Here's something nobody tells you before you step into a founding CS role: you think that you're ready because you have years of experience, you've managed customers, built relationships, and fixed broken processes. You were chosen for this role precisely because of that track record. So you walk in feeling confident.
And then, the reality hits.
Usually, if your previous roles, there’s something already pre-built. Processes existed that sometimes needed a fix, playbooks that needed updating, and a team that needed direction. Even when things were broken, you had something to work with, and you didn't have to build from scratch.
Founding CS is different because there is no playbook, most of the time, no one to ask, and there is no structure to inherit. There is just you, a list of customers, a product that is new to you, and a blank page. It's exciting and terrifying in equal measure.
I've been there. And I made most of the mistakes on this list before I figured out what actually works. Everything here comes from that experience: decisions, consequences, lessons. If you're stepping into a founding CS role, or you're already in one and something feels off, I hope this saves you some of the time it cost me.
Mistake #1: Building the CS function before you understand what you're building it for
This is really three mistakes that feel like one: building too fast, building before you know the product, and copy-pasting frameworks from companies nothing like yours. They all come from the same root, the urge to show up and deliver before you've done the work of understanding.
When you join as a founding CS hire, you want to prove your value immediately, so you start building everything: onboarding flows, welcome email automations, renewal playbooks, health score models, customer journey maps, all at once. You download frameworks from Gainsight, Zendesk, and ChurnZero because they look comprehensive and professional. And you start implementing them before you fully understand what your product does, what your customers need, or whether any of this applies to your situation at all.
I did all of this, I even know exactly how many times I used the playbooks I built in my first month – zero.
The health score story is the one I tell most often. In every company I'd worked at before, health scores existed. I knew how to build them: collect metrics, weight them, set thresholds, and build playbooks for each tier. I'd even led the implementation of a health score at a previous company. So when I joined as the founding CS hire, I didn't ask whether a health score made sense yet. I just assumed it did, because it always had before.
I spent about two weeks on it, chatting with ChatGPT, downloading templates, and figuring out how HubSpot's health score feature worked by speaking with their CSM. Eventually, I designed a formula with around ten metrics. Then I went to pull the data and realized I didn't have a single one of them. Back then, we didn’t have any data points connected, no NPS cadence running, our ticketing system wasn’t connected to the. I had built a perfect framework for a company that didn't exist yet.
The frameworks from large CS platforms have the same problem. They're built for teams managing hundreds of accounts, with dedicated ops support, mature tooling, and headcount you don't have. As a founding CS hire, you might have three to ten customers and no one to delegate to. Applying an enterprise playbook to that reality doesn't just fail: it actively misleads you, because it makes you feel like you're doing CS when you're really just performing a scaled-down version of what someone else built for a completely different context.
What to do instead: Before you build anything, give yourself permission to just learn. Spend the first two to three weeks understanding the product as a customer would. Go through onboarding yourself, step by step. Write down every point of confusion. Then sit with your Product team, your Sales team, and your engineers. You will learn more from those conversations than from any template. Ask: What does a successful customer actually look like at this stage, with this product, for this company? Only once you can answer that does it make sense to start building. And when you do, start with one thing. The most urgent thing. Get that right before you move to the next.
Use published frameworks as inspiration, not instruction. Read them to understand the thinking behind the approach. Then rebuild from scratch for your actual context. The answer will look nothing like a Gainsight template, and that's exactly right.
Mistake #2: Blurring the line between CS and Support
In the very early days of a startup, it often makes sense for one person to handle everything: CS, support tickets, renewals, and even sales. Because there's no one else, and the customer can't wait. So you wear multiple hats, and usually it’s fine, and you’re ready for it.
The mistake is letting that blur become permanent. When a dedicated support function eventually arrives, many first CS hires keep handling tickets out of habit, familiarity, or a genuine desire to help. The result is a CS function that has quietly become a reactive support function, and a CS manager who is too busy firefighting to do the proactive work that actually drives retention and growth.
CS and Support by default serve different purposes - support resolves problems, CS prevents them, drives adoption, and builds long-term value (this article is not about it). Of course, both matter, but there should be a separation between them.
What to do instead: The moment a support function exists, even one person, establish clear ownership:
- Agree on what goes to support and what stays with CS.
- Sync weekly to stay aware of ticket trends, recurring bugs, and common questions, because that context is invaluable on customer calls.
- Let support own the execution, join technical meetings - your job is to be proactive, not to be a second support queue.
- Help each other and not step on each other’s toes.
Mistake #3: Operating in silos with Sales
CS and Sales often develop into separate worlds, especially in startups where the teams are small, remote, or in different time zones. The typical dynamic looks like this: Sales closes the deal, hands it over, and CS takes it from there.
And it’s completely wrong (even if we are not talking about startups). When CS and Sales operate independently, customers feel it because they repeat themselves to multiple people. The messaging they receive is inconsistent; they arrive at onboarding with expectations no one in CS knew had been set. And believe me, you will feel awkward during such a call. The relationship that Sales worked hard to build starts to fall before CS has even had a proper introduction.
