Outpost Technologies
Risk Global commerce is a regulatory minefield. Without proper risk management, you're one compliance breach away from losing market access, banking partners, or customer trust. Outpost needs someone to own this. We operate as Merchant of Record across 58+ tax jurisdictions, handling payments, tax compliance, and customer experience for digital and physical goods. That means we sit at the intersection of payments, regulatory compliance, financial crime, and operational risk - across dozens of regulatory regimes simultaneously. This is the first risk hire. You'll build the risk function from scratch. The Role This is a Risk Manager role for someone who wants to build like a founder, thinks like a regulator, and operates like an operator. You'll own risk management end-to-end - from identifying emerging regulatory requirements to designing controls, embedding them in products, and ensuring we can scale safely across new markets. You'll work directly with the CEO, engineering, product, operations, and tax to turn complex regulatory frameworks into practical, scalable risk management. This isn't a role where you write policies and file them away. You'll be in the weeds: reviewing product launches, debugging compliance gaps with engineers, working with banking partners, analysing transaction data, and making hard trade-offs between speed and safety. You care deeply about building things the right way. You want to enable growth, not block it. What You'll Get Yes, the work is intense. But in return, you'll get training and exposure most people wait 10-20 years to access. You'll be working on global problems, dealing with regulators and banking partners, and owning strategic risk decisions across payments, tax, financial crime, and operations - from day one. We won't handhold, but we'll coach you hard. If you're hungry, you'll leave this role with a world-class risk skillset and the ability to scale fintech products in the hardest markets. What You'll Do Own the risk function: Build Outpost's risk management framework from scratch (policies, procedures, controls, and governance) Identify, assess, document, and monitor risks across payments, tax, financial crime, and operations Set risk appetite and tolerance levels in partnership with the CEO and founding team Make the hard calls: what's acceptable risk vs. what could kill the business Enable safe growth: Work with Product and Engineering to embed risk thinking into new product launches and market expansions Conduct pre-launch risk assessments for new products, markets, and banking partnerships Design practical, effective controls that protect the business without slowing it down Ensure we can say "yes" to merchants safely (not just say "no" to risk) Be the regulatory expert: Stay ahead of regulatory changes across payments, MoR, tax, and financial crime in key markets (EU, UK, US, etc.) Translate complex regulatory requirements into clear, actionable guidance for product and operations teams Represent Outpost in discussions with regulators, banking partners, and payment processors Build relationships with external stakeholders and maintain regulatory credibility Manage financial crime and operational risk: Design and implement AML/fraud controls across 58+ jurisdictions Monitor transaction patterns, investigate suspicious activity, and manage incident response Own the control environment for payments, settlements, and treasury operations Work with Operations to identify and remediate operational risk gaps Build the infrastructure: Develop KRIs (Key Risk Indicators) and MI (Management Information) to track risk exposure in real-time Implement risk incident management processes - logging, investigating, and remediating issues Create training and enablement materials so the whole team understands their risk responsibilities Build scalable systems and processes that grow with the business Example Projects Conduct risk assessment for launching in 5 new EU markets and design the compliance playbook Improve our AML transaction monitoring rules to catch real fraud without creating false positive nightmare Work with Engineering to build automated controls for payment routing and settlement risk Analyse six months of payment data to identify the top 10 risk drivers and build mitigation strategies Create a quantitative risk scoring model for new market launches based on regulatory complexity, fraud rates, and operational readiness Build automated KRI dashboards that alert on risk threshold breaches Build a data pipeline that aggregates risk signals from payments, tax, and operations into a unified view What We're Looking For Ideal background: 5-7 years in risk, compliance, or financial crime at a payments company or fintech (Stripe, Adyen, Revolut, Wise, or similar) Strong quantitative background - degree in STEM, economics, or similar (or demonstrable data science skills) Payments/fintech experience is mandatory - you need to understand how money moves and where risk lives Proficiency in SQL and at least one programming language (Python, R) for data analysis Experience in 1LoD (first line of defence) - you've owned risk, not just overseen it Bonus: MoR, marketplace, or cross-border payments experience Bonus: worked in a regulated environment with direct regulator or banking partner interaction Bonus: Experience building risk models, monitoring systems, or fraud detection algorithms Bonus: machine learning or statistical modelling experience applied to risk/fraud