After almost 6 years leading the PayPal Checkout Platform engineering team (Longest job I’ve ever held!) I’m excited to share that I’m changing roles to Head of Venmo Core Services. This is a big opportunity and a huge change, so as I prepare and reflect, I’d like to share some of my key learnings throughout my time in Checkout.
Collaboration over Individual Excellence
When I first joined Checkout, I found myself in the middle of a toxic political battle that went up 3 leadership levels. I heard statements from my team like “Y team is incompetent,” “We always have rollbacks because of them,” and “Their leader has no background in technology.” These statements were huge red flags of a dysfunctional non-collaborative culture full of mental masturbation. Instead of helping each other deliver faster, higher quality value to our customers, we were too busy scrimmaging petty fights with each other. I knew I had to quickly adjust the team’s mindset. We started a culture of blameless postmortems where we all learn from our mistakes collectively, including this other team. I introduced the team to feedback as a gift first toward each other, and then later using the same methodologies toward the other team. I’m proud to say the Checkout Platform team is now one of the most ego-less teams in Checkout, which is critical to our success being in the mid-tier with teams above and below us. We always get kudos from other teams on our excellent collaboration skills.
Ego-less leadership also allows me and my team to hire the best talent, hire those who are better than us. I left Checkout with a successor who I admire and who I believe exemplifies this statement — Ravi Chandrasekaran.
I started adding this Survey monkey link to the footer of my emails for many years: Send Tess Anonymous, Actionable Feedback. While I receive very few actual survey submissions, this note sends the message that I’m open and wanting of your feedback. Over the years many people have reached out to borrow the idea and show their appreciation for the sentiment. I stole this from someone at Intuit. (Please send me a note if you are that person so that I can give you credit!)
The Power of Human Connection
My very first job was hostess at a Chinese restaurant in Los Angeles. One day, an entitled, demanding customer walks in the door. Upon realizing their name is not on the waitlist, they demanded to speak to the manager. I was taken aback to see the manager give them the upmost customer service: Pulling up a chair inside the crowded wait room, offering some tea while they wait, and slotted them in before the end of the line. The most important thing I learned from that day is the customer is always right. I worked many side jobs in high school: Hostess/waitress, Sales rep on EBay/Amazon, Data entry/automation for an Import/Export company. It doesn’t matter where you work, this rule applies across the board. It’s never about you, and it never hurts to treat everyone how you want to be treated in return, no matter how entitled they are. I’d extend this learning also to treat coworkers like customers.
1st Impressions Matter — Trust is hard to [re]build and easy to lose. The first time you meet someone is prime time for setting the tone for the rest of your working relationship. Be prepared going into meetings, which many times is the first time you meet someone new. I set aside time every morning to plan my day, which sets the rest of my day up for success. The same tip extends to a related one: Dont skip 1:1s. These meetings are a small time investment, but they send an important message: “I care about you.”
Human Connection is also why customer empathy is so important, especially when you’re sharing a vision and strategy with a group of people expected to rally behind it. We’re all strongly motivated by emotions. So, when your Why speaks to someone else’s joy or pain, it can move mountains more than just a bare list of numbers or priorities can.
Data is King
Using the left brain is just as important as the right. Going through puberty in high school with overactive emotions, I had an internal battle: Which side is the better half, logical or emotional? I came to a conclusion that both sides are equally important, complementing each other. The right/emotional brain gives you that human connection inherent in all of us. The left/logical brain helps make sense of it all in a common language. This allows us to generalize individualism so that we can solve problems that appeal to the masses, to a larger group of similar people. When going into a negotiation room, equip yourself with as much data as possible because they are facts that speak to everyone equally.
Sometimes, however, a large number of data points can become overwhelming or hard to prioritize. This last year in Checkout we started KPI scorecards with around 20 different metrics and was told all managers would be measured on these KPIs. How do you decide which of the 20 to focus on? This simple framework worked wonders: Classify them into input and output metrics. By short-listing a set of north-star metrics — Active users, Revenue per Active, Conversion Rate — You can group all the other metrics as inputs to these. This also makes it easier to measure things that may not typically show up as a KPI such as “Number of clicks on this flashy new button”.
Confidence through Preparation & Persistence
When I first joined Checkout I asked my new manager what’s the secret to success? He said “Strength in leadership.” Immediately, I imagined myself doing a barbell shoulder squat with three fat 45 lb plates on each end, gritting my teeth, my face red under strain with veins popping out at the corners. While Strength may be the perceived output, I learned that the secret inputs are being extremely prepared with data and reasoning, as well as having the perseverance to stand your ground when no reasonable alternative data is shared. I’ve incorporated The High Performance Planner into my daily routine and it’s helped me always come prepared for each and every conversation planned for the day ahead. I highly recommend it!
Always be learning — No matter whether you’re a people manager or a technical leader, our craft centers around technology. By continuing to educate yourself with new technology (AI/ML, Cloud Computing, or Crypto), we continue to offer value to our employees, shareholders, customers, and, in turn, ourselves.
Wellness
After the events of the Covid-19 Pandemic we all talk about wellness like it’s a luxury or a perk, that’s readily taken away once we’re back to the office. In reality, wellness is a necessity. It means we put our own oxygen mask on first, because, like on an airplane, if you can’t help yourself, you wont be able to help anybody else. Wellness to me means I don’t compromise on exercise, daily meditation, and time with my loved ones.
Wellness also means sometimes saying no and setting boundaries. Say no when you know in your heart that a yes would mean no anyway. Say no when it means compromising on other higher priority commitments, including your own wellness. Being ok with sometimes running at 60% because you’re under the weather. Or running at 60% now because the next bout of push may be at 150% in another couple of hours. Saying no can also mean saying “not today.” I found that if I add more than 3 things to my daily todo list, I rarely accomplish more than 3. Being honest with myself on these facts help me with the daily self-appreciation needed to live a life with gratitude and joy. Yearn to undercommit and overdeliver, and do this for yourself as well as others.
Please drop me a note if you find any of these tips useful or if you’d like to hear more about these topics. What are some of your top reflections on the job?
