I found a good flow at Square, which is why I’ve stayed for 7.5 years (blog post about career before Square + odd jobs before college graduation). I can break down my time into a few chapters: payments terminal (2 years), ecosystem onboarding (4 years), food & beverage (1.5 years).
Square Payments Terminal – Product Analyst (2017-2019)
In my first role, I felt like I was on the ‘inside track’ of tech, in that I learned how things were ‘supposed’ to be set up in a strong, established tech company. I worked on a product team with a Product Manager (PM), Product Marketing Manager (PMM), a Designer, an Engineering Manager (EM), and a team of engineers. I learned more about tech product development: nuanced decisions / bets / strategy, product discovery research, experimentation, more specific marketing (new customer types / segments, cross selling / ecosystem products, etc), product launches across different platforms (iOS, Android, mobile vs desktop web, etc), feature logging, product roadmap planning, scoping, and adapting. I also learned about ETLs (Airflow), Python, insights ML (regression analysis, K-means clustering), Git, Looker, various databases (Vertica, Snowflake), using a Mac terminal, deploying/updating a developer environment, Jira, scoping projects, managing dependencies, and collaborating and searching for information in slack.
As a product analyst I learned to be part PM / domain expert and part data analyst where my ultimate goal was to add value to my product space via data (analytics hierarchy of needs). In product storytelling I found my niche around strategy and insights I didn’t know I was looking for. Terminal product also gave me an opportunity to work on broad areas of the business: I got to work on payment disputes functionality in our point of sale app, product discovery work around Terminal API, payment analytics on a major pricing change (article), and even work on US Census data that later ended up in Mary Meeker’s 2019 internet trends (slide 55). I also learned a lot of soft skills around communication including giving feedback upwards and across, working with different functional stakeholders, scoping out larger projects collaboratively, executive summaries / takeaways, and giving status updates even when I am mostly hyper-focused on a project. I learned what language and storytelling led to action and influence. This role expanded my capacity to frame problems – beyond smaller tasks / tactics to broader direction and strategy. I attended tech talks to learn from peers and joined Toastmasters to build confidence in public speaking. Over time, I grew very comfortable presenting and speaking up in meetings to stay engaged.
Some nifty, random tips and thoughts I remember from working with such talented product people:
- If engineers don’t understand why they are building something they won’t build it right.
- Often people think things go: ownership -> plan -> execution. When in reality they often go: plan -> execution -> ownership.
- Your capacity shapes the possibilities you see.
- I organize all my work in a spreadsheet with simple metadata, linking Jira tickets and including a category and completion dates – so I can find something I worked on six years ago in seconds.
- I also learned I need to make 1 on 1 docs and take notes / share summaries from a meeting afterwards to retain and build my internal understanding. Otherwise I would lose most of the specifics of what happened in meetings. Writing thijgs down was how progress was saved.
- Sometimes you don’t know your own capacity until someone you look up to leaves and you try to become that person in the room.
I got the sense that larger companies were made up of smaller companies and tribes, often having different languages and terminology. Big projects and migrations helped find tech debts, long held misunderstandings, and uncaught mistakes in old systems – but they required a vision and sponsorship, and data and metrics were often a common language folks could align on. The longer I stayed at Square, the more I realized when someone really strong I worked with left the company, people would start to ask me questions instead. I started using this analogy of being in a room with a hundred people of various ages, where suddenly a bunch of the oldest people leave, and though I am no different, the responsibility diffuses through the people still here. My first two years at Square felt like earning my unofficial MBA (working with so many MBA folks and learning how executives make decisions in real-time given resource constraints, etc).
As a bonus of working in a Bay Area tech company, I also got to visit a bunch of random SF offices (Slack, Uber, Dropbox, etc) and was finally able to pay off my student loans (5 years after graduating). The commute from Oakland to SF was time consuming, but the vibes at the Square office were amazing.
