Who Will Lead CS in 2031?
By Kristen Hayer
Hiring into customer success has stalled. Josh Crossman of Magnify told the Chief Customer Officer Summit in New York that openings were flat between 2023 and 2024, and that the roles cut in that period are not coming back. Which roles are going is clearest in an adjacent function. In late 2025, Marc Benioff said Salesforce had reduced its customer support organization from roughly nine thousand people to about five thousand, crediting Agentforce. Salesforce called this a rebalance rather than layoffs, and said it had stopped backfilling support engineer roles as case volume fell. Support is not customer success, though it has long fed into it, and the backfill language is what matters, because a role that is quietly never backfilled disappears as completely as one that is cut.
The same pattern is reaching entry-level customer success directly, because the work that filled a junior book of business is the work agents handle well. Almost everything written about this treats it as a story about capacity and cost. I want to ask a different question. If the junior book of business disappears, where does the person who runs your customer success organization in 2031 learn to do it?
I am not the first to raise this. The World Economic Forum, Training Journal, and Seramount have all published versions of the argument this year, converging on the point that entry-level roles were never only about output. What I have not seen is anyone working through what it means for customer success, where the apprenticeship had an unusually specific shape.
It is worth being precise about what that first book of business taught, because it was not what the job descriptions claimed. Nobody needed a year to learn the product, the health scoring methodology, or the QBR template, all of which can be taught in a week. What it taught was judgment, which comes from exposure that is hard to manufacture. Someone managing forty small accounts saw forty versions of the same situation in a year, and somewhere around the fifteenth they stopped consulting the playbook and started recognizing the shape of the thing. Most importantly, they learned to make a mistake that mattered, own it, and repair it, in an account small enough that the mistake ended no one's career.
My own version came from VerticalResponse, where I was the sales vice president when I inherited the support team, twenty-five reps handling every issue raised by the roughly fifty thousand customers active in a given month. That volume taught me that my instincts were not reliable at that scale, and that the only honest way to know what was happening was to measure it. Gut feel is a fine instrument for forty accounts and a useless one for fifty thousand, and I learned where that line sits by standing on both sides of it. Volume does not simply sharpen intuition, it calibrates it. I used that to turn our account managers into customer success managers, and later, at JazzHR, I inherited the support team and added the CSM function alongside it. Those years were not a stage on the way to leadership. They made the leadership work possible.
The consequence takes about five years to arrive, which is why almost nobody is planning for it. Senior CSMs came from junior CSMs, team leads from senior CSMs, and directors from team leads, and the gap between a first customer success job and a first leadership role has run five to seven years. Remove the bottom rung in 2026 and the shortage does not appear in 2027, while the mid-career population is still moving upward. It appears around 2031, and by then it cannot be fixed, because the people who would have filled those roles needed to start five years earlier.
Two objections deserve a hearing. The first is that you can hire senior people and let someone else develop them, which works until enough companies cut back on junior roles at once and the pool everyone draws from stops being replenished. The second, and stronger, is that AI makes junior people senior faster, since a new CSM with capable tools can produce work that once took years of experience. That is partly true, and what it misses is that output quality and accumulated judgment are different things. Juniors built judgment by struggling to produce the analysis, getting it wrong, and finding out why, and when the analysis arrives already correct, the output improves and the learning does not. I have spent a decade building customer success training, so I have every interest in claiming that training closes this gap, and it does not, because judgment comes from consequence.
That last point contains the solution. Volume used to generate developmental exposure by accident, and the answer is to design it deliberately instead. Give junior people the situations where the systems are weakest rather than the tidiest ones, because ambiguity, organizational change, conflict, and executive relationships are where machines stay weak and judgment is built. Use AI output as a teaching instrument rather than a delivery mechanism, asking a junior person to critique a generated analysis and defend the correction, because evaluating a recommendation builds judgment in a way that accepting one does not. And give real ownership with real consequence, because people need to own something they can lose.
If you lead a customer success organization, there are three decisions worth making before your next planning cycle.
Protect some junior headcount explicitly as a development line rather than a capacity line, because a role defended on capacity grounds loses that argument every time and one defended on succession grounds might not.
Write down what the first two years in your organization should teach, then audit whether the role still teaches it.
Ask whether the people two or three years in are accumulating judgment or output, because that cohort is the last one that entered under the old model.
A leadership pipeline is built five years before anyone notices it is missing, which is what makes this problem so easy to defer and so expensive to defer. Organizations treating junior roles purely as capacity to be automated are making a decision about 2031 right now, and most do not know it. The decision looks correct on every metric available this quarter, and will keep looking correct until the year it does not.
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Kristen Hayer - Kristen is the Founder & CEO of The Success League, a global, customer-focused consulting and training firm. Kristen’s background includes leading award-winning sales, marketing, and customer success teams in early and growth-stage tech companies. She is the host of several podcasts on CS and leadership, and has written over 100 articles on the field of customer success. The book she recently co-authored with 5 other CS thought leaders - The Customer Success Talent Playbook - recently hit #1 on Amazon in 5 categories. Kristen received her MBA from the University of Washington and splits her time between San Francisco and San Felipe, Mexico.