The Deliverability Problem That Almost Killed Robly (Plus, 3 Things We Learned)

 In School of Hard Knocks

New York City, May 2014

It was a crisp, late spring morning the day that Google almost killed our company. It was five months after we’d brought Robly to market, and we were already struggling.

As is the case with many startups, we were far too optimistic pre-launch.

We had projected that we would acquire 800 customers our first month in business. A laughable forecast in hindsight – this was my first time leading the charge, and like many green entrepreneurs, I knew nothing.

That optimism faded mere weeks later. We didn’t have nearly the traction we had hoped for, and this was the balls-to-the-wall low point.

We were struggling. To find customers, to convince them to buy our product, to keep them, and to build monthly recurring revenue.

After four months, we were stuck at about 150 people paying us $15 per month…not nearly enough to cover our expenses.

We were burning through our all our savings. Our spouses and partners were questioning why we had quit our lucrative finance jobs to chase an out-there internet dream.

These were dark, dark days.

But that day in May, things got even darker.

Gmail’s Phishing Phenomenon

We learned from our customers that Gmail was labeling all the email that came off any of our IPs as spam. This came seemingly out of nowhere. At the time, Gmail had around 20% of the email market.

It wasn’t that all our mail was going into the spam folder. This was much worse.

Our emails were going into people’s inboxes, but labeled as phishing scams. You know, this thing:

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(via Elite Daily)

Can you imagine how devastating this would be?

We were all already on the brink of financial ruin, sales were at a standstill, and suddenly we couldn’t do the one job we had to do for our customers.

To make it even worse, we had no idea why.

So What Happened?

Gmail made a big change that messed up inbox placement for everybody.

We did what anyone with our level of experience would do in this situation: we panicked.

We scrambled; asking everyone we knew who knew anything about email if they knew what was going on and how to fix it.

As it turns out, we weren’t the only ESP feeling the pain. Gmail had made a sudden, unannounced change to their algorithm for inbox placement, and it affected almost every ESP across the board.

A Glimmer of Hope (Courtesy of Campaign Monitor)

About 24 hours later, Campaign Monitor put out a blog post that shed a tremendous amount of light on what was happening, which I believe laid the foundation for many of the deliverability best practices and lessons that are embraced today.

The folks at Campaign Monitor were part of a meeting with Sri Somanchi, the then-head of Google’s Anti-Spam team, who explained the recent changes to a group of representatives from the largest ESPs in the industry.

Here’s the summary of what we learned about Gmail’s new methodology, and what it means for you.

Lesson #1: Send Emails That Your Subscribers Will Love

Somanchi explained that rather than looking at any individual email that went to the spam folder and trying to figure out why, you should look at the email campaign holistically and try to figure out what you could do to make your subscribers love the content more.

This aligns with everything I’ve ever heard Google say about SEO. Rather than try to game search engines, you should focus on creating content that people actually want to read or watch.

The bottom line? The more your subscribers love your emails, the more emails will land in the inbox. And, I’m afraid, the opposite is true as well.

Focus less on why a spam filter might have routed the email to spam and more on why your subscriber might hit the spam button in the first place. Maybe they’re bored to tears. Maybe you send too much. Maybe that call to action in all caps is making their eyeballs bleed.

Lesson #2: Engagement is now the MOST important thing

Gmail takes engagement very seriously.

Opens are good, but re-opens, clicks, forwards, and especially replies, are much better.

According to Somanchi, if the user doesn’t hit the spam button, there is little reason to trigger future spam filters from the same sender. However, high engagement will lead to messages mistakenly classified as spam by Google to be moved back to the inbox.

How do you design for higher engagement?

  • Make sure you include large, clear, strong calls to action (big buttons are great)
  • Ask subscribers to reply directly if they want to get in touch with you
  • Use mobile responsive templates with a single-column design

Lesson #3: Send Frequently to Hyper-Engaged Contacts Only

It was clear Gmail was trying to make people aware that while some people are okay with receiving more email in the beginning, most people tire from frequent email sends quickly.

That doesn’t mean you can’t send often. What it does mean is that if you do, you need to segment your list by engagement (that is, people who are opening and clicking your emails) and only send frequently to the most engaged contacts.

Sending frequently can mean different things to different people, and every email sender is different.

If you’re looking for rough guidelines, here are our recommendations on sending frequency vs. engagement. If you’re sending:

  • More than 5x day: If a subscriber goes an entire day without engaging, move out of “most engaged,” send only weekly or monthly newsletters
  • 3 to 5x day: If a subscriber hasn’t engaged in five days, move out of “most engaged,” send only weekly or monthly newsletters
  • 2x day: If a subscriber hasn’t engaged in one week, move out of “most engaged,” send only weekly or monthly newsletters
  • Daily: If a subscriber hasn’t engaged in two weeks, move them out of “most engaged,” send only weekly or monthly newsletters

Another pro tip for frequent senders is to route your unsubscribe link to a preferences page where the user can update their preferences for desired send frequency. Here’s one Robly customer that does this particularly well:

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How We Ultimately Fixed Our Near-Fatal Deliverability Issue at Robly

So back to Robly.