Reading Books / Audiobooks
Square has a really strong reading culture. People I respected were always recommending books (e.g. soft-skills reading list). I rarely read before Square, but here I started following through on almost all book recommendations. What really changed things for me was audiobooks, which let me read on my commute, while doing chores, etc – I used to value listening to audiobooks below reading physical books until at some point I noticed that I could actually recall more information from audiobooks (content and which books I read). Maybe it was my ADHD, but I seemed to have a hard time focusing while sitting down – I needed to move around to think. I started writing reviews for books I read on Goodreads and really got hooked. In 2018 I read 100 books, and in 2019 I read 94. In just two years, I had read more books (and audiobooks) than in the previous 27 years of my life (blog post on top 5 books by year). I felt so liberated when I finished an 800 page (37 hour) audiobook (The Brothers Karamazov by Fyodor Dostoevsky) – I had been trying to read it since college after a philosophy professor said to me when I was feeling existentially lost that it contained everything I would need to know about life – but I just could not sit and focus long enough to make it past a few chapters.
Square Ecosystem Onboarding – Product Data Scientist (2020-2022) – Part 1 (Getting Established and Getting Lost)
I joined the ecosystem onboarding team a few months before the March 2020 Covid pandemic shut down. I remember our last meeting before the work from home mandate started, we had no idea how long it would be, but many were aware that it was not just going to be a few weeks…
I joined the onboarding team after it had moved from a specific product team to a neutral, seller experience team. More broadly Square had a General Manager (GM) structure, with multiple orgs that focused on specific products like Square for Restaurants, Square for Retail, Developer APIs, Payments, etc. Moving onboarding to a new org emphasized that it was meant to prioritize what was best for Square, not a specific product team. I was able to leverage my time at Square to help navigate the ~35 product teams in the ecosystem, including their quirks, where they fit well together, and where they competed for space – later writing up an ecosystem history doc from my conversations over the years to help unify some of the common tribal language across different product organizations. While my time working on Square’s payments terminal was a collaboration across product teams, ecosystem onboarding became a collaboration across teams of teams.
My first year, I worked on ALL Square onboarding across ALL platforms – that includes general web onboarding (desktop and mobile), product specific variant web pages, and the mobile (iOS and Android) software development kit (SDKs). The idea was to prioritize the Square ecosystem over any specific product, and balance a smooth and simple onboarding process (e.g. identity verification for payments activation, hardware ordering, etc) with an introduction to the broader ecosystem and potential upsells and upgrades. This was the team owning the experience for nearly all new merchant signups across multiple countries (mostly US), a product intent model, and a setup guide after the onboard web pages or app screens in our merchant web dashboard. The space was pretty broad – and very quickly my focus became on building a clear framework to create feature logging, experimentation, and dashboards as well as documentation for folks to self-serve data on the platform.
Square was growing rapidly in 2020-2021 – so I did a lot of interviewing (reaching 200+ interviews at Square). At this point in my Square career I had become a pretty established product data scientist (after 4+ years), so I spent more time onboarding folks, mentoring, and working with the neurodiversity community (Linkedin spotlight) and a few extracurriculars (e.g. revamping external DS blog posts). Folks were also pretty stressed about the pandemic layoffs and madness of the broader world when they joined Square – so I tried to help make Square feel safer for those around me and leverage my tenure to help teach others in a remote culture. I began to develop a reputation as a ‘clarifier’ in different projects – focusing on teaching and documenting as a way to better understand some complex systems. I also had developed enough trust in relationships to become pretty productive in most spaces and enough experience to start becoming a leader in a lot of projects. I started seeing corporate alignment/politics as all the 1 on 1 meetings before the big meeting. I spent a lot of time aligning success metrics across different product teams (ecosystem success metrics blog post) – which felt sort of like building a home owners association (HOA) policy, where some people wanted X and another wanted Z and I tried to find common ground to settle on Y.
