Are your digital success plans even working?

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Hey CS Pro,

Ever created a success plan…only to watch it disappear into a slide deck graveyard..⚰️ 

You are not alone. This week I sat down with Alana Stoltzfus from Okta, and she broke down the exact system they use to make success plans a living, breathing digital experience that drives adoption, renewals, and actual value.

Let us get straight into it.

But first, today’s sponsor

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From CSM to building digital CS from the ground up

My favourite part of Alana’s story is how normal it is. She did not move into digital CS because it was trendy. She moved into it because she was tired of doing the same thing twenty times a week. Same onboarding call. Same emails. Same resources. Same questions.

And instead of accepting that repetition as “just how CS works,” she started building:

• A basic self service help center

• Weekly onboarding webinars instead of constant one to one calls

• Reusable email programs so she did not rewrite the same message every day

And here is the real takeaway.

Digital CS wasn’t even a recognised function back then. She simply followed the path that solved the pain. That path became her niche, and eventually led her to Atlassian and then Okta, where she now runs Automation and Scaled Insights.

If you have ever looked at your week and thought, there has to be a smarter way to do this, listen closely to what she built next.

What digital success looks like at Okta, and why it works

If you think digital CS is only for low ARR customers, this part will challenge you. At Okta, digital is not a segment; it is a layer across the entire customer base.

Here is how they structure it:

• Basic, everyone gets the foundational digital experience

  • Digital onboarding, in-app guidance, learning content, and a stripped-down Success Hub for clarity on what they bought and what they should do next.

• Silver, paid digital experience with personalised plans

  • They get a more interactive Success Hub, tailored videos, and a checklist driven by their selected business goals.

• Gold, CSM plus digital

  • They get everything above, plus a named CSM, plus digital tools that actually support the human experience, not replace it.

There is also a pooled CSM model that jumps in when signals show the customer is stuck. So support is both proactive and efficient.

Now let me explain the part that impressed me the most.

The Success Hub

Customers reported the same pain we all hear:

So the Success Hub gives them a single place that pulls together:

• Onboarding progress

• Adoption recommendations

• Renewal guidance

• Tailored content based on their actual usage

• A clear view of their SKUs, contacts, and entitlements

Then they layered in business goals.

When a customer selects a goal, the entire experience shifts.

• They get a personalised checklist tied directly to that goal

• Emails and in app journeys adapt to match that goal

• Their quarterly value snapshot reframes metrics around the outcomes they care about

And this next part is the best bit.

Admins get links into the product with guided steps.

Executives get industry benchmarks, risk insights, and outcome narratives.

Same customer. Different messages. Zero extra manual work.

That is how digital should work.

The tech and AI behind it, and what you can steal today

A lot of teams want a digital program like this, but do not have the infrastructure. The reality is, neither did Okta when they started. They did what most of us would do, they built version one in Salesforce Experience Cloud because that is where their help center lived.

It worked, but it was limited.

So they layered EverAfter on top to power the interactive components. Customers do not see two systems.

And of course, AI is starting to amplify everything.

One example she shared, which honestly blew me away.

They are using AI to create account research packs that combine:

• Usage data

• 10K filings and public company goals

• Industry trends and threats

• Identity maturity scores

• Competitive insights

Then it summarises the whole thing into a SWOT analysis and next step recommendations.

The lesson here, they did not start with a sophisticated AI powered engine. They started with the scrappy version. Then they layered. Then they iterated. Then they scaled.

That’s it for this week! You do not need Okta’s tooling to start.

You just need to stop treating your success plan like a deliverable and start treating it like a system.

When you are ready for the full breakdown of how Okta built theirs, listen to the full episode with Alana. I think it will spark a lot of ideas for your team:

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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