What happens when customers ask for something your organizational structure doesn’t support?

I need to write this down while it’s fresh, because I’m still processing what just happened.

Last week, I got asked a simple question at Google Cloud: Would I be interested in joining a discovery call with a potential customer?

My answer was immediate: Sure, why not?

I didn’t think much of it. I love talking to customers. I had time on my calendar. Seemed straightforward.

The call itself was fine. An interesting use case, strategic conversation, the kind of thing I genuinely enjoy. But it was the call afterwards with my manager that caught me off guard.

“Why did you join that call?” he asked.

I didn’t understand the question at first. “I was asked to join. I had availability. Thought it would be valuable to understand the customer.”

“But is that your job?” he pressed. “We don’t make purchasing recommendations. Customer Success operates post-sales. There are plenty of other types of calls you should be having.”

And look, he’s not wrong. At least not according to how we’re structured. CSMs live in the post-sales world. Sales own discovery calls. We have swim lanes. Clear responsibilities. Defined metrics.

I tried to explain that it was just one call, that I was being helpful, that it didn’t impact my other work. But his concern wasn’t really about this specific call. It was about what happens when boundaries start to blur about precedent.

I respect that. He’s managing a team within a framework that makes sense for most CS organizations. And honestly, I didn’t push back hard. It was one call.

Except it became a bigger deal.

When the Customer Asks

A few days ago, the customer reached out again. They wanted a follow-up call to dive deeper into their strategic planning.

But here’s where it gets interesting: they didn’t just ask for a follow-up call. They specifically requested that I be on it.

The request didn’t come through our internal channels. It came directly from the customer.

And it went everywhere. To the AE. To his manager. To his senior manager. Over to my senior manager. Down to my manager. Like a game of telephone across organizational hierarchies.

Then I got the call from my manager.

“Did you go around me on this?” There was definitely tension in his voice.

“I have absolutely no idea what you’re talking about,” I said, genuinely confused.

That’s when he forwarded me the email, the customer’s request, now copied across what felt like half of our leadership, explicitly asking for me to be part of their strategic planning conversation.

My manager wasn’t happy about the approach. He felt this was circumventing the structure he was trying to maintain, blurring lines that should stay clear.

But he also recognized that we didn’t really have a choice.

The customer was asking. And when customers make reasonable requests, you generally say yes.

What I’m Noticing

I’ve been on three calls with this customer now. Working alongside the AE and SE, helping them think through their cloud strategy, their business outcomes, and their implementation approach.

And here’s what’s becoming clear to me: I’m not doing sales. I’m not doing SE work. I’m doing something different.

I’m helping them see what’s possible. I’m connecting their business challenges to our platform capabilities in ways that go beyond features and functions. I’m thinking with them about their adoption journey before they’ve even signed a contract.

The AE is handling the business mechanics, including pricing, contracts, and legal matters. The SE is architecting the technical solution. And I’m… orchestrating the strategic narrative? Helping them envision their future state?

I don’t even know what to call it yet.

But the customer keeps asking for it.

The $300K Question

Two days ago, the deal closed.

$300,000 annual contract.

And suddenly, the conversation changed.

My senior manager reached out yesterday, asking me to put together a proposal for “trying this on a wider basis.” A team structure that would include CSMs in the value-building process from the beginning, not just post-sale.

I said yes, but I’m not sure what I’m proposing yet.

What I do know is this: something happened in those conversations that doesn’t happen when CS only enters after the deal closes.

Continuity. By the time they signed, I already understood their business. They didn’t have to explain everything again to a new person. There was no handoff. No information lost in translation.

Trust. They made their buying decision with someone who would actually be part of their implementation journey. I wasn’t a stranger introduced after the fact.

Strategic alignment. We weren’t just selling them a product. We were co-creating their roadmap before they even became a customer.

The Tension I’m Sitting With

Here’s what I’m struggling with: Is this scalable? Or was this just a one-off situation that worked because of specific circumstances?

My manager’s concerns are legitimate:

• If CSMs are in discovery calls, what happens to their capacity for existing customers?
• How do we measure success across traditional stage boundaries?
• Does this change how we think about quotas and compensation?
• Where do responsibilities actually begin and end?

These aren’t trivial questions. They’re the kind of operational complexity that makes organizations default to clean swim lanes and clear handoffs.

But there’s another question I can’t shake: What if the way we’ve structured customer-facing teams serves our organizational convenience more than our customers’ actual needs?

What the Customer Showed Me

The most revealing moment wasn’t when I was invited to the first call. It was when the customer specifically asked for me on the follow-up.

They were telling us something: This is valuable to us. This perspective helps us make better decisions.

Organizations can either listen to those signals or ignore them.

I’m figuring out, actually, what it means to listen.

Where I’m Headed

I have a proposal to write. I don’t have all the answers yet, but I have some hypotheses:

Hypothesis 1: The artificial boundary between “sales” and “success” creates friction that customers shouldn’t have to navigate.

Hypothesis 2: Strategic customer advocacy is valuable at every stage, not just post-sale.

Hypothesis 3: When we give customers continuity across their journey, we accelerate everything that follows.

Hypothesis 4: The cleanness of our org chart matters less than the coherence of the customer experience.

I might be wrong about all of this. This could be a unique situation that won’t translate. The operational complexity may outweigh the benefit.

But I can’t ignore what just happened either: a customer asked for a strategic partnership from the beginning. We provided it. They closed a significant deal. And now leadership wants to know if we can do it again.

The Uncomfortable Part

Here’s what makes this complicated: I genuinely respect my manager’s initial concern. He wasn’t being obstructionist. He was protecting team capacity and role clarity.

The challenge is that customers don’t care about our internal structure. They experience us as one company. And when they find someone who adds strategic value to their decision-making process, they want that person involved, regardless of what stage we think they “should” enter.

So the question becomes: Do we design our processes around our organizational preferences, or around how customers actually want to engage with us?

What I’m Thinking About

As I start drafting this proposal, a few ideas keep surfacing:

What if CSMs weren’t just post-sales resources? What if they were part of cross-functional teams that maintain continuity across the customer lifecycle?

What if we stopped thinking of the customer journey as a handoff and instead saw it as a continuous partnership?

What if the role of Customer Success isn’t to manage post-sale customers, but to be strategic partners who help customers unlock value from the first conversation through long-term growth?

I don’t know if this will work. I don’t know if leadership will actually want to experiment with restructuring customer-facing teams. I don’t even know exactly what I’m proposing yet.

But I know this: That discovery call showed me something that our current structure doesn’t accommodate.

And if one customer benefited from it, there are probably others who would too.

An Invitation

I’d like to know if others in the CS community have experienced something similar. Have you been pulled into pre-sales conversations?

Have customers specifically requested your involvement before they were officially “your” customer?

What did you learn from it?

I’m figuring out whether this is an anomaly or a signal: a one-time success or a blueprint for something bigger.

I’ll share more as I develop this proposal. For now, I’m sitting with the question: What happens when we let customers pull us where they actually need us, instead of limiting ourselves to where our org chart says we should be?