Oh those college years.

2007-2013

The line between work and play was pretty blurry.

Paypal was a playground.

Ask someone you know who worked at PayPal - and you must, because PayPal is like the Six Degrees of Kevin Bacon game - and they’ll probably tell you it was a lot like college. Formative. Wide open. Hard fun, hard work.

It was like college in that you made friends for life. I saw everyone as an extension of my family. The supportive environment helped me push boundaries.

Jacqueline Cisneros
Co-founder, Circora

make time for free think.

patent play

What really got me going was innovation, and it helped to have an organization that supports it, that gives you space to experiment.

Fast pay (2010 - US20120158528A1)

NOT APPROVED

In 2010, PayPal was still very much eBay transactions and online sales.

Wesley Hsu and I brainstormed ideas for in-person payments. The identifier could be a QR code. It could be printed on bills. What if it connected to restaurant seating software?

While our patent did not get approved, it was a great experience that I’ll never forget. 

I helped introduce the QR code concept, restaurant seating integration, and put together the deck and presentation materials.

PayPal’s early legacy of 'leap ahead' innovation was the engine behind disrupting, then setting the standard, for the payments industry. When the company shifted its focus toward incremental improvements, it opened the door to a new wave of disruptors.

paypal innovation showcase

Dar and I have discussed the frustrating lack of follow-through on product ideas. He was helpful on many fronts, from innovation to product management to program management.

About three years after our Fast Pay patent was submitted, PayPal built out an innovation showcase.

We experimented with many emerging technologies and ideas, experiencing both successes and failures. It still amazes me how many of those concepts are now part of everyday life.

IT’S THE THOUGHT THAT COUNTS.

paypal here offline (2013)

NOT SUBMITTED

Here’s why ‘the thought’ counts: your ideas are part of a larger process of innovation, where you continuously refine your own creative thinking. Keep at it, you’ll land on something.

I worked up these crude wireframes in a few minutes to illustrate an idea around receiving payments without an internet connection.

PCI compliance was difficult back then, and it was determined that storing the credit card info was problematic (even if temporarily).

you champion the experience, not a design.

This isn’t revelatory wisdom, but an important motto that you should hang in the hallways of your office.

Account Level Holds (2011)

I hadn’t been at PayPal for more than.a couple weeks when I heard of PayPalSucks.com. The Risk group used predictive models and blanket policies that could suddenly freeze funds - and piss off customers.

Adam Braasch and our UX team removed seller goals from payment holds, and everyone was happier.


Results:
Reduced contact volumes by 20k/month, decreased number of sellers impacted by adverse actions by 145k/month from 2.3% in Dec. 2011 to 0.5% in Q4 2012. csNPS 20 point improvement from 11% baseline for legacy and 31% for new experience.

I helped the team with research, supported them in the effort to change the experience, and advised on messaging.

PayPal was a company that grew really big, really fast -- the kind of environment where teams cranked out new features constantly to keep our lead in the payments space. We could get away with "good enough" for a long time. But as we were growing, we had to go back and reconcile all these disparate parts.

C.A.R.E. (2013)

While Rachel is referencing a different project in the above quote, it is a great lead-in to the Compliance & Risk Enablement initiative.

Hendrik Kleinsmiede came into PayPal around this time, and we were on him pretty quickly about these inconsistencies. He was head of Global Design, so he had some sway to address this. He formed C.A.R.E., looking to create a shared framework that not only found efficiencies with the tech, but also improved the experience for our customers.

The Risk group was centered in San Jose, and Compliance in Singapore. It was decided we’d send a small group out to Singapore for a meeting to tackle this large challenge. We shipped off a designer (Brian Folsom), writer (Janice Ishizaka), and a PM (Elizabeth Belda).

up and down the fidelity scale

A mistake that has been commonly made in design is to see fidelity as a linear progression (from napkin sketch to pixel perfect in a straight line). Now in 2026, most design organizations know better, but 10+ years ago that was not the case.

For C.A.R.E., we went up and down the scale when we felt it was appropriate.

Content maturity and visual fidelity are not a three-legged race.

We swapped in and out high fidelity action items to see how customers interpreted the content.

We had this big cool project with Singapore, and I all I got was this kinda cute keychain.

a foundation

Ultimately our designs did not see the light of day. A new design leader came in before they were launched, and ushered in a completely different style. However, the most important part - evaluating the use cases and starting work on a technical framework - is the legacy we left the next team who finished the job.

Solve once, help many?

X-Y (2012 - US10775964B2)

I had been listening to customers complain about managing all their refunds and disputes. 14 years ago, automation was not standard, particularly for small merchants. So, in my evolving UX mind, I centered on an interaction to help solve the problem. I had been thinking about an efficient way to pair an action with a transaction line item. I took the idea to Egan Schulz, the mobile design director at the time. I wanted his expertise on selecting actions based on tapping where a column and row intersected.

Russell and I overlapped at PayPal around 2010-2013. During that period, I led a team of UED professionals through a reorganization design effort .




Russell was part of our task force and focused more on “what we had to gain vs what there was to lose.”
Trying to inject Operational Excellence into creative processes can be a recipe for disaster, but Russell helped us navigate the balance. 


Working with Russell and the UED team was one of my favorite projects at PayPal!

Ah, thanks Lou.

Lou is far more generous about my skills and contributions than I deserve - and while I made mistakes involved in organizational change - I both learned and provided some value.

I owe a debt of gratitude to a number of folks who helped me learn:

First, I want to thank William Clarke for giving me the shot to lead a design team at PayPal.

Much gratitude to the program managers and natural organizers - like Bernice Lee.

I learned a lot about design from a lot of people (Brian Folsom, Christie Lau, Jacqueline "Jac" Cisneros).

Rachana Rele was a source for much learning for both the design and research domains.

fútbol is life.

Our jobs at PayPal really mattered to us, and fútbol helped us balance out the stress of working in tech (at minimum we told ourselves that to justify our hours spent playing 🤣). eBay understood this - or more to the point the VP of HR Sal Giambanco did - as he was the one who greenlit the construction of the pitch.

There were 3 simple rules to surviving a soccer game at PayPal:

1. Give me the ball and get out of the way.

2. Do not listen to anyone giving you nonsense advice during the game like: “easy passes” …”back and forth” … or “we need runners!” … if they insist kick them in the soccer ball!

3. Be nice to people! …. before and after the game … never during!

So many great folks I met on the pitch. If I missed anyone, please let me know… I’m not connected to everyone on LinkedIn and I have a 56-year-old memory!

Bram Flowers, Mateo Graziosi, Germán Scipioni, Ruslan Timostsuk, PJ Balin-Watkins,Yani Brankov, Schubert Lobo

"PayPal taught me that innovation isn't a department — it's a mindset.

You were always either pushing an idea forward or killing one fast enough to try the next. Either way, you were moving.

Working alongside people like Russ reminded me that the best innovation comes from people who are genuinely curious.

the best swag

Darrell built out the PayPal product for Canada. This was a vast undertaking - and quite successful - and I supported him on one small project. He and Jonmichael Moy needed content support for the launch of Website Payments Pro, and I was doing content design at the time.

For my efforts they made me a personalized PayPal jersey. I break it out 2 times a year when I go to a Barracudas or Sharks game. My favorite piece of swag to be sure.

Me and my youngest at a ‘Cuda game.