Yesterday I went live to break down the State of the Customer Success Job Market based on data from the last two years of Job Drops.
How would I rate the market right now?
I opened with a gut check: How would you rate the market right now, 1 to 10, where 1 is "Cutomer Success is cooked" and 10 is "you could get hired off the street."
My rating was a 6. It's not easy out there, but there's more good than bad. Let’s break it down:
The market is growing
Compared to 2025, every single month in 2026 has been bigger than the year before. March, April, and May ran roughly double.
I say quality roles because all Job Drops are curated to meet my criteria: remote, salaried, primarily US. There are more of them in 2026, not fewer.
Salaries are steady
Unlike volume, salaries are not increasing at any meaningful rate. But they also aren’t decreasing.
If it were up to me, I’d like to see a bit higher salaries in 2026, but there was one thing I was worried about going into this year that I’m not seeing: companies pulling roles and relisting them at lower numbers to take advantage of desperation. If that were happening at scale, I’d be able to spot it. And it’s not.
A note on inflation
Inflation was 4.2% from 2025 to 2026, and only senior CSM and break-into-CS roles beat that, while everything else came in under. So while salaries are steady in number, our buying power is going down.
See the Customer Success Salaries report for a breakdown by category and experience level.
Hiring feels confusing right now
We can probably all agree on this one.
Three things are driving it:
Templated job descriptions. Every JD sounds the same now. Someone generated one with ChatGPT, someone else copied it, and the same generic language is everywhere. Nobody's saying what they actually want.
Hidden requirements. Because the JD says nothing specific, you don't find out what kind of CSM they want until you're deep in the process. Sometimes they haven't decided themselves.
Intentional friction. More hoops. Extra questions, video submissions, more complicated ATS. I heard about a company that bought Workday specifically because making people create a login and re-enter their resume would cut down on applications. They could have cut the volume by writing a clearer job description instead.
Customer Success roles are shifting
It's not just the process. What the market wants from each role is changing too. Here it is role by role.
CS Operations is growing
I started tracking Ops again in March because it came back after nearly disappearing, and I expect a wave of these roles by the end of the year.
Right now, Operations means AI. Companies want someone to lead AI enablement internally, build AI workflows and automation, and operationalize success without adding headcount. AI fluency is sometimes valued more than operations experience itself.
It's also becoming an IC path for leaders who want out of people management, especially if you've led an AI rollout.
Onboarding & Implementation is getting more senior
SMB and Mid-Market Onboarding is being folded into the CSM role, and that segment is the first target for AI and ops automation.
What remains skews enterprise: more technical, more senior, and increasingly titled Implementation. I counted 208 roles named implementation versus 47 named onboarding. Sometimes that means a genuinely more technical ask; sometimes it's just a rebrand of the same motion with a more technical-sounding name.
The Customer Success Manager the role is forking
This is my biggest category, and it's splitting in two. Most companies want one or the other, rarely both:
More commercial.
Expansion shows up in over 65% of CSM roles, and upsell or cross-sell in about a quarter. Standalone Renewals and Commercial Account Manager roles are declining; they want the CSM to own more revenue.
Pre-2020, I knew CSMs who weren’t responsible for retention at all. It would be extremely difficult to find a role like that today.
More technical.
Deep vertical expertise, AI fluency, and Forward-Deployed-Engineer-style roles where a deep expert embeds with the customer to build.
Break into Customer Success is not entry level
Almost nobody reading the Job Drops is truly entry level. You might not have SaaS or Customer Success experience, but you have work experience and transferable skills, and this category is about using them:
Any customer experience. Retail, hospitality, restaurant, or call center from outside tech; or support, sales, or project management from inside it.
Non-tech vertical experience. I've seen roles built for teachers, RNs, PTs, paralegals, and medical billing experts to step into a CSM seat in their field.
Leadership: coach to operator
It's a tough time to be a manager. Teams are growing, scope is growing, and expectations are growing.
The shift I see is from coach to operator: more direct reports, more player-coach setups where you own a book of business too, more strategy and AI transformation on your plate, and less room to actually develop your people.
Most of the growth on the leadership side is in Director roles, which now make up about 40% of leadership openings year to date, and "Director" increasingly lands on IC roles too. Manager has stayed flat at roughly a quarter of roles, and I just saw a surge in VP openings in June that I'm keeping an eye on.
The big picture
Step back and there are two forces under all of this: the inescapability of AI, and the employer's market.
Both trace back to executive whims. Leadership is captivated by AI and it's trickling into every role and every hiring process.
The same decision-making drove the roughly 100k tech layoffs in 2026. I don't buy that AI is so good it's taking the jobs; that's a convenient story for what are really short-term, margin-driven, stock-price decisions.
But whims are fleeting. AI is inescapable right now; we're in an employer's market right now.
Worth knowing: only about 19% of the job descriptions I track even mention AI. It feels everywhere because the hype is everywhere, not because the actual roles demand it.
If you've been in tech a while, you've watched this movie before, with Web3, with blockchain, with headless commerce. Someone in power gets excited, everyone scrambles, and then something new and shiny comes along, and we start the process over.
Markets that swing toward employers always swing back. I can't tell you the day, but a candidate's market is coming. The hard parts are real, and they're temporary.
What’s next
Get an edge in an employer’s market.
The 2026 job market is an employer's market. There are a lot of qualified Customer Success candidates, and hiring managers can afford to be picky.
Insider is your edge.
More jobs, right on time. Two Job Drops a week means you’re seeing roles right after they’re posted. In a market where good jobs close fast, that timing matters.
Strategies that get you hired. The Playbooks turn nebulous advice like “post on LinkedIn” into real tactics you can do today. You stop second-guessing every move and start taking action with confidence, even on the parts of the job search that feel yucky.
The pulse of the market. After years as a Director of Customer Success and two years running this newsletter, I know how this market moves. I share what I'm seeing every week so you're not guessing.