15 Best SaaS Winback & Re-engagement Email Strategies & Optimisations (2025)

💬 Email can be a key driver as part of a winback and re-engagement campaign - and with testing different angles, messaging, variants in terms of design/layout, and other elements that I highlight through this checklist, you can increase your chances of better winback/re-engagement performance.

Numerous experiments for elements across design, messaging, angles, offers and more for re-engagement and winback SaaS emails

💬 Most of the tactical areas I share below have example references from top SaaS brands I've seen - hoping there are some areas that can spark some other thoughts/tests that you can run for your product. :)

Setup automated sequence campaigns like this to stay top of mind to freemium/free-plan user segments about paid features and capabilities they’re missing out on. 

It can help create FOMO, especially when using the right messaging (highlighting USPs/pros), social proof and use cases.

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• This is a great reference from Zoom, reminding users (in this case past paid users) of what they've been working on, and showcasing exciting new features

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I always speak to clients/companies I consult with to ensure to have at a minimum, product update emails to send to all segments - where it’s a chance to highlight new product releases, bug fixes, upcoming features, reminder for feedback, resources to share and other relevant announcements.

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• A nice "block based" sections example from Asana
• Really like the personalisation of the copy ("grab a coffee and let's catch up) at the top
• Testing between variants in layout and CTAS, such as Zoom above in the first checklist point and this Asana version this are good - measure CTR and conversions

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• Good reminder email from Skillshare combined with a great offer
• Highlighting new features section with USPs

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• Another example to remind segments is from Brainfm
• Good use of two CTAs, as well as like the copy of "see benefits in 15 mins.." - personally, I'd make this clearer as it highlights a result to encourage users to try

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I’m a big fan of initiatives like this where you keep things more “human” and away from just the typical promo/automated sequences. 

If you want to get cut-through and generate engagement/replies for something that is critical to get feedback/engagement from users and customers, then plain-text founder emails like this example from Rand Fishkin can be effective.

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• Good style of email to prompt users to reply with 2 simple questions
• Points out how Rand and Casey review each email - which helps reassure people know that their replies will be read (especially if users go to the effort of replying) - helps them feel valued
• Nice reminder about updates with features on SparkToro

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Check out case study

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To help with ‘winning’ back those who are on freemium plans after they downgraded, or didn’t commit post free-trial period, experiment with emails focused on top features, backed with relevant and focused customer review(s). 

Key recommendation: based on the attributes you have available, choose ICP-aligned reviews to those key segments you’re sending to.

• Like the simplicity done here by AllTrails, highlighting one of their main features "Navigator" with a relevant testimonial

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I’m a big believer of using social proof elements like reviews, publication logos, UGC-type content (videos and/or images), thought-leader quotes (etc) wherever possible across emails. 

In this case, sending dedicated emails focused just on social proof can work very well for re-engagement for inactive/low activity-based audiences. 

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• Love this from Picmonkey using various reviews from different sources, including publications, 3rd-party review platforms, and real customers
• Also like the fact they've combined reviews alongside key USPs

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You can achieve higher re-engagement rates from users/audiences who have become inactive when you share more stories, which relate to key solutions and your primary ICP’s. 

• Great example here from Kajabi with the co-founders of Bossbabe - combining story and social proof with key USPs

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If you’re wanting to push for more conversions, sometimes you have to dangle the carrot to get people to commit - and that’s where sharing incentives/offers can help. 

Reminder: Tailor offers and messaging by key behavioural segments.

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• Simple layouts like with a clear CTA are effective

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• This is a good example from Linktree - especially for their audience which are D2C (so they're used to "coupon" email styling like this from eCommerce).

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• I like what Appsumo have done here with their elements throughout - incl. video CTA/embed, member perks and USPs, offer section with products, and to round it off, a nice testimonial.

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As mentioned earlier in this checklist, utilising social proof elements like testimonials and reviews can help accelerate trust-building and credibility, which is important to make noticeable for those deeper in the funnel.

And the tactical experiment I’m pointing out here is to utilise social proof with a core offer in one email. 

From experience, emails like this tend to perform quite well as it’s focused on one core CTA.

• One of the best I've seen with reviews-specific alongside an special offer is from Sling TV

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If you have ‘templates’ or some sort of ‘use case’ library that’s part of your product offering, experiment with this angle to remind users of how ‘easy’ it can be to apply templates to specific solutions/use cases. 

Ensure to tailor send outs with templates that are broken down by segment goals/attributes - (for e.g. send project management templates to operation managers).

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• Like this 'nudge' email from Dropbox with their product - templates are a good 'reminder tactic' to help reactivate

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Sometimes, all you need is a simple email with one focused CTA, with minimal and succinct copy to inactive/low-active segments. 

Have tested this in the past and it can work - sometimes less ‘clutter’ can help with certain pockets of audiences.

• Just like this example from Asana - simple GIF with a nudge to say Asana is 2x faster (faster than ever!)

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Many of the top SaaS startups use this tactic for those who were on free trials and never upgraded. 

Highly recommend to incorporate this into the mix of your SaaS email strategy. 

Recommendation: run the first one with no offer, and for those who don’t uptake, test combining with an offer at a later date.

• Harvest keep it to the point, with clear reasons why people love the software, and next steps

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Sometimes just a simple prompt reminder is all you need to get a % of users to come back - especially in a busy inbox, just focusing on one simple action can help get some users back. 

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I always get impressed as a user with these types of “end of year” data-based emails - whether related to my specific use, or just knowing the benchmarks/data from the company about how their users across the board have utilised the product, I find interesting.

• Loom always do a good job with these types of digest/summary emails - both monthly and end of year
• Like how they've positioned it with "Loom personality" - good to highlight what users are affiliated as ('Time Saver' in this example)
• Also good to see top collaborator and 'quick hits' from the year

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Related to the above checklist point, a good way to get people back are through summary reports from the company and/or product. 

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• This is up there with one of the best designed emails I have seen - kudos to the design and marketing team at Grammarly.

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With any sort of event/webinar or conference you’re planning to run, you want to ensure to send tailored and dedicated emails to segments that are inactive or those who have previously downgraded plans. 

You can use this as an opportunity to angle ‘exciting new updates’ and other messaging focused on why they should attend, tied with social proof.

• Like this example from Webflow which utilises social proof for their conference

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Sharing any sort of milestone or celebratory anniversary is a great way to nudge and stay top of mind to users. 

I actually wrote a checklist on different types of milestone/anniversary experiments that you can test.

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