I still ship most days.
I spent a decade building Square's commerce infrastructure, developer platform, and partner ecosystem. What started deep in payments, building the financial infrastructure backing Square's products and devices — led to platform leadership spanning all Square products and geos. I helped rewrite Square's core financial services into its modern public APIs, set direction leading to today's public developer offerings, and led organizations as Head of Product, Developers & Partners. In my early days at Square, the platform was a bold bet. Ten years later, the platform processed $18B+ a year in payment volume (GPV) through its APIs and supported nearly half of Square's mid-market seller volume.1 The platform's ecosystem grew to a thousand managed Partners,2 thousands of app Developers, over half of new sales leads,3 while powering 71% of Square's enterprise Sellers.4 The platform has come to be known as Square's superpower.5
After years building the platform and guiding the products it powers, I was selected to lead product for Square's Developers & Partners business. The business: a ~200-person organization with a distinct P&L, operating in all eight Square countries.6 The public portfolio included Square's entire public developer surface:7 Seller commerce APIs across payments, banking, orders, catalog, customers, and staff; SDKs in seven languages;8 documentation and guides, sandbox, webhooks & eventing, AuthN/Z, GraphQL, mobile & web payments SDKs,9 developer monetization, the App Marketplace;10 developer support, and platform AI products.11
This portfolio was built on an invisible, but deep foundation. Our teams owned and maintained internal libraries, style guides, deploy and release processes, versioning, API governance, App review & launch operations — while maintaining public SLAs / SLOs. I was lucky to build teams with incredibly brilliant people who loved delivering a better tomorrow for each of our Sellers & Developers.
In 2019 I moved into the Developers organization, leading products across Square's public API portfolio and supporting AuthN/Z systems. Through partnership with key developers, we shipped Square's latest financial services as generally available public APIs and SDKs. While Square's Marketplaces offering was ultimately shut down (the story), this product's sunset helped refine focus on Square Sellers' greatest needs.
Sellers need connective tissue between their POS and essential services. By enabling Developers to deliver Apps directly to Square Sellers — small retailers quickly connected to their preferred shipping services, restaurants to on-demand delivery services,12 and more.13
Enterprise Sellers often need solutions tailored to their business.14 By expanding beyond payments to Square's broader commerce offerings (Square Online, appointments, inventory, customers, staff, loyalty, catalog15) — Sellers in need of custom solutions for their business were able to build their own, or hire an agency16 to get the job done. POWDR, for example, ran commerce across its ski resorts on nearly all of the platform's developer APIs.17 This was a direction many of us set and one still guiding the platform strategy.18
In this era we also changed how Square built APIs: product teams across Square designed and shipped their own public APIs — a surface spanning more than 30 commerce APIs.19 Our teams provided the standards, style guides, review processes, shepherding, and governance. Along the way, this included shipping Square's public GraphQL API (alpha, 2022)20 while driving the platform's developer-security work.21
Square hired me into a role tasked with growing the upmarket payments business. I founded the Payments Intelligence team, responsible for building the transaction-cost data and custom-pricing capabilities behind Square's move upmarket and across verticals. This team's transaction-cost models supported the first change Square ever made to its flagship 2.75% rate,22 and our ML models predicting per-transaction interchange cost were patented (US10402807). The full story: You can't price what you can't cost.
In 2017, I was chosen to lead product for Square's next big bet: public payments & financial Developer infrastructure powering online marketplace businesses, with Eventbrite signed as our hero customer23. Delivering a suite of services powering complex online marketplaces was some of the deepest technical work of my career: with colleagues across payments and the platform, we rewrote Square's core financial services so these same systems could serve Square's own engineers and outside Developers alike. This meant shipping a broad set of financial capabilities marketplaces and other developers demanded, like multiparty settlement,24 while laying the foundation of Square's modern (V2) API surface which launched publicly over the following years: Payments (2019), Bank Accounts and Disputes (2020), and Cards among them25.