The gap is especially pronounced when your Sales team is in a different country or time zone. Without deliberate effort, the distance turns into silence, and silence turns into misalignment.
What to do instead: Build a real handover process with Sales from the start. Before doing it, you should make sure you understand what’s important for you to know. At minimum, CS should know what's in the pipeline before deals close, understand what was promised during the sales cycle, and have a structured conversation with the sales rep after every new customer signs. Ideally, CS gets involved even earlier, during the evaluation or POV stage, so the relationship begins before the contract is signed. Share customer feedback back to Sales regularly, too. The voice of your existing customers is some of the most valuable input they can receive, and it builds the mutual trust that makes collaboration work.
I prefer having a meeting cadence with a sales rep and follow-up on the upcoming deals, upsell opportunities (if they’re part of it), and other priorities. Believe me, building relationships with the sales team is as important as building relationships with any other department.
Mistake #4: Going without a senior executive when you're stuck
In most early-stage startups, there is no CS leader above you. There may be a VP of Sales, but their focus is on new logos. There is no senior CSM to shadow, no internal benchmark for whether what you're building is working. Many first CS hires respond to this by putting their head down and figuring it out in isolation, which leads to slower progress, more repeated mistakes, and a lot of unnecessary stress.
The CS community exists precisely for this situation. There are thousands of practitioners who have built CS functions at companies just like yours: same size, same challenges, same constraints. Many of them are genuinely happy to share what they learned.
What to do instead: From your first week, find two or three CS communities where real practitioners share real experiences, not just thought leadership content, but actual conversations about challenges and how people solved them. Show up regularly. Ask specific questions. Share your own challenges honestly. The guidance you will get on frameworks, tools, metrics, and stakeholder management will be more practical and more relevant than almost anything you can find by Googling. Don't wait until you're stuck to reach out. Make community part of how you work.
Mistake #5: Reaching for CS tools before you have the data to use them
There's a category of mistakes that costs you time without feeling like a mistake at all: onboarding CS tools too early and thinking it will make your life easier. You're evaluating platforms, setting up dashboards, and building reports. But if you don't yet have clear metrics, defined milestones, and a solid understanding of what you're tracking and why, the tools just give you a more organized view of your confusion.
Tools amplify clarity; they don't create it. If the foundation isn't there, no platform will build it for you.
Again, when I started, I thought that I knew so many great tools I’ve used before, and I will be able to improve the current situation tremendously by bringing them on board. In reality, if you don’t have enough data, baseline metrics, and a source of truth, no tool will help you.
What to do instead: Before evaluating any CS tooling, sit down with your Product team and align on what data you actually have access to: usage metrics, feature adoption, login frequency, whatever your product surfaces. Then define what milestones a customer should hit, and by when? What signals suggest a customer is at risk? Only once you can answer those questions does tooling become useful.
And sometimes you will realize that you don’t need anything extra, and you will be fine with what you have. Speak with people and check what they’re using on a day-to-day. I came to the realization that the existing setup with Hubspot + Gong will be good enough for our client base. Then eventually I brought some missing tools that can help me to scale and automate processes, like n8n for creating automations and workflows and Storylane for imporving our technical documentation and demos.
For example, if you have fewer than 20 customers, you almost certainly don't need a dedicated CS platform. A well-configured CRM is enough to start, and more than enough to prove out your processes before you invest in something more complex. Get your data right first. The tools can wait.
Mistake #6: Taking on commercial conversations without a commercial framework
At some point, your leadership will want to see upsells and expansions, which will probably be part of your KPI/bonus as well. That's reasonable: CS should contribute to revenue growth. The problem is that in an early-stage startup, the commercial infrastructure often doesn't exist yet. There are no clear pricing packages, no defined upgrade path, and no agreed-upon criteria for what triggers an expansion conversation. Sometimes there aren't even features to upsell to.
So you end up in calls with customers, expected to drive expansion, with no playbook for what that actually means at your company. Then you start to improvise and make it up as you go. It can put you in a very uncomfortable situation where you can be sure if and when you can get extra dollars, which leads to being inconsistent with your customers.
What to do instead: Before you take on any commercial responsibility, get aligned with leadership on the basics. What are you actually selling? At what price? What triggers an upsell conversation, and who owns it: CS or Sales? What does a successful expansion look like at this stage? If those answers don't exist yet, your first job is to help create them, not to go into customer calls without them. Push for clarity internally before you commit to outcomes externally.
I recommend creating a simple Google shared file with all possible features, their usage, and price per feature. Your executive team must approve it, and only then you can start speaking pricing with the customers. It will make your conversations with them sharper, and it will protect you from being held to metrics you were never set up to hit.
A final note
Building CS from scratch doesn't have a finish line. There are always open challenges: better segmentation as you grow, tighter feedback loops with Product, and finding the right balance between high-touch engagement and scale.
But if there's one thing I'd want every first CS hire to take from this: stop trying to build the CS function of the company you wish you were. Build the one your current company actually needs. It will look less polished than the playbooks suggest. It will be more manual than you'd like. And it will work far better than anything you could have copied and pasted from someone else.
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