Sales / Go to Market

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 need to sell internationally, turned into infrastructure. Tell us what you are selling. We will 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 Sales / Go to Market role for someone who wants to close deals, build pipeline, and help shape how Outpost sells. You will report directly to the CEO and own full-cycle sales. Prospecting, qualifying, closing. Inbound and outbound. You will sell directly to merchants expanding internationally and help develop B2B2B channels where Outpost powers partner platforms. This isn’t a pure sales role. You will also help build the GTM engine: refining pitch decks, shaping positioning, creating materials that help close deals. You will work across sales and product marketing because that’s how early-stage companies work. 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 learn fast and communicate clearly.

What You Will Get

Yes, the work is intense. But in return, you will get exposure most people wait years to access. You will work directly with the CEO, close deals that shape the company’s trajectory, and help build the commercial playbook from the ground up. If you want to grow fast in a high-ownership environment, this is the role.

What You Will Do

• Close Deals
• Own full-cycle sales from prospecting to close
• Build and manage your own pipeline. Inbound and outbound
• Run discovery calls, demos, and negotiations
• Navigate deals with multiple stakeholders and complex requirements
• Generate your own leads through outbound prospecting
• Work inbound leads and convert interest into pipeline
• Identify target accounts and build account-based plays
• Develop B2B2B opportunities where Outpost is embedded in partner platforms
• Help refine pitch decks and sales materials based on what works in the field
• Contribute to positioning and messaging as you learn what resonates
• Build case studies and proof points from closed deals
• Feed insights back to product and marketing

Example Projects

• Close your first 10 deals and document what worked
• Build an outbound sequence targeting e-commerce brands expanding to Europe
• Refine the pitch deck based on objections you are hearing in calls
• Develop a B2B2B partnership with a platform that serves your target segment
• Create a one-pager for a specific vertical or use case
• Turn a successful deal into a case study that helps close the next one
• Identify a new segment and build the business case to go after it

What We Are Looking For

Ideal background:

• Sales at a B2B fintech, payments company, or e-commerce infrastructure platform
• Full-cycle sales experience. Prospecting through close
• Experience generating your own pipeline. Inbound and outbound
• Bonus: sold MoR, tax, compliance, or cross-border products

Signals we care about:

• You have built pipeline yourself. You don’t wait for leads
• You can run a sales process and close deals independently
• You are curious about the product and want to understand how it works
• You can communicate complex ideas simply
• You are comfortable with ambiguity. Early-stage means figuring things out
• You want to do more than just sell. You want to shape how we sell
• Bias for action. You move fast and learn by doing

What this role is not:

• Not a role where you wait for inbound leads
• Not pure sales without touching GTM materials
• Not someone who needs a defined playbook to be effective
• Not someone who waits to be told what to do

Why This Role Is Different

Most early sales roles are about executing someone else’s playbook. This role is about helping write it. You will close deals, build pipeline, and shape how Outpost goes to market. You will work directly with the CEO and have real influence on commercial strategy. If you want to grow fast at a company solving a hard problem with real momentum, this is it.

Outpost Team

Our team were leaders at Revolut, Airwallex, Adyen and Wayflyer, and we are 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 is where the hard problems are. If you want to close deals and build the GTM engine for global commerce infrastructure, we would love to hear from you.