The Unfiltered Truth About Building a Customer Success Practice in SaaS
Two years ago, I dove headfirst into the adventure of building a Customer Success (CS) practice for an as-a-service business. Little did I know it would feel like juggling flaming swords—some of which were set ablaze by office politics. But hey, that’s part of the thrill, right? …Right?
Today, I’m peeling back the curtain on what really happens when you try to revolutionize your business and define one of the most misunderstood roles in SaaS—the Customer Success Manager (CSM). Spoiler alert: it’s rarely glamorous, frequently chaotic, and eerily similar to assembling IKEA furniture without the manual. But trust me, it gets good.
The Struggle is Real: Welcome to the As-a-Service Circus
First things first—switching from a perpetual licensing model to an as-a-service setup is not for the faint of heart. It’s like waking up one day thinking you’re flipping pancakes in your kitchen, only to realize you’re now running a Michelin-starred restaurant with a full dinner rush… every single day.
It’s not as simple as slapping together a new comp plan or hiring a Customer Success team and calling it a day. Nope. You’re rewiring the entire company mindset. And when I say mindset, I mean:
New personnel.
New processes.
And yes—sometimes breaking the news to Paul from Ops that his 'renewals are boring' attitude isn’t going to cut it anymore. Sorry, Paul.
The worst part? Most companies treat this transformation like that one extra LEGO piece left after assembling the Death Star. 'Oh, look… CS! Where do we put this?' Spoiler: it needs to be front and center. Otherwise, you’re building on a foundation of stress and unanswered Zendesk tickets.
CSMs vs. The World
Let’s talk about the role itself—Customer Success Managers. Or, as I like to call them, the Swiss Army knives of SaaS.
Hot take: choosing between technical CSMs and business-focused CSMs is the workplace equivalent of debating whether pineapple belongs on pizza. No matter what you pick, someone is going to be dramatically upset.
On one side, you’ve got tech whizzes who’ve spent years debugging code. Now you’re telling them, 'Hey, upsell and be extra charming while you do it!'—which, let’s be honest, is like asking a cat to bark. Then, you have the business-focused folks who can work a room like a pro but wouldn’t know an API from a KPI. No judgment!
And here’s the kicker—pre-sales engineers would actually make the best CSMs. They know the tech. They have that 'trusted advisor' swagger. So why isn’t this happening? One word: money. CSMs get paid less, there’s no clear career path, and many CS leaders are laser-focused on hiring from the post-sales talent pool instead of looking upstream. And that, my friends, is a major missed opportunity.
CSM Roles = Swiss Cheese
Unpopular opinion: The CSM role might just be the most undefined job in modern business.
Seriously, I’ve seen CSMs handling everything from tech support to sales enablement to post-purchase therapy sessions for cranky clients. Why? Because this role was born out of sheer panic—SaaS companies waking up one day and realizing, 'Oh no, churn exists!'
Cue the chaos. Half of the tasks in a CSM’s job description are hand-me-downs from Sales, Pre-Sales, and Post-Sales teams, leaving them as a catch-all department. It’s the corporate version of 'We forgot to label this, so let’s just stick it under CS and hope for the best!'
Post-Sale or Sales 2.0?
Okay, story time. I once heard someone ask, 'If CS is responsible for renewals and upsells, why don’t we just put them in the Sales department?' And to that, I say… good question.
Technically, CS is post-sale. But let’s not forget that these CSMs are also setting up the next sales opportunity. They’re the unsung heroes of the recurring revenue model. But lumping them under Sales? That’s like asking a vegan to run the BBQ pit—technically possible, but deeply questionable.
And why does this even matter? Because if CS is categorized as a 'post-sale' function, it becomes a cost center—just another line item in the budget. That means instead of tracking real business impact, we end up obsessing over utilization rates. And that, my friends, is how you take an invaluable team and reduce them to spreadsheet fodder.
The CSM Manifesto
After two years of battling the SaaS trenches, here’s my manifesto for building a modern CS practice:
The as-a-service shift is permanent. Stop treating retention like an afterthought. CS shouldn’t be a department—it should be baked into your company’s DNA.
Pay your CSMs what they’re worth. We talk about customer success like it’s the backbone of SaaS, yet we compensate them like they’re the appendix. Time to fix that.
Define the role—sooner rather than later. Decide upfront what you want your CSMs to do. No more 'we’ll figure it out as we go' energy.
And finally, if you treat CS like an afterthought, your customers will feel like one too. And they’ll take their money elsewhere. Don’t do that to Paul in Ops. He deserves better.
