Enterprise Account Executive

United States (Remote) · Full-Time

Enterprise supply chain is a $16B software market still held together by human duct tape. Every invoice, contract, shipment, and exception still requires someone to read an email, reconcile mismatched data, chase a vendor, and make a time-sensitive call with incomplete information. ERPs and S2P tools track the work. They don't do it.

Freehand does. We build AI Teams — agentic systems that replace staff and software across logistics, procurement, direct materials, MRO, and services spend. Our customers include Meta, GE, Apple, Pfizer, J&J, Cardinal Health, and Unilever. We are recognized by PwC, McKinsey, Deloitte, Gartner, and Kearney. We are early, we are growing fast, and the category we are creating is real.

We are now looking for an Enterprise Account Executive who can sell into the complexity — and win.

This is a full-cycle, enterprise sales role. You will own a territory of F500 and large enterprise accounts, run deals from first call to close, and drive expansion inside the accounts you land. You will be selling to VP and C-suite supply chain, procurement, and ops finance leaders who have lived the problem firsthand. That context matters. You will need to speak their language fluently, not learn it on the job.

Our top performers — Shawn (168% of plan), Aroop (131%), and Rey (122%) — share three things: deep supply chain domain knowledge, relentless prospecting, and a consultative discovery muscle that earns trust before pitching a solution. That is the bar. We are looking for someone who can match it.

You will build and execute account plans for a defined territory of enterprise targets, running multi-threaded outreach across procurement, supply chain, and ops finance.

You will run discovery that goes deep — understanding spend categories, organizational pain, data infrastructure, and decision-making dynamics — before you show a single slide.

You will own live data demos. Freehand is not a deck product. The most compelling moments in our sales cycle happen when a prospect sees their own supply chain data processed in real time. You will be comfortable driving that conversation and building credibility through it.

You will manage complex, multi-stakeholder deals with $500K–$3M+ ACV potential, navigating procurement, legal, IT, and the business simultaneously.

You will close, forecast accurately, and work closely with the Forward Deployed Product Engineering team to run structured pilots that convert.

You will build the kind of relationships that drive expansion — across spend categories, geographies, and use cases within your accounts.

• You have 5+ years of enterprise SaaS sales experience, with at least 2 years carrying and consistently hitting a $1M+ quota. Overachievement in at least one year matters to us.

• You have real supply chain or procurement domain experience — not surface-level familiarity, but the kind earned by selling to, working in, or building for logistics, P2P, sourcing, or ops finance teams. A background at a carrier, 3PL, shipper, or supply chain software company is a meaningful advantage.

• You sell through domain depth and business value, not relationships. You can walk into a room with a VP of Procurement at a Fortune 100 company and demonstrate, quickly, that you understand their world.

• You are technically comfortable. You can run a live data demo with confidence, ask smart questions about data infrastructure, and hold your own in conversations that go beyond talking points.

• You use AI tools in your own workflow today. You can articulate what AI-native means to an executive who has heard every vendor claim a version of it.

• You prospect. You do not wait for inbound to carry your number.
  

This is not a role for someone who needs a brand name to open doors or a large SDR team to fill their pipeline. Freehand is a company where the product opens doors — if you can demonstrate it. The people who thrive here are self-directed, intellectually curious about the problem space, and energized by building in a category that is still being defined.

We offer a competitive base salary, uncapped commission, equity, and full benefits. Compensation is calibrated to your experience and location. OTE range for this role is $280,000–$300,000, with no cap on upside for overachievers.

Freehand is an equal opportunity employer. We are committed to building a team that reflects the diversity of the customers and industries we serve.