Head of Sales

Deligo • Boston, MA

3d • 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! 🚀 As Head of Sales, you will partner with the founders and the founding sales team on go-to-market strategy, secure lighthouse customers, and build the commercial engine for the company's next phase of growth. Combining hands-on enterprise selling with strategic leadership — team development, revenue ownership, and creation of scalable sales playbooks.

Requirements

• Early-Stage Revenue Leadership: 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.
• Sales Leadership Experience: 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.
• Business Acumen: Ability to deeply understand needs and incentives across customers, partners, and the broader ecosystem — orchestrating win-win-win scenarios.
• Talent Magnet: 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

• 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.

Benefits

• Opportunity to join at a critical growth stage, making a visible impact as we scale in the U.S. market.
• Real influence on how our sales organization, GTM strategy, and overall business evolve.
• A collaborative, ambitious, and transparent culture where ownership and impact are recognized.
• Work closely with experienced founders and a world-class team building a new category.
• High-tech equipment.
• Flexible working setup with a hybrid approach and frequent travel to customers.
• Competitive salary and equity package aligned with your impact.
• Relocation support available.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed