Better Tomorrow Ventures
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. Pick only what you need - tax, payments, treasury, or operations - and unlock new markets without the overhead. Sometimes we act as Merchant of Record, taking on tax and compliance risk. Other times, we give you the tools to do it yourself. We operate across 58+ tax jurisdictions for digital and physical goods. That means we own the full stack - payments, tax, compliance, treasury, and merchant experience. Sell anything, anywhere. Without compromise. The Role We're looking for our Head of Operations: the person who owns how Outpost actually runs. Today, operations at Outpost is a set of processes held together by a small group of very good people. Merchant onboarding, KYC/KYB, market launches, tax registrations, payouts, treasury approvals, chargebacks, merchant support - it all works, but it works because people push it. Your job is to turn that into a machine. This is a hands on leadership role, not a management layer. You'll own the operational stack end to end: onboarding and activation, merchant operations, payments and treasury ops, compliance monitoring, and new market launches. You'll design the processes, build the tooling requirements with engineering, write the playbooks, and then run them yourself until they're good enough to hand over. You'll hire and grow a small team behind you, but for the first stretch you are the team. If your instinct when something breaks is to open the dashboard and fix it rather than schedule a meeting about it, you'll do well here. You'll work directly with the CEO and founding team, and you'll have a real say in what Outpost builds - operations is the sharpest source of product signal we have. What You'll Get Yes, the work is intense. But in return, you'll get scope and exposure most people wait 10-20 years to access. You'll own a core function of a company solving one of the hardest problems in global commerce, work with senior stakeholders across PSPs, banks, tax authorities and merchants, and build a team from scratch. We won't handhold, but we'll coach you hard. What You'll Do Own the operational stack Own merchant onboarding end to end: applications, KYC/KYB, risk review, activation, time-to-live Run merchant operations day to day - support escalations, payouts, settlements, disputes Own treasury operations: proceeds requests, money movement, reserves, reconciliation Monitor merchant risk and compliance thresholds (chargebacks, fraud, refunds) and act before they become losses Own payment operations alongside engineering: auth rates, routing, decline recovery, chargeback and fraud strategy Build the system, not just the output Turn manual processes into documented, repeatable, measurable playbooks Define the operational metrics that matter and build the reporting so the company can see them Work with engineering to spec and prioritise internal tooling - you are the customer for our internal ops platform Kill work: automate, template, or delete anything that doesn't need a human Make Outpost able to double merchant volume without doubling ops headcount Launch and scale Launch new markets with full legal, tax, payments, and operational setup Onboard new PSPs, banking partners, and local acquiring in new geographies Build the operational side of new products and merchant segments before they go live Feed market and merchant reality back into the product roadmap Lead Hire, onboard, and grow a small operations team Set standards: what good looks like, how fast we respond, what we never get wrong Be the operational voice in company planning - what we can support, when, and at what cost Example Projects Redesign merchant onboarding to cut time-to-live by 50% without weakening KYB Build the operational launch playbook for three new markets and run the first one yourself Debug delays in payouts and fix them across engineering, ops, compliance, and PSPs Design reserve and settlement logic for a new merchant segment and implement it Build the ops metrics dashboard: onboarding funnel, time-to-live, ticket volume, payout SLA, chargeback rate Cut chargeback rate through better fraud tooling and merchant policy Spec the next version of our internal ops tooling with engineering and ship it Write the merchant VAT compliance playbook across EU markets with the tax team Hire and onboard the first two operations analysts and get them productive in 30 days What We're Looking For Ideal background: 6-10 years in operations at high-growth fintech, payments, or e commerce infrastructure (Revolut, Stripe, Adyen, Wise, Mollie, Airwallex, or similar) Has owned a function or a large slice of one - onboarding, merchant ops, payment ops, or risk ops - not just executed within it Experience building processes from zero, not inheriting them Bonus: MoR platforms (Global e, Digital River, Paddle), cross border tax exposure, or PSP/acquirer operations Comfortable with data - SQL, spreadsheets, dashboards. You measure before you decide Signals we care about: Ridiculous bias for action - you solve, not observe Systems thinker who still does the work - you fix the ticket and then remove the reason it existed Analytically strong - you can quantify a process, not just describe it Strong EQ - you know how to read a room, a customer, or a blocker Exceptionally hard working - you see work as a core part of your purpose Fluent in ambiguity and chaos - startups are not neat, this will be hard Curious and resourceful - you can figure anything out Comfortable getting hands dirty - your default mode is to do, not delegate Clear, quantified achievements on your CV (not vague descriptions) What this role is not: Not a people management role where you run a team that does the work Not a process maintenance role - nothing here is finished Not a single function specialist who wants to stay in payments, or compliance, or support Not someone who needs defined processes and hierarchy to be effective Why This Role Is Different This isn't about maintaining processes - it's about building the operating system of Outpost from the ground up. You won't just be in the room, you'll be writing the agenda. Operations at an MoR is not a back office function. It is the product. How fast merchants go live, whether money arrives on time, whether we catch risk before it costs us - that's what customers buy and where our margin lives. You'll own it. 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. 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 a senior leadership role A culture of builders, not talkers Working Style We work together in person in London 5 days a week. We believe the hardest problems are solved in the room. Reach Out Learn more Outpost Culture Outpost founder Outpost is where the hard problems are. If you want to help build the engine behind global trade, we'd love to hear from you.
