‘We’ll Be Unstoppable’ — How Pinwheel’s Head of Engineering Empowers Her Team to Thrive

Jennifer Chao shares her approach to leadership, cultivating culture and inspiring growth.

Written by Olivia McClure
Published on Dec. 08, 2023
‘We’ll Be Unstoppable’ — How Pinwheel’s Head of Engineering Empowers Her Team to Thrive
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As an early-stage startup, Pinwheel lacks the reputation, resources and advantage of a larger, more established organization. 

But none of that matters to Head of Engineering Jennifer Chao, as she believes that the company has two key ingredients for success.  

“We have talent and agility, and if cultivated well, we’ll be unstoppable,” she said. 

Since its inception in 2018, the company hasn’t slowed down in its efforts to help consumers access better and fairer financial products. And according to Chao, this means engineers who join the startup get to help build innovative technology with real-world impact. 

Chao explained that to empower the company’s engineers to help shape the future of fintech, she strives to lead by example every day. When she’s not openly discussing business needs during weekly meetings, she’s identifying growth opportunities for team members, ensuring they have access to the individuals and resources they need to pursue their career goals.

Chao may have joined the company a mere three months ago, but she has already had a major impact on her team’s culture and is eager to continue building it up, drawing on her own leadership vision to do so. And while many elements of the company have stuck out to her since stepping into her role, she has been most impressed by the people she gets to work alongside every day. 

“The best thing about my onboarding has been confirming that my team is as talented and hungry as they seemed during my interview process, so cultivating our high-performance culture is going to be a lot of fun,” Chao said. 

Below, Chao describes her approach to leadership, culture and growth and shares the value proposition for those interested in joining Pinwheel. 



Guided by the aim to create a fairer financial system, Pinwheel offers an API platform that’s designed to securely update direct deposits and access income data. By unlocking the data that exists within payroll systems and providing direct access to paychecks, the startup aims to help entrepreneurs build financial products that increase access for the underserved while supporting its partner fintech organizations, banks and lenders.


What’s your vision for leading your team?

Jennifer Chao
Head of Engineering • Pinwheel

My vision for Pinwheel’s engineering team is to ensure everyone knows what our strategy is for winning and how we know we’re making progress. Understanding this unlocks agency in determining how we get there. 

Instead of being told, “Ship feature ‘X’ on time,” I want engineers to be asked, “How do we keep our customers happy and make Pinwheel even more valuable for them?” Because at the end of the day, that’s what really matters, and I want my team to be focused on solving problems that matter.


How do you build team culture, and why is that important for the work that you do?

An important way to build team culture is to always offer context regarding what the business needs and what we should be focused on. This isn’t something that I wait to do in an all-hands meeting. I talk about it in daily standups, one-on-ones and everyday conversations to connect topics that can feel abstract with day-to-day work and decisions. 

I’m also big on leading by example. I’ll let my team watch me struggle with a hard problem and ask questions out loud to dig deeper in an area I don’t fully understand yet. My hope is that they’ll see that everyone is a work in progress, and anyone can become an expert.


“I’ll let my team watch me struggle with a hard problem. My hope is that they’ll see that everyone is a work in progress, and anyone can become an expert.”


How do you help your teammates pursue their professional goals?

The most important step is to have an explicit conversation to understand each employee’s career goals. Managers often skip this step and make wrong assumptions. Some employees are clear-eyed about their career goals, while others need help defining them. 

Once we’re on the same page, I weave in projects and conversations to support them in their goals. I’ll look for role models I know across the company or industry, and I’ll encourage people to guest star on other teams if there are opportunities to grow in ways that match their ambitions.



While there are many principles that Pinwheel team members embrace, Chao considers two in particular to be of utmost importance. “There are two values that I focus on when building my team’s culture: living an underdog mentality — being hungry, humble and curious — and having a strong sense of agency,” she said. Chao believes these traits are critical to have in an early-stage startup environment, where priorities and projects evolve quickly.


What’s the employee value proposition for those thinking about joining Pinwheel? 

Pinwheel has a meaningful mission: We’re building a new category of software that enables financial institutions, including banks, to offer better and fairer products to consumers, even those with no credit history. That makes Pinwheel a good fit for people who want to spend their time on work that matters in the real world.

Engineers who join get to have their hands all over the software lifecycle, from spinning up their own services to monitoring their work in production. We also have some of the smartest, most go-getter and caring individuals you will ever work with, and we know that surrounding yourself with a great team is one of the indicators of career success.



Responses have been edited for length and clarity. Images provided by Pinwheel.

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