Over the span of nearly two decades in B2B SaaS and customer-success leadership roles, I’ve held nine jobs. Each move was intentional or inevitable, but none of them followed a straight line.
As I search for my next opportunity where I lead Customer Success in a stable, high-impact environment I’ve reflected more than ever on what all those jobs taught me.
I won’t bore you with the personal details of each company or title. Instead, here’s:
- How I learned what to care about
- What I’m looking for
- What matters most to me.
In no particular order…
1. You become the “new guy” a lot
Entering a new company nine times means you spend a lot of time introducing yourself, earning trust, deciphering culture. That gives you agility, resilience, and an ability to land softly. But it also changes how you view work.
After a while, you realize you’re not just doing a job, you’re often laying groundwork, building relationships, aligning expectations and being forced to show up with credibility immediately.
And if you’re doing that again and again, you ask: what kind of environment allows me to settle and lead more deeply, rather than just arrive and shake things up again?
2. Authenticity isn’t optional
I’ve always believed: I am the same person at work as I am at home, with my family, or with friends. I don’t try to slip on a different “work persona.” Maybe I’ve changed over the years (I know I have) especially as a father, as someone who’s grown.
But I’ve always felt strongly that being myself is a strength.
When you lead teams, you build trust by showing you’re real: that you’re honest, that you give your opinion, that you’re not hiding. It takes courage, especially when you’re new to a company or when you feel like you have something to prove. But over nine roles, that approach has reinforced itself: authenticity matters more than title or tenure.
3. Loyalty, longevity, and the “one-company” ideal
I look at the ideal of staying ten years+ at one company and I think: aspirational, yes. But it hasn’t been my path so far.
On one hand, moving roles frequently has been a strength: constant learning, broad exposure, adaptability. On the other hand, business culture often rewards loyalty and tenure. My career may appear less linear or “steady” than some. I’ve often shown up thinking long‐term, working to build something meaningful, but things don’t always line up. Sometimes you leave because you’re pushed, sometimes because you choose, sometimes because something better comes along. In every case, I’ve shown up with the best long-term intentions.
4. What matters isn’t only the next title or company
Through each role I’ve asked myself:
What does this teach me about who I am, what I value, and how I spend my time?
For me it’s always been: do the best possible work and lead teams toward meaningful impact, Grow personally and professionally. The notion of “climbing the ladder” might have been there implicitly, but I’ve realized the next step isn’t always upward in the traditional sense. Sometimes it’s forward in a different dimension: stability, leadership, autonomy, meaningful relationships, and a culture where I can bring my full self.
Great, what’s your point?
So I’m now looking for my next opportunity in a stable, high-impact SaaS organization but also asking: what kind of life do I want alongside it? What kind of team? What kind of product? What kind of growth? And what kind of relationship between work, family and impact?
5. The long-term vision: building stability while staying agile
Having had nine jobs has given me a perspective I didn’t believe I’d ever have. I’ve seen many contexts: small startups, scaling teams, enterprise challenges. That gives me versatility. But I also crave stability: a place where I can plant roots, build deep relationships, influence culture, and help a company win over the long run. That desire is growing in me, even as I hold onto the agility and curiosity that my journey has given me.
I don’t know exactly what’s next. Whether I’ll stay at one company for ten years, or whether I’ll once again change course. But I do know this: I’ll continue to show up as my true self, bring my leadership, deliver the best work I can, and stay alert to the life I want to lead alongside the career I pursue.
Once you’ve been through many roles, you’ll ask yourself “What’s next?”
Know that you’re not alone. Changing jobs isn’t just about changing companies. It’s about changing your view of work, your view of yourself, your view of life. And sometimes, that perspective is the greatest gift of all.
Robert Statsky 