Head of Sales

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

[email protected]

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.