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. Pick only what you need - tax, payments, treasury, or operations - and unlock new markets without the overhead. Sometimes we act as Merchant of Record, taking on tax and compliance risk. Other times, we give you the tools to do it yourself. We operate across 58+ tax jurisdictions for digital and physical goods. That means we own the full stack - payments, tax, compliance, treasury, and merchant experience. Sell anything, anywhere. Without compromise. The Role We're looking for our Head of Operations: the person who owns how Outpost actually runs. Today, operations at Outpost is a set of processes held together by a small group of very good people. Merchant onboarding, KYC/KYB, market launches, tax registrations, payouts, treasury approvals, chargebacks, merchant support - it all works, but it works because people push it. Your job is to turn that into a machine. This is a hands on leadership role, not a management layer. You'll own the operational stack end to end: onboarding and activation, merchant operations, payments and treasury ops, compliance monitoring, and new market launches. You'll design the processes, build the tooling requirements with engineering, write the playbooks, and then run them yourself until they're good enough to hand over. You'll hire and grow a small team behind you, but for the first stretch you are the team. If your instinct when something breaks is to open the dashboard and fix it rather than schedule a meeting about it, you'll do well here. You'll work directly with the CEO and founding team, and you'll have a real say in what Outpost builds - operations is the sharpest source of product signal we have. What You'll Get Yes, the work is intense. But in return, you'll get scope and exposure most people wait 10-20 years to access. You'll own a core function of a company solving one of the hardest problems in global commerce, work with senior stakeholders across PSPs, banks, tax authorities and merchants, and build a team from scratch. We won't handhold, but we'll coach you hard. What You'll Do Own the operational stack Own merchant onboarding end to end: applications, KYC/KYB, risk review, activation, time-to-live Run merchant operations day to day - support escalations, payouts, settlements, disputes Own treasury operations: proceeds requests, money movement, reserves, reconciliation Monitor merchant risk and compliance thresholds (chargebacks, fraud, refunds) and act before they become losses Own payment operations alongside engineering: auth rates, routing, decline recovery, chargeback and fraud strategy Build the system, not just the output Turn manual processes into documented, repeatable, measurable playbooks Define the operational metrics that matter and build the reporting so the company can see them Work with engineering to spec and prioritise internal tooling - you are the customer for our internal ops platform Kill work: automate, template, or delete anything that doesn't need a human Make Outpost able to double merchant volume without doubling ops headcount Launch and scale Launch new markets with full legal, tax, payments, and operational setup Onboard new PSPs, banking partners, and local acquiring in new geographies Build the operational side of new products and merchant segments before they go live Feed market and merchant reality back into the product roadmap Lead Hire, onboard, and grow a small operations team Set standards: what good looks like, how fast we respond, what we never get wrong Be the operational voice in company planning - what we can support, when, and at what cost Example Projects Redesign merchant onboarding to cut time-to-live by 50% without weakening KYB Build the operational launch playbook for three new markets and run the first one yourself Debug delays in payouts and fix them across engineering, ops, compliance, and PSPs Design reserve and settlement logic for a new merchant segment and implement it Build the ops metrics dashboard: onboarding funnel, time-to-live, ticket volume, payout SLA, chargeback rate Cut chargeback rate through better fraud tooling and merchant policy Spec the next version of our internal ops tooling with engineering and ship it Write the merchant VAT compliance playbook across EU markets with the tax team Hire and onboard the first two operations analysts and get them productive in 30 days What We're Looking For Ideal background: 6-10 years in operations at high-growth fintech, payments, or e commerce infrastructure (Revolut, Stripe, Adyen, Wise, Mollie, Airwallex, or similar) Has owned a function or a large slice of one - onboarding, merchant ops, payment ops, or risk ops - not just executed within it Experience building processes from zero, not inheriting them Bonus: MoR platforms (Global e, Digital River, Paddle), cross border tax exposure, or PSP/acquirer operations Comfortable with data - SQL, spreadsheets, dashboards. You measure before you decide Signals we care about: Ridiculous bias for action - you solve, not observe Systems thinker who still does the work - you fix the ticket and then remove the reason it existed Analytically strong - you can quantify a process, not just describe it Strong EQ - you know how to read a room, a customer, or a blocker Exceptionally hard working - you see work as a core part of your purpose Fluent in ambiguity and chaos - startups are not neat, this will be hard Curious and resourceful - you can figure anything out Comfortable getting hands dirty - your default mode is to do, not delegate Clear, quantified achievements on your CV (not vague descriptions) What this role is not: Not a people management role where you run a team that does the work Not a process maintenance role - nothing here is finished Not a single function specialist who wants to stay in payments, or compliance, or support Not someone who needs defined processes and hierarchy to be effective Why This Role Is Different This isn't about maintaining processes - it's about building the operating system of Outpost from the ground up. You won't just be in the room, you'll be writing the agenda. Operations at an MoR is not a back office function. It is the product. How fast merchants go live, whether money arrives on time, whether we catch risk before it costs us - that's what customers buy and where our margin lives. You'll own it. 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. 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 a senior leadership role A culture of builders, not talkers Working Style We work together in person in London 5 days a week. We believe the hardest problems are solved in the room. Reach Out Learn more Outpost Culture Outpost founder Outpost is where the hard problems are. If you want to help build the engine behind global trade, we'd love to hear from you.
Better Tomorrow Ventures
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.