When Customer Success starts struggling, one of the first instincts is usually to look at the team. Do we need another CSM? Does someone need more training? Are people being proactive enough? Is Implementation moving quickly enough?
Sometimes, yes. But when the same problems keep showing up across multiple customers, I start looking at the system around the team.
I also think headcount decisions need to reflect the company’s stage, budget, actual customer load, and how much project management your CSMs are carrying. Account ratios matter, but “one CSM should manage X accounts” is rarely useful without context.
Ten highly complex enterprise accounts with multiple stakeholders, integrations, dependencies, and workstreams can create more work than 100 lower-touch customers.
Before opening another role, I want to understand whether the team truly lacks capacity, whether the account model makes sense, whether project management responsibilities are clear, and whether inefficient processes are creating unnecessary work.
Hiring ahead of what the business can realistically support can create a much bigger problem later, especially if that growth turns into layoffs six or twelve months down the road.
After more than a decade working across Customer Success, enterprise onboarding, implementation, experimentation, personalization, and AI, these are the first five places I look.
1. The handoff
A lot can go wrong before the post-sale team ever meets the customer.
What did Sales promise? What was scoped? What does the customer believe they bought? Who are the important stakeholders, and what internal politics are they bringing with them? What does success look like to them?
A weak handoff creates confusion immediately, and CS or Implementation usually spends the first few weeks trying to piece the story back together.
It also creates unnecessary project management. When scope, timelines, stakeholders, and expectations are unclear from the beginning, someone has to chase all of that down later. That “someone” is very often the CSM.
2. Ownership
Post-sale gets messy very quickly when ownership is vague.
Who owns the technical implementation, and each task within it? Who owns project management? Who handles product questions? Who is responsible for customer communication? Who makes the call when something gets escalated? Is there a reliable Product feedback loop for bugs and feature requests?
I’m also very careful about the phrase “the CSM owns the customer.” That can easily turn into the CSM owning every meeting, follow-up, timeline, dependency, internal chase-down, and escalation by default.
Someone absolutely needs to keep the work moving. That responsibility just needs to be intentional.
Customers do not care about your org chart. They care that someone knows what is happening, who owns the next step, and when it is getting done.
3. The definition of success
“Launch” is not a customer outcome.
Neither is completing training, finishing an integration, or checking every task off an onboarding plan.
I want to know what the customer needs to be able to do, what first value looks like, and how we will know they are making progress toward the reason they bought the product.
That definition also gives your project plan somewhere meaningful to go. Otherwise, you can have a beautifully managed implementation with every task completed on time and still end up with a customer who is not getting value.
The team needs that clarity before everyone gets buried in tasks.
4. The repeatable process
Great people can compensate for a messy process for a while. Eventually, things fall through the cracks, especially as the company starts to scale.
Kickoff agendas, handoff documentation, implementation plans, stakeholder maps, meeting cadences, status updates, escalation paths, risk tracking, decision logs, clear owners and due dates. The repeatable parts of the customer journey need some structure.
Project management is a big piece of this. Your team needs a consistent way to track what is happening, what is blocked, who owns what, and what needs a decision. Otherwise every customer becomes its own little operating system.
This also matters when you look at account ratios. If every CSM is manually rebuilding decks, chasing internal updates, creating custom onboarding plans, following up on overdue tasks, and tracking customer health in five different places, their book of business is going to feel much heavier than the raw account count suggests.
A good playbook gives people a foundation so they can spend more time applying judgment where it actually matters.
5. Customer health
I love a good Customer Satisfaction (CSAT) score, but I would never use it alone to tell me whether an account is healthy.
I want to understand the relationship, product usage and adoption, especially how those are measured, stakeholder engagement, business outcomes, and commercial health together.
A customer can love their CSM and still churn. I’ve seen that as recently as a month ago. They can use the product regularly and still question the ROI. You need enough context to see the full picture.
Good health data also helps you design a smarter coverage model. Some accounts need frequent strategic involvement. Others need more hands-on project management during onboarding and much less after launch. Some can thrive with a lighter-touch motion.
Treating every customer exactly the same can put unnecessary pressure on the team and make your staffing model much harder to understand.
The common thread
Healthy post-sale organizations have clear ownership, shared context, repeatable processes, strong project management, and a clear understanding of what value looks like for the customer.
When those pieces are missing, even excellent CSMs end up spending too much time chasing information, coordinating work, fixing avoidable problems, and manually holding the customer journey together.
That can make a team look understaffed when part of the capacity problem is operational.
So before adding headcount, I’d look at the system, the account ratios, customer complexity, project management load, the coverage model, the company’s stage, and what the budget can realistically sustain.
Sometimes another CSM absolutely is the answer. When it is, you want to know you’re hiring because the business genuinely needs the capacity, and that you’re bringing someone into an operation that can support them long-term.
Good people deserve that stability, too.
Want to build a stronger post-sale operation? Book a free consultation and let’s talk through what’s working, what’s getting in the way, and where there’s room to improve.
Christine Borkowski
Christine Borkowski is the founder of The SaaS Post-Sale Studio, a consulting practice helping Series A/B SaaS companies build post-sale systems that stick. She has 14+ years of experience in enterprise CS, onboarding, and implementation, with clients including Sony Pictures, Disney Cruise Line, Yum! Brands, and Activision Blizzard.