Have you ever wondered: what really happens when the startup you work for gets acquired?
Does everyone get to cash out and eventually retire on a beach? Or does it end up being a huge letdown?
I used to wonder the exact same thing earlier in my tech career.
I'd hear stories about employees walking away with life-changing amounts of money (millions) when their company went public or got bought, and in the tech industry it’s easy to imagine that’s the rule and not the exception.
Then I was part of a company that got acquired and I got to experience it all for myself.
Spoiler alert: your mileage may vary. Especially when you're a seller.
There's also a lot of variables in this equation like your tenure, role and the comp you negotiate when you join, so it's nearly impossible to fully predict the outcome of something like this (unless your a founder and have majority ownership of the company getting acquired).
In this week’s edition of Sales Players, I’m going to share my personal experience of joining a growing software startup that then got acquired by one of the biggest tech companies in the world (Meta). I’ll share both the lessons I learned and a ballpark figure of what I pocketed from the whole experience.
I'm sharing this to shine a light on the reality of what happens (good and bad) during a liquidity event. In many ways, my experience was a case of being in the right place at the right time and if it could happen to me, it might happen to you too at some point.
First, Some Background
A few years back, I was working at another startup when a recruiter reached out. At first, I ignored him. But about six months later, my curiosity got the better of me and I took the call.
The company was Kustomer (yep, spelled with a K), a CRM platform in the CX space. They had a strong reputation, good product market fit, proven founders (who had sold multiple companies before launching Kustomer), and plenty of funding. During the interview process, it was already clear that Meta (still Facebook then) was planning to acquire them.
I decided to roll the dice. I put together a 90-day action plan for my interview rounds, landed the role, and suddenly found myself not just at a fast growing startup, but on track to possibly be part of a FAANG company.
The Transition
Not long after starting, I got something called a “comfort letter” outlining how things might look post-acquisition. It included the basics: how much stock I’d receive, how the benefits package compared, and assurances that I'd have a path into Meta once the deal closed.
A few months later, Meta officially acquired Kustomer. Overnight, I went from being a rep at a 300-person startup to one at a company of 70,000+ employees. I even got a @facebook.com email address (which, came in pretty handy when doing outbound).
What I Actually Earned
Here’s the part most people want to know: what’s the financial upside when the startup you work for gets acquired? Again, this will vary depending on a number of factors. For me, it looked like this:
- Equity: I was able to vest several hundred restricted stock units (RSUs) each quarter. My process was to automatically sell off a portion of those shares on the vest date to diversify, while still holding onto a smaller percentage of shares for the longer term. META has had a really good run over the past few years, but as of now, I no longer hold any of these RSUs. The equity I received from the Meta acquisition ended up being worth over six figures, most of which has since been reinvested into other funds and still continues to grow as part of my long-term goals.
- Bonuses: I received both a sign-on bonus and a "transition" bonus as part of my integration into Meta. Together, those added up to mid five figures. I spent the entire transition bonus on a family trip to Europe (totally worth it).
- Retirement Savings: For the first time in my career, I had access to a 401(k) with a generous company match. I maxed it out two years in a row and rolled it into a Traditional IRA and it has since grown to just shy of six figures with no any additional contributions.
- Commissions: I still closed deals, including a big strategic one that paid out a high five-figure commission. Being under Meta’s brand often accelerated deals rather than slowing them down.
In total, the combination of commissions, bonuses, RSUs, and retirement contributions came to about a quarter million dollars of financial upside in less than two years, and that's not factoring in base pay, benefits and the many other cash perks offered by FAANG i.e. home office stipend, paid gym membership etc.
So, by no means “get a yacht” money and not even "f-you money" either but definitely a substantial boost to my retirement plan and a major milestone in my family's financial security.
What I Learned
Here’s the truth: most employees don’t walk away with massive life-changing payouts from acquisitions. The stories you hear about making millions are usually the outliers.
That said, there are real advantages to experiencing one:
- You learn how a big tech company operates from the inside.
- You get access to world-class benefits that startups rarely offer.
- You suddenly have a household-name logo on your resume, which opens recruiter doors left and right.
- And yes, you can pad your bank account and retirement savings along the way.
For me, the most valuable part was perspective. I confirmed that while I enjoy the perks of big tech, I’m wired for startups.
I like scrappy teams, early-stage chaos, and building from the ground up. But having Meta on my resume, and the financial runway that came with it, made me a stronger, more confident seller.
Final Thoughts
If you ever get the chance to work at a company that’s heading toward an acquisition or IPO, don’t assume you’ll be in the market for a yacht or private island. But also don’t underestimate the upside and longer term growth you'll experience. Between the financial benefits, the credibility boost, and the lessons you’ll take with you, it can be a career-defining chapter for sure.
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Stay classy SP,
-Jesse