Joining Skylight

After nearly four years at Block - first Square, then its sibling company Cash App - I made a thoughtful and grounded decision to leave in order to join an organization called Skylight to work as a Principal Product Designer in the public health space ✨


Skylight is a digital consultancy that helps government agencies deliver better public services, and I was drawn to how closely their operating values align to mine, the enthusiasm of everyone I spoke with during the hiring panels, and the meaningful impact their their team delivers.

I couldn’t be more excited to start working with a passionate, tight-knit team of technologists to help advance the tools and technologies that epidemiologists at the CDC use to solve some of our country’s most pressing public health challenges.

Why a Change Now?

Last year, I started examining the trajectory of my career and also how it aligned with my personal values and motivations. I was becoming less certain I was spending my skills and expertise in a space that was delivering meaningful value. When you’re spending 40 hours of your waking life feeling mis-aligned….well, it’s time for some soul-searching.

I’m not getting any younger, and I’ve been regularly thinking “what might the second half of my life look like?” I consistently came back to a vision of working in service of others, and started brainstorming the next steps on my path.

I ended up applying to a masters program in social work, and a masters program in clinical mental health counseling. And in November 2023, I was extraordinarily excited when I was accepted to both programs! I figured I could spend three years doing school part time on the weekends, another two years of post-degree supervision, and then after becoming fully licensed as an LPC or LCSW, I might move into private practice or start an affordable-care practice providing clinical mental health programs for underserved communities.

But I thought long and hard about what would be a long, slow pivot into an entirely different field. It’d be exhausting to juggle a full workload and another graduate-level program. And my husband works in mental healthcare, specifically within behavioral health and substance use disorder treatment in hospitals pulling 12-hour shifts in an emotionally charged environment, and I’ve learned a lot from him about what can be an incredibly rewarding, but also exhausting career.

So I took a step back, declined to move forward with both educational programs, and paused. Surely I could pursue something else that aligned closer to the trajectory I was already on, that leveraged the masters degree I already had, my years of professional experience as a designer and lead, and my ambitions for working for social good and public wellness. I chatted with some folks I consider mentors, and I really narrowed down what I felt motivated by and what was a non-starter.

And that’s where civic tech comes in. After interviewing with Skylight and their aforementioned team of talented, passionate and attuned professionals this year, it was a no-brainer to jump on the opportunity to work with their team of people who are really motivated by making positive change for the American people by positively influencing how the government serves folks in today’s digital world. I get to work in an impactful area, with incredible people, in an affirming and flexible working environment, and toward a mission and goal I 100% align with.

Leaving Block

And of course, starting something new typically means ending something else. I really value the time I had at Block, and I’m 100% sincere when I say I’ll miss my colleagues tremendously. I spent nearly four years collaborating with a bunch of amazing people, and their impact on me will never fade.

I got to meet and work with some of the most talented, funny, inspiring, passionate, creative, and supportive folks in my career. I’m also so lucky to have built a small but mighty circle of people who I consider mentors out of that group - I love that we connect regularly and I can bounce ideas off of them to help inform the way I approach a problem.

But that’s the best part about working at a huge company - you do meet so many amazing people, and you build a network of incredible, talented, kind, likeminded folks. It’s indisputable that the last ~4 years here has strengthened me by fire (I mean let’s be real, working in a huge company obviously has its challenges) and I’m coming out of my time there with a refined sense of leadership and design principles, a sharpened concept of how I’ll want to lead teams and departments later in my career, and what makes a positive or negative culture as you ebb and flow through change. More reflection on this later.

Onward!

KM