Signals we care about: Data-driven decision making - you use statistical analysis and modelling, not just intuition Technical fluency - you can write SQL queries, build dashboards, and work with engineers on data pipelines Quantitative rigour - you understand statistical significance, false positive rates, and model performance metrics Pragmatic risk mindset - you enable growth safely, not block it bureaucratically Regulatory fluency - you can read complex regulations and translate them into practical action Bias for action - you build controls and frameworks, not just write policies Comfortable in chaos - you thrive when building from scratch in ambiguous environments Commercial awareness - you understand the business model and make risk decisions that balance safety and growth Strong communicator - you can explain risk to engineers, merchants, and regulators equally well What this role is not: Not a pure 2LoD oversight role (you need to build and own, not just review) Not someone who needs a team or established processes to be effective Not a specialist who only wants to work on one risk domain (AML, fraud, etc.) Not someone who sees risk as "saying no" (your job is to enable safe growth) Why This Role Is Different This isn't about managing an existing risk function. It's about building the risk infrastructure that powers global commerce from the ground up. You won't just be in the room, you'll be defining how we manage risk. You'll have exposure to every part of the business: payments, tax, compliance, treasury, operations. You'll work directly with the founding team. You'll shape the controls that let us scale safely into new markets. The problems are hard. The scope is massive. The impact is real. We expect whoever is in this role to grow rapidly, and we'll back you every step of the way. 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. Team member Role Experience Will Mahon-Heap CEO / Founder ex. Revolut, ex. Wayflyer, ex. lawyer Artur Zheykars Head of Engineering ex. Revolut, ex. Align Technology Stef van Heugten Founding Head of Tax ex. Adyen, ex. VU Amsterdam Anca Maszni Founding Strategy and Operations ex. VC, ex. Ophelos, ex. Wayflyer What We Offer Equity and salary in a well-funded startup Ability to own your work and move fast World-class training from operators who've scaled globally A global mission with real impact Low politics, high output Chance to grow into Head of Risk as we scale A culture of builders, not box-tickers Working Style We work together in person in London or Amsterdam, 4-5 days a week. We believe the hardest problems are solved in the room. Reach Out Outpost is where the hard problems are. If you want to build the risk function that enables global trade, we'd love to hear from you.
Risk Global commerce is a regulatory minefield. Without proper risk management, you're one compliance breach away from losing market access, banking partners, or customer trust. Outpost needs someone to own this. We operate as Merchant of Record across 58+ tax jurisdictions, handling payments, tax compliance, and customer experience for digital and physical goods. That means we sit at the intersection of payments, regulatory compliance, financial crime, and operational risk - across dozens of regulatory regimes simultaneously. This is the first risk hire. You'll build the risk function from scratch. The Role This is a Risk Manager role for someone who wants to build like a founder, thinks like a regulator, and operates like an operator. You'll own risk management end-to-end - from identifying emerging regulatory requirements to designing controls, embedding them in products, and ensuring we can scale safely across new markets. You'll work directly with the CEO, engineering, product, operations, and tax to turn complex regulatory frameworks into practical, scalable risk management. This isn't a role where you write policies and file them away. You'll be in the weeds: reviewing product launches, debugging compliance gaps with engineers, working with banking partners, analysing transaction data, and making hard trade-offs between speed and safety. You care deeply about building things the right way. You want to enable growth, not block it. What You'll Get Yes, the work is intense. But in return, you'll get training and exposure most people wait 10-20 years to access. You'll be working on global problems, dealing with regulators and banking partners, and owning strategic risk decisions across payments, tax, financial crime, and operations - from day one. We won't handhold, but we'll coach you hard. If you're hungry, you'll leave this role with a world-class risk skillset and the ability to scale fintech products in the hardest markets. What You'll Do Own the risk function: Build Outpost's risk management framework from scratch (policies, procedures, controls, and governance) Identify, assess, document, and monitor risks across payments, tax, financial crime, and operations Set risk appetite and tolerance levels in partnership with the CEO and founding team Make the hard calls: what's acceptable risk vs. what could kill the business Enable safe growth: Work with Product and Engineering to embed risk thinking into new product launches and market expansions Conduct pre-launch risk assessments for new products, markets, and banking partnerships Design practical, effective controls that protect the business without slowing it down Ensure we can say "yes" to merchants safely (not just say "no" to risk) Be the