Strategic SaaS Account Executive - AI Estimator

Gelato has created the world’s largest global network for on-demand production of custom products – from t-shirts and mugs to books and wall art. We empower a new generation of ecommerce entrepreneurs to share their creativity worldwide while embracing local, sustainable production. By producing locally and perfectly matching supply with demand, we eliminate waste and reduce carbon emissions.

At Gelato, we don’t own production facilities – we build the software that connects them. With over 140 production partners in 32 countries, our network can deliver custom products to five billion people in just 72 hours. It’s smarter, faster, and greener.

With GelatoConnect, our SaaS platform, we’re driving innovation in print production. GelatoConnect simplifies operations for print producers by automating procurement, workflows, and logistics into one seamless system. By boosting efficiency and cutting costs, it helps businesses scale to meet market demands. Together, these products represent a full commercial stack for print businesses, from day-to-day quoting efficiency to end-to-end digital transformation.

As an Account Executive, you will own the full sales cycle across both GelatoConnect products, managing a commercial portfolio that spans both transactional and strategic sales. The ability to shift between these motions, and to sequence them intelligently, is central to how this role creates value. This is a high-ownership role for sellers who are motivated by variety, learning, and commercial impact.

• Sales Execution and Deal Ownership
• Own the full sales cycle across both products, from prospecting and qualification through to close.
• Drive outbound prospecting into priority accounts while converting inbound demand efficiently.
• Apply a Challenger-led approach for AI Estimator deals, moving quickly from discovery to close in 10-20 day cycles.
• Lead deep, consultative discovery for GelatoConnect deals, engaging commercial, operational, and technical stakeholders across 3-6 month sales cycles.
• Apply MEDDIC qualification rigorously across the pipeline.
• Design and articulate tailored solutions that map to complex customer workflows and operational needs.
• Navigate multi-stakeholder buying processes, procurement, and approvals on enterprise deals.
• Identify cross-sell opportunities and build pathways from AI Estimator adoption into broader GelatoConnect engagement.
• Collaborate closely with Product, Solutions, and Leadership on strategic deals.
• Consistently meet and exceed monthly and quarterly sales quotas.

• Pipeline Management and Forecasting
• Manage a mixed pipeline of transactional and strategic deals simultaneously, with accurate forecasting across both.
• Maintain excellent CRM hygiene to ensure pipeline visibility and actionable sales insights.
• Act as an AI builder, actively utilizing AI tools to enhance sales processes and increase execution speed across the funnel.

• Customer Value and Market Feedback
• Provide frontline feedback to Marketing, Product, and Partnerships to continuously improve our go-to-market approach.

Who You Are

You have a start-up mentality, incredible stamina, discipline, resilience, and grit. You're a doer. You change until you win. You feel comfortable getting your hands dirty while never losing sight of long-term ambition. You are confident in your abilities and experience, yet humble and curious in your execution.

Our Requirements Include

• 5+ years of full-cycle, quota-carrying closing experience in B2B SaaS or cloud-based platforms.
• Demonstrated experience closing deals of £/€100k+ annually.
• Demonstrated success in both transactional/high-velocity and consultative/enterprise sales motions.
• Strong discovery skills; you know how to uncover real business pain through curiosity.
• Proven track record of meeting or exceeding revenue targets.
• Familiarity with MEDDIC structured sales qualification methodologies.
• Excellent communication and relationship-building skills.
• Entrepreneurial mindset with a strong bias toward action and ownership.
• Experience using CRM systems (e.g. Salesforce, HubSpot) and sales reporting tools.
• Fluency in English; additional European languages are a plus.

We are a customer-obsessed team with the ambition to change the world by connecting technology to the printing industry and making it much more sustainable. Everyone who joins our team must feel genuinely intrigued and motivated by our mission. We expect a lot. We are a driven team with big goals, so we seek individuals who are genuinely passionate about their work and possess an entrepreneurial spirit.

At Gelato, we pride ourselves on our global presence with 14 offices worldwide, fostering a dynamic and diverse work environment. Our culture is unique and we live by our values, so it's worth learning more about our culture and how we work before presenting your application.