Hi all,
Happy Sunday. I just arrived in Wisconsin for my quarterly lecture & can’t wait to jam with all the students at the University of Wisconsin-Madison Business School this week.
If you think you’re cold in NYC, don’t come here lol.
Many complex problems totally block companies from growing fast.
Today’s newsletter highlights one I see far too often: poor communication to your customer about their progress makes them feel like there’s little to no progress at all.
This leads to high churn, bad reviews, slowed word-of-mouth, and lower revenue. Here’s how to fix it.
P.S. If you like this newsletter topic, you’ll love these past favorites, which all anchor on designing customer behavior:
First: what founders get wrong about retention
The model people want to believe goes like this: Product good → customer happy → customer stays. Build more features, reduce churn. Make the product better, reduce churn. Hire more CSMs, reduce churn.
If you’ve ever built anything, you know that’s not reality.
And that’s because retention is also half a perception problem.
Your customer needs to feel improvement, like their life is getting better because of your product. It’s your job to architect and design this feeling.
Many professionals get paid to show customers their progress.
Personal trainers. Therapists. Financial advisors. Coaches.
Every single one has developed a ritual for reflecting progress to their customers: before-and-after photos, session notes, charts, milestones.
They know customers will notice the right progress milestones on their own, so they architect the moment of recognition.
Your software product is the same. Your customers need to know they are accomplishing something & you can design these moments.
Unstructured progress isn’t easy to realize. When wins are stacked and surfaced, progress compounds.
Here are 4 interesting ways to build and reinforce customer progress.
1. Cement the “before” state
What it is: Where your customer started before you came into their life
I encourage you to ask yourself: if a customer cancelled today and you wanted to show them how far they'd come, what would you point to in the product or comms?
If your best answer is that you’d have to have a conversation with them and talk through how much better their life/workflow is because of your product, I can promise your retention has a ton of upward potential.
Your customer cannot feel progress if they have no baseline to measure against.
Think this sounds obvious?
Opportunity:
Consumer companies have crushed this: You start at level 0 and start to work up. This is reinforced with milestones, levels, progress bars, points systems.
B2B companies are totally behind here.
The only B2B company I know that crushes at this is Rilla ($0 to $70M ARR in 7 years, 7th fastest growing SaaS company in history, in the Knight Vision portfolio). Rilla’s software has streaks, and users can unlock goals.
Rilla was built with all the winning consumer tactics, and it’s undoubtedly one of the reasons they have grown so fast.
2. Set users up for the “aha” moment via “best known working state”
What it is: Not when the customer gets value. The “aha” moment is when they KNOW they're getting value. These are not the same thing. This is the moment customers consciously experience the magic of your product.
Everyone reading this newsletter should know what the “aha” moment is. What’s actually new to most people is that the user needs to be set up to meet this “aha” moment in a conscious state.
At Citizen, we spent multiple quarters anchoring on the “best known working state” – i.e., everything the user needed to get to the aha moment. This boiled down to:
Location always on
Notifications on
Latest version of the app
If the customer had these 3 permissions enabled, their experience was measurably better, as obvious in metrics like:
User time in the product
Exiting the product and re-entering
Number of sessions per hour and day (e.g. did you open the app 5x today)
Sharing of content to friends outside of the app
Every product has a “best known working state.” This is a critical input to the “aha” moment.
So, what do you need from your customer to have the best experience and reach their “aha” moment?
Maybe it's:
Certain permissions enabled
Connecting their email
Uploading foundational documents to build their profile
Customizing their settings
Whatever it is, make sure you’re setting up your user for success so when they reach the aha moment, they actually know what’s going on. If the product is operating at its full level of excellence, it only matters if the user actually understands.
Opportunity: Tease the aha moment to the user before they reach it. Try things like:
Customer success stories
Progress tracker that frames expected outcomes
What’s been won vs. lost by using the product
Tell the user what the “aha” moment is so they know what they are goaling against and working towards, so when it happens to them, it’s an immediate “brain click” moment + confirmation that the product is working exactly as promised.
3. Save users from disasters (and tell them)
What it is: Articulate the worst things that would happen to customers if your product disappeared tomorrow
Opportunity: Tell your customers about the bad outcomes you’re preventing
Example: "Grammarly caught 62 errors in your writing this week, including 3 that would have been pretty bad and made you look stupid."
It’s your job to make your product value visible.
The “saved from disaster” pillar works well in security, compliance, infra, and fintech tools, any product where the value is partly about what didn't happen.
But any and all products should do this. You’re shaping your enemy.
Dating apps lean into this with the disaster being you’re single for life
Netflix: the disaster is missing the shows everyone talks about
Lightfield: the disaster is missing deals & revenue around you because you couldn’t spot that they even existed…
my personal disaster would be having to go back to a normal CRM after using Lightfield. I literally will not and using HubSpot after Lightfield would make me regress and feel stupid (real).
4. Create milestones
What it is: Constructed moments that force customers to recognize their own advancement
Consumer companies have weaponized this. Duolingo's streaks. Strava's segment PRs. Peloton's milestone rides. These are deeply embedded into the psychology of these products. The whole thing is gamified.
B2B has been embarrassingly slow here. Your customers hit meaningful milestones constantly. Here’s exactly how you can surface them:
Type | Example | Trigger |
Volume milestone | “You’ve processed 10k invoices in 10 minutes vs. 10 hours” | User does a lot of the core product actions |
Time milestone | “90-day streak” | User does something consistently |
Efficiency milestone | “You saved 40 hours this month” | User’s life is better because of X |
Social milestone | “Top 5% of all power users” | When the user ranks against other ppl |
Opportunity: Bring these milestones to life in different ways, including:
In-product: Show case studies based on customers’ usage
Founder emails: "Customer story every Tuesday" or “here’s where I’m at, here’s where you can be too”
Peer matching: "Customers like you" segmentation (industry, size, use case) hit X, and you hit X
The end goal for achieving milestones is to end up with the same experience as one of your products' “super users”. These are REAL customers who you are the best examples of successful stories + you can articulate it.
The rotation should go like this:
Cement the "before" → Set up for "aha" → Hit milestones →
Celebrate wins (case studies) → Reinforce with founder voice →
Protect with "disaster avoided" → Wrap in brand vibes
Well, How’d I Do?
On the surface, I bet when you hear these terms, you believe you already know them.
If you read this newsletter today, I guarantee you learned something new.
These concepts are easy to understand but incredibly difficult to crack and granular to get to level 10.
Many of the best founders can build products, but forget to teach the user about the journey they are on when using the product.
It’s my job to make you better than that, so you never miss these wins.
I hope you have an excellent and productive week.
Julia
