Editor’s note: Longtime contributor Rocky Agrawal announced this morning that he was joining PayPal as Director of Global Strategy. While he won’t be writing for us nearly as much, we’re happy for him — and wanted to hear why he’s making this move. Here’s his story.

After several years focused on helping small businesses and entrepreneurs understand and respond to the changes in commerce and payments, I’m joining PayPal — to continue to help small businesses and entrepreneurs.

We’re at a big turning point in commerce and the future of money. Back when I made my first sales on eBay in the mid-90s, the process was something like this: I’d go through a lot of work to describe the item, wait seven days for the auction to close, send an email bill to the buyer, wait a week for a money order in the mail, try to determine if it was legitimate, deposit the money order, hand write a shipping label and take it to the UPS store.

The first time I used PayPal, it was like magic. The money appeared in my account minutes after the auction closed. I could ship the next day. Stuff out of my house faster; goods to the buyer sooner.

We’re at a similarly magical time. New payment experiences are coming into the market that can reduce friction and drive real value to consumers and merchants. We’re seeing new marketplaces like Uber and Airbnb that take advantage of mobile to create new businesses.

While a lot of the industry hype has been focused on technology solutions that technologists love, those solutions often leave consumers scratching their heads to what the real value is. There is a lot of consumer value to be created by taking a customer-centric view of the problem. If a payments solution doesn’t save consumers time or money or both, is it really a solution?

PayPal has a lot of unique assets to bring to bear on the problem. First and foremost is scale. Payments is fundamentally a scale business. In 2013, PayPal processed more than $180 billion in transactions; that’s roughly equivalent to the GDP of New Zealand.

I’ve been truly impressed by PayPal’s leadership in the last several years. Two years ago this week, I wrote a post on VentureBeat titled “PayPal’s new POS service is a Piece Of Sh*t”. But PayPal isn’t a company that shirks from criticism.

I’ve had the opportunity to spend time with much of PayPal’s leadership, including president David Marcus, vice president of growth and strategy Stan Chudnovsky, and chief product officer Hill Ferguson. All three are dyed-in-the-wool entrepreneurs who want to get things done.

Marcus said at a recent ReadWriteMix that if you have scale and you can iterate quickly, no one will be able to catch you. I agree.

Just as important is the response from close friends who work at PayPal, as well as VCs I know and trust. When I shared the opportunity with them and asked for their input, their advice was that I should absolutely join PayPal.

As important as the opportunity to create magic and the great team is the ability to continue to help entrepreneurs and small businesses. I’m a big believer in what I call “long-term capitalism.” It’s relatively easy to create businesses that exploit short-term opportunities at the expense of your customers; it’s much harder (but also more lucrative long term) to create real value for businesses.

A personal example to illustrate the difference: A VC friend once asked me to sit on a pitch from a payments startup. If the company was interesting, he said would offer me a consulting agreement to help with the due diligence. Fifteen minutes into the meeting, I knew it didn’t make sense to invest. A short-term capitalist would go for the consulting agreement and say “no” after spending weeks analyzing the situation. I gave him an answer immediately: No. That meant I got no consulting arrangement, but it built a long-term relationship that continues to pay off. It’s that VC who introduced me to my new boss at PayPal.

Part of my role at PayPal will be to help small businesses and entrepreneurs understand online commerce and payments. There is a lot of nuance in commerce that goes beyond just APIs and technical implementation. If you can show a customer how to reduce chargebacks or mitigate fraud and as a result that business is more successful, you become more successful. If you can teach a customer to market better and they sell more, you will be more successful. The best APIs and the prettiest interfaces don’t mean much if your customers are still struggling with the rapidly changing retail environment.

That process also goes in the other direction, too: continuing to educate PayPal on the needs of those merchants and entrepreneurs. I see too many companies that are trying to revolutionize businesses without ever having talked to those businesses.

It’s an exciting time to be in commerce and I can’t think of a better place to be.

Obviously, picking a company to join is not an easy decision. In the spirit of my previous “how to” pieces, I thought I’d share how I evaluated companies I was considering joining.

Big companies vs. startups

It’s a competitive labor market out there and big companies offer different reward/risk profiles. (I’ll talk more about that in the compensation below.) I talked to large companies and startups of various stripes.

I’ve worked at both and know the tradeoffs. I’ve been at a startup that was running on fumes, but I’ve also had the frustration of working for big companies that couldn’t execute on great ideas that were handed to them on a silver platter.

But for someone who wants to work in local or payments, the opportunity for the biggest impact is in a company that has a lot of scale already. (Assuming they can execute.)

Does the company deliver value?

I’m a big believer in Tim O’Reilly’s saying, “create more value than you capture.” I’ve written extensively in the past about companies that — I believe — extract too much value from the ecosystem at the expense of their customers; I just can’t do that.

In the long run, companies that don’t deliver value don’t stick around.

Is there a good fit with my skills and a good role?

I keep a list of things that I’m great at and love doing, things that I’m great at but don’t like doing, and things that I suck at. I share this list with potential employers. (No, my greatest weakness is not that “I work too hard,” as people often say in interviews.) Obviously, I try to optimize for roles where the bulk of my time is spent on things I’m great at and love doing.

Often there isn’t an immediately obvious role, especially if you have an unusual combination of skills. Although many companies claim to “think outside the box,” few do. In PayPal’s case, they didn’t have a role, but created one around my skills.

Will this company be fun to work for?

Life is too short and workdays are too long to be at a job you hate. I’ve quit high-paying jobs in the past because I just hated what I was doing or didn’t believe in what they were doing.

Will I learn from the people I will be working with?

There’s the old joke about what you should do if you find out you’re the smartest guy in the room: Find a new room. I’ve always placed a premium on companies and roles where I can learn from those around me (and they can learn from me).

If anything, launching compelling products is getting harder, not easier. What you could have launched in 2004 isn’t good enough in 2014. Although we have better tools and distribution mechanisms than we did ten years ago, so does everyone else.

The best, most innovative products com not from people vehemently agreeing, but from people disagreeing and challenging conventional wisdom.

We are in a really exciting time in the labor market for technology employees. People can choose from a range of options. I’ve been advising friends who are looking not to settle or to try to shoehorn themselves into jobs they can’t get excited about.

As much as I hated to leave a sunny warm day in Honolulu this week, I was even more excited to start my new job.

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