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Pinterest has been kicking its product tires since 2010. Along the way, they’ve made some huge improvements and innovations in interface, experience, and email. Let’s Explore.

Bart King
Published in
11 min readSep 23, 2016

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To satisfy moms collecting recipes and designers collecting interface is a lot to ask of a product. (It would be only slightly harder to create a bacon teleporter.) And while product improvements don’t always go hand-in-hand with email improvements, Pinterest has made email a largely integrated experience.

Let’s see how they do it, shall we?

New user sign-up was quick. I gave them my email and indicated my gender (male). Then I selected a handful of interests, including architecture, tiny houses, woodworking projects, furniture, green homes, travel and men’s hairstyles (my Gen X solution to a mid-life crisis).

While I was browsing through the inspiration feed generated by my selections, the first email arrived…

No-fuss confirmation email

SUBJECT: Please confirm your email
(Day 1, 1:24 p.m.)

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I like the clean, straightforward design. Though I wonder why they doubled up on the logos. I also like that the footer doesn’t have a bunch of pointless legalese. Is it broken though? It seems oddly spread out.

The copy doesn’t offer much. Pinterest strikes me as a brand with good copywriting. But here could be a good opportunity to promise value in exchange for confirmation. Or perhaps more personalization. (Everyone likes to see their name in print, right?)

What’s the strategic intent? Confirm the email, and get the user back to the site. (Move along, nothing to see here.)

First new-user email

SUBJECT: Happy first day of Pinterest!
(Day 1, 1:39 p.m.)

Fifteen minutes later, this beauty arrived. Even though I’m one of those weirdos who doesn’t like watermelon, it’s still an enticing image.

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The copy introduces what boards are all about. It seems narrow to define a user’s motivation as: “finding ideas to try,” but brilliant to establish the link to aspirations.

Maybe I just have a guilty conscience, but the call to action (CTA) sounds morally instructive, rather than encouraging. A shift to future tense might help: “Create boards you’ll love.”

Also, maybe let me know it’s “easy” or “simple” to do. (I’m easily daunted.)

Oh, here’s another one

SUBJECT: 8 most popular home decor Pins this week
(Day 1, 1:39 p.m.)

Back-to-back emails within the same minute. Interesting…

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It’s another good layout. But that last pin throws off the balance. I assume these must have been selected algorithmically for content, not size.

It’s cool that Pinterest is beginning to curate for me based on the home-related interests I indicated during sign-up. But what’s up with that secret gun table? I definitely didn’t select “firearms” as an interest. I guess it fits with “furniture” and “woodworking projects.”

Speaking of which, do furniture and woodworking really count as home decor? I just recently got around to hanging a wall clock I got for Christmas in 2012, so I wouldn’t exactly say I’m into decorating.

But of the 36 content categories on the site (see image below), I suppose that’s the one best aligned with my interests. (Maybe my mid-life solution is to get to know my inner decorator better!)

Regardless, the strategic intent is clear: Drive engagement with curated content.

Ahh, it’s a search engine!

SUBJECT: Feast Your eyes on Pinterest’s unique visual search
(Day 2, 8:19 a.m.)

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When I first used Pinterest, it didn’t really occur to me that it’s essentially a search engine. So I think this message is spot-on: Show the user what can be done with Pinterest to make life better.

As for design, the previous email’s balance issue is gone with this layout. I’m guessing these images were selected by the design team to accompany these (and lots of other) suggested search options. But if that’s the case, I’m surprised a human selected that visually confusing kitchen image for “home renovation.” The other images are so much cleaner and more effective.

As for the copy, I’ve got to be honest. That headline sounds exhausting. How about: “Search our 50+ billion Pins” instead.

Regardless, the CTA is solid. (Try a search, you’ll love it!)

Now it’s getting personal

SUBJECT: More Pins for your board Inspired homes
(Day 2, 12:30 p.m.)

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These suggested pins are all relevant to the first board I created, called “Inspired homes.” And I LOVE what I’m seeing: first the tiny beach huts (yes!), then the red homes with snow, then the waterfront anomalies. They even found a different image of the first home I pinned to the board (that thing that looks like the love-child of a sailboat and a Jetstream on stilts).

Pinterest crushed it with this one! With just five emails (and very little engagement on my part), they’re suddenly delivering images I want. I can feel the hook going in a little deeper! Pinterest emails are actually serving me. Amaze.

I’ve just got one complaint… The user-generated text below the images ended up being random and confusing in this instance. It seems like the design could be cleaner and just as effective with only the light grey copy: “From the board…”

Of course there’s a mobile app

SUBJECT: Give our fast, fun app a try
(Day 9, 2:04 a.m.)

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There was a seven day gap between messages here. I appreciate the breathing space, Pinterest. But I’ll be honest, I didn’t think about you.

Maybe I need an app to make this relationship more convenient…

Great timing for this message! I wonder, if I had already found the app on my own, would I have gotten this message? If not, that’s impressive.

Terrific, simple design to this email, too. Communicates the intent without an overload of detail. And it’s on trend.

What happened? Things were going so well!

SUBJECT: Top 8 trending Pins in home decor
(Day 9, 2:04 a.m.)

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I should note that by Day 9, I hadn’t done any more pinning. Perhaps if I had, the system would have served me fresher, better-targeted content.

Speaking of “targeted,” look, more hidden guns! A Glock and an assault rifle to be specific. This was before Orlando and Dallas. But still, WTF? And the hide-your-shotgun-from-dinner-guests table is back, as well as two other other pins from Day 1.

