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Email & SMS Marketing

What Marketers Get Wrong About Email, According to Media’s Newsletter Guru

September 6, 2022
Mae Rice

“It’s much easier to find brands doing a bad job than brands doing a good job,” says Dan Oshinsky, who's launched newsletters for the New Yorker and BuzzFeed.

Table of Contents

Email marketing is powerful.

For one thing, it reaches a ton of people. Facebook has 2.7 billion monthly active users around the world — but Campaign Monitor estimates that globally, there are 3.8 billion email accounts.

That’s about half the people in the entire world

For another, it’s one of the highest-ROI marketing channels. When you spend a dollar on email marketing, you earn an average of $42 in return, Litmus found in a 2019 survey

Why? Well, once a brand has a customer’s email address, they have indefinite, free access to that customer. (Unless you count the price of email software and strategists.) They don’t have to pay per click or impression, the way they have to with ads. 

It’s what marketers call an “owned” channel. 

This is email’s core advantage. “If I get someone's email address today, tomorrow, two years from now, 10 years from now, I might be able to still have a relationship with that person,” Dan Oshinsky told MarketerHire. 

Keyword: “might.” Email marketing is powerful, but not easy. Oshinsky would know. 

Though he doesn’t call himself this, it wouldn’t be a stretch to call him a newsletter guru. He’s led newsletter development at The New Yorker and BuzzFeed. Today, he consults on email strategy through Inbox Collective, and publishes a beloved monthly Google Doc on the same topic, Not a Newsletter.

“I will confess that a lot of brands just send terrible emails,” he said. “It's much easier to find brands doing a bad job than brands doing a good job.”

"I will confess that a lot of brands just send terrible emails."

So how do brands mess up the most popular, highest-performing digital marketing channel? A channel they could leverage to basically print money?

Here’s what Oshinsky’s noticed — and how to fix it. 

How Marketers Get Email Wrong

They think they actually own the channel. 

In the end, your reader owns their inbox.  

“Think about the inbox as this really personal space,” Oshinsky recommended. “It's like a living room that your reader lets you into.”

“It's like a living room that your reader lets you into.”

Yes, marketers own space in their customers’ inboxes more than they own space in their customers’ Facebook feeds. But ultimately, email recipients own their inboxes — and can revoke marketers’ access at any time.

That means marketers should behave like guests. Instead, a lot of marketers behave like Viking invaders. 

To be more specific...

They hard-sell right out of the gate. 

No pleasantries?!

“A lot of marketers get [your] email address and you just start getting bombarded with asks,” Oshinsky said. 

Many companies call these ask emails “blasts” or “pushes” — the kind of aggressive words rarely used to describe two-way conversation.

Hard selling via email has gotten so normalized, though, that not even the New Yorker is above it. When Oshinsky first started working there, the magazine’s email automations were aggressive, to say the least. 

“As soon as someone was signing up for a New Yorker newsletter, suddenly they would start getting all sorts of asks from Condé Nast.”

Subscribe to Bon Appétit. Check out this two-for-one package. Sale! Sale! Sale! 

It was too much, too soon. At that point in the New Yorker’s email flow, “we hadn’t even gotten them to pay for the New Yorker yet,” Oshinsky said. 

He helped the magazine completely revamp its approach to email — but Oshinsky still sees plenty of brands treating email the way the New Yorker once did. 

They send emails that sound like the voice of an organization. 

So — dull. 

What does it mean for an organization to write an email? From an existential standpoint, who knows. From a practical standpoint, though, it usually means the email is boring. 

The problem is simple. “Really big brands often have a lot of people invested in email,” Oshinsky said. “There are a lot of cooks in the kitchen.”

Often, email marketers who know best practices for email creative have to make concessions to other parts of the organization that want to hit certain quotas or broadcast certain brand messages.

It’s also just hard for anything interesting or cohesive to get through a labyrinthine corporate approvals process to the reader. 

So in the end, brand emails “often don’t have a unique voice,” Oshinsky said. 

They think of personalization as a substitute for personality. 

No one has a parasocial relationship with an algorithmically-generated email send. From a bank.

There’s nothing wrong with personalization — in fact, we predicted it would be one of the biggest marketing trends of 2021

But sending emails packed with just-for-the-reader tips and deals alone won’t kindle a connection the same way personalization plus personality will, Oshinsky said. 

That’s especially true when you’re onboarding a new subscriber, competing for their attention and loyalty with a million other email marketers. Personality is a differentiator; personalization is increasingly table stakes. 

But often, brands focus exclusively on the latter in their emails — “which I think is a mistake,” Oshinsky said. 

They fixate on inbox placement...

If you’re not going to spam, you’re fine. 

Oshinsky hears it a lot: “How do I get to the good part of the inbox?” 

This could be a “Primary” or “Priority” or “VIP” tab, depending on the reader’s email provider. Whatever it’s called, Oshinsky said, it’s silly to fixate on. 

