After creating and leading LinkedIn’s business operations, strategy and analytics teams through a period of breakneck growth, many colleagues and friends were surprised when I accepted a job at a startup company with fewer employees than the entire department I was running.

If I’m being honest with you, even my wife was concerned at first about my move from a company that is a global brand to a startup that shows promise but isn’t a household name -- at least, not yet. Beyond the comfort that comes from working with a marquee company, she knew I loved my work at LinkedIn and the deep pride I felt with all that my colleagues and I had accomplished during my five years with the company. Why give that up?

The hard-earned comforts of a good job can taste like sweet fruit found at the summit of a long career climb. Then one day you look around and realize you’ve grown fat and you’re stuck on a plateau, not a peak. You miss feeling hungry.

Related: Richard Branson on Knowing When to Quit Your Day Job

It’s a common problem for executives. David Marcus, the former president of eBay’s PayPal division, surprised some with his move to lead a much smaller team at Facebook.

Marcus said that he had missed being an entrepreneur managing  a small team of people

“Going from managing a few hundred people at best in my entrepreneurial career, I suddenly found myself leading 14,000,” he wrote on his Facebook post explaining his departure. “So after much deliberation, I decided now is the right time for me to move on to something that is closer to what I love to do every day.”

Here are some factors to help you know whether the biggest play of your career may be moving to a smaller operation:

What is your appetite for risk? This is the first question an investment advisor asks when assessing your stock portfolio and should be the first question you ask yourself when deciding whether a startup or smaller company is a better fit than an established company.

The risks you take in your career are equivalent with the potential rewards. What you lose by going from a large company to a startup -- namely job security and financial rewards less vulnerable to market whims -- you gain in perhaps the only currency that truly matters in building a strong career: Experience.

In a small company, you get to wear more hats. That has a downside – you’ll have less support staff,  longer hours and most likely bigger stresses. And the immediate gains are often smaller. A recent study showed that only about half of companies with 200 employees or fewer have benefits. (Although that’s less true in the Silicon Valley, where even startups need great perks to compete for talent.)

Related: 7 Ways to Survive and Thrive at a Startup

But as a manager at a large company, you’ll spend more time managing employees and their career path, and also more time sitting in cross-functional meetings and traversing the natural politics that arise. If that’s your thing, great. If not, then the enthusiasm you once had for your work will be constantly challenged.

What is your vision for your career? It’s hard to know if an opportunity at a smaller company is right for you unless you have a long view of what you want to get out of your career.

When NerdWallet's co-founder Tim Chen wanted to meet with me about best practices for scaling a company, I wasn’t looking for a new job. But a few months before we met, my wife and I discussed my career. I told her I would probably want to leave LinkedIn in a couple of years to pursue something more entrepreneurial.

I was proud I had taken my LinkedIn team from one person in 2009 to 120 people by the time I left. Yet I was hungry to get back with a smaller team where I could have a greater impact. I had no idea that opportunity would come so soon. But I wouldn’t have recognized the moment had I not known which direction I wanted to go.

Does the opportunity align with your interests? Making a risky move requires a deep belief in the venture you’re joining. (You can’t throw your heart into your work if you don’t believe in the mission.) NerdWallet struck me as a great fit because its mission to provide personal financial tools to the masses dovetails with my investment banking background and past work at several startups that expanded financial services into the Internet space.

How many times in my career would I have an opportunity to help people in a way that combines my experience in banking and technology with the entrepreneurial zeal of a startup -- and be given the responsibility to run its daily operation? For me, the stars aligned when I took that meeting with Tim.   

What will you learn? I’ve found that if I focus my career on maximizing my skillset the outcome takes care of itself.

And as much as I learned in my years at LinkedIn, I knew that I’d learn much more as COO of NerdWallet. The startup reminds me of LinkedIn in the early days, where you have a tremendous amount of raw talent and a huge potential for success. I can help shape that success in a way more fundamental than any influence I can now wield at LinkedIn.

Related: 7 Reasons to Ditch the Corporate World for a Career at a Startup