Feature Story
I get asked some version of this question almost every single week, should I leave my job, and I never have a clean answer for it, because it is not a clean question, it is not about red flags or green flags or some checklist you run your role against at two in the morning when you cannot sleep and you are lying there trying to talk yourself into or out of something. It is personal, it is yours, and instead of giving you an answer, let me give you five, because I have left five companies, and I left every single one of them for a completely different reason.
The first time, I hit my ceiling.
I spent five and a half years at my first SaaS company, walked in as a CSM and walked out as VP of Customer Success and Practice Development, and for about four years of that run I had a leader who raised me, and I mean that in the real sense, the kind of leader who shapes how you think about the work for the rest of your career. Then he moved on, and when the next leader showed up, I knew almost immediately that he was not my leader, not because he was bad at his job, but because there was nothing left in that seat for me to grow into. I had learned everything the role had to teach me, and staying would have meant getting comfortable, and comfortable was never the plan.
The second time, it was misalignment.
I walked in thinking I was going to build, that is the role I thought I had signed up for, autonomy, a blank canvas, the chance to architect something from scratch, and instead I found infrastructure that was already built, a strategy that already existed, a vision that was already someone else's. And look, that is a perfectly good job for the right person, it just was not the job I wanted, because I did not want to carry someone else's vision to the finish line, I wanted to be the one drawing the map, and once I realized that gap was not going to close, I left.
The third time, I ran, but I ran smart.
I want to be careful with how I say this, because I tell people all the time to run to something, not from something, and that is still true, but this is the exception that proves the rule matters even more than the rule itself. I was working for a toxic leader, gaslit, degraded, blamed for things that were never mine to carry, and I stayed longer than I should have because I kept trying to force that situation into the "run to, not from" framework, as if patience was the thing that was missing. But I did not walk out into nothing, I resigned with a new job already lined up, because even in the middle of a genuinely bad situation, I still protected myself enough to leave on solid ground instead of leaving on a cliff edge. Sometimes the healthiest exit is still a planned one.
The fourth time, I saw it coming, and I was at peace with it.
This one was different, a PE acquisition was on the horizon, and with it, changes to the leadership team that I knew would not include me in the way I had been operating, and I loved the work, I loved the team I had built, but I could read the direction the business was heading, and it was not a direction I wanted to go. There was no drama here, no villain, just two paths splitting, mine going one way and the company's going another, and I left with a clear head, which honestly might have been the hardest kind of leaving, because there was nothing to be angry at, just a decision to make.
The fifth time was the hardest thing I have ever done professionally.
Five years as Chief Customer Officer at ClientSuccess, leading the entire post sales org, and if you have followed my journey you already know this chapter, and if you have ever met Dave Blake, you know exactly why this one was hard, because he is one of the best humans I have had the privilege of working for, and that team was not a team to me, it was family. I loved the work, I loved the customers, I loved the community we built inside that company, and there was no ceiling, no misalignment, no toxicity, no acquisition forcing my hand, I left something genuinely good, on purpose, because it was time to go build my own thing. That is a different kind of leaving, you are not leaving because something is wrong, you are leaving because something else is calling, and staying, even somewhere good, would have meant staying small.
The Takeaway
Five companies, five completely different reasons for walking away, a ceiling, a misalignment, a toxic leader, a shifting business, and finally, a calling that had nothing to do with anything being broken.
Here is what ties them together, every single one of those decisions was mine, not reactive, not someone else's timeline, not a script I was following because it is what you are supposed to do at year three or year five, and I knew, each time, because I asked myself honestly what I needed and I believed the answer even when it was inconvenient. Even the exit I ran from, I still ran with a plan.
If you are sitting in a role right now turning this over in your head, I am not going to tell you what to do, but I will tell you this, your reason does not have to look like anyone else's, and it does not even have to look like your last one.
THE RESOURCE
Five questions to ask yourself before you make your next move, not as a scorecard, but as a mirror.
Am I still growing? Growing in scope, in mastery, in exposure to problems you haven't solved before. If you've hit the ceiling and there's nothing left to reach for, that's real data, not restlessness.
