Head of Sales

Head of Sales

About the opportunity

A Y-Combinator-backed AI company transforming how global supply chains manage freight spend. The platform applies AI to freight audit and payment — catching detention, demurrage, and accessorial overcharges before they happen and recovering historical ones — for shippers, logistics service providers, and drayage carriers. Post-pivot, the company sells enterprise outcomes (audited invoices, fair payment, vendor scorecarding), not software seats, and is on a path to profitability with a defined liquidity horizon.

The role

As Head of Sales, you own the go-to-market engine end to end. You'll carry the enterprise number yourself while building and leading the sales function, running partnerships, and helping shape the broader GTM motion (including marketing at the exec level). You report directly to the CEO and sit on the exec team. This is a builder's seat at an inflection point — you inherit early traction and real enterprise logos, and you get to define how a modern, AI-first sales org runs.

What you'll do

• Own and hit the enterprise revenue number — lead by example as a hands-on seller while you build the team
• Build, hire, and coach the sales function; bring structure to pipeline, forecasting, and process
• Run partnerships and co-selling motions that extend reach into new enterprise accounts
• Shape GTM strategy across sales and marketing; represent marketing at the exec table
• Embed AI into the sales motion — leverage the company's documentation, code, and recorded-call library to build AI-assisted selling workflows (the "AI CRO" vision)
• Partner with product and operations as the company expands from single-mode to multi-mode, multi-geography freight audit
• Give the CEO leverage — take ownership of the revenue org so leadership can scale

What we're looking for

• Proven B2B SaaS / tech sales leadership — has built or scaled a sales function and personally closed enterprise deals
• Genuinely AI-forward — already uses AI in their own workflow and is excited to build it into the GTM motion
• Comfortable as a hands-on, player-coach leader in a lean, fast-moving startup (not a big-company overlay manager)
• Strong on partnerships and multi-stakeholder enterprise selling
• Some marketing fluency / willingness to own GTM broadly
• New York based, or ready to be there — the team is in the NY office
• Plus, not required: logistics, supply chain, freight, or AP-automation background