Read time: 4 min, 22 secs
This is for you if you run an agency or SaaS and you want to stop customers leaving

Hey there - it's Brian 👋

“Our customers are leaving… 😢
How do we get them to stay?”

In 2019 I worked with a $4.3B SaaS fintech.

They had an INSANE churn problem. Typical churn for a SaaS sits around 3%. These guys were around 30%.

But they had SUCH incredible marketing they could acquire customers like crazy.

So we were on a mission to figure out how to get customers to stay and use other products.

So we transformed their customer success program.

I took those retention methods and

At the end of this issue you'll know:

• Why poor onboarding directly causes 20-25% of all customer churn

• How to spot the warning signs your onboarding is failing (before it's too late)

• Which 5 retention strategies your Customer Success team needs to focus on

This is for you if you want your customers to pay you for longer and buy more of your stuff.

Note: if you run an agency, this is your “account manager”
If you run a SaaS this is your “customer success manager.” Same concept.

Keep customers paying you longer. Get them to upsell.

Let's make your business an outlier: 👇

P.S. prefer the video version? Here you go!

For my friends: What’s going on with Brian?

My sister graduated!

So I went back to Boston for a few days to see her graduate and celebrate.

Now I’m back in Playa del Carmen building.

We’re focused on building out AI agents in-house to make our business as efficient as possible.

Our first focus is content. I know how nerdy you guys are so we want to make content that has even more research, citations… in more formats (audio, video, text etc).

I’ll let you know how our experiments go.

Let's get into it: 👇

Poor onboarding directly causes 20-25% of all customer churn

This blew my mind.

Bad onboarding is the single largest avoidable churn factor after product-market fit issues.

Think about that for a sec.

You build a product people want. You spending money on marketing and sales to get customers in the door.

Then you lose them because your onboarding sucks.

It's frustrating.

Here's what you need to understand:

The first 30 days are make-or-break.

90% of customers decide whether to stick with your product in this window.

But most companies treat onboarding as an afterthought.

On average you see 3-5% of your customers leave every month… and a lot of those come from never getting properly onboarded.

Why?

"But isn't churn more about product quality than onboarding?"

Well… no.

You can have the best product/service in the world but if customers don’t know that, who cares?

A good onboarding process helps customers ACTUALLY understand your value and learn to get the most out of it.

Customers don’t want to put in work. So they skip tutorials. Don’t listen to terms. etc etc

They just want the outcome.

But if they skip the parts where you teach them what makes you so valuable, you’re in trouble.

They don’t get what makes you amazing. And they leave.

That’s where a good customer success rep fills the gap.

They help customers get the most out of what you offer.

Get this right and they’ll boost your revenue by 25%…

So if you’re doing $1M ARR that’s $250,000.

Not bad on a $2k / month investment.

🚨 So what warning signs do Customer Success Managers (CSMs) look for to tell a customer might leave you? 🚨 👇

🧔🏻‍♂️ Brian’s nerdy side rant:
“Wait. Do I need a CSM?”

Well… it depends.

So there’s 3 types of customer success management.

1) High-touch
Completely customized. You assign a CS person to manage a few accounts. They build relationships etc.

This is for you if you have fewer customers, bigger deal sizes.

2) Low-touch
It’s a white glove, personalized human touch at scale.

This is for you if you have more customers than high touch, but you want a human to build a relationship with your customers at scale. This person builds relationships with far more clients and helps them see your value, pay you longer, refer friends, and buy your other offers.

Low-touch is what we’ll focus on in this issue.

3) No-touch
Fully automated. This is reserved for the highest volume, lower ticket items.

It’s usually called “tech-touch” but I hate jargon. I just share good ideas.

Most of our CSM clients are “low-touch.” More of my CMO consulting clients are high-touch.

What are the warning signs that customers leaving in your first few weeks is a problem?

So how do you know if YOUR onboarding is broken?

Look for these red flags:

1) How long does it take customers to get their first win?

If customers don’t get their first win in week 1… they’re out.

If you have a more complex solution, that’s HARD! So we need to re-design you process to figure out what feels like a quick win to your customer and get it to them ASAP.

It doesn’t have to be anything big. But we need to build momentum.

2) How many customers are actually finish onboarding?

Some percent won’t finish and that’s fine.

Benchmark:
If 80% or more finish, that’s good news.

Less than 80%? We’re in trouble.

3) How long does it take to finish onboarding?
3 weeks? A month?

Way too long.

(But it also depends on how you define onboarding and how complex your product is. A lot of people mix up onboarding + adoption.

If you’re not mixing those up, we have a problem if it takes people a month to learn how you work and what makes you valuable).

🧔🏻‍♂️ Brian’s nerdy side rant:
Okay I’ll give you a few more “obvious” ones so I don’t get yelled at for missing stuff.

4) Bad survey scores?
How to survey customers during/after onboarding isn’t obvious. At all.

It’s actually hard to get the process right.

But if you’re ALREADY doing surveys (NPS / CSAT is the most common)…
bad survey results = bad onboarding.

5) A ton of the same questions coming in?

However you get questions (support tickets, emails etc). If you get a lot of questions that should be answered during onboarding… it’s not working.

Common objection:
"Our product is self-serve; customers don't need a personal CSM."

Idk. It depends.

Are you leaving money on the table from a CSM not hosting group calls and trying to ascend people and keep them paying longer?

Hot take but I struggle to see a situation where a no-touch business can’t get a HUGE boost from a CSM if it’s done right.

Someone prove me wrong. Reply and convince me otherwise.

I’ll update my thinking next week.

So what tricks do we do to boost retention and upsells during onboarding?

Great.

So which CSM activities actually move the needle?

Here are the five:

1) Data-triggered outreach
When a user hasn't completed critical setup steps within 5-7 days, the CSM personally reaches out. This prevents early abandonment at the most vulnerable stage.

Examples:
• Collecting data on how customers use your platform. Reaching out based on usage.
• Too many days inactive
• Reaching milestones (more below)
• Renewal conversations

2) Group onboarding webinars
Regular live sessions where one CSM can train many customers simultaneously. This scales knowledge efficiently - one hour of CSM time can benefit dozens of customers.

Examples:
• Teaching how to use the product
• Teaching something related to your product
• Meeting industry experts

3) Quick success check-ins
Brief (15-minute) calls with higher-value accounts around day 14-21 to verify progress. This builds relationship while confirming adoption is on track.

4) Milestone celebrations
Personalized notes from CSM when customers achieve key setup or usage goals. This reinforces positive behavior and creates emotional connection.

5) Post-onboarding review
CSM conducts short assessment call or email at day 30 to confirm completion and plan for ongoing adoption. This ensures smooth transition to regular use.

These 5 things are targeted, personalized and they scale.

The CSM isn't holding anyone's hand through the entire process - they're stepping in precisely when it matters most.

How to implement this method in your SaaS

Ready to slash your early-stage churn during onboarding?

If you’re doing it at scale, it’s a balance between automation and personal touch.

Find that balance, and you'll watch your early churn numbers drop dramatically.

See you next Thursday 👋

Brian
[email protected]
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TalentHQ

P.S. Struggling to figure out how you balance automation + human touch to retain, refer, and upsell?
Give me a call.
Happy to help you think through it

P.P.S. Ignore the title of that calendar. it’s my LatAm hiring one. It’s just easier to keep it in one place.

🙋 Vote: How did we do?