Job Opportunities API

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 opti