Episode 3 | The Hidden Cost of Scaling Across Borders w/ Andrew Trout

Hacking Borders continues with Episode 3. Once a company can hire almost anywhere, "can we hire there?" stops being the hard question. The harder ones come after: why this market, what it really costs, and what the rest of the company has to have in place before the first offer goes out. This episode features Andrew Trout, Head of People and Talent at Odyssey, who over the last decade has scaled teams at Square, Goldman Sachs, Gusto and FalconX, across fintech, crypto and frontier AI. He and host Tony Le talk through what actually changes when companies scale across borders, and what talent leaders are rethinking in the AI era. In this episode: • Why the first question about any new market should be why: commercial reach, labor cost or a new product. • Why "20 engineers for the price of 4" no longer holds, and why the comparison has to go two or three levels deeper than "software engineer". • What time zones and always-on operations do to a team, and why a heavy Slack culture is not the same as working async. • How talent acquisition became T-shaped, with entities, payroll, offer letters and compliance now landing on the recruiting desk. • Why leaner, flatter companies make every hire matter more, and why adaptability now matters more than experience. • How backfill policies and manager incentives decide whether internal mobility actually works. • Why metrics like "regrettable attrition" can hide what is really happening. Episode chapters 0:00 — Intro & Andrew's background 1:42 — How TA and hiring have changed over a decade 6:32 — Signals that a hiring strategy can actually scale 11:58 — How companies choose where to hire: Square, Goldman, FalconX 15:16 — What leaders get wrong about distributed teams: time zones, async, Slack 20:00 — "20 engineers for the cost of four" and TA as an operational advisor 26:05 — Fully remote, PEOs, EORs and compliance surprises 29:36 — The pendulum back to the office & talent density 32:09 — What executives underestimate: delayering and hiring for adaptability 38:31 — Quality of hire, retention & internal mobility 44:22 — Regrettable attrition and vanity metrics 47:30 — Advice before scaling internationally for the first time 49:48 — Closing & where to find Andrew About Hacking Borders Hacking Borders is a podcast for Talent, People, and Engineering leaders building teams across borders. Hosted by Tony Le, a talent acquisition expert with more than 20 years of experience in software companies, the show explores the decisions, systems, and tradeoffs behind scaling global teams. Hacking Borders is made possible by CodersLink, helping companies build and scale engineering teams across Latin America. Follow us on substack: hackingborders.substack.com