TL,DR - too long, didn’t read? Listen on YouTube instead!
Why do we onboard at all?
Two core reasons - first, because a user who understands how the platform works, what it’s good for, and the underlying problem that it solves/value it delivers is a “good” user. Someone who is more likely to be engaged, to use it, have the best experience, and (of course) renew.
Second, the pure cutthroat answer, because good customer training is seen as the fastest way to offer Time To (first) Value (TTV). The moment where a customer really sees why their new purchase is “worth it,” heading off the Buyer’s Remorse high-churn step of someone bouncing off a tool because they can’t figure it out.
When does onboarding fail?
When it’s not there for them when, and where, they need it.
That’s a pure, simple answer, but let’s unpack a few cases where that would be:
A user opens a platform for the first time, with a very specific need. An un-skippable onboarding slideshow plays. A 20 minute AI “conversation” sets up their account for the first time. It takes so long to get set up that the moment passes, and the user churns because of a barrier to adoption.
A new lead takes over after the person who was onboarded by the company (you) originally. The company doesn’t offer remedial/follow-up onboarding, the help documentation and support aren’t robust enough to fill in the gap, the new lead drives a churn because they can’t figure out the platform. This can happen if someone is replaced at a customer’s company, but it could simply be that the people who went through the first onboarding weren’t the people who were really going to be using it.
Someone skips the tutorial, doesn’t remember the onboarding, there’s no reference in-platform to fill in the gaps (and they used it rarely enough to forget everything) - the customer churns because they don’t use the tool enough.
There’s a crisis. The customer REALLY needs the thing to work, fast - and it doesn’t. Support and documentation aren’t fast enough to get them there, immediate churn (and an low-sentiment one) because you weren’t there when they needed you.
A feature changes, significantly, from what was covered in onboarding.
What’s the common thread?
Flexibility. Speed. And most of all, timing.
All of this is where Customer Success absolutely shines, because one thing Customer Success can offer is the depth of product-knowledge, training skill, and simple reachability, being there when critical questions come up on the customer side.
This is from Mozilla Firefox’s Help page. I stared at this for a full minute trying to decide which option it had been…
So how do you fix it?
There are two very strong solutions, and a combination of both is (I think) by a mile the strongest approach.
First, flexible, responsive onboarding. You don’t template and cookie-cutter an implementation flow, you don’t cover every single feature in-depth. Instead, you offer the bare-minimum training a user base needs to get up and running in your tool. Repeat, reinforce, make sure it’s memorable.
And then you build in help tools that work.
Support chat, help documentation, feature walkthroughs. These need to understand the question, and get the user an answer real-time. Automated, live, honestly that doesn’t matter, as long as it meets the core goal of being there when and where the customer needs it (see the trend?)
This is an excellent case for AI, because tools that can understand what question a user is asking real-time in a platform, and actually walk through through the solution live, are the best possible solution to most of the issues above.
That’s straightforward, and it’s what nearly every company out there sells (even before AI) …but it’s a rare company whose help tools actually deliver on that promise.
At all, let alone when it really matters.
Second, Customer Success.
The thing that ties it all together, the team that follows up with the strategic conversations, that’s close enough to, and involved enough with, both your product and your customers that they can have real strategic conversations when and where they’re the most impactful.
They’re the people who can make sure your onboarding/help tools are working as needed, and go even further in actually acting on where, why, and how customers are asking for help.
Pure automation will (for now) lose to LLM’s speed and convenience paired with human interaction and insight.
What’s going to win is the team that’s there, always there, and the customers who always have what they need in the moment.
Founder of the Week
Leta Lista, of the fundraiser positioning company keep building
The entire purpose of my Founder of the Week spotlight is to showcase exceptional founders - great products, great ideas, great practices.
But most importantly, it’s to offer something to other founders. Last week, it was how to build in public like a pro, with Ilai. Before that, it was to challenge the 10-ton gorilla in a product niche with Luca.
With Leta, it’s how to break in with funders - and I do mean “break” in
Leta is a founder. But a founder whose entire company and work is around very literally helping founders. To quote keep building’s website:
+ you don't want to burn your warm intros and go through 30+ convos to refine your narrative and approach
+ you don't want to keep tweaking your deck - you want to raise and get back to building your business
+ "it's not a good time for us" is not a real reason - there's always an answer behind it, and you'd prefer to know it
It’s what to say, to put your best foot forward.
It’s where to say it, to not waste your time.
It’s how to fully process the feedback you do get, and how to take it without letting you slow down.
Leta’s content and personality are strong. Punchy, to the point, nothing held back. She’s that voice in the room who will say, out loud, what you really need to hear.
Founders need that.
But Leta goes even further, vocally calling out VC’s and investors on LinkedIn for practices that hold founders back. Challenges opinions in ways that founders themselves can’t, making her an incredibly valuable advocate for the entire founder ecosystem, and well deserving of the shout-out!
She calls out the really good stuff too, but that’s something anyone can do.
Everyone has been saying “SaaS is dead,” but sass remains a superpower, and Leta masters that for good and profit.
Post of the week
beehiiv’s own Tyler Denk is always a good source for punchy, to the point breakdowns of the business moves he’s making. This week though he hit a particularly good one, about how Substack and Patreon are hurting themselves by making the platforms actively unfriendly to creators.
As I said in a comment, that’s a common sight among well-established software platforms out there, but while it will result in increased profits briefly, long-term it will have very negative effects on the growth of the business.
Taking advantage of the creators who are your platform’s product might as well be literally writing Tyler’s marketing releases for beehiiv!
News tidbit of the week
Salesforce alum Gregg Johnson posted some interesting insight on Salesforce’s acquisition of Fin (formerly Intercom) this past week, and how it speaks to the overall strategy of Salesforce and their in-house Agentforce.
This is one I’m watching closely, because Salesforce/Intercom was (some time ago) the single best Customer Success tech stack I’ve ever used. The two merging has upsides and downsides, both of which will depend on how well they’re integrated as platforms, and how much attention is put in to their overall product design.
That’s especially interesting to watch as Salesforce is moving to dump their UI entirely, which is an excellent idea… IF they can pull it off in a functional way.
Until next time!
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