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HEAD OF LEGAL @ OUTPOST 🌍 About Outpost Global expansion is broken. Without a local entity, conversion rates fall, costs rise, and compliance gets messy. Outpost fixes it. Selling internationally is a maze of tax, payments, and operational friction. Most brands avoid it or expand slowly and expensively. Outpost is your modular back office for global commerce. We operate as Merchant of Record for digital and physical goods across 58+ tax jurisdictions. That means we own the full stack: payments, tax, compliance, and customer experience. Outpost recently raised a €15M Series A (bringing total funding to €17.5M) from investors including Index Ventures, Balderton Capital, Ribbit Capital, Seedcamp, and Better Tomorrow Ventures to scale the platform globally and accelerate product development. Sell anything, anywhere. Without compromise. 🧠 The Role This is a Head of Legal role for someone who wants to evolve and scale the legal and regulatory foundation of a fast-scaling fintech, not manage process in a mature organisation. Legal at Outpost operates as part of the Tax & Legal team, reflecting the fact that our platform sits at the intersection of legal structuring, indirect tax compliance, payments infrastructure, and global commerce. You'll report to the Head of Tax & Legal and work closely with the CEO and leadership team, owning legal across the business: commercial contracts, payments regulation, AML, corporate governance, and fundraising. You'll handle most work in-house and manage external counsel in new jurisdictions as we expand. We operate at the intersection of payments, tax, and global commerce. That means Visa/Mastercard scheme rules, EMI and PSD2 frameworks, AML programme design, and commercial agreements with enterprise customers. You need to be fluent across all of it. This isn't a "review and advise" role. You'll draft, negotiate, build programmes, and make judgment calls. You'll shape how Outpost operates in new markets and help us navigate the regulatory complexity that comes with being a Merchant of Record globally. 🧗 What You'll Get Yes, the work is intense. But in return, you'll get ownership most lawyers never experience. You'll further develop and scale our legal infrastructure legal infrastructure, work directly with the CEO on high-stakes decisions, and shape how we scale internationally. If you want to grow beyond pure legal into compliance, regulatory strategy, and international commercial operations, this is the role to do it. 🧩 What You'll Do Commercial & Contracts - Own all commercial agreements: MSAs, merchant contracts, partnership deals - Draft and negotiate directly, not just review - Build contract templates and playbooks that scale - Support enterprise deals where legal diligence is part of the sales process Payments Regulation - Own our regulatory posture across EMI, PSD2, and equivalent frameworks globally - Advise on scheme rules (Visa, Mastercard) and ensure compliance across our payment operations - Navigate regulatory requirements as we expand into new markets - Work with external counsel in new jurisdictions and manage those relationships AML & Compliance - Oversee and continuously improve our merchant onboarding and monitoring framework, including risk classification, ongoing monitoring, and escalation processes aligned with scheme rules and regulatory expectations - Ensure alignment between merchant onboarding, transaction monitoring, and third-party requirements (e.g. acquiring banks, PSPs, and card schemes such as Visa and Mastercard) Corporate & Governance - Lead legal on fundraising: term sheets, investment documents, board matters - Own corporate governance as the company scales - Manage cap table, equity, and corporate structure across entities - Handle board documentation and investor reporting obligations International Expansion - Assess legal and regulatory requirements for new market entry - Structure our appr