Head of Sales

About the Company

Outpost is building the AI global trade engine. We operate as Merchant of Record or Tax of Record across 58+ tax jurisdictions, providing full liability transfer or tax layers to help companies sell anything, anywhere.

Responsibilities

• Take over founder-led sales and own the pipeline
• Run full-cycle sales from prospecting to close
• Build and manage inbound and outbound pipelines
• Design the sales process, playbook, and tooling
• Hire and develop the sales team as the company scales
• Build compensation structures and performance frameworks
• Own PSP relationships and drive revenue through payment partners
• Build B2B2B channels where Outpost is embedded in partner platforms
• Focus on landing new logos globally

Requirements

• Sales leadership experience at a B2B fintech, payments company, or e-commerce infrastructure platform
• Proven track record of building and scaling sales teams
• Experience with PSP, payments, or platform partnerships
• Experience closing complex deals with long sales cycles and multiple stakeholders
• Ability to act as a player-coach, carrying a bag while building the function
• Experience building sales infrastructure and processes from scratch

Preferred Qualifications

• Experience selling Merchant of Record (MoR), tax, or compliance products