regulatory expert: Stay ahead of regulatory changes across payments, MoR, tax, and financial crime in key markets (EU, UK, US, etc.) Translate complex regulatory requirements into clear, actionable guidance for product and operations teams Represent Outpost in discussions with regulators, banking partners, and payment processors Build relationships with external stakeholders and maintain regulatory credibility Manage financial crime and operational risk: Design and implement AML/fraud controls across 58+ jurisdictions Monitor transaction patterns, investigate suspicious activity, and manage incident response Own the control environment for payments, settlements, and treasury operations Work with Operations to identify and remediate operational risk gaps Build the infrastructure: Develop KRIs (Key Risk Indicators) and MI (Management Information) to track risk exposure in real-time Implement risk incident management processes - logging, investigating, and remediating issues Create training and enablement materials so the whole team understands their risk responsibilities Build scalable systems and processes that grow with the business Example Projects Conduct risk assessment for launching in 5 new EU markets and design the compliance playbook Improve our AML transaction monitoring rules to catch real fraud without creating false positive nightmare Work with Engineering to build automated controls for payment routing and settlement risk Analyse six months of payment data to identify the top 10 risk drivers and build mitigation strategies Create a quantitative risk scoring model for new market launches based on regulatory complexity, fraud rates, and operational readiness Build automated KRI dashboards that alert on risk threshold breaches Build a data pipeline that aggregates risk signals from payments, tax, and operations into a unified view What We're Looking For Ideal background: 5-7 years in risk, compliance, or financial crime at a payments company or fintech (Stripe, Adyen, Revolut, Wise, or similar) Strong quantitative background - degree in STEM, economics, or similar (or demonstrable data science skills) Payments/fintech experience is mandatory - you need to understand how money moves and where risk lives Proficiency in SQL and at least one programming language (Python, R) for data analysis Experience in 1LoD (first line of defence) - you've owned risk, not just overseen it Bonus: MoR, marketplace, or cross-border payments experience Bonus: worked in a regulated environment with direct regulator or banking partner interaction Bonus: Experience building risk models, monitoring systems, or fraud detection algorithms Bonus: machine learning or statistical modelling experience applied to risk/fraud Signals we care about: Data-driven decision making - you use statistical analysis and modelling, not just intuition Technical fluency - you can write SQL queries, build dashboards, and work with engineers on data pipelines Quantitative rigour - you understand statistical significance, false positive rates, and model performance metrics Pragmatic risk mindset - you enable growth safely, not block it bureaucratically Regulatory fluency - you can read complex regulations and translate them into practical action Bias for action - you build controls and frameworks, not just write policies Comfortable in chaos - you thrive when building from scratch in ambiguous environments Commercial awareness - you understand the business model and make risk decisions that balance safety and growth Strong communicator - you can explain risk to engineers, merchants, and regulators equally well What this role is not: Not a pure 2LoD oversight role (you need to build and own, not just review) Not someone who needs a team or established processes to be effective Not a specialist who only wants to work on one risk domain (AML, fraud, etc.) Not someone who sees risk as "saying no" (your job is to enable safe growth) Why This Role Is Different This isn't about managing an existing risk function. It's about building the risk infrastructure that powers global commerce from the ground up. You won't just be in the room, you'll be defining how we manage risk. You'll have exposure to every part of the business: payments, tax, compliance, treasury, operations. You'll work directly with the founding team. You'll shape the controls that let us scale safely into new markets. The problems are hard. The scope is massive. The impact is real. We expect whoever is in this role to grow rapidly, and we'll back you every step of the way. 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. Team member Role Experience Will Mahon-Heap CEO / Founder ex. Revolut, ex. Wayflyer, ex. lawyer Artur Zheykars Head of Engineering ex. Revolut, ex. Align Technology Stef van Heugten Founding Head of Tax ex. Adyen, ex. VU Amsterdam Anca Maszni Founding Strategy and Operations ex. VC, ex. Ophelos, ex. Wayflyer What We Offer Equity and salary in a well-funded startup Ability to own your work and move fast World-class training from operators who've scaled globally A global mission with real impact Low politics, high output Chance to grow into Head of Risk as we scale A culture of builders, not box-tickers Working Style We work together in person in London or Amsterdam, 4-5 days a week. We believe the hardest problems are solved in the room. Reach Out Outpost is where the hard problems are. If you want to build the risk function that enables global trade, we'd love to hear from you.
