Changing the Color of Money

As PayPal services Venmo and Braintree conquer the digital payment sphere, Rob Pelkowski ensures that the company’s innovations stay within the lines

Technology has transformed the identity of the green dollar bill into a colorless entity, making it easier than ever to divide a dinner check or pay a friend or colleague. As long as you use a smartphone application connected to your debit card or bank account, you may never need your wallet again.

There are a few major players responsible for this in the booming digital commerce market, but PayPal’s Venmo may be the most popular. Venmo’s charm comes from transforming payments into a social and memorable experience. The app encourages users to include a message with each transaction, which then gets broadcast over the company’s payment social network. In short, users can see how their friends are also paying.

Josh Criscoe, head of corporate affairs and communications at Venmo, believes this experience not only removes the awkward feelings that are sometimes associated with a friend covering a bill, but also provides an easy and fun way to pay someone back.

This mentality has transformed Venmo from the little giant that could into one of PayPal’s top assets. PayPal initially obtained Venmo after the 2013 acquisition of Braintree, a global payments platform that processes billions of dollars annually for merchants such as Uber, Pinterest, Airbnb, and Yelp in more than forty countries and 130 currencies.

Venmo is projected to process about $20 billion in 2017 alone, all while the company’s team devises new ways to strengthen the service’s memorable model, and big banks try to keep up.

Rob Pelkowski, head of legal at Venmo and Braintree, is a pivotal expert within these developments. Digital commerce is still new and loaded with potential, and Pelkowski serves as a bridge between compliant innovations and the marketplace. He also helps deflect problematic or illegal moves.

Pelkowski’s journey to Venmo actually started about eight years ago when he began working with law firms. At the time, Pelkowski discovered that he had a passion outside of private practice and more toward the commercial sector.

“I prefer the commercial work, which tends to be less adversarial and more results-oriented,” Pelkowski says. “With litigation, you generally have two sides that don’t like each other; it’s a fight to win or punish the other side. With commercial work—product work in particular—it’s about achieving something together and building relationships, as opposed to breaking them down.”

Pelkowski made his first move into the corporate world with American Express. While there, he focused on prepaid payment products, including reloadable prepaid cards and gift cards. He was also challenged to learn the ins and outs of payment law, complex corporate organizational structure, and gained the confidence needed to help the company move forward at its desired pace.

“You need to be comfortable playing in that gray space [of the law], give definite guidance, and stand behind it,” Pelkowski says. “For me, it was about becoming comfortable with being uncomfortable. There may not be the concrete or easy answers for the innovations you’re looking to bring to market, but you still have to provide effective guidance quickly and stand behind it so your clients can make their next move with confidence.”

This education came of great use when Venmo was searching for payment lawyers in early 2016. Pelkowski was impressed by the company’s rapid growth, and after meeting with the team at Venmo’s headquarters, he got a sense of how passionate they are about their work.

“It was infectious and made me want to join them even more,” he recalls. An opportunity to join Braintree revealed itself shortly after he was hired by Venmo, and he instantly jumped aboard.

Pelkowski is responsible for keeping up to date on current laws, advising the Venmo and Braintree teams, and anticipating legal changes that have not yet occurred. Mastery of the law is essential in all of these roles, so he constantly reads industry journals and key rulings, and keeps an eye out for notices of proposed rulemaking sent out by government agencies. Additionally, he attends industry events, where he can hear directly from regulators and listen to panelists, as well as other important figures who can share their viewpoints and challenges firsthand.

“It’s about achieving something together and building relationships, as opposed to breaking them down.”

Pelkowski stresses that both Venmo and Braintree’s expert leadership teams supply the guidance and support needed to help him succeed.

“I’m fortunate at Venmo and Braintree,” Pelkowski says. “I’m tapped into PayPal’s industry leaders in business, legal, compliance, government relations, communications, and other areas, and they all do an incredible job supporting me. It’s a team I’m very proud to be a part of.”

Venmo’s open-office environment also encourages more natural and fluid interaction with his colleagues. Pelkowski says people are rarely sitting down and aren’t gripped to their computers all day, even though technology dominates much of their work.

On top of the office environment, Pelkowski enjoys the frequent—and somewhat sudden—challenges sparked from the changing legal landscape and new product developments. One might even say he finds them invigorating.

“You never know what you will be asked to weigh in on or deal with,” he says. “Some people might find that lack of predictability concerning, but I think it keeps things fresh, new, and exciting. Every day is a potential new experience and an opportunity to learn something, and I think that’s the best part about it.”

Earlier in his conversation with Modern Counsel, Pelkowski uses the instantly quotable phrase, “Pressure is a privilege.” While many may disagree, this head of legal could use those words as his mantra, given his respectable position and success at Venmo and Braintree.