We eventually got past the deliverability issue and Robly blossomed into the successful business it is today.

What did we do to fix it?

Post panic attack, we carefully considered the following:

  1. Do a forced, one-time sunset (more on this in a minute) of Gmail users. Specifically, those who hadn’t opened an email in over a year for all our customers. This was around 15% of the total number of Gmail emails in our system.
  2. Start educating our customers about the benefit of sunsetting.
  3. Create features that would allow our users to sunset on their own.

We hoped that by reducing the overall number of sends with the same level of engagement, and didn’t send to any unengaged emails, our problems might get solved quickly.

Lucky for us, they did.

What is Sunsetting and Why Should I Care?

Sunsetting is eliminating inactive users from your email list who haven’t engaged in a long time. As our data shows, they will probably never engage again.

Sunsetting is against our best interests. We make far less money if people do it, but we preach it all day long. We actually added a popup for it in Robly. Every six months or so it displays: “Do you want to lower your bill?” and actively encourages users to cut the dead weight from their list.

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We ran the data on every account we have between 100k and 500k contacts in Robly to figure out the odds of whether or not a sunset subscriber would ever come back.

If a subscriber engaged at any point in 2016, then didn’t engage for all of 2017, there was only a 3.7% chance they would engage in 2018.

The gain in overall engagement and inboxing you will get from the virtuous cycle that will come from chopping 30% of your list that is unengaged will FAR SUPERCEDE the potential loss from the 3.7% of subscribers that might engage if you didn’t eliminate them.

As you can see, if someone hasn’t opened your email in a year, there is virtually no chance they will open it again.

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Another Bonus of Sunsetting

Another HUGE benefit of sunsetting is it can help you clean spam traps off your list.

A spam trap is an email address that is intentionally planted online or elsewhere. The purpose is to help expose illegitimate senders or those who are scraping emails from places they shouldn’t be. Old, abandoned email addresses or defunct domains can be turned into spam traps. This means your list may have them if you have lists with old contacts that you haven’t sent to in a while.

If you’ve got a bunch of spam traps, and your sending reputation is important to you, you need to take a hard look at your list building practices. That’s where spam traps start.

Hitting spam traps hurt your email reputation more than just about anything else. You’ll land on blacklists. Your emails will go to spam folders. You’ll spend hours filling out delisting forms and explaining to ISPs why you’re not a spammer.


Spam traps don’t engage with emails. You’ll never see a spam trap email open anything.

Assuming you send to your entire list, if you eliminate all unengaged emails that haven’t opened in three months, you’ll eliminate spam traps from more than three months ago.

One of the main types of spam traps are called “recycled” spam traps. ISPs recycle email addresses that haven’t been used for 90 to 270 days. They know if you’re bulk emailing them, then you got that email address from an old list you rented or bought.

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Source: Litmus

Create a Virtuous (Not Vicious) Deliverability Cycle

Simply put, the quickest and easiest way you can improve your engagement in the eyes of ESPs is by sunsetting.

By not sending to unengaged users, your campaign is going to a much higher percentage of engaged users. In the long run, this leads to better inbox placement and even more engagement.

This is the virtuous deliverability cycle that every serious email marketer who is consciously managing their sending reputation strives for.

If you don’t sunset, and as your list grows over time, you will likely have a higher percentage of unengaged users than when you started with a few hundred subscribers.

On the flip side, if you’re not proactive with your list hygiene, you can create a vicious engagement cycle. Your overall percentage of unengaged users will go up, which is interpreted as lower engagement. This in turn leads to decreased inbox placement, followed by further erosion of engagement.

Create a Plan (They’re Different for Everybody)

Best practices can help you determine the frequency and magnitude of your sunsets. If you’ve never sunset your list before and are a low volume sender, trimming those who haven’t opened in the last six months is a good place to start.

If you’re sending with very high frequency and your list building practices are in what we might call a grey area, your only hope may be to sunset users after a day or two of not engaging.

If you have explicit, double-opt-in permission from your users, you aren’t sending with high frequency, your subscribers love your content, and you’re sending them exactly what they expect with the frequency they expect it, you may not actually need to sunset. However, we think it’s always a good idea because:

  1.     Gmail cares so much about engagement
  2.     Sunsetting does, in fact, lead to a virtuous engagement cycle

Both Robly and have great engagement tools that do all of this in one step.

If you’re using another ESP, here’s how you do it:

  1.     Segment your list into customers that have opened any campaign within X number of months
  2.     Download the segment into a CSV file
  3.     Upload it as a do not mail/suppression list
  4.     If your ESP doesn’t segment by engagement, contact their customer support and request a list of unengaged contacts based on your criteria, go to step 3

If you send more than 100k emails per month, the team would love to help you come up with a complimentary list hygiene plan based on your business type, sending frequency, content, and audience. We’ve been doing this for years at Robly. We’ll show you a few things that will leave you with a virtuous engagement cycle and ever-improving  inbox placement.

Go to and book a call now!

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