The Customer Success Playbook for Building the Relationship with the Decision-Maker

(Transcribed by TurboScribe. Go Unlimited to remove this message.) One of the most common problems I hear from customer success leaders when I talk to them about their teams is that their CSM is not connected with the decision-maker. They've built great relationships at the user level.

Some of them have champions at the operational level. But the person who actually signs the contract, the one who decides whether this stays in the budget next year, the one whose priorities determine whether this account expands returns, that person is a stranger. And the CSM figures out how much that matters exactly when they can't do anything about it. And the fix isn't what most people think.

It's not about sending more emails or being more persistent to get that connection. It's building the relationship on purpose from the start. Today, we're breaking down how customer success teams should be building the decision-maker relationship deliberately from the moment that the account lands through every quarter after that. Stick around because at the end, I'll share where the shift is hardest and where the right kind of support actually changes the trajectory.

Let's get into it. Welcome to the CSRepSpeak podcast. I'm Angeline Gavino. I spent 17 years leading customer success inside B2B SaaS, most recently as a VP of CS.

And today, I coach customer success leaders one -on-one on the exact challenges you're navigating right now. Everything I share in this podcast comes from time actually doing the work and time spent helping other leaders lead better. I talk about building credibility, turning customer success into a revenue engine, scaling your team, and navigating the leadership challenges nobody prepares you for. Let's dive into today's episode.

Let's start with defining what I mean by decision-maker here. I'm talking about the person who actually has budget authority over your product. That might be a department head, a VP, an executive sponsor, or the economic buyer who signed the original deal. In some accounts, it's a C-level executive.

In others, it's probably a director or a senior manager. It depends on the size of the deal and how the customer's org is structured. What matters is that it's definitely not the user. It's not the day-to-day champion, though sometimes the champion has influence over this person.

It's the one whose priorities determine whether this line item stays in the budget and grows or gets cut. Now, let's talk about why this relationship is so often missing. The user relationship and the decision-maker relationship are two completely different things, and most CSMs default to the one that's easier. The user relationship is comfortable.

The people using the product every day want to talk to your CSM. They have questions, they need help, they're grateful for the support. The conversations are natural, they just happen a lot, and the CSM gets constant positive feedback. Every hour they put into that relationship pays back in warmth and engagement.

Now, the decision-maker relationship is harder. The person doesn't need help using the product. They probably haven't logged in this quarter. Or more realistically, they never even need to use the product at all.

They're busy running a function, hitting a number, or navigating or a politics. They don't want another vendor check-in on their calendar. The conversation has to be earned, and the value has to be obvious. So, what do CSMs do?

They spend their time where they get the most immediate feedback. They go deeper with the users. They build stronger relationships with champions. And they tell themselves that the decision-maker will hear about the value through those relationships when it matters.

Except that's not how it works. When the renewal comes up, the decision-maker isn't thinking about how much the user loves the product. They're thinking about whether this budget line is worth what it costs. And if the first real conversation they've ever had with your CSM is happening 60 days before renewal, the CSM is trying to build trust and prove value at the same time in a compressed window under commercial pressure.

That's a hard place to negotiate from. And the reason it happens isn't because the CSM missed something. It's because the relationship was never built deliberately from the beginning. Here's another thing.

Most CSMs feel uncomfortable engaging at the executive level. They worry about not having enough to say. They worry about wasting a busy executive's time. They worry about coming across as junior or unprepared.

Or they've been taught that engaging with an executive requires matching them with another executive from your org. So they assume the customer's executive won't take them seriously without a title match. Let's put that aside for a second. Think about your own executives.

They're running departments. They're running the business. They have priorities that stretch across the whole org. Imagine if they had to join every customer call because the CSM felt they needed exec cover to have a real conversation.

That's not scalable, and frankly, it's not necessary. We need to move past that outdated notion. Your CSMs need to be empowered to engage at every level of the customer org, including the executive level. They're not too junior for that room.

