Designing Retention for SaaS
Keeping new users active and engaged via email strategy
MyCheckins was the answer to every “Did we really need a meeting for this?” In other words, an async, text-based check-in tool designed to replace unnecessary meetings with clear, structured updates. It helped teams stay aligned while freeing up time to focus on actual work instead of calls.
The Problem:
People were creating accounts...
and disappearing.
The Solution:
A set of emails sent over the course of a month addressing common concerns.
Written from the founder’s point of view, the email journey was built around a simple idea: help people understand the product in a way that feels relevant to them. For leaders, it was about saving time, keeping teams aligned, and figuring out how to get everyone to adopt something new. For team members, it was about having fewer meetings, clearer priorities, and a controlled workday.
Instead of just nudging people to come back, each email tried to be genuinely useful. It showed how to write better check-ins, how to build the habit, and what kind of results to expect. It also addressed the real reasons people drop off like not knowing where to start or not seeing immediate value. The idea was to reduce that friction step by step and make it easier for people to stick with it.
Each email set expectations for what was coming next, creating a sense of continuity and helping users stay engaged throughout the journey.
The journey ended with a custom wrap-up of the hours saved in a month using MyCheckins. If users failed to use the product, they were nudged to give it a chance in the next month with a predictive wrap-up of the hours they could possibly save.
Tone of Voice
Conversational, approachable, and grounded
For founders and team leaders, the tone leaned into shared understanding . It acknowledged the reality of leading a team and the constant need to stay informed without disrupting work.
For team members, the tone was practical and relatable. It focused on the everyday benefits of writing things down, such as staying organised, keeping track of goals, and saving time otherwise spent trying to piece together tasks.
Route 1:
Founders & Team Leaders
Emails explaining how
MyCheckins helps teams
Scenario A:
Team makes regular check-ins
Scenario B:
Team does not make regular check-ins
Wrap-up email with monthly hours saved and other stats
One last nudge with predictive hours saved
Route 2:
Team Members
Emails describing how MyCheckins helps stay organised
Scenario A:
Team member make regular check-ins
Scenario B:
Team member doesnn’t make regular check-ins
Wrap-up email with monthly hours saved and other stats
One last nudge with predictive hours saved
Click to Read E-mails
Route 1
Subject: Your meeting-free journey begins today.Subject: How long does it take to see results from MyCheckins?
Subject: In an alternative meeting-free universe...
Route 2
Subject: All meetings cancelled.
Subject: Do you know what your team is up to? - 3/8
The Result:
Uncertainty was reduced
Users were able to understand what to do with MyCheckins, why it mattered, and what would come next rather than simply being reminding to return.
Activation rate increased from
Improved Week 1 retention from
Reduced early drop-off from
Increased product adoption from
32% → 41%
11% → 16%
23% → 18%
27% → 38%
For the first email, achieved an
open rate of
Throughout the
journey, achieved
an open rate of
Maintained click through rates of
48%
32-42%
6-8%
Designing Retention for SaaS
Keeping new users active and engaged via email strategy
MyCheckins was the answer to every “Did we really need a meeting for this?” In other words, an async, text-based check-in tool designed to replace unnecessary meetings with clear, structured updates. It helped teams stay aligned while freeing up time to focus on actual work instead of calls.
The Problem:
People were creating accounts... and disappearing.
The Solution:
A set of emails sent over the course of a month addressing common concerns.
Written from the founder’s point of view, the email journey was built around a simple idea: help people understand the product in a way that feels relevant to them. For leaders, it was about saving time, keeping teams aligned, and figuring out how to get everyone to adopt something new. For team members, it was about having fewer meetings, clearer priorities, and a controlled workday.
Instead of just nudging people to come back, each email tried to be genuinely useful. It showed how to write better check-ins, how to build the habit, and what kind of results to expect. It also addressed the real reasons people drop off like not knowing where to start or not seeing immediate value. The idea was to reduce that friction step by step and make it easier for people to stick with it.
Each email set expectations for what was coming next, creating a sense of continuity and helping users stay engaged throughout the journey.
The journey ended with a custom wrap-up of the hours saved in a month using MyCheckins. If users failed to use the product, they were nudged to give it a chance in the next month with a predictive wrap-up of the hours they could possibly save.
Tone of Voice
Conversational, approachable, and grounded
For founders and team leaders, the tone leaned into shared understanding . It acknowledged the reality of leading a team and the constant need to stay informed without disrupting work.
For team members, the tone was practical and relatable. It focused on the everyday benefits of writing things down, such as staying organised, keeping track of goals, and saving time otherwise spent trying to piece together tasks.
Click to Read E-mails
Route 1
Subject: Your meeting-free journey begins today.
Subject: How long does it take to see results from MyCheckins?
Subject: In an alternative meeting-free universe...
Route 2
Subject: All meetings cancelled.
Subject: Do you know what your team is up to? - 3/8
The Result:
Uncertainty was reduced
Users were able to understand what to do with MyCheckins, why it mattered, and what would come next rather than simply being reminding to return.
- Activation rate increased from 32% → 41%
- Improved Week 1 retention from 11% → 16%
- Reduced early drop-off from 23% → 18%
- Increased product adoption from 27% → 38%
- For the first email, achieved an open rate of 48%
- Throughout the journey, achieved an open rate of 32-42%
- Maintained click through rates of 6-8%