About the job
Head of Sales
About Outpost
Imagine if expanding your business globally was as easy as local sales. Outpost is revolutionizing international commerce with our AI-powered global trade engine, simplifying the complexities of international sales by providing comprehensive infrastructure that covers every regulatory aspect.
As a Merchant of Record or Tax of Record in over 58 tax jurisdictions, we manage the entire process—from analysis to setup—allowing you to sell anything, anywhere, without the usual compromises.
The Role
We are seeking a dynamic Head of Sales who is ready to build a robust sales function from the ground up in a pioneering fintech environment. Reporting directly to the CEO, you will inherit a founder-led sales strategy, actively closing deals while also creating a scalable team and sales playbook.
Your focus will be on driving new business globally, targeting direct sales to merchants, forming PSP partnerships, and exploring B2B2C channels. Our ideal clients are companies eager to expand internationally without the traditional hurdles of tax, payments, compliance, and liability—complex issues that require a sophisticated sales approach.
In this player-coach position, you will not only close deals and generate leads but also construct the sales infrastructure encompassing processes, hiring, compensation plans, and tools, ultimately leading to the growth of your own dedicated sales team.
What You'll Get
While the role is challenging, you will gain ownership of the sales process in a company with proven product-market fit, substantial funding, and significant market potential. This is your chance to work closely with the CEO in shaping the commercial strategy and truly have an impact on how the company scales.
What You'll Do
Close Deals
- Take charge of founder-led sales and manage the pipeline.
- Conduct full-cycle sales from prospecting to closing.
- Develop and oversee your pipeline, both inbound and outbound.
- Handle complex deals involving multiple stakeholders.
Build the Function
- Create the sales process, playbook, and necessary tools for success.
- Recruit and train your sales team as the function grows.
- Implement compensation structures and performance metrics.

