Red Flags Most CSMs Miss (Until They Get Laid Off)
Too many talented CSMs ruin their careers chasing startup dreams that turn into nightmares.
I’ve guided dozens of CS pros through transitions, and I’ve seen the same costly mistakes repeat. The allure of equity, rapid growth, and “building something from scratch” can blind you to critical red flags.
Here’s your practical playbook for making smart decisions about startup CS opportunities.
The Startup Reality Check
Early-stage startups (pre-Series A) are high-risk ventures.
They promise excitement and potential upside, but often lack the infrastructure to support proper customer success functions.
You'll likely become the "catch-all" for every customer-facing problem, working 80+ hour weeks while wearing multiple hats that have nothing to do with actual customer success.
Late-stage startups approaching IPO offer more stability but come with their own challenges.
If they have specialized teams for renewals, onboarding, and upsells, your role might be reduced to relationship management.
This makes you vulnerable during cost-cutting phases when companies start showing warning signs of imminent layoffs.
You didn’t build your career just to become the first name on a layoff list.
The Revenue Responsibility Test
The most critical question to ask during interviews: "What specific revenue activities will I own?"
If you're not directly responsible for renewals, expansions, or upsells, you become an easy target for layoffs.
Companies that view CS as a "retention mechanism" rather than a revenue driver will cut your role first when budgets tighten.
Why This Test Actually Works
A CS pro I worked with was considering two offers: a Series B company promising equity upside and a Series D company with lower equity but clear revenue ownership.
She used the revenue responsibility test and discovered the Series B role was purely relationship management with no expansion responsibility.
She chose the Series D company instead.
Six months later, the Series B company laid off their entire CS team during a funding crunch, while she hit 127% of her expansion targets and earned a $35k bonus!
Basic Red Flags That Scream "Run Away"
The "Opportunity to Build" Red Flag
When hiring managers say you'll have the "opportunity to build the CS organization," what they really mean is you'll do everything while they figure out their business model.
This sounds exciting but usually means unclear expectations, resource constraints, and burnout.
The Multi-Functional Role Trap
"Multi-functional" is startup code for "you'll own problems we haven't even discovered yet".
Being versatile is valuable. But beware of roles where responsibilities are completely undefined unless you have the founder/builder mindset.
The Series Stage Warning
Anything below Series D carries significant risk.
Even Series D companies face resource demands that can overwhelm CS teams. The earlier the stage, the higher the likelihood of sudden layoffs or pivots that eliminate your role entirely.
Key Questions to Ask
About the Product:
What's your current retention rate?
How do customers typically achieve success with your product?
About the Business:
How do you measure CS impact on revenue?
Who currently handles renewals and expansions?
For more comprehensive interview preparation, check out my customer success manager interview questions guide to make sure you're asking all the right questions.
These basics will help you avoid the worst startup traps, but there's so much more you need to know to make strategic career moves that actually advance your earning potential.
What you're missing without the complete framework:
A downloadable checklist you can use during every interview to spot red flags early
The exact questions that reveal if leadership understands CS value (hint: 90% of startups fail this test)
How to negotiate equity packages that could net you $200k+ at IPO
The insider strategy for making yourself layoff-proof even at risky startups
My step-by-step evaluation framework that's helped CS professionals land $100k+ roles
The conversation scripts that position you as a revenue driver from day one
The CS professionals who consistently land the highest-paying roles don't just avoid red flags.
They know how to identify and negotiate the opportunities that fast-track their careers, especially when transitioning to customer success from other fields.
🔐The Advanced Due Diligence Framework
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