Head of Sales

Deligo•Boston, MA

18h•Hybrid

About The Position

Deligo is a leader in visual AI self-checkout for the convenience retail industry, trusted by global brands like Compass, Sodexo, Marks & Spencer, and Spar. We build advanced visual AI — developed by a top-notch machine learning team — to recognize food and retail items instantly. No barcodes, no manual scanning. Just place your items and tap to pay — it’s that simple. The result: a magical experience that improves everyday lives by saving time standing in checkout lines. But this isn’t just exceptional tech: We are a tight-knit team of curious, passionate and ambitious builders who take pride in our craft and value trust in everything we do. If you’re looking to join a rocket ship and help redefine the future of AI-powered checkout, we’d love to meet you! 🚀

Requirements

Successful track record of leading enterprise sales through critical growth stages — ideally $5M→$10M and $10M→$30M+ ARR.
Ability to thrive in ambiguity and fast-moving early-stage environments.
5+ years leading enterprise sales teams in a scale-up with full ownership of revenue targets, pipeline, and forecasting.
Demonstrated success hiring, developing, and building scalable playbooks and repeatable revenue engines.
Ability to deeply understand needs and incentives across customers, partners, and the broader ecosystem — orchestrating win-win-win scenarios.
The best go-to-market talent wants to work with you, and you have the network to find them.

Nice To Haves

Experience in retail technology, convenience retail, food service, enterprise SaaS, AI-driven platforms, or adjacent operational technology sectors is highly preferred.
Experience working across both U.S. and European markets.
Strong product intuition and taste.

Responsibilities

Partner with the founders and the founding sales team on go-to-market strategy.
Secure lighthouse customers.
Build the commercial engine for the company's next phase of growth.
Combine hands-on enterprise selling with strategic leadership, including team development, revenue ownership, and creation of scalable sales playbooks.
Develop a deep understanding of our segments, geographies, and sales motions.
Partner with founders and the founding sales team on go-to-market strategy.
Support Series A fundraising with a credible plan.
Lead lighthouse deals in US Convenience Retail.
Personally lead and close first convenience store deals on top of our Verifone partnership.
Build a pipeline, strategy, and repeatable sales motion for large enterprise chains.
Lead and develop the sales team; foster a great sales culture.
Own EU and US revenue growth — qualified pipeline, consistent execution, forecast accuracy, and revenue targets.
Develop the Deligo Sales Playbook across Segments, Geographies, and Motions (direct, channel).
Grow the sales team across Europe and the US to support our growth objectives.