Head of Sales

Head of Sales

Location

Boston, MA; New York, NY

Employment Type

Full time

Location Type

Hybrid

Department

Sales

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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! 🚀

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Role at a glance

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.

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How you’ll make a difference in the first 12 months

Develop a Deep Understanding

• Deeply understand our segments, geographies, and sales motions

Strategy

• Partner with founders and the founding sales team on go-to-market strategy and 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

Sales Leadership

• 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

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What makes you a great fit

• 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

Bonus:

• Industry Knowledge: 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

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Why join us

• 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

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Details

• Start: As soon as you are ready
• Location: US East Coast, with a preference for Boston / NYC area (relocation support available)
• Set up: Hybrid
• Contract: Permanent
• Travel: Up to 50%
• Compensation: Competitive package including salary, bonus, and equity

If you’re ready to help build a truly seamless and magical checkout experience, we encourage you to connect and explore future opportunities with Deligo. We’re looking forward to receiving your application!