I think the algorithm fell asleep on this one. I didn’t click on any suggestions in the first “home decor” email. Wouldn’t it make more sense to try another category aligned with my other chosen interests — maybe gardening or travel? (Sounds like I’m ready for retirement when I say it like that.)

I deserve to be shamed

SUBJECT: 10 new Pins for your Inspired homes board
(Day 9, 2:04 a.m.)

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This is the same body template as the previous email. But I love what they’ve done with the footer here. That simple graphic is a brilliant way of prodding me to get busy filling my first board.

Instead of rehashing the same subject line and headline from Day 2, they could have reinforced that prod. It would require another layer of dynamic content, but how about something like: “This board only has one lonely pin. Why not give it some friends?”

One question: If Pinterest has 50+ billion pins, why are they suggesting four of the same ones they showed me a week ago?

Here’s a new twist

SUBJECT: Hi, Bart! We found new Tiny House Storage and Tiny House Pins and boards for you!
(Day 9, 2:05 a.m.)

First I’ve got to say something about the timing of this and the three previous messages. They all arrived at the same moment in the middle of the night.

I can understand wanting a message to be at top of my inbox in the morning. But four before the coffee kicks? Risky. Makes me think there must have been a glitch in the system, especially considering the seven previous days of silence. Anyway:

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This is the pivot I was expecting earlier — content curated to one of my other interests. Lots of interesting tiny homes stuff here.

Speaking of small, I like how this email is a microcosm of the site with both pins and boards. It also shows me what the future of my boards could be like.

This design conveys a lot of options without being crowded or confused. Essentially, it’s the body template from before (with a CTA), followed by a module for featuring boards (with a second CTA).

I like how the featured boards are divided into a main image and three smaller ones. Reminds me of the Martha Stewart color swatches you can take home from the hardware store. (Wow, home decor really is my thing. Pinterest might know me better than I know myself!)

Oh, and they used my name for the first time in the subject line. Gives me that warm, fuzzy feeling.

And now for something completely different

SUBJECT: You’ve got 25+ new Pins waiting for you
(Day 10, 2:02 p.m.)

Well, that first image was unexpected. All the other pins are clearly related to my indicated interests, but since I haven’t clicked through from any recent emails, it’s possible Pinterest is just trying to activate me with content their algorithms associate with my segment. It would be really interesting to know what other user segments the system has me in at this point!

The focus on “new” pins in this email is intriguing. As a copywriter, I recognize the compelling strength of newness. But as a Pinterest user, I’m more interested in seeing the most-loved pins, regardless of age.

Also, when I clicked through via the CTA, it didn’t actually take me to these pins. And it’s not obvious how to find new pins in general. Based on the number of likes, the pins in my feed all appear to be older.

Am I missing some functionality, or is the focus on “new” just a copywriting tactic to drive engagement?

This is the last time I’ll mention this: That 404 message seems like another good reason to do away with the user-generated pin descriptions.

Not new, but trendy

SUBJECT: Top 8 trending Pins in men’s fashion
(Day 11, 2:05 p.m.)

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This email is another pivot. Men’s fashion was probably triggered by my interest in hairstyles. (Sadly, when I try to grow a thick hipster beard, it just looks like I have dirt on my face.)

The ability to pivot is a huge strength. If they keep rotating through my interests, they’re bound to reel me in eventually. For instance, I had to click on the how-to graphic for the “Trinity” necktie knot. It looks a little wide (and complicated) for me, but I feel way hipper for knowing about it.

After receiving those four earlier messages at 2 a.m., now I’ve received two at 2 p.m. Were the first four a mistake? Are they automating 2 p.m. based on my initial signup and browsing time on Day 1? I’d like to know more about their timing tactics.

After a handful of emails, I’m starting to see how this series relies on repeated subject lines and headlines to set up the regular delivery of algorithmically generated content. Seems like a smart, scalable copywriting approach and a good way to establish expectations.

However, as a user, I skipped right over the body copy (“So many Pins, so little time…”), which I’ve already seen. I’d be happy with just the repeated headline followed by a new set of pin suggestions.

OK, that’s random…

SUBJECT: This week’s top Pins
(Day 11, 2:05 p.m.)

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If this arrived in my actual mailbox, I’d check the address to see if the mail carrier screwed up.

I have no idea why they suggested any of these pins. Admittedly, I’ve engaged very little with the emails or the site to this point, so they don’t have a lot to work with. But rather than a completely random selection, how about:

  • surveying me on my interests
  • suggesting I find what my friends are pinning
  • showing me what relevant celebrities or brands are pinning
  • pivoting again to one of the other interests I initially selected

It’s possible too that this selection was generated from my browser history or advertisers, though there would need to be some type of “sponsored pin” indication for the latter. Both are possibilities, according to the user settings.

Let’s wrap this up

Twelve emails in 11 days. That seems like a good place to stop, though it’s clear a steady flow of emails will continue.

I had the floodgates open in my account settings. As a user, I would likely dial down the frequency of emails over the long term to receive only a weekly digest. But for people who want daily inspiration, Pinterest is primed and ready.

The automated emails aren’t perfectly tuned from a selection, design, timing or copywriting standpoint, but the foundation is impressive to say the least. It’s pretty amazing how well they can target and deliver to a new user based on the selection of just a few interests. And I suspect with more time and interaction, the system would learn to stop showing me firearms and expand on the discovery of my emerging passion for home decor!

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PR consultant and copywriter for green building, sustainability and cleantech. Principal @ New Growth Communications.