Outpost Technologies
Legal Counsel About Outpost What if going global was as simple as going local? Outpost is building the AI global trade engine. The accumulated knowledge of every rule you'd need to sell internationally, turned into infrastructure. Tell us what you're selling. We'll tell you how to sell it everywhere. We operate as Merchant of Record or Tax of Record across 58+ tax jurisdictions. Full liability transfer, or just the tax layer. We do the analysis, we handle the setup, we absorb the liability. Sell anything, anywhere. Without compromise. The Role This is a Legal role for someone who wants to build their career at a fast-scaling fintech and grow with the company. You'll report directly to the CEO and work across the full legal scope: commercial contracts, payments regulation, AML, corporate governance, and fundraising. You might go deep in one area and build breadth across the others. The shape of the role will evolve as you do. We operate at the intersection of payments, tax, and global commerce. That means Visa/Mastercard scheme rules, EMI and PSD2 frameworks, AML programmes, and commercial agreements with enterprise customers. You'll learn fast and own real work from day one. This isn't a support role. You'll draft contracts, advise on regulatory questions, help build compliance programmes, and work on fundraising. You'll shape how Outpost operates in new markets. As the company grows, so will your responsibilities. What You'll Get Yes, the work is intense. But in return, you'll get exposure and ownership most lawyers don't see until much later in their careers. You'll work directly with the CEO, touch every part of the legal function, and help build the infrastructure that lets Outpost scale globally. If you want to grow into a legal leadership role at a category-defining company, this is where you start. What You'll Do Commercial & Contracts Draft and negotiate commercial agreements: MSAs, merchant contracts, partnership deals Build contract templates and playbooks that scale Support enterprise deals where legal diligence is part of the sales process Payments Regulation Advise on regulatory posture across EMI, PSD2, and equivalent frameworks Learn scheme rules (Visa, Mastercard) and ensure compliance across payment operations Work with external counsel in new jurisdictions AML & Compliance Help build and maintain our AML policy and compliance programme Support KYC/KYB processes and regulatory obligations Prepare for audits and manage documentation Corporate & Governance Support fundraising: term sheets, investment documents, board matters Help manage corporate governance as the company scales Assist with cap table, equity, and corporate structure across entities International Expansion Research legal and regulatory requirements for new market entry Work with local counsel and help build the external network we need Advise on entity structure, licensing, and local compliance Example Projects Draft the MSA template for enterprise MoR customers and negotiate your first deals Research EMI equivalents in three new markets and summarise the licensing options Build the first version of our AML policy documentation Support a funding round by coordinating diligence and reviewing investment documents Review Visa/Mastercard scheme obligations and flag compliance gaps Manage external counsel in a new jurisdiction and synthesise their advice Create the legal playbook for merchant onboarding What We're Looking For Ideal background: In-house legal at a payments company or fintech (Adyen, Stripe, Revolut, Wise, Nuvei) Or private practice with fintech regulatory focus wanting to move in-house Exposure to payments regulation, commercial contracts, or AML Bonus: experience with EMI/PSD2 frameworks Bonus: exposure to fundraising or corporate governance Signals we care about: You want to go deep on fintech legal and build real expertise You can draft and negotiate, not just review and comment You're curious about payments, tax, and how cross-border commerce actually works You're comfortable with ambiguity. Startups don't come with playbooks You want to own your work, not wait for instructions You see this as a path to leadership, not just a job 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 big team or defined processes to be effective Why This Role Is Different Most junior legal roles are about supporting a larger team. This role is different. You'll work directly with the CEO, touch every part of the legal function, and own real work from day one. As Outpost grows, you'll grow with it. If you want to build a legal career at the intersection of fintech, payments, and global commerce, 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 A culture of builders, not talkers Working Style We work together in person in London. We believe the hardest problems are solved in the room. Learn More Outpost Culture: Outpost founder: Outpost is where the hard problems are. If you want to build your legal career at a company defining global commerce infrastructure, we'd love to hear from you.
