What I Learned About Resilience From Being Laid Off 3 Times

I've been laid off three times.

I'm saying it plainly because the version of this story that gets told on LinkedIn - "I was caught in a restructuring, which led to my greatest opportunity, and here's the leadership lesson" - tends to skip over the part where you're sitting in your car in a parking lot at 11 AM on a Wednesday not entirely sure what to do next. The LinkedIn version is tidier. This one is more useful.

So let me tell the real version.

The CloudKitchens Exit

In December 2023, CloudKitchens restructured. I was Head of Sales for Central U.S., managing 4 teams across 15 markets with tens of millions in annual revenue flowing through my region. The performance was real - 300% increase in outbound demos during my tenure. But the company was reorganizing regionally and my role was consolidated in the restructure. It was a company decision, not a performance decision.

That's the factual version. The personal version: it's disorienting to have a team you've built, results you can point to, and a clear sense that you were doing the job well - and then have it end because of decisions made above you in an org chart you had no visibility into. You spend a few days running back through every decision looking for the thing you missed. Eventually you realize the org chart just moved. That's all. It's not more complicated than that, even when it feels like it is.

What it taught me: the things you control and the things you don't are genuinely different categories, and conflating them is a waste of energy that would be better spent on what's next. I took a month to be honest about what I wanted from the next chapter before I started pursuing it. That month was useful. It produced more clarity than I would have had if I'd immediately started interviewing at the first available opportunity.

The Prokeep Exit

In November 2025, I was let go from Prokeep. I had been Senior Director of Sales since November 2024. In that year, we expanded pipeline significantly, restructured the new business sales team, and shifted focus toward higher-value, upmarket prospects. By any measure, the business outcomes were strong.

The decision was a strategic headcount move. The company was in a stage transition that required different cost structure decisions. Hitting milestones doesn't make you immune to those decisions. The relationship between performance and security is real but not absolute - and every sales leader learns this eventually, usually the hard way.

This one was harder to process than CloudKitchens, honestly, because the results were clearer and more recent. It's one thing to be restructured out of a role. It's a different thing to have built something measurable and still have the outcome be the same. There's a particular kind of quiet that follows that conversation. You sit with the numbers - the pipeline, the verticals, the revenue contribution - and they don't change anything. They're just numbers now.

What it taught me: the best protection against this is building things that demonstrate your value independently of any single company's decision. Which is part of why I started building.

The One That Came Before

I'm not going into detail on the third one because it involves people who are still in my network and the specifics don't matter for the lesson. What I'll say is that it was the first time it happened, it was genuinely unexpected, and the three weeks between the conversation where I was told and the first serious conversation with a new potential employer were the longest three weeks I've experienced professionally.

What happens in those weeks: you run through every decision you made that might have led here. You second-guess conversations. You wonder what you missed. Eventually - and this part matters - you run out of things to second-guess and you start thinking clearly about what's actually next.

The clarity comes after the noise, not before it. That's not a cliche. It's a sequence. You have to get through the noise first.

What Companies Should Know About Leaders Who've Been Through This

Here's the thing that most hiring conversations handle backwards: a layoff is treated as something to explain away, a gap in the narrative that needs to be smoothed over. It should be treated as evidence.

A sales leader who has been laid off - particularly in a company decision rather than a performance decision - has been through something that produces a specific kind of toughness that you cannot manufacture in a stable career. They know what it feels like to have external circumstances affect something they built. They know how to recover. They know what things actually matter and what things are noise (and the associated insomnia from figuring out which is which).

The leaders I've seen come out of disruption with genuine growth tend to have three things in common. First, they stay close to what they're actually good at - they don't panic-pivot to something that sounds safer. Second, they use the transition period to build something, anything, that keeps them active and thinking. Third, they're honest with themselves about what they want from the next chapter instead of just taking the first thing that calls.

The leaders who don't recover tend to let the identity disruption become the story. They spend the transition defending their record instead of building their next one.

The Honest Part

The weeks between roles are genuinely hard in a way that's difficult to describe to someone who hasn't been through it. Sales leadership is an identity-intensive job. You're the person with the number. Your team looks to you. Your calendar is full of calls where you are the center of the decision-making. And then one day it stops.

The silence is the hardest part. Not the logistics - the logistics of finding a next role are manageable. The silence of not being needed in the specific way you were needed for the previous two or three or five years. Your phone still works. Your email still works. The particular kind of being-needed that you had on Tuesday just isn't there on Wednesday.

I'm telling you this because the polished version of this story isn't useful. The version where it was hard and you got through it anyway - that one might actually be useful to someone reading this at 11 AM on a Wednesday in a parking lot, trying to figure out what to do next. You're not the first person in that parking lot. You won't be the last. The car does eventually start.

What I'm Building Now

The three exits - the CloudKitchens restructure, the Prokeep strategic decision, the one I'm not detailing - produced a consistent question: what can I build that doesn't depend on someone else's organizational decisions?

The answer I've been executing on is joepeck.ai. AI tools for sales leaders - the Deal Coach, the Forecast Truth Machine, the Autonomous SDR architecture. Built because I needed them. Built to demonstrate what's possible with the tools available right now. Built as the kind of work that compounds regardless of any single employer's org chart. The Mac Mini running my AI agent hasn't been restructured once. It hasn't asked for a day off or updated its LinkedIn to "open to work."

I'm also doing fractional CRO work - stepping into revenue organizations as a senior operator who has done this at scale and can help them move faster and make fewer expensive mistakes. That work is interesting to me in a way that a traditional full-time role isn't right now, because it lets me work with multiple companies simultaneously and build the kind of varied experience that a 20-year career in one lane doesn't produce.

The three exits, viewed from here, look less like failures and more like forcing functions. The CloudKitchens exit produced clarity about what I wanted next. The Prokeep exit produced the urgency to build independently. The first one produced the knowledge that I could recover - which makes every subsequent disruption materially less frightening.

That's not a motivational reframe. It's just what happened.

If you're building a revenue org and want someone who's been through the fire - let's talk. calendly.com/joseph-p-peck.