If they're bringing business contacts, strategic perspective, and real value to the conversation, the executive doesn't care about title match. They care about whether the meeting is worth their time. Now, to be clear, there's absolutely a place for getting your own executives on a call with the customer's executives. Executive-sponsored programs, strategic account reviews, high-stakes escalations.

Those moments matter, and using your execs deliberately in those situations is a strong strategy. What we want to avoid is having a CSM lean on exec cover just because they don't feel qualified to be in the room. That's a very different reason to bring an exec in, and it holds your CSMs back. Building a decision-maker relationship is its own skill.

It's not just an extension of the user relationship, and it has to be built deliberately. Here's what most customer success leaders don't fully appreciate. The strongest first step to getting access to the decision-maker isn't something that the CSM does alone. It starts at the moment that sales closes the deal.

Think about it. What happens in a great sales cycle? The account executive builds a real relationship with the buyer. They understand what the decision-maker cares about, what they're trying to accomplish, how they measure success, who they answer to internally.

By the time the deal closes, the AE has weeks or months of context with that executive that took real work to build, and then the deal closes. In most orgs, what happens next is the AE hands the account over to a CSM that the executive has never met and then quietly steps out of the relationship. The executive goes back to their day job. The CSM gets an internal handoff document, maybe a call with sales, and starts fresh at the user level.

That transition is one of the most expensive things happening in your CS org right now. Because every ounce of executive relationship that AE built just evaporated, and your CSM is now expected to rebuild it from scratch with no history and no context. The fix is a real sales to CS handoff of the executive relationship, not just the operational context, the relationship itself. Here's what a great handoff looks like.

Before the deal closes, sales and CS should be aligned on how the executive is going to be transitioned, not after, before. The AE should be teaming up the introduction as part of how they position the post -sale experience to the buyer. So, something like, our CSM is going to be your partner in getting the value you signed it for, and I want to introduce you to your CSM personally in the first two weeks. Then, in the first two weeks of the account, there should be a warm introduction call, a dedicated call where the AE personally introduces the CSM to the decision maker, positions them as a strategic partner, and hands off the relationship in a way that the executive experiences as an upgrade, not a downgrade.

And I do believe that the AE should stay warm in the relationship for the first quarter, not to stay in the account, to signal continuity. Let's say a brief check-in from the AE at 90 days that reinforces the CSM's role. Small moves that tell the executive this is a coordinated team, not a bait and switch. The reason most CS orgs don't do this is because sales and CS haven't sat down together and designed the handoff.

Sales sees the deal as closed, CS sees the account as new, neither one owns their relationship transition, and the executive relationship falls in that gap. If you're a CS leader listening to this and thinking, we don't have anything like this today, that's actually the biggest lever that you have, building a real sales to CS handoff process and making sure that the executive relationship is part of what gets transitioned changes the trajectory of every account from day one. Now, let's be realistic.

Most CSMs are inheriting accounts today where the sales to CS handoff never happened, or if it did, the decision maker was never really engaged to begin with. So the question is, how does a CSM earn access to that decision maker on their own? This is where credibility matters more than persistence. The most common mistake is sending an email cold with no contacts and no value that says something like, I'd love to schedule some time to introduce myself and understand your priorities.

That kind of email gets ignored, and it should. There's nothing in it for the executive. It's asking for their time without offering anything in return. But a good outreach email can absolutely work if it's earned.

The difference is what comes before it. If the champion has been talking about you, if you've delivered something that the executive has already heard about, if the email leads with an insight or a specific reason that they should care, not with the requests for time, then the email isn't cold and it isn't generic. It's a natural next step in a relationship that's already been quietly building. The lesson isn't that you should never send an email.

It's that the email lands based on what you've built before. So how do you build that foundation? There are four specific ways, and I want to spend real time on the first one, because it's the most underused and the most powerful. So first, deliver real value to the champion.

I want to unpack what that actually means, because most CSMs think they're doing this and they're not. Your champion is the person who uses the product every day, or at least manages the people who uses the product every day, right? The one who advocates for it internally, the one who reports up to, or has real proximity to the decision maker. That relationship is one of the most valuable assets your CSM has, and most CSMs underinvest in it.