Legal Counsel About Outpost What if going global was as simple as going local? Outpost is building the AI global trade engine. The accumulated knowledge of every rule you'd need to sell internationally, turned into infrastructure. Tell us what you're selling. We'll tell you how to sell it everywhere. We operate as Merchant of Record or Tax of Record across 58+ tax jurisdictions. Full liability transfer, or just the tax layer. We do the analysis, we handle the setup, we absorb the liability. Sell anything, anywhere. Without compromise. The Role This is a Legal role for someone who wants to build their career at a fast-scaling fintech and grow with the company. You'll report directly to the CEO and work across the full legal scope: commercial contracts, payments regulation, AML, corporate governance, and fundraising. You might go deep in one area and build breadth across the others. The shape of the role will evolve as you do. We operate at the intersection of payments, tax, and global commerce. That means Visa/Mastercard scheme rules, EMI and PSD2 frameworks, AML programmes, and commercial agreements with enterprise customers. You'll learn fast and own real work from day one. This isn't a support role. You'll draft contracts, advise on regulatory questions, help build compliance programmes, and work on fundraising. You'll shape how Outpost operates in new markets. As the company grows, so will your responsibilities. What You'll Get Yes, the work is intense. But in return, you'll get exposure and ownership most lawyers don't see until much later in their careers. You'll work directly with the CEO, touch every part of the legal function, and help build the infrastructure that lets Outpost scale globally. If you want to grow into a legal leadership role at a category-defining company, this is where you start. What You'll Do Commercial & Contracts Draft and negotiate commercial agreements: MSAs, merchant contracts, partnership deals Build contract templates and playbooks that scale Support enterprise deals where legal diligence is part of the sales process Payments Regulation Advise on regulatory posture across EMI, PSD2, and equivalent frameworks Learn scheme rules (Visa, Mastercard) and ensure compliance across payment operations Work with external counsel in new jurisdictions AML & Compliance Help build and maintain our AML policy and compliance programme Support KYC/KYB processes and regulatory obligations Prepare for audits and manage documentation Corporate & Governance Support fundraising: term sheets, investment documents, board matters Help manage corporate governance as the company scales Assist with cap table, equity, and corporate structure across entities International Expansion Research legal and regulatory requirements for new market entry Work with local counsel and help build the external network we need Advise on entity structure, licensing, and local compliance Example Projects Draft the MSA template for enterprise MoR customers and negotiate your first deals Research EMI equivalents in three new markets and summarise the licensing options Build the first version of our AML policy documentation Support a funding round by coordinating diligence and reviewing investment documents Review Visa/Mastercard scheme obligations and flag compliance gaps Manage external counsel in a new jurisdiction and synthesise their advice Create the legal playbook for merchant onboarding What We're Looking For Ideal background: In-house legal at a payments company or fintech (Adyen, Stripe, Revolut, Wise, Nuvei) Or private practice with fintech regulatory focus wanting to move in-house Exposure to payments regulation, commercial contracts, or AML Bonus: experience with EMI/PSD2 frameworks Bonus: exposure to fundraising or corporate governance Signals we care about: You want to go deep on fintech legal and build real expertise You can draft and negotiate, not just review and comment You're curious about payments, tax, and how cross-border commerce actually works You're comfortable with ambiguity. Startups don't come with playbooks You want to own your work, not wait for instructions You see this as a path to leadership, not just a job 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 big team or defined processes to be effective Why This Role Is Different Most junior legal roles are about supporting a larger team. This role is different. You'll work directly with the CEO, touch every part of the legal function, and own real work from day one. As Outpost grows, you'll grow with it. If you want to build a legal career at the intersection of fintech, payments, and global commerce, 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 A culture of builders, not talkers Working Style We work together in person in London. We believe the hardest problems are solved in the room. Learn More Outpost Culture: Outpost founder: Outpost is where the hard problems are. If you want to build your legal career at a company defining global commerce infrastructure, we'd love to hear from you.
