a rolling three-month window and the last two weeks of December are written off for meetings as so many people are on holiday. If you want to be part of the conversation for their Quarter 1, now is the time to offer test access to your service or a way to demonstrate your expertise. 

The other option is gamification. Send out a light-touch holiday greetings for Halloween, with the chance to win a prize. I have done this before with “spot the vamp,” or “match three in row” on a landing page (AI makes coding these things much easier).   

November is good for…

  • End-of-year reports
  • Cheatsheets, doodles and summaries
  • Human connection (refuge from the endless sales!)
  • Last-chance follow-ups

People are fatigued by the time November rolls around. The lack of daylight and the stress in the build-up to Christmas and ThanksGiving takes it’s toll. 

December is good for…

  • Personal reports: how the year has gone for your company
  • Seasonal greetings and gifts
  • Quizzes and infotainment
  • Waitlists for January
  • Advanced meetings for January

It’s human nature to put off workplace decisions when there’s a break in sight. You can use this to your advantage to build a lunch list for your new feature or product, or else create opportunities for your sales team. The other thing that’s very popular (and you can re-use in January) are end-of-year reports, written from your viewpoint. You can summarize how the year has gone for the industry (people rarely remember specific details from, say, March), give your viewpoint for the future or weigh in on a controversial topic.

Offices shut down from the third week onwards in December. However, people still check their emails on a casual basis, or drop into work between Christmas and New Year to catch up and enjoy the peace. This is where infotainment - a lighthearted quiz or video - works wonders.    

Your Calendar

Month Date(s) Occasion / Theme Campaign Ideas
September 1 Sept Labor Day (US/Canada) North American partner acknowledgments, early fall campaigns
September 18 Sept National Teaching Assistants' Day (UK) Education sector B2B offers, recognition messages
September 21 Sept International Day of Peace CSR, culture, or wellness communications
September 29 Sept National Coffee Day (UK/US) Invite to webinars, “coffee break” quick insights, light networking
October Early October Autumn Planning Q4 planning & logistics update, industry reports
October 1 Oct International Coffee Day Engagement, creative touchpoint for clients
October 10 Oct World Mental Health Day HR/employee resources, workplace wellness guides
October 20–21 Oct Diwali Seasonal greetings, themed insights for relevant clients
October 25 Oct Clocks Go Back (UK) Timely reminders, promote time management tools
October 31 Oct Halloween Fun content, holiday marketing teasers
November 5 Nov Guy Fawkes Night (UK) “Spark” creativity, themed offers or event invites
November 11 Nov Singles’ Day (China/global) Early-bird offers, B2B savings campaigns
November 11 Nov Remembrance Day (UK/CW)
Veterans Day (US)
Sensitive content, commemorate service, promote peace
November 27 Nov US Thanksgiving Thank you messages, holiday cards
November 28 Nov Black Friday  Q4 offers (renewals, assessments, bundles)
November 29 Nov Small Business Saturday Spotlight SMB clients, celebrate partnerships
December 1 Dec Cyber Monday Last-chance Q4 deals, highlight digital solutions
December 8 Dec Green Monday Deadlines for year-end contracts, final order push
December 14–22 Dec Hanukkah Holiday greetings to relevant partners
December 18 Dec (est.) Last Royal Mail Posting (UK, 2nd class) Shipping/service cut-off reminder
December 20 Dec Super Saturday Final push: digital products, last-minute signups
December 24 Dec Christmas Eve Appreciation emails, year-in-review wrap-ups
December 25 Dec Christmas Day Automated greetings, relationship-building touchpoint
December 26 Dec Boxing Day (UK) Renewal reminders, Q1 teasers, post-season offers
December 31 Dec New Year’s Eve Thank-you messages, preview upcoming 2026 initiatives

Good luck with your planning!

If you’ve found this blog useful, check out our free mini-course on No-Excuse List-Building. 

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