October 1, 2026
Planning season has started.
Much of your 2027 is being decided over the next few weeks.
- Headcount.
- Tools.
- Priorities.
- Who gets the benefit of the doubt.
And much of it is being decided in rooms where Customer Success is represented by a slide, not a voice.
The question is not whether CS has a plan.
The question is whether anyone in that room can see what CS actually needs.
The Problem
Budgets may be loosening. Forrester’s 2027 planning research found that more than 80% of leaders expect their budgets to increase over the next 12 months, and 55% of CX leaders anticipate spending growth of 5% or more, up from 39% a year ago.
That sounds like good news.
It is only good news for the functions that can make a clear case.
The same research carries a warning: new investment does not pay off without the organizational readiness to use it.
Finance knows this. That is why planning conversations tend to reward clarity over effort.
So CS leaders walk into planning with what they have.
Activity volumes. Health scores. A list of initiatives.
A request for more headcount because the team is stretched.
And the request gets heard as a cost.
What Planning Rewards
Three kinds of information show up in a planning conversation:
What gets noted. Activity. QBRs delivered, tickets closed, accounts touched. Proof the team is busy.
What gets debated. Requests. More headcount, a new platform, a bigger program. Asks without a clear line to outcomes.
What gets funded. Clarity. Where the function creates value, where it is exposed, and what a specific investment would change. A picture leadership can act on.
Most CS plans are built in the first layer.
Budget decisions are made in the third.
The Shift
Less visible: Arrive with a request.
Visible: Arrive with a diagnosis.
There is a real difference between a CS leader who asks for resources and one who shows leadership what the organization needs, and why.
- One says “we need two more CSMs.” The other shows which segment is under-covered and what that gap is putting at risk at renewal.
- One presents last year’s activity. The other names the capability gaps that will limit next year’s results if nothing changes.
- One defends the team. The other gives the executive room a reason to invest in it.
The leaders who come out of planning season with what they need are rarely the ones with the longest deck.
They are the ones who did the honest assessment before anyone asked.
One Move This Week
Before your first planning conversation, write down three things on a single page:
- Where is my organization creating value that leadership may not see?
- Where are we exposed, in a capability, process, or coverage gap, that could show up in 2027 results?
- If I could fund only one change next year, what would it be, and what outcome would it move?
If you can’t fill that page with confidence, that tells you where to look first.
Not leading the team yet? Bring these three questions to your next 1:1 with your leader.
A Note from Bev
This is the work the Customer Success Leadership and Performance Diagnostic was built for. In two weeks, it gives CS leaders a clear, evidence-based picture of where their organization is strong, where it is exposed, and what to prioritize, in time to bring it into planning.
If that would be useful this season, start a conversation and we can talk it through.
Know a CS leader heading into planning? Share this with them.
Question for Reflection
If your CFO had to describe your CS organization in one sentence during planning, what would it be, and is it the sentence you want?
Until next time,
Beverly Hathorn, PMP, PHR
Customer Success Leadership Consultant
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