Around 2022, after 2 years in ecosystem onboarding, I started to get really lost. I didn’t know where to go from here and had never stayed at one company or place so long (longer than college even). I did some random things in my existential confusion like manage an intern to test the waters and see if I wanted to become a manager, and I become a PM for a month after someone sponsored me to potentially join their product team. It was also hard for my lead to help me since I didn’t know what I wanted. I also started sharing my writing more (e.g Square blog post on success metrics for product analytics), which later led to this blog!
During this time, the tech bubble appeared to have finally burst (blog post), and I was glad Square had a clear monetization strategy from day one – something I always appreciated about the company. I realized also that there was no clear end destination I was going towards, like executive or manager or something – there were just a process of assessing options around me and making a decision for what to do next. I had also let myself become ‘out of shape’ with interviewing – as I wasn’t sure if I wanted to still be a data scientist at this point (note: staying sharp blog post). Being lost was difficult and frustrating, but it led me to develop a better framework for my own career and wants, whereas a sense of progress was more clear and set up for me earlier in my career. Career growth went from progressing up a skill ladder to more of a tree, where each branch was a focus that was further along only if I wanted to go that direction.
Note: this is also the time when the product analyst role became product data scientist (partially to distinguish from business intelligence analysts and machine learning engineering roles), and Square inc became Block inc.
A Detour on Therapy
Shortly before the pandemic, I started more seriously diving into cognitive behavioral therapy (CBT) therapy. I had never felt I had to space to do so before this time in my life. Therapy took a little focus away from work, but was a very strong investment in my identity, relationships, and balance. I learned how better to recognize when I was emotionally dysregulated as well as more subtle interpersonal dynamics. I noticed how anxiety-driven productivity was often praised, but struggles with depression were less openly acknowledged – despite often being the other side of the same coin. I journaled after most therapy sessions and over time started to feel like I was seeing in color after years of seeing in black and white (e.g. blog post I wrote up on debugging soft skill gaps). As an analogy I like to describe the impact of therapy as having a jar of water with a bunch of dirt settled at the bottom, therapy shakes up the bottle and explores all the pieces that had been settled for a long time which had given the appearance of showing the whole picture as clear water. Understanding my childhood identity and history better helped me feel more confident and see reality (and others) more clearly.
Some random learnings from therapy and communication in relationships:
- Sometimes people mistake wants and needs. For example, you NEED to eat. But maybe you WANT to go to McDonalds. The NEED is non-negotiable, but the WANT is. You could eat somewhere else!
- When someone comes to me stressed about a problem, it is not inherently my problem. Similarly if they come to me angry about a problem, often times I perceive the problem as THEM, not whatever they are upset about, unless they can convey it to me in a way that lands.
- A really good quote from a college professor I had: ‘In every problem you cannot solve, there is a smaller problem you cannot solve: find that.’ Sometimes people are feeling emotionally/socially disconnected (i.e. a need is not being met). Though their conscious brain might be trying to solve a work problem, their subconscious mind is trying to solve the disconnection problem. Their cognitive resources are at odds. I think the pandemic/remote work has enhanced this, since some folks used to get that social need met by having lunch with coworkers, small talk with desk mates, etc.
- When I ask something in a channel, people instinctively want to help, but that distraction has a cost – so me being impulsive and sort of ‘using people’ to rubber duck and get started on a problem can be disruptive.
Ultimately therapy was a solid investment in my relationships, life, AND career. I am grateful I had the space in my life to invest that time and effort into self-awareness and emotional regulation. It helped me address problems more efficiently, communicate more directly, and better understand interpersonal dynamics.
Square Ecosystem Onboarding – Product Data Scientist (2023-2024) – Part 2 (My Data Science Comeback)
What drove my comeback into data science was a gradual recognition that I had fallen behind technically in my existential confusion and generally getting ‘out of shape’ in data science over the years. My value had become more specific knowledge around Square’s ecosystem and I had lost some industry data science technical skills like statistics and programming. Basically, similar to when I was at SoFi, I was wondering if I would be able to get my own job if I applied externally (discounting relationships and focusing purely on the technical bar). I decided to reinvest in my technical skills and adapt / commit to the more senior/staff data science role – mostly forming my goals based on external interviews and where I struggled the most.
