Many companies use events like Black Friday and Cyber Monday to mass market to their prospects and customers, usually through a series of email blasts promoting sales or discounts. That somewhat SPAMmy approach can sometimes be effective if you're selling directly to consumers; it's almost always ineffective if you're selling to businesses.

This is not because your email blasts won't get opened. Quite the contrary, business emails sent on Thanksgiving Day, or during holiday weekends in general, tend to have usually high open rates. (I explain why later in this post). 

So an email blast will get a lot of opens, but the response will be tepid or even negative because email blasts are inherently impersonal and thus set the wrong "tone" especially over the holidays. 

Your challenge when using email marketing during the holidays is to take advantage of the statistically high open rate that you'll get but without coming off like a typical sales jerk. This is an exaggerated example of the general rule that when you're selling to businesses, you should avoid anything that sounds, looks, or feels "sales-y." Most people distrust salespeople, so "sales-y" communications--which very much include email blasts--tend to create resistance to buying.

Here's what does work over the holidays: personalized emails to customers and prospects with whom you've already worked and therefore have a pre-existing relationship. By personalized, I mean something that you've crafted specifically for each individual rather than something that's automatically personalized (which, BTW, is an oxymoron). Some quick examples:


Dear Jim  McReady ,

I hope you are well this holiday season, Jim.. We are offering a Cyber Monday deal especially for  Acme Industries, Inc., LLC which you, Jim , should know about...



Do you remember that proposal we discussed last June? The reason I ask is that we're offering a special price on that product as part of a Cyber Monday promotion...



Can you maybe give me your opinion on an idea? You were pretty outspoken at the user conference and I'm curious whether we're still on the same wavelength. We're running a Cyber Monday special that, if I've done the numbers right, should create the better ROI that you suggested...

Needless to say, writing a personalized email takes a lot more time and effort than creating an email blast. You'll need to check your notes, do some research, and use your imagination to segue from something unique about that client into the offering that you're promoting.

The potential benefits of doing that extra work, however, are enormous, especially if you put yourself into the shoes of the client and write about something that will be immediately relevant to that individual.

This is especially true during the holidays because here's a secret: decision makers get antsy when they're not actively working and are sometimes grateful for an email that distracts them from the rigor of enforced down-time.

I want this post to be very "actionable" as they say, so the following are the specific steps I'd take If I were building a campaign for Cyber Monday:

  1. Build a list of my 20 best clients or prospects.
  2. Rank them according to the closeness of our relationship. 1 (highest) to 3 (lowest)
  3. Rank them according to their likelihood of buying from me. 1 (highest) to 3 (lowest)
  4. Rank them according to the size of their potential spend. 1 (highest) to 3 (lowest)
  5. Add the rankings for each client.
  6. Sort the clients from then best (the 3s) to the worst (the 9s).
  7. Cross out the bottom half of your list. They're not worth the effort.
  8. Research (check LinkedIn, news, etc.) for an update on the remaining 10 clients.
  9. Write a highly-personalized email to those 10 clients.
  10. Send those emails either on Thanksgiving afternoon or on Black Friday mid-morning.
  11. If you get a response, segue to setting up a meeting.
  12. If you don't get a response, wait until late Saturday morning and send a "just wanted to make sure you saw this" email, and appending the original email.
  13. If you get a response, segue to setting up a meeting.
  14. If you still don't get a response, queue up  a "heads up that time's running out on this" email (appending the original email) so that it will hit the client's inbox at 2am Cyber Monday.

I could explain the logic behind how I've timed of those email but it would involve a lot of boring statistics about open rates, response rates, and conversion rates. You'll just have to take my word for it.