9 Things That Surprised Me as a First-Time CEO


Last month, I celebrated my five-year anniversary as CEO of Verblio. As my first time in the CEO role, it’s been an incredible journey so far, but there have been more than a few unexpected surprises.

In no particular order, here are nine things that caught me off-guard about becoming a first-time CEO:

1. Approving my own PTO requests is bizarre.

“Good for you, Steve. Nice to see you taking some time off.”

“Thanks, Steve. Looking forward to it.”

“Got any fun plans?”

“Heading to the ultimate frisbee nationals, actually, so I’m pretty stoked.”

“Oh, cool! Congrats, good luck.”

“Thanks, Steve.”

2. There’s no job description. At all. 

As Verblio grows, anytime I get good at something, the job changes to show me how bad I am at something else.

It helps to know I’m not alone in this: I talked with Drift founder and CEO David Cancel on our podcast, and he shared how much his job has changed for him since the company’s earliest days to today, as they scale up to 600+ people.

“My job is totally different. Someone who was with us in the early days will look at me and be like, ‘What do you do now?’ …Because my job has been to give away all the things that I was running personally, so I’m not doing any of those things now.”

And sometimes that non-existent job description includes having the company warehouse in your basement.

3. It’s crazy how many projects I unknowingly start with poor communication.

Me, spontaneously musing: “Wouldn’t it be nice if….?”

The team one week later: “We did it.”

But hey, we’re in year two of our podcast now, so that’s cool. 

4. I’ve worn way more hats than I ever expected.


5. I have the feeling that I’m accidentally breaking a precious vase in the founder’s house on at least a weekly basis.

I often describe the experience of taking over a company from founders as moving into somebody else’s house who’s been living there for 70 years. You love the foundation, the way it looks, everything about it—but there are sconces in the bathrooms and pink carpet and other stuff that just needs to be changed. And while I know it’s my job as CEO to make those necessary changes and take the house to the next level, that doesn’t mean the process is always easy.

6. I underestimated how satisfying and wonderful it would feel to hire one amazing person after another.

When I joined Verblio, it wasn’t even Verblio yet. Our entire team consisted of 11 FTEs and no contractors. My first responsibility was making a couple of key hires, who helped create a culture that then acted as a magnet for other awesome people. Those rockstars then attracted more great people, who attracted more great people….and on and on the cycle goes.

Fast forward five years to today. We’re 33 FTEs strong with some powerful contractor partners and nowhere close to slowing down. Check out our open positions (and watch our video on how amazing we all are.)

7. I still have to change the toner and am also somehow in charge of Costco runs for the office

That aforementioned rockstar team needs their LaCroix.

8. Seeing my personal cell number posted online in a fraud scheme is unnerving. 

Scammers suck. One responsibility I definitely didn’t foresee was having to address fake job postings that pretend to be from Verblio. It’s an ongoing issue that cropped up this past year, and we’re doing our part to prevent more people falling victim to the fraud.

9. I may be in charge, but I still get vetoed on company swag decisions. 

Vests are still cool, right? No? Darn…

Regardless, I’m grateful for a team that saves me from myself. (And for my fourth anniversary, they made me branded frisbees, so I really can’t complain.)

Thanks to the team for making this an incredible experience. Here’s to the next five years, and the next thousand learnings. Want to catch them in real-time? Say hello and follow me on LinkedIn.

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Steve Pockross

As CEO, Steve brings more than 20 years of startup, nonprofit, and Fortune 500 experience to not only running the business of Verblio, but also setting the culture, vision, and purpose of the team. Outside the office, Steve enjoys ultimate frisbee, telemark skiing, hosting jazz concerts, and spending time with his two boys.

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