I spent a decade on Square's developer platform — from designing its first public payments APIs to serving as Head of Product, Developers & Partners, leading product across a ~200-person organization. The APIs we built processed $17B+ a year in payment volume, and Block reported that nearly 50% of its mid-market volume (Q3 2022) came from sellers connected to the platform. I still ship working software most days.
Selected by Square's executive team to lead product for the Developers & Partners business — a ~200-person organization with a distinct P&L, operating in all eight Square countries. The portfolio ran from the public APIs & SDKs, developer docs and funnel, and the App Marketplace to developer monetization, in-person & online payments SDKs, and ML products. 16 direct reports; promoted six leaders across levels.
Keynote speaker at Square Unboxed 2023, Square's developer & partner conference. The era is a memo: Running the platform.
Designed and shipped Square's modern public payments APIs — Payments (2019), Bank Accounts and Disputes (2020), and Cards among them (the founding memo) — and led Marketplaces, the Stripe competitor we ultimately shut down; I can tell you exactly why. Championed and shipped Square's public GraphQL API (alpha, 2022), and drove the platform's developer-security work: OAuth revocation webhooks and short-lived, limited-scope authorization, both on Square's developer blog.
Founded the Payments Intelligence team, and built the transaction-cost data and custom-pricing capability behind Square's move upmarket. My team's transaction-cost models supported the first change Square ever made to its flagship 2.75% rate, and our ML models predicting per-transaction interchange cost were patented (US10402807). The full story: Knowing the cost of every payment.
Hired as a freight broker. Taught myself to code after hours and built a route-optimization program good enough that the CEO moved me into product. Went on to build and lead the 45-person product & engineering team whose web and mobile products supported Coyote — a $2.1B-revenue business — through its $1.8B acquisition by UPS.
The founding, the failure, the pricing engine, and the org — written as decision memos, not build logs: problem, insight, named trade-offs, honest numbers, and what I’d do differently. Five minutes each.
Developers weren’t a business at Square; I was chosen to build one. The API decomposition, the partner bet, and the SEC-filed result: nearly 50% of mid-market volume (Q3 2022) from sellers connected to the platform.
Read the memo → Decision memo · 2018 – 2020Square invested $25M in Eventbrite; we shipped twelve APIs and a ten-marketplace alpha. Then I recommended shutting it down — and I can tell you exactly why. The owned failure, accounted for structurally.
Read the memo → Decision memo · 2016 – 2019Square charged 2.75% for everything and couldn’t see per-payment profit. Cost data, patented interchange ML, custom pricing behind the move upmarket — and the first change ever to the flagship rate.
Read the memo → Decision memo · 2022 – 2025Head of Product for a ~200-person business: the ML recommendations bet that beat a doubled north star, the operating-model rewrite that unstuck years-in-alpha products, and the feedback that made the job possible.
Read the memo →Promoted six leaders across levels, including two people I brought into product from customer support and account management. I ran Square's PM mentorship program, conducted more interviews than anyone in the Developers & Partners org in 2024, and managed 16 direct reports across product and platform operations.
The story I'd tell first: a week before a major launch, a conflict between the docs and engineering teams escalated to me, each side certain the other was the problem. The launch wasn't the problem — the teams had turned tribal — so instead of ruling on the escalation, I coached the two leads and ran a joint offsite. Not a single similar escalation since.
And the record travels: 40+ engineers I helped train now work at Google, Palantir, Amazon, and Bloomberg — that venture is just below.
Co-founded Eskalate (2020), the product arm affiliated with A2SV — a Google-backed 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 Africa and 120+ offers at the world's top technology companies.
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.
Payments infrastructure invented at Square and Block — each patent granted, each one click from the public record.
Advisor to founders building early-stage product and payments companies.
The cost of turning an idea into working software fell to almost nothing, and strategy and building stopped being separate jobs — so I kept doing both. Each of these is real, shipped software, built solo and end to end with AI-native tools, mostly on nights and weekends. It’s not a hobby; it’s how a product executive stays honest about what building actually costs.
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. 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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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.