Here's why delivering real value to the champion matters so much. The champion is the fastest and warmest path to the decision maker. Executives may not go directly asking, is this vendor working? But they see how their team is using the product.

They notice which tools show up in reports. They notice when someone on their team says, we're crushing this initiative because of X. And they notice when a member of their team can point to a concrete wins and confidently explain how a vendor helped drive them. The kind of visibility only happens when your champion has real substance to share.

But that only happens if your champion actually has something to say. And they only have something to say if your CSM has genuinely helped them look good, achieve their goals, and get real outcomes. That means going beyond product support. It means understanding what your champion is being measured on, what they're trying to accomplish this quarter, what pressure they're under from their leadership, and then actively helping them navigate that.

Bring them insights. Bring them wins. Bring them stories they can tell upward. Make it easy for them to look competent and effective in front of their boss.

And when the timing is right, coach your CSM to ask the champion directly. Something like, I know your VP is focused on X this quarter. Would it be helpful if I put together a quick summary of how what we're doing supports that? Or I'd like to make sure your leadership team sees the impact your team has been driving was the best way to do that in your org.

That kind of conversation puts your CSM in a completely different position. They're not asking for access. They're offering the champion a way to advocate more effectively. And when your champion goes to the decision maker and says, you should meet with the CSM at this vendor.

They've been really valuable to us, and they have some things I think you'd want to hear. That requests Lance as a warm introduction, not a cold ask. Second, show up with business contacts, not product contacts. Every time the CSM talks to anyone in the account, they should be showing that they understand the business, not just the product.

What the company is trying to accomplish, what's happening in their industry, how the product connects to what the executive is measured on. Business contacts is what makes a CSM worse in executives' time. Product contacts is what makes a CSM look like a vendor. Third, bring insight to the account that the customer couldn't have come up with themselves.

This is the piece most CSMs under use. If a CSM can bring a benchmark, a pattern from similar customers, an observation about how the team's usage compares to what a great outcome looks like, that's not a meeting request. That's a reason to meet. Executives take meetings when the meeting itself will make them smarter.

So bring something to the table. Fourth, you want to share key milestones proactively. When your team hits a major milestone in the account, whether that's successful onboarding, a first value moment, an adoption threshold, or a strong QBR outcome, that's a natural, non-sales-to -reason to reach out. And it works even better when your champion is sharing those wins internally at the same time.

The executives start seeing evidence of progress from two directions, one from you and one from their own team. That's how credibility compounds without you ever having to ask for a meeting. The pattern across all of this is the same. The executive relationship isn't earned by trying harder to get the meeting.

It's earned by making the account and the champion so valuable to work with that the meeting becomes the natural next step. Coach your team to that mindset. It changes what every account looks like. Let's talk about what happens once you get in the room, because a lot of CSMs get access to the decision maker and then waste the meeting by treating it like a bigger version of a user check-in.

The decision maker doesn't want a product update. They don't want a walkthrough of adoption metrics. They don't want a status report on open initiatives. They already have a full plate of things demanding their attention.

And if the CSMs meeting sounds like every other vendor meeting they sit through, they won't take another one. What the decision maker actually wants from your CSM are three things. Number one, they want business to impact. They want to know if this investment is producing outcomes that matter to their business, not features used, not tickets closed.

Outcomes, revenue influence, efficiency gain, risk reduced, time saved. If your CSM can walk into that meeting and clearly connect the product to the executive's world in the executive's language, that's what earns the next meeting. Two, they want strategic perspective. Again, not a status update.

They want a point of view. So something like, based on where you are in your journey, here's what I'd recommend focusing on next quarter, and here's why. Executives are drowning in people who tell them what happened. They pay attention to people who tell them what to do next.

Third, they want a partner who makes them look good. This one gets overlooked, but it's real. Executives sit inside political environments. Their credibility depends on the decisions that they've championed working out.