Do I still feel fulfilled by the work itself? Not happy every day, that's not the bar. Do you still love the profession. Are you proud of what you're building and who you're building it for.
Am I respected and empowered to do the job I was hired to do? Do people trust your judgment or do they just tolerate your title. Are you actually shaping outcomes, or executing someone else's plan you never fully agreed to.
Is this environment protecting my wellbeing or costing me? Be honest here. Tired is normal. Diminished is not. If you're being gaslit, blamed, or degraded, that's not a growth opportunity, that's an exit sign.
Do I still believe in where this is headed? Not just the role, the business. Leadership, direction, the next chapter of the company. You can love the work and the people and still watch the road bend somewhere you don't want to go.
Answer all five honestly before you answer the bigger question everyone actually wants you to answer.
AI in CS
Here's an angle on this most people aren't thinking about yet. AI is changing the timeline on which people realize it's time to go. It used to take a couple of bad quarters, a couple of leadership changes, or a slow accumulation of frustration for someone to admit they'd hit a ceiling. Now, tools can surface that reality faster because they're absorbing the manual, reactive work that used to take up so much bandwidth that people didn't have room to think about their own trajectory.
Once a CSM or a CS leader isn't drowning in health score spreadsheets and manual QBR decks, they have space to ask a harder question, is this role still growing me, or am I just executing tasks a system could increasingly do on its own. That's uncomfortable, but it's also clarifying. AI isn't going to make the decision for you, but it is going to remove some of the noise that used to bury the signal.
For leaders, this means the "am I still growing" conversation is going to come up more often, and sooner, in your one on ones. Build space for it instead of dreading it. The people who feel safe enough to ask that question out loud are the ones you actually get to help grow. The ones who don't ask, just quietly start looking.
COMMUNITY INVOLVEMENT
Why Companies Fail at Growth Despite Departmental Success
Many organizations celebrate departmental wins, while their companies still struggle with retention, growth, or profitability.
Why?
Because departments are often optimized for their own metrics rather than aligned around shared customer and business outcomes.
Learn how your organization can negate silos, conflicting priorities, and fragmented customer experiences in the August CS Mastermind, The Alignment Problem: Why Companies Fail at Growth Despite Departmental Success.
Join hosts me and Andrew Marks, along with a panel of CS experts, as they dive into how CS leaders can bring teams together around a unified vision of customer and company success.
Wednesday, August 19, 2026 at 11am PT / 2pm EST
During this online event, the panelists will discuss:
→ Why companies struggle with growth, while individual departments appear successful
→ Examples of departmental goals that unintentionally work against each other
→ Metrics and KPIs that encourage company-wide alignment and cross-functional collaboration
→ The role Customer Success plays in strategic conversations across Sales, Marketing, Product, and Support
And more!
Register today and mark your calendar to learn why organizations fail to grow despite apparent departmental success, how misaligned incentives create hidden friction, and what CS leaders can do to bring teams together around a unified vision of customer and company success.
CAST YOUR VOTE
Atonom has launched their awards program recognizing the leaders shaping the future of customer experience and I’ve been nominated.
I’d appreciate it if you could take a few minutes and vote for me. It would mean a lot.
A NEW CS EVENT
AI is redrawing the commercial landscape.
Frontier by Planhat brings together 400+ commercial leaders for one day focused on deploying AI to win. Hear stories direct from executives and builders at OpenAI, Wiz, Framer, Granola, Fyxer, 20VC and more as they trade market-tested tactics and explore the technologies powering tomorrow's post-sales winners.
November 10, 2026, London
Get your tickets at planhat.com/fontier
A FINAL NOTE
CLOSING WITH KRISTI
I didn't leave any of these companies because I stopped caring. I left because I kept listening to myself, even when the answer was inconvenient, even when it meant walking away from something good to go find something that was actually mine.
If you're in the thick of that decision right now and you want a thinking partner who isn't going to hand you a script, that's a lot of what Advisory and Coaching with me looks like. Not telling you what to do, helping you get honest about what you actually want. You can find both, along with Education & Enablement and Speaking, at kristifaltorusso.com.
See you next Tuesday,
Customer Success. Revenue Follows.