I started focusing on my largest gap: technical skills, especially around statistics and python. I was aiming to get an ‘informal’ masters in statistics – where I felt comfortable navigating those types of problem spaces. I read a few statistics textbooks and wrote up some docs and asking peers for review (e.g. Essential probability & statistics concepts for data science). I started writing code and sharing in a public repo (Github). I started collaborating on more technical problems (e.g. taking over an onboarding production recommendation model in Python) and writing a few interviews (SQL, Python pair programming, etc) as well as creating criteria and standards for crowd-sourcing the submission of new technical screens. Later, with Block’s functional re-org (from a GM structure), I worked on revamping Square’s DS technical interview set and career ladder with some very strong technical DS peers (blog post on data science career progression).
This was partly an identity shift – committing to a deeper understanding of data science concepts (beyond just data analytics and product storytelling) – which helped me decide which projects to dive deeper into and which to let go. I thought deeply about which career areas has a low skill vs high skill cap, e.g. where are areas where 10 years of experience count more than 5? Thinking through what areas would be more fruitful for developing skills, i.e. which branches of that ‘career tree’ I wanted to climb (four graduate degrees I wish I could download into my brain) – given the reality of paint-drip people as opposed to just generalists and specialists. I also, with therapy, began to accept that I might lose some marketability for happiness and it is important to know my boundaries and principles and what I was more willing to sacrifice to reach certain goals (e.g. ironically you can sometimes go more in-depth mentoring people as an IC than a manager, because you don’t have to spend so much time dealing with the logistics of managing!).
Square Food & Beverage – Product Data Science (2024-2025)
2024 was a transitional year at Block, with a functional re-org from the GM model. The tech bubble had burst and it was clear before this point that Block inc’s stock was not recovering like some other tech companies had without some more drastic actions. During this chaos I was ready to move on after a little over four years on the ecosystem onboarding team – so I applied around and ended up in the food & beverage team (still within Square), where the company was still heavily investing and growing (competing with Toast). Here I worked on some pretty cool / high impact projects like the launch of the orders platform (including bar tabs), work on kitchen printer reliability (i.e. involving 3rd party printers, Square’s point of sale, and connectivity between the two), and continuing to revamp Square’s DS interview set and DS career ladder. I appreciated the technical depth of the restaurant problem space, the clear customer and business focus, and the team!
2025 has been chaotic so far (a family loss, political turmoil, etc), but all things considered I feel good about my career today. Maybe it won’t last, but I have confidence that my community and I can adapt. A lot of my career so far has been developing relationships, luck, and timing. I’ve tried to focus on the things I can control, like working to maintain good relationships, building up a solid sleep, exercise, and meditation routines as well as develop a more consistent ‘fitness’ around technical skills. Really I have no idea what comes next – I’m just trying to learn step by step and stay adaptive, curious, and reflective: I wanted to write up these few blog posts to re-ground myself in where I came from and what I learned.
I’m not going to cite all the quotes and collaborators and amazing people from my career at Square (the list is very long), but special shout-out to some mentors over the years: Xavier Shay, David Talach, Alyssa Henry, Mary Kay Bowman, Anne Yeung, Michael Higgins, Edmond Chan, David Feng, Inna Kaler, Vibhor Chhabra, Morgan Engel, David Oddy, Claudia Ng, Rachel Fisher, Prashant Jois, Alexander Statnikov, Victor Umansky, Giovanni Landini, Cynthia Johanson, Claire Meyer, Fan Zhang, Cy Villaflores Shaw, Rob Wang, Lisa Melnik, Christine Hsiao and many more.
Prequels: blog post about career before Square & odd jobs before college graduation
Daeus Jorento 