Coyote — Chicago's technology-first freight brokerage — hired me as a freight broker in 2012. I taught myself to write code after hours and built a multi-shipment route-optimization program addressing carriers' needs when direct routes weren't an option — work contributing to the service recognized with a 2012 Chicago Innovation Award.26 After proving the model with our production fleet, Jeff Silver (CEO) moved me into product to improve Coyote's technology suite. Our teams shipped Coyote's new customer-dedicated web Transportation Management System (TMS), automated carrier payments and improved route visibility through Coyote's carrier facing mobile App, and delivered machine-learning shipment recommendations to optimize carrier routes. Part of this work is preserved in a patent application I co-invented (US 2015/0213402: automated advance payments, dynamic load routing).
By the end of 2014 I moved into the role as Coyote's Software Development Manager, leading a 45-person product & engineering organization — while founding Coyote's first international development teams in Pune, India. These international teams grew to carry the majority of Coyote's codebase. The products these teams built — CoyoteGO, the carrier app we launched in 2013,27 the web freight platform, payments, and tracking systems — supported a $2.1B-revenue business through its $1.8B acquisition by UPS,28 then the largest acquisition in UPS's 108-year history.29
Anyone can list outcomes. I wrote these to show the work behind them — how the calls got made, what shipped, and what the public record says happened next. Five minutes each.
The products I'm proudest of are the leaders who shipped them. At Square I managed 16 direct reports across product and platform operations, with skip-level scope from L3 to L7 — building teams that ran their own rooms across all eight Square countries.
I promoted six leaders across levels, including two people I brought into product from customer support and account management — talent shows up before the title does. I ran Square's PM mentorship program and conducted more interviews than anyone in the Developers & Partners org in 2024: finding and growing people is the part of the job I protect first.
And the record travels. At Coyote I led the 45-person product and engineering org and founded its first international teams in Pune. Through A2SV, the first 40+ engineers I helped train now work at Google, Palantir, Amazon, and Bloomberg30 — that venture is just below.
Co-founded Eskalate (2020), the product arm affiliated with A2SV — a Google-backed31 nonprofit training Africa's top engineers — and served as A2SV's Head of Product, the title A2SV's own 2021 mission film puts on screen.
We trained by shipping real products — including TrackSym, a COVID-19 symptom-tracking app built with Ethiopia's Ministry of Health — and the first ~40 engineers we placed landed at Google, Palantir, Amazon, and Bloomberg. What A2SV has since grown into: 1,200+ engineers trained across 22 African countries and 120+ offers at the world's top technology companies.32
Strategic advisor to HeritageXplore, the London platform opening Britain's independently-owned historic houses — founded by Violet Manners, backed by Nick Hanauer and Anya Hindmarch, and covered by Forbes, Tatler, and Town & Country. I advise on zero-to-one product, payments, and engineering — I wrote the JD for the company's founding engineer and helped hire the role.
Payments infrastructure invented at Square and Block — each patent granted, each one click from the public record — plus the first application, co-invented in the Coyote years.
Advisor to founders building early-stage product and payments companies.
Building software is the part of the work I never gave up — I genuinely love it. Each of these is real, shipped software, built end to end on nights and weekends: to solve a problem in my own life, to keep my hands on the newest tools, and because nothing beats the feeling of shipping something people use.
Two of the largest onchain lending protocols, wrapped in a single REST API a fintech could actually ship against: OAuth-style keys, webhooks, rate limits, request logs, SDKs, a sandbox where no real funds move, and a self-serve dashboard. The developer-platform craft from a decade at Square, applied end to end to a brand-new domain.
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Drop a pin on any patch of ocean — even a spot you keep secret — and Shaka fuses satellite and model data into a live read of that exact point. One 0–100 score. Nothing else scores an arbitrary lat/long.
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Every other monitor sells you hardware and rents you your own data. ApneaWatch turns any pulse oximeter from Amazon into an overnight monitoring system: live vitals on any screen anywhere, thresholds calibrated to a child's age, and a one-page report a clinician can act on.
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83% of Android apps ask for the internet.33 Monk ships without it — so the OS itself guarantees your messages never leave the phone. It silences the noise across 25 messaging apps and answers on your behalf while you're heads-down. Open source, 1.4 MB, zero servers — a zero-knowledge core other developers can rebrand and build on.
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After a decade heads-down at Square, I’m taking my first real break — you’ll find me exploring with my family, while still finding time to ship most days. I’m exploring my next product-leadership role and advise a small number of founders. If you’re building something that needs a platform, get in touch!
