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 youd need to sell internationally turned into infrastructure. Tell us what youre selling. Well 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.

Youll 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. Youll 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. Youll carry a bag close deals and build pipeline. Inbound and outbound. Youre used to making your own leads not waiting for them. At the same time youll build the sales infrastructure: process hiring comp tooling and eventually a team.

What Youll Get

Yes the work is intense. But in return youll own sales at a company with real product-market fit strong funding and a massive market.

Youll 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 Youll 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 platforms cross-border capability

Build the business case framework that helps buyers get internal sign-off

What Were 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:

Youve built pipeline yourself. Inbound and outbound. You dont wait for leads
You can close deals and coach others to do the same
Youve built sales process and infrastructure not just inherited it
You understand fintech buyers: their pain points objections and decision-making
Youre 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. Youll 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.

Youll take over founder-led sales and turn it into a repeatable function. Youll close deals build partnerships and hire the team. Youll 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 were backed by top-tier investors who have built or backed some of the worlds 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 Culture: Outpost founder: is where the hard problems are. If you want to build the sales engine for global commerce infrastructure wed love to hear from you.

Required Experience:

Director