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SaaS Onboarding Email Blog

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FreshBooks Onboarding Email Series Pt.2

The FreshBooks free trial is 30-days long and covers plenty of ground. The first 15 days are profiled in Part 1, and the second 15-day stretch is explored below.


Series Overview

The second half of the FreshBooks free trial onboarding email series spanned 15 days and included four onboarding emails plus two winback messages. In comparison, FreshBooks sent 10 emails in the first 15 days.

Here is the cadence for days 16–31:


And to review, here is the schedule from Part 1:


Day 19: Use Case


Subject Line: And the Award for Best Invoice Goes to…You

Sender Name: Rachel Guloien, FreshBooks

Send Time: Day 19, 8:53 AM CST

Objective/Content: Talk about more ways to make invoicing easy

CTA: Try them on an invoice


FreshBooks onboarding emails show a good evolution of the customer journey, even though they are just time-based. Whereas in the first half of the onboarding series FreshBooks focused on making the first invoice, they’ve now moved on to optimizing invoices. Instead of “make your first invoice” it’s “are you ready to make your next invoice your best one yet?”

They also use bold headlines in a simple but very effective way. Emails gotta be scannable.

What to learn from it:

  • The information and benefits included in the onboarding emails should evolve as the trial progresses. Consider what a user needs to know to get started vs. use the product more effectively

  • Make sure emails are scannable

Day 22: CTA


Subject Line: Have You Seen the Difference FreshBooks Makes?

Sender Name: FreshBooks

Send Time: Day 22, 8:51 AM CST

Objective/Content: Encourage users to select a plan

CTA: Select a Plan


As the end of the free trial approaches, FreshBooks is starting to draw more attention to selecting a paid plan. In this email, they outline some of the benefits of the service before asking trial users to select a plan.

Since there are still nine days left, though, they’re keeping it light and breezy. Nothing too urgent yet. Underneath the CTA button, they’ve linked additional resources. This email plants the seed of the nearing end in the mind of the user.

What to learn from it:

  • Plant the seed about the end of the trial before it’s too close to the cutoff date

  • Support your ask with benefits and resources

Day 24: Offer


Subject Line: Same Great Features, Even Better Price

Sender Name: FreshBooks

Send Time: Day 24, 10:04 AM CST

Objective/Content: Offer a discount for selecting a higher tiered plan

CTA: Upgrade Now


Similarly to, FreshBooks offers free trial users a discount with a twist. While monday offered a discount on annual plans, FreshBooks offers 30% off their two higher-tiered plans. Perhaps the hope is that a user will think “hey, why not get the beefed-up version for the same price I was going to pay for Lite” and then eventually become hooked on the bonus features and continue with the more expensive plan. FreshBooks also sweetened the deal by adding that users don’t have to pay until the trial is up (which is only a few days away).

It’s also convenient that the Plus plan is the most popular, complete with the confetti explosion. A trial user will see the discount for the pricier plans but think “I don’t need THE most expensive one. I’ll take the middle of the road/the cheaper of the more expensive.”

What to learn from it:

  • Use discounts to move people towards pricier plans, either at a higher tier or for a longer commitment

Day 27: Final CTA


Subject Line: You Have 4 Days Left on Your Trial

Sender Name: FreshBooks

Send Time: Day 27, 10:04 AM CST

Objective/Content: Remind users of discount and end of the trial

CTA: Upgrade Now


This email is chock full of great copy! First, the subject line is abundantly clear. Then, the inside reads like a motivational letter. Maybe it’s the impending New Year that has me in the spirit of change, but I appreciate the FreshBooks pep talk. They also follow up with the offer from the previous email. It’s always good to remind people of the end of the trial and any discounts.

What to learn from it:

  • Let users know that you believe in them and that your tool can help them reach their goals

  • Paint a picture of the ideal future and plant your product in the thick of it all

Day 31: Winback


Subject Line: Your Trial Is Over. It’s Time to Upgrade

Sender Name: FreshBooks

Send Time: Day 31, 10:04 AM CST

Objective/Content: Alert user that the free trial is over, plus a discount with a 6-month upgrade

CTA: Upgrade Now


It’s important to let trial users know what will happen to their account and any work they did once the trial is over. In this case, FreshBooks does that while simultaneously using the info to lure me back. If I want my data, I need to upgrade.

Luckily, they give me a discount if I select a 6-month plan. I get a discount, and they get a customer for at least six months. Win-win.

I think this is also a case where a few CTA buttons work well. They say what they need to, and then give me a chance to upgrade. Then they give me even more info and let me select a plan within the email.

What to learn from it:

  • I’m not telling you to hold your trial users’ work hostage, but if that’s how your product is set up, let them know + offer an upgrade discount

  • Multiple CTA buttons (especially strategically colored ones) can work together

Day 34: Winback


Subject Line: Why Not Save 30%?

Sender Name: Rachel Guloien (FreshBooks)

Send Time: Day 34, 10:04 AM CST

Objective/Content: Alert user that the free trial is over, plus a discount with a 6-month upgrade

CTA: Upgrade Now


This is a perfect follow up to the previous winback email. The first post-trial email went into detail about the different account features and the discount at hand. This one, however, is a simplified and personal follow-up.

What to learn from it:

  • Follow up important and complex email with more relaxed and concise messages

Day 36: Winback


Subject Line: This Offer Goes *Poof* in 2 Days

Sender Name: FreshBooks

Send Time: Day 36, 10:06 AM CST

Objective/Content: Alert user that the free trial is over and the upgrade offer is about to expire

CTA: Upgrade Now


FreshBooks is laying on the urgency copy thick here. The offer is about to go “*Poof*” and “tick. tock. time’s running out” are all meant to make me think “ruh-roh I better speak now or forever hold my peace.”

Design-wise, they went back to the chart from the first winback email.

What to learn from it:

  • There are many phrases that say “hurry up and do something before it’s all over”

Series Review:

FreshBooks emails have clean design, useful lists/information organization, and enticing CTA buttons on lock. While this second half of the trial definitely features fewer emails than the first half, I think all of them were strong. Information was always presented in an organized way and help was always offered.

Want to know when to send SaaS emails and what to say?

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