Head of Sales
At a glance
Leadership Sales Leadership role at Deligo. Boston · full-time.
Pay not stated
Growth Roles summary, based on the employer's posting.
What you'll do
- Shape go-to-market plans with the founders and founding sales group while supporting the Series A fundraising story
- Personally win early convenience-store accounts in the US, building on the Verifone partnership
- Create enterprise pipeline and repeatable selling motions for large retail chains across direct and channel routes
- Own European and US revenue performance, including pipeline quality, forecasting, execution, and targets
- Hire and develop sales talent while building a scalable playbook for segments, regions, and motions
What you bring
- At least five years leading enterprise sales teams at a scale-up with revenue, pipeline, and forecasting accountability
- A record of guiding enterprise revenue through major growth stages, including transitions from $5M to $10M and beyond $10M to $30M+ ARR
- Evidence that you have hired, developed, and built repeatable sales systems and revenue engines
- The ability to operate well amid ambiguity and understand incentives across customers, partners, and the wider ecosystem
Who this fits
You’ll suit a hands-on sales leader who can close enterprise deals while developing teams, playbooks, and commercial strategy. The role spans US and European markets and is based on the US East Coast, with Boston or New York preferred and relocation support available. It is hybrid, permanent, and involves travel to customers of up to 50%.
From the employer
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! 🚀
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.
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
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
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
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!
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