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SaaS Onboarding Email Blog

What are you in the mood for? I’ve got onboarding email breakdowns, strategy how-tos, and SaaS email marketing best practices. Or, just browse the latest down below. Onboarding Email Breakdown is a team and project management app that offers a 14-day free trial. Let’s see how they take a user from hello to hooked.


Series Overview

During the 14-day free trial, I received eight emails, including the initial authentication message. All of the emails were time-based since I didn’t complete any action within my trial account that could have triggered action-based messages. It’s also interesting to note the send times of the emails. Many of the other onboarding series I’ve recorded have been delivered in the morning, but monday mostly sent emails at night. Monday also sent three winback emails once the trial was over, in which they offered an additional week free.


Day 1.1: Authentication


Subject Line: Confirmation code for 493–895

Sender Name:

Send Time: Immediately after signup

Objective/Content: Account authentication

CTA: Enter the code into the website. In case you closed the window, click here.

Strengths:’s account authorization requires the trial user to enter an email code on monday’s site. They make this extremely easy by including the code in the subject line. No need to even open the email.

If you do open the email, they’ve placed a link back to the relevant page. Thanks, team!

What to learn from it:

  • Include authentication codes in the subject line

  • Make sure you link back to the page a user needs to visit to enter the code

Day 1.2: Introduce the Building Block


Subject Line: Hey Stephanie — build your first board, and get your team started!

Sender Name: team

Send Time: Immediately after authentication

Objective/Content: Hold

CTA: Hold

Strengths: keeps this email brief, and it’s quite nice. They pop in with a helpful video that offers an overview of the service. Cognizant of the reader’s busy schedule, they send small bits of information at a time. also sets an expectation of what’s to come. By stating that they’ll “be in touch,” the user knows there will be more information and onboarding emails to come.

This is also the first email of many that cite their ten-minute response claim. That’s impressive! From the very first emails, I feel that respects my time and is truly available to help, and that’s powerful.

What to learn from it:

  • Be respectful of a reader’s time

  • Set expectations about future communication

  • You don’t have to have a lightning response time to make user’s feel like you’re ready and willing to help


There’s a bit of a disconnect between the subject line and the email content. Based on the subject line, I expected this email to focus solely on’s “building block.” Building a board seems to be the foundational feature of the service.

Instead, it offered a broader overview of the entire product. The email in and of itself was useful and worthy of a spot in this early email. However, the subject line could have alluded to the contents better.

What to learn from it:

  • Make sure subject lines are both eye-catching and accurate. It should give reader’s a clear idea of what to expect inside the email

Day 1.3: Bookmark


Subject Line: don’t lose this

Sender Name: Hold

Send Time: Day 1, 11:21 AM CST

Objective/Content: Provide a direct link to my account

CTA: Log in


This was the third and final email I received on Day 1. I don’t recall receiving any other SaaS emails that had the sole purpose of being bookmarked for easy account access. This would be useful for all new services I’m getting into the habit of using. However, this is extra helpful since assigns all users their own URL.

What to learn from it:

  • Make it as easy as possible for new users to return to your product

Day 2: Use Case


Subject Line: manage projects @stephanie39 + more

Sender Name: Team

Send Time: Day 2, 3:14 AM CST

Objective/Content: Introduce templates and use cases from real customers

CTA: Go to Monday stories, See template


This email is an effective combination of use cases & social proof testimonials. While shows off ways to use their tool, they’re also sharing real-life success stories. Trial users get to hear how useful the product is from peers, not the marketing team.

The headlines, visuals, and CTA buttons are also nicely organized and straightforward.

What to learn from it:

  • When possible, let happy customers sell your product


Once again, I think the subject line doesn’t do the email justice. The email itself is great, but I think a subject line along the lines of “see how monday users manage their projects” would have been truer to what’s inside.

The email copy talks about the community and their happy customers, which should have been carried to the subject line.

What to learn from it:

  • Use the strengths of the email copy and content, such as social proof, in the subject line

Day 4: Value-Add Content


Subject Line: join us for a webinar?

Sender Name: Team

Send Time: Day 4, 8:38 PM CST

Objective/Content: Get users to register for a webinar that focuses on the benefits of implementing monday

CTA: Save your spot now


As the monday onboarding sequence progresses, the subject lines look more and more like messages from friends or coworkers. It’s an interesting tactic, and I’m curious what their open rates and click-through rates are like.

Overall, I really like the idea of using a webinar to show trial users the ideal future that’s possible with monday. It’s a great way to sell the product and answer customers questions all at once. There are multiple days to sign up with, but there are also limited slots. monday is finding the balance between flexibility and scarcity.

What to learn from it:

  • If you don’t have any value-add content already created to send along, why not try a webinar? You can talk about the product in a more personal and direct way, as well as answer customer questions. Responding to user questions helps customers and you. They get help, and you gain valuable insight into user thoughts and concerns.

Day 9: Discount


Subject Line: fyi

Sender Name: Team

Send Time: Day 9, 8:04 PM CST

Objective/Content: Entice trial users to sign up for an annual plan at a discounted rate

CTA: Click here to check it out in your account


A trial user is already able to access your product for free for two weeks, and now you’re giving them a discount? monday says yes. On Day 9 I received a short email letting me know there was a 48-hour promotion.

