Careers at Pilot5 · Now hiring

Enterprise Account Executive, Strategic AI.

Carry a category-defining product into your market, early, with no ceiling on what you build.

The market in 2026

In 2026 the hard part is no longer getting an answer. It is trusting one. Across strategy, finance, legal, operations, risk and product, leaders now need a strategic analysis layer for any answer too important to take on trust. Demand is opening across every sector at once, and a new category of AI is being defined right now.

Pilot5 defines it. The window to own a territory in it is open today, and we are looking for exceptional operators to carry Pilot5 into their markets early, with no ceiling on what they build anywhere in the world.

About Pilot5

Pilot5.ai is your Strategic AI. You get one complete report: a clear recommendation, traceable evidence, and the preserved dissent. Behind it, five independent AI models (Claude, GPT, Gemini, Grok, Mistral and more) reason, disagree, and converge, with you in the loop. You make the call. Disagree to decide.

We are scaling globally and building a network of independent Enterprise Account Executives.

The role

You sell Pilot5 across two clear models. You own your pipeline, you work your network, you close. Fully remote, independent contractor, open worldwide.

Two simple models

Both models are uncapped. No draw. You are paid on what you close.

Enterprise

You sell Pilot5 directly to organisations who use it as their strategic analysis layer.

You earn
Attractive recurring commission on the revenue billed during each client's first 12 months.

Partners

You sign software editors, IT and AI development firms, integrators and consultancies who embed or resell Pilot5 to their own clients.

You earn
Attractive commission on partner-generated revenue.

A mature product that fits any client environment

One deliberation layer, three ways to reach it. This is your strongest proof point in the room: Pilot5 adapts to the client, never the other way round.

  • On the platform

    A neutral home to run, record and govern every analysis at pilot5.ai.

  • In their tools, via MCP

    A panel invoked from inside the assistants teams already use: Claude, ChatGPT, Cursor, Gemini, Perplexity, Copilot, Le Chat, Zed.

  • In their stack, via API

    Launch, stream, steer and close a deliberation over plain HTTPS.

Contractual basis

Every Enterprise Account Executive engages with Pilot5 as an independent business operating under their own registered self-employment or company status in their country of residence. You invoice Pilot5 directly for your commissions. Holding valid independent status in your own jurisdiction is a condition of the engagement.

Who we are looking for

  • Independent "hunters" with an active book of non-competing B2B or SaaS clients.
  • A track record selling to executives in strategy, consulting, finance, or operations.
  • Comfortable carrying a category-defining product (deliberative AI), not a commodity chatbot.
  • Enterprise Account Executives across EU, MENA, APAC and LATAM equally welcome, each under their own national independent status.

What we provide

  • Attractive, fully transparent, uncapped commissions.
  • Private access codes and a live demo environment for your prospects.
  • Sales assets, our blog (pilot5.ai/blog), and direct product support.
  • Leads we send you in your sector.
  • A category-defining product that sells on trust: five independent AI models that reason, disagree, and converge into one report your clients can defend.

Why this is worth your network

If you have spent years earning the trust of decision-makers, this is the product that rewards that trust, and the moment to put it to work. Your territory, your book, your upside. We provide the category, the product, and the proof. You bring the relationships and the hunger.

Another way to contribute

Your network is your asset, and you create value through advice and high-level introductions. You are a Strategic Advisor. Pilot5 also runs an Ambassador program built for exactly that. Tell us in your note if that fits you better, and we will share how it works — or see the partner & ambassador program.

How to apply

Apply through the listing or send a short note and your track record to contact@pilot5.ai. In your message, tell us three things:

  1. 01Your registered independent business status and country.
  2. 02Whether you have an active book of B2B or enterprise clients.
  3. 03Which markets and segments you currently cover — and whether you sell to enterprises, partners, or both.

Your territory. Your book. Your upside.

Apply now →