10 former Square payments leaders
These ten people led payments teams or payments work at Square and have since left the company. A reader can learn how payments work was run at a company like Square from people who did it there.
Professionals to explore
Dareyn Stilwell
LinkedInExperience: Payment Product Partnerships & Enablement · Square
Dareyn Stilwell is a former Payment Product Partnerships & Enablement lead at Square, where the role ran from 2019 to 2025, and the profile highlight for that role describes leading the team that worked with payment networks, acquirers and service providers. Dareyn Stilwell has been Director, Financial Partnerships at Airwallex since 2025.
Justine Korpi
LinkedInExperience: Head of Product, Square Payments + Point of Sale · Square
Justine Korpi is a former Head of Product, Square Payments + Point of Sale at Square, holding the role from 2023 to 2024, and was Head of Product, Square International there in 2024 and Head of Product & Globalization, Square International from 2024 to 2026. Justine Korpi has been Head of Product, Pay Group at Gusto since 2026.
Kevin Wei
LinkedInExperience: Senior Product Manager, Payments · Square
Kevin Wei is a former Senior Product Manager, Payments at Square, holding the role from 2023 to 2025, and the profile highlight for that role describes owning money movement for Square Payroll. Kevin Wei was Product Manager, Payments Risk at Coinbase from 2021 to 2022 and has been Principal Product Manager, Productivity at ServiceTitan since 2025.
Kyle Callender
LinkedInExperience: Payment Operations Manager · Square
Kyle Callender is a former Payment Operations Manager at Square, holding the role from 2016 to 2019, and held tax, operations and financial analyst titles there from 2011 to 2014. Kyle Callender was Vice President - Head of Payments at Monzo from 2019 to 2022 and Director - Payment Operations at Yapstone in 2019.
Layla Liang
LinkedInExperience: Lead Product Manager, Payment Onboarding · Square
Layla Liang is a former Lead Product Manager, Payment Onboarding at Square, holding the role from 2023 to 2025, and was Senior Product Manager, Payment Onboarding there from 2022 to 2023 and Group Product Manager, Growth & Identity from 2025 to 2026. Layla Liang has been Director, Product Management at Ripple since 2026.
Samina Hussain-Letch
LinkedInExperience: Head of Payment Partners & Operations, UK · Square
Samina Hussain-Letch is a former Head of Payment Partners & Operations, UK at Square, holding the role from 2023 to 2025, and was Head of Payment Partnerships and Industry Relations, AU there from 2020 to 2023. Samina Hussain-Letch has been Head of Europe & UK Payments and Card Acceptance at PayPal since 2026.
Sean McClain
LinkedInExperience: Product Manager - Payments · Square
Sean McClain is a former Product Manager - Payments at Square, holding the role from 2021 to 2023, and was Product Manager - Square Point of Sale there in 2023 and Product Manager - International Development from 2023 to 2024. Sean McClain has been a Product Manager at Carrot since 2025 and is based in San Francisco, California.
Sudheer Anne
LinkedInExperience: Head of Engineering, Remote Payments · Square
Sudheer Anne is a former Head of Engineering, Remote Payments at Square, holding the role from 2021 to 2024, and was Engineering Manager of Managers, Invoices there from 2019 to 2021 and Head of Engineering, AI and ML in 2024. Sudheer Anne has been Head of Engineering - Capital Core at Stripe since 2026 and was Head of Engineering - Fintech, Mobile at Gusto from 2024 to 2026.
Thomas Isaacs
LinkedInExperience: Head of Strategic Payment Partnership, Australia · Square
Thomas Isaacs is a former Head of Strategic Payment Partnership, Australia at Square, holding the role from 2024 to 2026, and was Manager, Payment Partnerships there from 2022 to 2024 and Program Manager, Risk from 2020 to 2022. Thomas Isaacs has been Director, Head of Acceptance Products at Visa since 2026 and is based in Melbourne.
Travis Raila
LinkedInExperience: Lead Product Manager · Square
Travis Raila is a former Lead Product Manager at Square, holding the role from 2020 to 2024, and the profile highlight for that role describes being the founding PM of Square Credit Card, a business credit card backed by AmEx, and leading product strategy, partner integration and launch execution. Travis Raila has been Member of Product Staff at Instagram since 2024 and was Senior Product Manager at Uber from 2019 to 2020.
Choose the right perspective
Match the person's area to your question, since payments product, payment partnerships with networks and acquirers, payment operations, onboarding and payments engineering roles each saw a different part of seller payments. Check the years of their Square role and where they work now, because payment products and network rules change quickly.
Questions to take into the conversation
- 01How did you work with card networks and acquiring partners when launching payments in a new market?
- 02Which measures told you whether seller payments and onboarding were working well?
- 03What would you build first for seller payments at a younger company with a small team?
Reaching former Square payments leaders
How can I contact one of these former Square payments leaders?
Pick one of the 10 people on this page and choose "Book a paid call", or describe your project to find others. You offer a fee for a 15-minute call or a written answer, Instant Expert finds the person's work email and sends the invitation, and they decide whether to accept. The list covers 1 company: Square, based on profile data retrieved on October 24, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach former Square payments leaders?
You choose the offer, starting at $5 per person. The offer is what the person receives, and Instant Expert's fee is added on top, so a $100 offer costs you $125. The fee is 20% of what you pay. You're charged only when the person books the call or sends the answer.
What if they don't reply?
You pay nothing. Instant Expert sends follow-up reminders, and if the person hasn't booked or answered within 7 days, the request expires and any hold on your card is released. You can invite several of the 10 people on this list at once and cap your total spend, so you pay only for the ones who accept.
Can an AI agent ask one of these former Square payments leaders a question?
Yes. An agent with a USDC wallet on Base can ask one question without an Instant Expert account. It names the person, for example by the LinkedIn URL on this page, and pays per ask over x402 (HTTP 402). The person answers in writing or by voice note, and if nobody answers within 7 days, the payment goes back to the wallet automatically. Claude and ChatGPT can do the same through the Instant Expert connector: setup is at /docs/mcp for Claude and /docs/chatgpt for ChatGPT. x402 docs
About this directory
This is a professional research starting point based on business profile data retrieved on . Titles and companies reflect that source snapshot; roles marked former had ended by then. Check the linked profiles for current details. Inclusion does not imply Instant Expert membership or availability.
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