Moonlight’s Weekly Digest

Spotlight on Email #1: Your newsletter is your product


Posted 3.18.21

This is the first entry in an ongoing series of interviews and case studies on excellence in application email.

Moonlight is an online community matching software developers to remote contracting and full-time opportunities. It was acquired by PullRequest in 2020.

We realized that our weekly newsletter got something like two times as many people looking at it every week as our entire website.

I spoke with Moonlight's co-founder Philip Thomas about Moonlight's application email strategy: specifically, their weekly newsletter. A lot of companies treat weekly newsletters as part of their marketing email strategy. Instead, Moonlight improved engagement by treating them as application email, making the content customized per user and tightly integrated into the product experience.

The Email

Moonlight sends a weekly newsletter to developers and companies on their platform, customized to each user. First, the userbase is divided into four groups:

  1. Developers who are active jobseekers
  2. Developers who have not yet finished onboarding
  3. Companies with paid subscriptions
  4. Companies with inactive subscriptions

Every Tuesday, users on Moonlight receive an email with a custom subject and introductory paragraph written specifically for that week and that segment of users. This human touch is important, Philip says: "People are good at spotting things that come from a robot. You don't want to growth hack yourself into ostracizing your audience."

After that human-written introduction, everything in the email is automatically generated based on the user's interests.

The following is an example email sent to a jobseeking developer:

Moonlight's Weekly Digest Email

This email is plain text only. It is clear, relevant, and speaks to why developers are on the Moonlight platform in the first place. "We didn't have a fancy header," Philip told me. "We got great results with some lightly styled plain text. We were really focused on user value rather than making it super designed."

Moonlight made sure the information hierarchy in the email was clear and the copy was always crisp and readable – no need for headers, fancy or otherwise.

The content of the email after the opening section (from "Featured Job" on down) is automatically generated when the email is sent. Job matches and contracting opportunities are generated for each user based on a machine learning algorithm. Content about updates to the website is also automatically generated: "We hooked it into it bunch of different feeds, like our blog and our product updates from Headway," Philip said.


We thought of our newsletters as a way to build a long-term relationship with our customers.

Philip says this newsletter was originally sent as a static marketing newsletter, with everyone receiving the same content. Developers additionally received one email for each new job opportunity. As the Moonlight platform grew, user inboxes started getting flooded with job matches, many of which weren't relevant to their skills or interests.

The solution was including customized opportunities in the weekly digest email. "We realized that our weekly newsletter got something like two times as many people looking at it every week as our entire website." Since most people aren't looking for jobs 365 days a year, most developers rarely logged in and only interacted with Moonlight through emails. If the emails keep them engaged, then when they come back on the job market, they'd think of Moonlight first. Philip says Moonlight "thought of our newsletters as a way to build a long-term relationship with our customers."

General Advice

Philip has a lot of good advice relevant to anyone sending application email. Here are three highlights:

  1. Watch your open rate, but don't obsess. Philip said that monitoring open rates is useful for monitoring email deliverability. Philip recommends Postmark's free DMARC monitoring tool which helps make sure spammers don't send email under your domain. Beyond this though, a high open rate "isn't an end-in-and-of itself." Moonlight always avoided subject lines with clickbait, which might drive short term results but would alienate their audience over the long term.
  2. Use fine-grained unsubscription management. Moonlight was originally sending newsletters and other emails through Intercom, but realized that "when users click unsubscribe on Intercom it turned off all emails, even though you might just be getting an onboarding campaign that you didn't want anymore." They switched to using an unsubscription system where users can unsubscribe from a specific category of email without losing access to ALL application emails. (Mailclerk does this for you automatically.)
  3. Use a dedicated IP address. When you send with services like Mailgun or Sparkpost, you have the option of sending on a shared IP address or a dedicated IP address. Moonlight started on a shared IP address for cost reasons, but had trouble migrating to a dedicated IP address when the time came because of the high volume of email they were sending. (This requires "warming up" the IP address and is a topic for a future Mailclerk blog post!) Philip says that "I would recommend generally to founders that they invest in an IP before they have tens of thousands of emails going out because making that transition over is much easier."

Which team owns application email?

Philip says application email is "really cross-functional," touching many different functions within Moonlight. Specifically for the weekly newsletter:

  • Product was involved in identifying that the existing static newsletter was driving engagement and identify it as a good candidate for further investment.
  • Engineering was involved in figuring out how to increase the relevance of the emails using a recommendation engine.
  • Design was involved, more for copy than layout, making sure information is presented clearly and naturally.
  • Marketing was involved in keeping the subject lines and introductions fresh each week to keep the experience authentic


We think Moonlight's weekly newsletter shows the benefits of treating email as an extension of your app's user interface. Since many developers didn't visit Moonlight's website for months at a time, the website had to go to them in their inbox.

By sending a customized, relevant, and thoughtfully designed email, Moonlight could nurture its relationship with audience over time so that, when developers need Moonlight's service again, they immediately thought of them.

Philip says this email was absolutely crucial to Moonlight's growth and success. "We ended up with just crazy open rates and crazy clickthrough rates on it because the email was customized." It kept developers engaged and coming back to the platform.

Interested in early access?