[Un]Churned · 3 Jun 2026 · From the week of 1 June
What Happens When CS Teams Cross the Commercial Line ft. Chael Banks (Okta)
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Chael Banks, Senior Vice President of Customer Success at Okta, an identity security company with around 20,000 customers, describes how his customer success organisation is structured and why it never does commercials. He covers the identity maturity model, how Okta is using AI to make people more effective rather than just efficient, the digital motion for the long tail of customers, how value realization hands off from sales, and a personal story about swimming in Lane 6 that shaped how he leads. The central argument is that customer success should carry the value narrative and act as trusted tour guides, because in identity security trust is everything and money as the motive damages it.
For founders
- Chael's team draws a hard line: customer success carries the value narrative and never sells, because he believes trust is tarnished once money becomes the motive.
- Chael describes AI tools Okta is building that would use product telemetry to show which capabilities a customer has fully or partially adopted, so that even junior staff can ground value conversations in data.
- Chael says Okta uses AI to remove low-value tasks so staff can have higher-level conversations, with the stated goal of effectiveness and not headcount reduction.
- Chael says the Okta team is building many overlapping AI tools and expects consolidation, with the challenge of scaling one consistent experience across all customers.
For revenue leaders
- Chael says Okta's account executives own the commercial conversation and customer success owns value realization after the first purchase, with the commercial line drawn after the sale.
- Chael says Okta avoids renewal procurement talks by running value conversations throughout the year, so the renewal is not a price negotiation three months out.
- Chael describes Okta's long-tail motion as using data signals on adoption to find stalled customers and deploying early-career staff to have those conversations.
- Chael says the content and tour guiding should be the same whether the person delivering it has been in the industry for 25 years or for four years.
What was said 22, most useful first
Okta's customer success team will never do commercials. Listen
Chael Banks says his customer success team at Okta does not sell, and that this is a rule he has set with the senior executive team. He argues that trust comes with thought leadership and a tour-guide role, and that it is tarnished if the motivation is money. The team instead drives value realization and gets to a point where it can flag a potential opportunity for the account executive or sales engineer.
“This team will never do commercials.”
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Okta's long-tail digital motion uses data signals to find customers who are not adopting. Listen
Chael says Lawrence, who runs the long-tail digital motion, looks at data signals in the install base by customer to find where they are not adopting, where they are adopted, and where they are stalled. Early-career staff are deployed to have conversations about why and how to help. Chael says this began a couple of years ago and that AI now helps these staff get smarter faster.
“look for data signals in that install base and by customer, where are they not adopting?”
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Lower-tier customers often receive little support from software vendors because churn is less painful there. Listen
Chael says reps at the lower end of the market may have hundreds or thousands of buyers in their territory and do not receive much support from software companies. He attributes this to churn at that level not being as painful for the company. He presents Okta's digital long-tail motion as a response to that gap.
“because the churn at that level isn't as painful for a company”
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The content and tour guiding for customers should not depend on the experience of the person delivering it. Listen
Chael says a 25-year-old early in their career must be able to drive the same discussion with a CISO who is personally liable as a senior person does. He says the content and tour guiding should be the same whether the company is a giant bank or a tiny regional lender, because the liability is the same. He says this is why his team needs to teach early-career people the content.
“the content and the tour guiding should be the same.”
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Chael draws the line between commercial and non-commercial conversations after the sale. Listen
Chael says the line between commercials and not commercials is drawn in post-sale conversations, which he describes as a different discussion. His team carries the value narrative, is prescriptive with industry benchmarks and next steps, and leaves product purchase conversations to others. He says that separating these roles keeps the purity of the trusted relationship.
“That's where I ultimately draw the line of commercials and not commercials because that's a different discussion.”
Listen to the episode Sales process & deals Link to this Report a problem
Okta's customer success organisation is split into technical account management and customer success. Listen
Chael says technical account management focuses on adoption and on winning technical buyers so they believe the value they are getting is worth the spend. The customer success side focuses on business buyers and drives the narrative that the customer has joined the Okta family and where they started. He describes the two together as the tour guides of the customer's identity security journey.
“One is a technical account management crew.”
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Okta's identity maturity model uses product telemetry to show customers their adoption status. Listen
Chael describes the identity maturity model as a progression that each stage of value builds toward, similar to how other vendors describe a path to a full customer view. He says product telemetry can show a new person which capabilities contribute to a compliance requirement and where they are fully or partially adopted. He says this lets junior staff have senior-level context in conversations with customers.
“You're fully adopted on these two. You're partially adopted here”
The goal of AI at Okta is to make people more effective, not just more efficient. Listen
Chael says Okta uses AI to remove low-value tasks so people can have higher-level conversations, and that the efficiency gains are in service of effectiveness. He says the time freed is meant to be used, not to reduce the number of people in the team. He adds that he does not expect the gain to come from cutting headcount.
“make people more effective, not just more efficient”
Okta is prototyping an AI tool that guides junior staff through senior-level customer conversations. Listen
Chael describes a real-time app he saw demoed that prompts a junior person on what to say and where to go in a conversation, with guardrails for complex, regulated topics. He says the intent is to let more junior people have senior discussions without the experience. He describes this as in prototype and in flight rather than fully deployed.