Outpost Technologies
Head of Sales About Outpost What if going global was as simple as going local? Outpost is building the AI global trade engine. The accumulated knowledge of every rule you'd need to sell internationally, turned into infrastructure. Tell us what you're selling. We'll tell you how to sell it everywhere. We operate as Merchant of Record or Tax of Record across 58+ tax jurisdictions. Full liability transfer, or just the tax layer. We do the analysis, we handle the setup, we absorb the liability. Sell anything, anywhere. Without compromise. The Role This is a Head of Sales role for someone who wants to build a sales function from scratch at a category-defining fintech. You'll report directly to the CEO and take over a founder-led sales motion. That means closing deals yourself while building the team and playbook to scale. You'll own new business globally: direct sales to merchants, PSP partnerships, and B2B2C channels. We sell to companies that want to expand internationally without the pain. Tax, payments, compliance, liability. The problem is complex, the buyers are sophisticated, and the deals require someone who can navigate both. This is a player-coach role. You'll carry a bag, close deals, and build pipeline. Inbound and outbound. You're used to making your own leads, not waiting for them. At the same time, you'll build the sales infrastructure: process, hiring, comp, tooling, and eventually a team. What You'll Get Yes, the work is intense. But in return, you'll own sales at a company with real product-market fit, strong funding, and a massive market. You'll work directly with the CEO, shape the commercial strategy, and build the revenue engine from the ground up. If you want to define how a company scales, this is the seat. What You'll Do Close Deals - Take over founder-led sales and own the pipeline; Run full-cycle sales from prospecting to close; Build and manage your own pipeline (Inbound and outbound); Navigate complex deals with multiple stakeholders. Build the Function - Design the sales process, playbook, and tooling; Hire and develop the sales team as we scale; Build comp structures and performance frameworks; Create the infrastructure for repeatable, scalable sales. Partnerships & Channels - Own PSP relationships and drive revenue through payment partners; Build B2B2B channels where Outpost is embedded in partner platforms; Identify and develop new partnership opportunities. New Business - Focus on landing new logos globally; Understand buyer pain points across tax, payments, and compliance; Position Outpost against alternatives and win competitive deals. Example Projects Close the next 10 enterprise deals and build the playbook from what works Build an outbound motion targeting e-commerce platforms expanding internationally Develop a PSP partnership that drives consistent deal flow Hire and onboard the first two sales reps Create the sales process documentation and CRM structure Negotiate a B2B2B deal where Outpost powers a platform's cross-border capability Build the business case framework that helps buyers get internal sign-off What We're Looking For Ideal background Sales leadership at a B2B fintech, payments company, or e-commerce infrastructure platform Built and scaled sales teams before Experience with PSP, payments, or platform partnerships Closed complex deals with long sales cycles and multiple stakeholders Bonus: sold MoR, tax, or compliance products Signals we care about: You've built pipeline yourself. Inbound and outbound. You don't wait for leads You can close deals and coach others to do the same You've built sales process and infrastructure, not just inherited it You understand fintech buyers: their pain points, objections, and decision-making You're comfortable with ambiguity. This is building, not optimising You want to own the number and the function Bias for action. You sell, you learn, you iterate What this role is not: Not a pure management role. You'll carry a bag Not someone who needs a big team or mature process to be effective Not a sales leader who only works inbound Not someone who waits to be told what to do Why This Role Is Different Most Head of Sales roles are about scaling an existing machine. This role is about building it. You'll take over founder-led sales and turn it into a repeatable function. You'll close deals, build partnerships, and hire the team. You'll shape how Outpost grows commercially. If you want to own sales at a company solving a hard problem with real traction, this is 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 A culture of builders, not talkers Working Style We work together in person in London. We believe the hardest problems are solved in the room. Learn More Outpost Culture: Outpost founder: Outpost is where the hard problems are. If you want to build the sales engine for global commerce infrastructure, we'd love to hear from you.
