Should CS be involved in the sales process?
Yes, when the deal calls for it. If you sell to mid-market or enterprise companies, or your deal cycles run long, bringing CS into the right late-stage deals shortens the close and sets onboarding up to go well.
If you’re selling lots of smaller deals at scale, it will probably just slow you down. Either way, don’t roll it out as a rule. Pilot it first, and make sure your CSMs know how to show up before you put them in front of a prospect.
I learned this as a frontline CSM, and I kept making the case for it once I was leading CS.
What happens when CS stays out of the deal?
When I was a CSM, my sales team asked me so many questions about their deals that I finally said, “Why don’t you just bring me into the call?”
They said no. Very politely, but it was a no. Sales leadership was worried I’d overshare and say something that would derail the close. So I handed over the talking points they asked for and stayed off the call.
The deal closed, which was great for the rep. But then onboarding took forever. The customer had made a pile of assumptions because they didn’t know what questions to ask, and nobody answered the questions that never came up.
Guess what? Every one of those assumptions turned into extra work for my team after the close, and a slower road to value for the customer. That’s the part Sales never sees.
How do you get Sales to say yes?
I took that deal back to sales leadership. I didn’t ask them to make it a rule. I asked if we could test it on deals where the prospect needed post-sale context.
On the next one, the AE and I spent 15 minutes aligning before the call. Our average time to close was roughly 60 days, and that deal closed in about 45 to 50. The prospect got what they needed from the conversation and stopped entertaining calls with competitors. That enterprise customer then onboarded inside our 30 to 45 day target, when enterprise usually ran longer, and became one of our biggest advocates.
When I became a CS leader, I brought this into every conversation with a CRO or VP of Sales, along with what I’d seen work before and why I believed it could work there. Then I asked for a pilot, with two kinds of deals in it:
Deals with a verbal commit that were stalled in procurement, legal or security. Bringing CS in there adds real value to the deal, and it gives us a head start post-sale.
Competitive deals where we were stalling or the buyer was leaning toward another solution. In the post-sale organizations I designed, the experience we created was a real differentiator, so it belonged in the room.
The pilot also showed us which deals actually deserved this and who on the team should be doing it. Even at companies where it never became a full program, everyone adopted some version of it.
When should CS stay out of the sales process?
I always say it depends, because there are so many factors to consider.
If your deals are mostly below a certain value and you’re trying to scale, this probably isn’t your move. If the prospect’s questions are about pricing, contract terms or a quick feature check, that’s the AE’s conversation.
If you sell to mid-market or enterprise, your cycles are long, and the prospect is asking about implementation, resourcing or what working with you is actually like, bring CS in.
And it shouldn’t always be the CS leader on the call. Customers want to talk to the people they’ll actually be working with, which means you have to train your frontline CSMs to do this well.
How does CS on a sales call go wrong?
I’ve absolutely seen this go sideways, and it’s usually with the best intentions. CS knows where things stall out and what customers are going to ask, so a CSM who wants the customer set up for success takes the conversation more technical, and suddenly it sounds complicated.
At the end of the day, they’re buying software to simplify their lives. Nobody buys software hoping for a second job. When that fear becomes real, they start thinking, “Maybe now’s not a good time. Maybe I don’t have the capacity to take this on.”
Under no circumstances are we trying to hide anything or mislead a buyer. But sales is an emotional stage of the buyer’s journey as much as a financial one, and CS has to respect that.
What should CSMs say when a prospect asks how much work it is?
Answer with discovery questions. “What’s in front of you right now? What are your competing priorities? How much time are you spending doing it the way you do it today?”
Those questions help the prospect see that the burden of not doing this is bigger than the burden of getting it stood up. Then be honest that there’s real effort up front, and that it’s the investment that makes everything downstream easier. Don’t let a CSM blurt out “this takes six months” without the context of what that depends on.
And I’m really intentional about the language. We don’t say “easy,” because it may not be easy. We say our job is to make it as simple as possible.
Steal this: the 15-minute pre-close conversation
Run it with your AE before any late-stage call that needs CS:
Their org and team structure
Their pain points and how they’re resourced
The expertise they have in-house, and what they don’t
Who else they’re evaluating
What they need to hear from CS to feel prepared
What CS won’t get into on the call
That last one is how you earn Sales’ trust. Pricing goes straight back to the AE, and CS stays out of narrow use cases. If a prospect asks about a really specific feature, it might be a seed a competitor planted, so don’t water it.
Then open the call by scoping it out loud: “Our call today is to help you understand what it will be like to work with us, what it’s like to use the product, and the success we’ve had with customers who look like you.”
The question for your next pipeline review
Pull up your late-stage deals and ask your sales leader one thing: which of these prospects is asking questions someone in CS should be answering? Pick two or three, call it a pilot, and see what happens to the close.
I promise you, those 15 minutes cost a lot less than the cleanup after the close.
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