I spent a decade on Square's developer platform — from designing its modern (V2) commerce 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 was Square's entire public developer surface: 20+ commerce APIs across payments, orders, catalog, customers, staff, and merchants; SDKs in six languages; docs, sandbox, OAuth, GraphQL; the mobile payments SDKs; the App Marketplace; developer monetization; and ML products — plus the machinery behind it all: the API gateway, and the internal frameworks, style guides, and review process every Square team used to expose a public API. 16 direct reports; promoted six leaders across levels.
Keynote speaker at Square Unboxed 2023, Square's developer & partner conference. The era's two biggest product bets are case studies — self-serve app submission and the Add-ons extensibility program — and the era itself is a memo: The operating model is the product.
Helped design and deliver Square's modern (V2) public API surface — Payments (2019), Bank Accounts and Disputes (2020), and Cards among them (the platform 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.
Square hired me into a role which didn't exist yet; I found the problem and founded the Payments Intelligence team, which 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: You can't price what you can't cost.
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.
Two product case studies with the real UI to show — the shipped self-serve submission system and the Add-ons extensibility bet — and four decision memos: transferable systems taught through the Square work that forged them, anchored to the public record. Five minutes each.
Product case study · 2022
Most platforms gate third-party app launches behind partnership meetings. We rebuilt Square’s as a self-serve product — paved path, automated validation, review workflow, operational tooling — and typical partner launch time fell from ~90 days to ~20. Live in the Developer Console today.
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Product case study · 2023
Let third-party developers extend Square’s own surfaces natively, instead of rebuilding 90% of a product to add 10% of new value. Conceived, advocated, funded, and proved in alpha with external partners — paused in a 2024 resource shift, and vindicated by the industry since.
Read the case study →Decompose the company into public primitives, sequence them so each layer funds the next, keep every contract for a decade. The system behind Square’s V2 commerce APIs — 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 – 2020How to decide when to kill a strategic bet: structural pre-mortems, kill criteria on day one, and owning the shutdown case yourself. Learned the expensive way, on the public record — Square’s $25M Eventbrite bet, which I led and then recommended shutting down.
Read the memo → Decision memo · 2016 – 2019Pricing power starts with unit-cost visibility: reconcile what every unit cost, predict what the next one will, then build the pricing surface. The system behind Square’s patented interchange ML — and the first change ever to the flagship 2.75% rate.
Read the memo → Decision memo · 2022 – 2026At scale, how a platform decides and ships beats any single feature. Two systems from running product for Square’s Developers & Partners business: conviction spent on evidence, and delivery decoupled from architecture ambition.
Read the memo → Essay · Developer platforms in the agent eraAgents are becoming the first consumer of every developer platform. The API-design system from a decade at Square, and what changes when the integrator is a machine — evals as acceptance criteria, error semantics, docs an agent can parse. The contract still has to hold for a decade.
Read the essay →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.
I ran PM hiring for my org and wrote the interview guides it ran on. The system screens for two things above everything else: self-awareness backed by concrete examples, and rapid, high-quality decision-making — the rare great answer. Bad logic is a fault. Bad ideas are forgiven.
My red flags are boring on purpose: meandering answers with no narrative behind them, features nobody can tie to business impact, job hops blamed entirely on other people, and paper seniority which doesn't survive questions about the actual work.
The bar itself is a system. An on-site is expensive, so a screen recommendation is a claim you defend to the panel. The pipeline matters as much as the interview: I built trial and conversion paths for strong people from adjacent disciplines, which is where the two conversions above came from.
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 — 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.
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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Born in Detroit. I built my career in Chicago, moved to San Francisco for Square, and stayed. Away from a keyboard I run a small machine shop. Through CNC and manual tools — I design, engineer and machine precision freediving equipment from raw materials. Manufacturing taught me design is often the easy part, and one repeatable bottleneck obviates every other optimization. I've always wanted to understand how things work: biology, chemistry, structural engineering, technology, history.
After a decade heads-down on one platform, I’m taking my first real break — time with my daughter, and still shipping 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.