Customer Success Has a Middle Management Problem

By Allison Tiscornia

It is 4:37 p.m. on a Thursday.

A Customer Success Director has three Slack threads open. One is an enterprise escalation that just went red. One is a Sales rep asking whether an expansion will close this quarter. One is a CSM asking for help preparing for a renewal call in the morning.

Her calendar for the week was supposed to include time for capacity planning. She intended to revisit the segmentation model. She even blocked two hours to review cost-to-serve by ARR band.

Those two hours disappeared by Tuesday. By 5:15 p.m., she will have resolved the escalation, reassured Sales, and improved the renewal deck. She will feel productive. She will not have moved the business forward. Worse yet, she will repeat the cycle next week.

This is not a performance issue. It is a structural one.

Customer Success Has a Middle Management Problem

For the past five years, Customer Success has been in a state of reinvention.

We layered in digital programs.

We added AI copilots.

We built segmentation models.

We gave CSMs expansion targets.

We told the board we now “own revenue.”

On paper, it looks like progress. But beneath all of that evolution, one layer has remained mostly untouched. The managers. Not the CSMs. Not the tooling. Not the dashboards. The layer in the middle.

And that layer is quietly becoming the bottleneck.

Most CS Managers Were Once Excellent CSMs

They were the ones you trusted with your largest accounts. They handled escalations calmly. They could rescue a renewal at 4:45 p.m. on the last day of the quarter. They built relationships that felt unshakeable.

So we promoted them.

It made sense. Who better to lead Customer Success than someone who had mastered it? But saving accounts and designing a portfolio are not the same skill. The job changes when you move from “my customers” to “the system that governs all customers.”

A CSM operates inside the portfolio. A manager is supposed to operate the portfolio. Too often, we never made that distinction explicit.

So managers stay close to what they know. They review QBR decks. They join escalations. They answer Slack messages. They double-check forecasts. They translate tension between Sales and Product.

They are busy. They are valuable. They are exhausted. But they are not running an economic engine.

And that gap is starting to show.

Tactics vs Strategy

When the manager layer operates tactically instead of strategically, the consequences compound quietly. Capacity planning becomes reactive. We add headcount when burnout becomes visible. We increase touch when customers complain. We rarely step back and ask whether our coverage model makes financial sense.

Segmentation drifts. Enterprise accounts get attention because they are loud. Growth accounts get attention because they are exciting. Smaller accounts get attention because someone feels bad ignoring them.

High touch becomes a personality trait, not a strategy.

Meanwhile, cost-to-serve creeps upward. Human time is our most expensive asset in Customer Success, yet it is often allocated emotionally rather than economically.

We tell ourselves that service is our differentiator.

But without margin clarity by segment, we are not differentiating. We are subsidizing.

Forecasts soften. Expansion projections lean heavily on optimism and relationship strength. Executives begin to sense that something feels less than rigorous. They may not know why. But they feel it.

And teams burn out.

Every customer feels urgent. Every renewal feels existential. Every request becomes a fire drill.

That is not a system. That is adrenaline disguised as dedication.

Now what?

If Customer Success truly intends to be treated like a revenue function, then its managers must operate like revenue leaders. That shift requires more than new dashboards. It requires redefining the job and training leaders to think and act strategically.

A modern CS leader is not just a team coach. They are a portfolio economist. They understand where margin is created and where it is quietly eroded. They know which segments justify high touch and which require a scaled model, not because of preference, but because of math.

They are capacity architects. They treat human attention as finite capital. They design coverage models intentionally. They understand how to say no to requests that do not align with strategy and are actually comfortable doing it!

They coach commercially. Not just on empathy or storytelling, but on economic positioning. On how to anchor value to budget owners. On how to frame expansion as a financial decision, not a relational favor.

And they interpret signals. Usage data, support volume, product engagement, budget cycles. They connect those signals to revenue risk and expansion probability. They move beyond dashboards into judgment.

That is a very different role from escalation manager.

And yet, in many organizations, we are still measuring managers primarily on renewal rates and team morale.

We say we want commercial rigor. But we manage for activity.

We say we want expansion ownership. But we coach for relationships.

Culture does not shift because of a strategy deck.

It shifts because the people in the middle operate differently.

Our Middle Managers Need Help

The uncomfortable truth is this:

We keep asking CSMs to think like revenue leaders. But if their managers are not managing like revenue leaders, the system will always pull them back toward reactivity. Customer Success will not become a durable revenue engine because we rebrand it as one. It will become one when the management layer matures into operational leadership.

That is the next evolution.

Not another dashboard.

Not another playbook.

Not another AI announcement.

A different standard for the people running the portfolio.

And that work starts in the middle.

The Success League is a customer success training and consulting firm. If you need help building your CS team, or learning how to manage effectively, we can help! Visit TheSuccessLeague.io to see our full suite of offerings.

Allison Tiscornia - Allison is a seasoned Silicon Valley executive with over 20 years of experience leading customer-facing teams. As Chief Customer Officer at ChurnZero, she scaled the customer experience organization and formalized implementation methodologies. At Sendoso, she built the customer experience function before transitioning to Chief Sending Operations Officer, aligning logistics with product and customer workflows. Previously, as VP of Customer Services at Zenefits, she led professional services and support for the platform. Passionate about scaling teams and driving customer success, Alli has held leadership roles at Medallia, Visa, Endeca (acquired by Oracle), and CA Technologies. She holds a B.A. in sociology and public policy from the University of Arizona, with certifications in scrum management, project management, and IT infrastructure. As a visiting lecturer at Pavillion’s CCO School, Alli specializes in customer onboarding. She resides in Scottsdale, Arizona, with her family and a lively Goldendoodle.