If your CSM can help them build a story of why this investment was a smart one, if they can give them numbers, wins, and framing that they can bring to their own leadership team, the CSM becomes an ally to their internal positioning. That's a relationship an executive protects. If your CSMs are getting in front of executives and defaulting to operational updates, that's your quotient gap because it doesn't matter how much they've earned the meeting. Once they're in the room, they have to know how to run a strategic conversation, not a status one, and that's a distinct skill.

The last piece is the one most CSMs don't do at all. Once they've built the relationship, they don't keep it up. And by the time that they need it, it's gone cold. So the mistake looks like this.

CSM gets access to the executive, has a good meeting, feels great about the relationship, then quarters pass. The user work keeps happening, the champion is engaged, and nobody talks to the decision maker for six months. When renewal comes, the CSM reaches back out, and the executive barely remembers them. Again, to fix isn't more meetings.

Executives don't want more meetings. The fix is intentional, low friction touch points that keep the relationship warm without demanding time. That could be a quarterly written update sent directly to the executive. Three sentences long, telling them the one thing that matters most in the account this quarter, not a monthly report.

A brief, high signal note that positions the CSM as someone with a pulse on their business. It could be forwarding a relevant piece of content with a personal note, a specific article, benchmark, or insight. The CSM knows this executive would care about with the one line why it thought of you. It could also be a shared moment at an industry event, quick coffee, a brief introduction to appear, a small gesture that reinforces the relationship without needing a formal meeting.

The point isn't the tactic. The point is that the relationship stays in the executive's peripheral vision consistently so that when the moment matters, they know the CSM. They trust the CSM, and they take the meeting the CSM asks for. The most common pattern I see when CS leaders start focusing on this is that their teams overcorrect.

They start asking for more executive meetings than they need. They flood the decision maker with communications, and the executive backs away. Keeping an executive relationship warm is a light -touch discipline. It's not a volume game, so you want to coach your team to that.

Let me bring this together. First, the decision maker relationship is different from the user relationship. It requires different conversations, different value, and different positioning. Most CSMs default to the easier one, and their accounts pay for it later.

Second, the strongest first step to building this relationship is a real sales-to-CS handoff of the executive relationship. If your work doesn't have one today, building it is one of the highest leverage moves that you can make. Third, when a warm introduction never happened, credibility earns success. Credibility earns access.

Deliver real value to champions. Show up with business contacts. Bring insight the customer couldn't have come up with on their own, and share key milestones proactively. That's what makes an executive want to take that meeting.

Fourth, what the decision maker wants once you're in the room is business impact, strategic perspective, and a partner who makes them look good. Your CSMs have to be trained to run a strategic conversation, not an operational one in that meeting. And fifth, keeping the relationship warm is the piece most CSMs skip. Build a light-touch discipline of staying on the executive's radar between meetings so the relationship is real when the moment matters.

The gap most CS leaders sit with after listening to this is going to be the same one. Your team is talented. Their user relationships are strong, and they know intellectually that the decision maker relationship matters. But building that relationship deliberately, at scale, across every account, is generally hard.

It takes shifting how CSMs think about their work, redesigning how sales hand off accounts, and coaching a level of executive fluency that doesn't come naturally to most CS teams. If you want to build this capability directly with your team, that's something I can help with. I design structured enablement programs customized to your specific contacts, your product, your customers, your buying centers, your accounts, not generic trading. It's a real program, a customized program, built around the way that your team actually works.

By the end of a program like this, your CSMs know how to spot decision maker access gaps early, run executive conversations with confidence, translate the product into business language your executives actually care about, and sustain the relationship long past the initial meeting. And they'll leave with the specific talk tracks, milestone frameworks, and executive-facing narratives tailored to your product and your customers so they can apply the work the very next day. If that's what you're looking for, head over to csrevspeak.

com forward slash enablement to learn more and schedule a consultation call. We'll walk through where your team is, where the gaps are, and whether a structured enablement program is the right fit. Thanks for being here. I'll see you in the next one.