Head of Sales Italy (Milan hub)

We are seeking a Head of Sales Italy to lead and scale our commercial operations across the Italian market, with a base in Milan. You will be responsible for defining and executing the national sales strategy, leading the local sales team, and driving revenue growth by closing strategic enterprise deals. This is a high-impact leadership role for a top performer who thrives in fast-growing environments and has a deep understanding of the Italian business landscape.
Key Responsibilities

• Define and execute the sales strategy for the Italian market, aligned with company growth objectives
• Lead, mentor, and scale the local sales team, fostering a high-performance culture
• Own and oversee the full enterprise sales cycle for key strategic accounts
• Build and maintain a strong pipeline through outbound initiatives, partnerships, and events
• Engage with C-level stakeholders, delivering high-impact presentations and product demos
• Collaborate closely with marketing, pre-sales, and product teams to tailor solutions to client needs
• Provide accurate forecasting and reporting to senior leadership
• Represent the company as a key commercial leader in Italy
  

Join Us If

• 8+ years of experience in B2B SaaS sales, with at least 3 years in a leadership role
• Proven track record of exceeding revenue targets and scaling sales teams
• Strong experience managing complex enterprise sales cycles
• Deep knowledge of the Italian market and business ecosystem
• Established network across key industries such as retail, finance, telco, or manufacturing
• Excellent leadership, communication, and negotiation skills
• Fluent in English (mandatory); Italian or any other language is a plus
• Based in Milan or willing to relocate
  

Nice To Have

• Experience in MarTech, AI, or enterprise content solutions
• Background in high-growth startups or scale-ups
• Familiarity with AI-driven platforms or digital transformation projects
  

What We Offer

• A competitive salary package aligned with your experience and seniority
• A generous stock option plan, reflecting the company’s strong growth trajectory and future exit potential
• The opportunity to play a key leadership role in a fast-scaling international company
• Direct exposure to top management and influence on strategic decisions
• A dynamic, innovative, and mission-driven work environment
  

Want a mini-spoiler on Contents?
Contents is a leading Italian scale-up providing an AI-powered content creation platform used by global brands in publishing, retail, luxury, financial services, and automotive. Our platform leverages LLMs to enable personalized content creation and seamless CMS/CRM/social integrations.
Contents is backed by leading European and American venture capital firms and is rapidly expanding its global presence and product offerings.
Contents is an equal opportunity employer. We evaluate candidates regardless of gender, ethnicity, sexual orientation, religion, or disability.

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