I have a feeling this promotion happens at this point for all trial users, but it nevertheless may be enticing to some users. People love discounts, and monday would still be getting a new annual subscription. It’s probably not a tactic every SaaS would want to use, but depending on your team’s goals it’s worth considering.


The promotion is also positioned smartly on their website when you click through. In reality, there’s always a cost benefit when you prepay for all twelve months at once. Therefore, the only new discount is the 8% early bird promotion. That may not be what your customer sees, though. They see an 18% discount PLUS 8% off, which seems too good to pass up.

What to learn from it:

  • If you‘re going to offer a discount, make it for a larger plan. Don’t give away a free trial and then a substantial discount on the first month. Users won’t value your product as much, and you’re unnecessarily missing out on profits. However, a discount on an annual subscription sits in the middle ground. A user gets their discount, and you get a user for the long haul (plus some cash flow).

Day 13: CTA


Subject Line: the end is coming

Sender Name: Team

Send Time: Day 13, 8:36 PM CST

Objective/Content: Remind users their trial is about to expire, and the consequences of letting it do so

CTA: Head to your account right now


monday’s subject lines got more unique as the series progressed. I think it’s entertaining, and its the kind of subject line I’ve grown to expect from the brand. It also puts a new twist on the classic end-of-the-trial-sense-of-urgency.

The lowercase + unique subject lines, along with this short form email, make monday seem relaxed and relatable. They aren’t selling hard as a distant corporation. It feels like a person on the other line whose just there to help.

What to learn from it:

  • Remain true to your brand identity

  • Let users know what happens once their free trial is over. Can they still access some of their information? Will all of their past work be erased?

Day 14: Final CTA


Subject Line: your trial ends today

Sender Name: Team

Send Time: Day 14, 8:42 PM CST

Objective/Content: A final reminder that the trial account will be read-only if you don’t upgrade

CTA: Click here


While yesterday’s subject line was unique, the final reminder was very straightforward. Much of the same information from yesterday was reiterated, but with more finality.

What to learn from it:

  • Don’t be afraid to repeat yourselves sometimes — not every person is going to read every email

Day 24: Winback


Subject Line: I want you back for good

Sender Name: Tom from

Send Time: Day 24, 7:18 PM CST

Objective/Content: Offer to extend free trial

CTA: Click here to extend your free trial


“I want you back for good” is a perfect example of using emotional pleas in winback emails. The email itself is also short and gets right to the point — the offer to extend your free trial.

What to learn from it:

  • Try playing up emotions in your winback emails — what have you got to lose?

Day 34: Winback


Subject Line: One more week, for free :)

Sender Name: Tan from

Send Time: Day 34, 3:22 PM CST

Objective/Content: Alert user about another free week

CTA: Go to


What do you do when a winback customer hasn’t clicked to take advantage of a free week? Go ahead and sign them up for it. There’s also a bit more to this email. They tried a simple reminder, and now they’re letting me know they’re there to help and will be sending resources. The CTA button is also interesting since there’s no doubt about where it’s taking you.

What to learn from it:

  • Try short and sweet first, and then follow up with more information as needed

Day 39: Winback


Subject Line: client management @ stephanie39

Sender Name: Tom from

Send Time: Day 39, 6:58 PM CST

Objective/Content: Introduce templates to use on the platform

CTA: Click this link to add this board to your account


Adding value through resources and content is always a strong move. They also have another great, descriptive CTA.

What to learn from it:

  • Be helpful and add value whenever possible

  • There are many different ways to approach winback emails

Day 54: Winback


Subject Line: Hey there…

Sender Name: Tom from

Send Time: Day 54, 7:05PM CST

Objective/Content: Mention new features and ask users to try the platform again

CTA: Click here to reset your trial


The beauty of this copy is that it’s possible this is an entirely automated message that has been in my fate since I signed up for the free trial, yet it doesn’t feel that way. It feels sincere and timely, and it makes me feel sympathy for the sender.

Perhaps he really did just make a list that included me, I have no idea. Not gonna lie, it does make me feel a little guilty. (Dear Tom, I didn’t leave because sucks, I was just running an experiment. Not sure if that makes you feel any better, but I feel the need to explain myself)

What to learn from it:

  • A scalable onboarding and winback series that feels one-on-one is possible

Series Review

The most memorable aspects of the monday onboarding email series are 1) their casual and forever-lowercased tone and 2) their persistence at the end of the trial. I also thought they had some unique tactics, such as offering an annual discount in the middle of the trial and using webinars to answer questions. The fact that most of their emails were simple text-based messages also goes to show that you don’t need fancy designs to start.

Overall, though, I wish they had talked a bit more about their features. There were some interesting videos and use cases, but there was plenty of breathing room in the middle of the sequence that could host a few feature spotlight emails.

What was your favorite email of the sequence?

Ready to create or upgrade your SaaS onboarding email series? Download What to Include in a 14-Day Onboarding Email Series (And When to Send Each Email) here.