Head of Sales About Outpost What if going global was as simple as going local? Outpost is building the AI global trade engine. The accumulated knowledge of every rule you'd need to sell internationally, turned into infrastructure. Tell us what you're selling. We'll tell you how to sell it everywhere. We operate as Merchant of Record or Tax of Record across 58+ tax jurisdictions. Full liability transfer, or just the tax layer. We do the analysis, we handle the setup, we absorb the liability. Sell anything, anywhere. Without compromise. The Role This is a Head of Sales role for someone who wants to build a sales function from scratch at a category-defining fintech. You'll report directly to the CEO and take over a founder-led sales motion. That means closing deals yourself while building the team and playbook to scale. You'll own new business globally: direct sales to merchants, PSP partnerships, and B2B2C channels. We sell to companies that want to expand internationally without the pain. Tax, payments, compliance, liability. The problem is complex, the buyers are sophisticated, and the deals require someone who can navigate both. This is a player-coach role. You'll carry a bag, close deals, and build pipeline. Inbound and outbound. You're used to making your own leads, not waiting for them. At the same time, you'll build the sales infrastructure: process, hiring, comp, tooling, and eventually a team. What You'll Get Yes, the work is intense. But in return, you'll own sales at a company with real product-market fit, strong funding, and a massive market. You'll work directly with the CEO, shape the commercial strategy, and build the revenue engine from the ground up. If you want to define how a company scales, this is the seat. What You'll Do Close Deals - Take over founder-led sales and own the pipeline; Run full-cycle sales from prospecting to close; Build and manage your own pipeline (Inbound and outbound); Navigate complex deals with multiple stakeholders. Build the Function - Design the sales process, playbook, and tooling; Hire and develop the sales team as we scale; Build comp structures and performance frameworks; Create the infrastructure for repeatable, scalable sales. Partnerships & Channels - Own PSP relationships and drive revenue through payment partners; Build B2B2B channels where Outpost is embedded in partner platforms; Identify and develop new partnership opportunities. New Business - Focus on landing new logos globally; Understand buyer pain points across tax, payments, and compliance; Position Outpost against alternatives and win competitive deals. Example Projects Close the next 10 enterprise deals and build the playbook from what works Build an outbound motion targeting e-commerce platforms expanding internationally Develop a PSP partnership that drives consistent deal flow Hire and onboard the first two sales reps Create the sales process documentation and CRM structure Negotiate a B2B2B deal where Outpost powers a platform's cross-border capability Build the business case framework that helps buyers get internal sign-off What We're Looking For Ideal background Sales leadership at a B2B fintech, payments company, or e-commerce infrastructure platform Built and scaled sales teams before Experience with PSP, payments, or platform partnerships Closed complex deals with long sales cycles and multiple stakeholders Bonus: sold MoR, tax, or compliance products Signals we care about: You've built pipeline yourself. Inbound and outbound. You don't wait for leads You can close deals and coach others to do the same You've built sales process and infrastructure, not just inherited it You understand fintech buyers: their pain points, objections, and decision-making You're comfortable with ambiguity. This is building, not optimising You want to own the number and the function Bias for action. You sell, you learn, you iterate What this role is not: Not a pure management role. You'll carry a bag Not someone who needs a big team or mature process to be effective Not a sales leader who only works inbound Not someone who waits to be told what to do Why This Role Is Different Most Head of Sales roles are about scaling an existing machine. This role is about building it. You'll take over founder-led sales and turn it into a repeatable function. You'll close deals, build partnerships, and hire the team. You'll shape how Outpost grows commercially. If you want to own sales at a company solving a hard problem with real traction, this is 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 A culture of builders, not talkers Working Style We work together in person in London. We believe the hardest problems are solved in the room. Learn More Outpost Culture: Outpost founder: Outpost is where the hard problems are. If you want to build the sales engine for global commerce infrastructure, we'd love to hear from you.