“a little thing in your ear telling you what to say, where to go, and what you're going to see.”
Running value conversations after the sale avoids a price-focused renewal conversation. Listen
Chael says that when value is tied to the customer and reinforced continuously by the technical account and customer success teams, there is no need to talk about procurement three months before renewal. He says a renewal conversation like that becomes a price negotiation, whereas Okta has support inside the customer that is not only contractual. He says the customer continues because the value is evident.
“what you're not doing is selling and then talking to them three months before renewal”
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Value realization at Okta is a relay that starts with account executives and continues with customer success. Listen
Chael describes value realization as a train where account executives are the engine, identifying value drivers in the sales cycle and framing value points with new customers. Customer success then hooks on and takes primary responsibility for value realization, with technical account managers validating the value the customer bought and driving adoption. He gives phishing resistance as one big value driver in identity.
“I look at it like sort of a train but those guys are the engine”
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Clarifying requirements early is much cheaper than fixing mismatched expectations at launch. Listen
Chael uses a consulting example in which a client says at the preview stage that the output is not what they meant. He says avoiding that early in the stage is infinitely cheaper and easier from an impact and money perspective. He says Okta hammers the values and the capabilities that support them, rather than the product, to avoid this.
“Avoiding that early in the stage is infinitely cheaper and easier”
Okta runs the same customer success motion at every segment, with more depth at the top. Listen
Chael says Okta does exactly the same thing from the top of the market to the smallest customers, covering value validation, adoption and telling customers how to be better. Higher-value customers simply receive more depth, because the rewards are high enough to justify heavier coverage. He gives the example of a customer with 17 business divisions and around 30 technical buyers.
“You do exactly the same thing from top to bottom.”
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With 20,000 customers, Okta can define benchmarks from patterns across its base. Listen
Chael says that with more than 20,000 customers, Okta can recognise patterns and define benchmarks in a very different way at its scale. He says this supports prescriptive guidance about what good looks like for a customer's industry, such as highly regulated finance or healthcare. He says the best practices change quickly as AI accelerates the market.
“you can recognize patterns and define benchmarks in a very, very different way at our stage.”
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Okta's big rock is to make the value conversation consistent across all segments through technology. Listen
Chael says Okta's main focus is putting tools in place to make the value conversation consistent and scalable across all segments of the business. He says the company is about 30% of the way to having that process instantiated in technology. He says the goal is for a consistent conversation whether the customer is large or small.
“I want to make it very painfully obvious that our job is value realization.”
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Customers want to buy from tour guides, not taxi drivers. Listen
Chael uses the tour guide analogy to describe how his team should guide customers through their identity security journey. He says customers are scared right now and want people to lead them through and tell them what is right. He contrasts this with a taxi driver who lets customers tell them what to do.
“Customers want to buy from tour guides and not taxi drivers.”
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In Okta's business, trust is the foundation of the customer relationship. Listen
Chael says that in identity security, trust is everything and that the customer must believe the vendor cares about their problems as much as they do. He says that if the vendor cannot protect the customer, the customer has no reason to keep talking to it. He frames this as the reason his team is separated from commercial selling.
“If you can't protect, why would I talk to you?”
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There are too many overlapping AI builds in his organisation and expects consolidation. Listen
Chael says there is a supernova of AI building across the world and that his team has many ways to solve the same problem. He says he is comfortable with that level of innovation because the best approaches will surface and can then be brought together. He says the broader challenge is that everybody has the power to build and the responsibility has not yet been worked out.
“we have nine ways to solve the same problem.”
Scaling AI tools requires one consistent experience and embedded best practice. Listen
Chael says the problem with building too many tools is that the result has to be scaled consistently so the experience is the same across all customers. He says that scaling in this way lets the company keep best practices embedded in the process. He describes this as the reason Okta is consolidating its many prototypes.
“The problem with building too much is you have to scale that through in a consistent way.”
His organisation of 400 to 500 people is too early in AI adoption for established best practice. Listen
Chael says his organisation is around 400 to 500 people and that they are very early in AI adoption. He says people are learning lessons by making mistakes, which is happening quickly and feels somewhat chaotic. He says he has been supportive and prescriptive in the areas that have worked.
“There's not a lot of best practice. People are learning lessons by making mistakes”
Grit and persistence drove his career, and that the Lane 6 story shaped his leadership. Listen
Chael says Lane 6 was an opt-in swim lane where every swimmer he knew of got at least one college scholarship offer, but swimmers who missed the intervals were removed and could never come back. He says he is not a talented person but has grit, and that work eventually wins. He says this shapes how he leads with a strategy and a focus on not being deterred.
“work eventually wins. You may make a thousand mistakes, but if you keep chipping away”
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A team can work hard without being sweaty and stressed. Listen
Chael says he believes people can work very hard and still do well without being sweaty and stressed. He says people do not perform optimally in a stressed state. He ties this to his leadership style of getting people bought into a strategy and having fun while they work hard.
“But you don't have to be sweaty and stressed. People don't perform optimally in that state.”
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