He’s seen a number of studies quantifying the engagement lift marketers get when they land in the main tab instead of the promotions tab, and “it’s relatively low,” he said. “People know to look to different parts of the inbox to find the stuff they want.” 

In fact, according to Return Path’s survey of 3 million anonymized Gmail inboxes, the advent of the Promotions tab barely dinged open rates — and emails in that tab are less likely to be marked as spam than emails in other tabs.

Source: Return Path

Oshinsky recommends that marketers embrace tab uncertainty, and avoiding “hacks and tricks” to improve visibility — like asking readers to drag your email to a specific tab, or add your email address to their contact list. 

Modern email inboxes are just too savvy for that, he said. If a reader rarely opens your emails, you’ll just get kicked back to the promotions tab, hack or no.

Everything besides deliverability and core engagement metrics — open rates, clicks, and replies — is basically window dressing, Oshinsky said. much that they sometimes try to build a new inbox.

Many have tried before.

Substack is beta-testing a proprietary inbox, presumably designed to boost its newsletters’ visibility — and it’s not the first company to try to reinvent email. 

“There have been a number of efforts over the years by media companies, by tech companies, to build a ‘better’ version of the inbox,” Oshsinky said.

Spoiler: None of them have taken off at scale yet.

“The majority of people don’t have really complex email needs,” he said. “The general public doesn’t actually see any real issue with the inbox.”

Sure, some journalists subscribe to 175 newsletters, and they might face certain difficulties — but most people who want to see email reinvented send emails.

A word of warning from Oshinsky: If your email strategy is tanking, a new product probably isn’t the answer. 

So… what is the answer? 

How Marketers Can Get Email Right

By highlighting their brand’s actual employees and warm, idiosyncratic voices. 

Humans like emails from humans.

Oshinsky loves a spokesperson. Or multiple spokespeople.

When we connected, he was working with a brand to overhaul their email onboarding series, making actual members of their team into public faces of the organization.

“Our bet is in the long run, the more that we can do to add that personality upfront... the more we’re going to see success in the long run with the big KPIs that we're trying to hit,” he said.

In general, Oshinsky said, “think about building your emails so that they feel like an email from a friend.” 

“Think about building your emails so that they feel like an email from a friend.”

That means prose with personality and voice — and, at the most basic level, a clear, individual speaker. It’s just easier for readers to connect with “real people who are doing interesting work” than with the abstract concept of a company, Oshinsky said.

By thinking of email as a two-way relationship. 

It's not a soapbox.

Ideally, email marketers have a relationship with their readers in which they aren’t the only ones talking. 

That means their emails should pose questions and elicit actual responses.

“Treat the relationship [with your reader] as a real relationship,” Oshinsky advised. “How can we be useful to this person? How can we get to know them? How can they get to know us?”

Getting replies boosts deliverability, on a technical level; on a more holistic level, it gets readers engaged on a deeper, more personal level. 

Ideally, brands set a conversational tone early, Oshinsky said, with a welcoming onboarding series. 

By opening with a warm, friendly onboarding series. 

Get to know your readers!

This was one of Oshinsky’s first projects at the New Yorker: creating a new onboarding series (that didn’t feel like a sales pitch for 26 magazines).

His team’s updated version focused on encouraging a subscription to the New Yorkerjust the New Yorker — and building a relationship with readers.

“Email at its heart is a relationship-building tool,” Oshinsky said.

"Email at its heart is a relationship-building tool."

He recommends prioritizing it in your onboarding series, whether you’re a magazine or a dog bed company.

There are a wide variety of relationship-building tactics to try. You might want to share your company origin story, or send a personal note from a founder or spokesperson, Oshinsky noted. You also might want to ask questions (or send a survey) to get to know them better.

A strong onboarding series can work wonders. 

By thinking bigger than ROI.

There are other KPIs to consider.

Yes, email is a high-ROI channel. But leveraged correctly, it can bring in customer insights as well as revenue.

If customers reply to your sends, their thoughts can improve everything from future marketing strategy to product development. 

Oshinsky has seen this firsthand. From its inception, Not a Newsletter had a conversation-starting email from Oshinsky built into its onboarding process. 

“As soon as you sign up, you get an email from me that says, ‘Do you have a newsletter? What are you struggling with right now? Write back to this newsletter. I want to hear from you,’” he explained.

People really replied, and he designed Not a Newsletter’s content— and his consulting business — to solve the problems they wrote in about. 

The responses have been “one of the secrets to Not a Newsletter’s success,” Oshinsky said.

In other words: It pays to treat email marketing as a feedback loop as well as a revenue stream. Email can do a lot more than make money. 

Mae Rice
about the author

Mae Rice is editor in chief at MarketerHire. A long-time content marketer, she loves learning about the weird and wonderful feedback loops that connect marketing and culture.

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