The posting
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 approach to operating in new jurisdictions
- Coordinate with local counsel and build the external network we need
- Advise on entity structure, licensing, and local compliance
💥 Example Projects
- Negotiate and close a Series B with governance provisions that protect founder control
- Build our AML programme from policy through to operational implementation
- Draft the MSA template for enterprise MoR customers and negotiate the first ten deals
- Assess EMI equivalents in three new markets and recommend our licensing approach
- Review Visa/Mastercard scheme obligations and ensure our payment operations comply
- Manage external counsel in Brazil on local regulatory requirements
- Structure our entity approach for US expansion
🧱 What We're Looking For
Ideal background:
- In-house legal at a payments company or fintech (Adyen, Stripe, Checkout.com http://Checkout.com, Revolut, Wise, Nuvei)
- Deep experience with EMI/PSD2 and payments regulation
- Commercial contracts in B2B or enterprise contexts
- AML programme design and implementation
- Fundraising and corporate governance
Bonus:
- Experience with international trade, customs, or cross-border commerce
- Exposure to tax-related regulatory frameworks
- Multi-jurisdictional licensing or market entry experience
Signals we care about:
- You draft and negotiate, not just advise
- You can explain scheme rules, interchange, and chargeback liability without hesitation
- You've built AML or compliance programmes, not just inherited them
- You've been through funding rounds and know what matters in term sheets
- You're comfortable with ambiguity. Startups don't come with playbooks
- You want to own more than legal. Compliance, regulatory strategy, commercial confidence
- Bias for action. You solve problems, you don't just flag risks
What this role is not:
- Not a pure corporate/M&A lawyer
- Not someone who only reviews and advises
- Not a "department of no". We need judgment, not just risk flags
- Not someone who needs a large team or defined processes to be effective
🚀 Why This Role Is Different
Most legal roles at startups are reactive. Reviewing contracts, flagging risks, managing outside counsel. This role is different.
You'll build the legal and regulatory infrastructure that lets Outpost operate as Merchant of Record globally. You'll shape commercial relationships with enterprise customers. You'll navigate the regulatory complexity of payments, tax, and international commerce and help us do things competitors can't.
If you want to grow beyond legal into compliance, regulatory, and commercial leadership, this is where you do it.
🦾 Outpost Team
Our team were leaders at Revolut, Airwallex, Adyen and Wayflyer, and we're backed by top-tier investors who have built or backed some of the world's leading fintechs.
🧾 What We Offer
- Equity and salary in a well-funded startup
- Ability to own your work and move fast
- Direct access to the CEO and founding team
- A global mission with real impact
- Low politics, high output
- Chance to grow beyond legal into compliance and commercial leadership
- A culture of builders, not talkers
🧭 Working Style
We work together in person in Amsterdam & London. We believe the hardest problems, especially ones involving regulatory judgment and commercial negotiation, are solved in the room.
🌎 Reach Out
Learn more
Outpost Culture http://notion.so/Outpost-Culture-18aa047bb9af800b8f6ff5f5c83174b1?pvs=21
Outpost founder https://www.littlegoatlabs.com/
Outpost is where the hard problems are. If you want to build the legal foundation of global commerce infrastructure, we'd love to hear from you.
Bonus points if you hassle us on whatsapp.
