Digital Attitude is the consulting company of Digital360 Advisory, the Business Unit of the Digital360 Group specialized in helping organizations harmonize the experience between people and technology. It is a Microsoft Solutions Partner for Modern Work and was recognized as Microsoft Partner of the Year 2025 for Copilot & Agents. The company supports the effective adoption of digital tools and advanced ways of working by combining technological expertise, organizational psychology, social sciences, and data-driven insights to enable measurable and sustainable change. Digital Attitude works with leading technology ecosystems and strategic partnerships, particularly with Microsoft, to integrate innovation, productivity, and workplace transformation. We support businesses, SMEs, and large organizations that are navigating digital transformation initiatives, AI adoption, workplace evolution, and organizational change in environments characterized by high complexity and significant impact on people. Digital Attitude is part of Digital360 Advisory, the consulting business unit of Digital360, which helps organizations define and implement transformation strategies and operating models. The Digital360 Group is a leading Italian company that supports businesses and public sector organizations in digital transformation, organizational innovation, brand enhancement, and market positioning. We are currently looking for an AI Literacy & Augmented Skills Trainer (Freelance) to join our network of trainers and facilitators and support learning and transformation programs focused on AI Critical Literacy, Augmented Leadership, and the evolution of professional, soft, and managerial skills in the age of AI. The role combines learning design, experiential facilitation, and training delivery in both physical and digital settings. We are looking for a practitioner who can challenge established perspectives, work confidently with senior and diverse audiences, and translate the impact of AI on cognition, leadership, professional identity, and organizational culture into learning experiences that create lasting change. Main

Responsibilities:
• Training design and delivery: Deliver in-person, virtual, blended, and asynchronous learning experiences on AI Critical Literacy, Augmented Leadership, and Augmented Skills, adapting facilitation style and content to different formats and audiences.
• Experiential facilitation: Design and run workshops that go beyond content transfer, including co-design sessions, simulations, reflective practices, strategic workshops, team reflection sessions, and group processes that drive shifts in perspective and behavior.
• Augmented Skills and managerial development:



Support organizations in understanding how AI is reshaping decision-making, communication, creativity, collaboration, critical thinking, leadership, and professional identity, helping participants develop the skills needed to navigate this change.
• Complex audience management: Facilitate skeptical, senior, mixed, and cross-functional groups with confidence, reading group dynamics and adjusting the approach in real time, both in person and remotely.
• Content and material development: Design and customize slides, exercises, simulations, labs, guides, and other learning assets for workshops and training programs; contribute to digital and video-based learning content where relevant.
• Program co-creation: Work closely with the internal Business Unit on program design, content co-creation, client customization, and continuous improvement of the learning offer.
• Quality and feedback: Support course coordination and contribute to customer satisfaction by collecting participant feedback and using it to improve future learning experiences. Skills and Competencies Required:
• Training expertise: Significant experience in classroom, experiential, digital, and blended learning delivery with managerial and organizational development audiences, supported by a strong understanding of adult learning principles.
• Facilitation

skills:
Proven ability to facilitate complex group processes with diverse and senior audiences, including co-design labs, strategic workshops, and team reflection sessions.
• Thematic depth: Solid grounding in at least one of the following areas: AI Critical Literacy; Augmented Leadership and AI-supported managerial development; soft skills and Augmented Skills in the context of digital and AI transformation.
• Intellectual curiosity and critical thinking: A well-developed perspective on what AI means for human cognition, professional identity, organizational culture, and the capabilities people need to work effectively with technology, with the confidence to discuss and defend that perspective before a critical audience.
• Learning design: Ability to transform complex concepts into clear, engaging, and experiential learning journeys, materials, and activities.
• Communication and presence: Excellent presentation and interpersonal skills, with the ability to connect with groups of different sizes,



seniority levels, and professional backgrounds.
• Collaboration and adaptability: Ability to co-create with internal teams and clients, incorporate feedback, and adjust content and facilitation to the needs of each project and audience.
• Organization: Strong planning skills, attention to detail, reliability, and autonomy in managing project-based assignments.

Requirements:
• Relevant experience as a corporate trainer, facilitator, learning designer, or organizational development practitioner.
• Experience working with corporate clients across different industries, organizational levels, and cultural contexts.
• Demonstrated experience in both in-person and remote delivery, including experiential and participatory formats.
• Full professional fluency in Italian and/or English is mandatory.
• Professional fluency in Spanish, Portuguese, German, French, or Mandarin Chinese is a significant plus.
• Availability to collaborate on a project basis, with the objective of building an ongoing and frequent working relationship over time. Application: A portfolio showcasing examples of learning materials, workshop designs, facilitation formats, or video training sessions would be highly appreciated.

Location:
Remote, with availability for in-person delivery depending on project and client requirements. Languages: Italian and/or English; Spanish/Portuguese/German/French/Mandarin Chinese are a plus. Why work with us:
• You will become part of a team that combines consulting, technology, and communication, working on tangible projects for both private companies and public sector organizations.
• You will have the opportunity to collaborate with professionals from diverse backgrounds and contribute to initiatives that bring together strategy, execution, and market development.
• You will work in a dynamic and evolving environment where experimentation and collaboration are integral to the way we operate.
• We leverage AI and advanced digital tools to support daily activities and enhance productivity and effectiveness.
•

We offer
flexible working arrangements and a culture that promotes autonomy, accountability, and ownership.
• We invest in our people through continuous learning opportunities and professional development programs, helping them grow both personally and professionally. This search complies with Italian Legislative Decree 198/2006 and is open to individuals with disabilities, regardless of gender identity or expression, sexual orientation, age, ethnicity, or religious beliefs. This job posting has been created in accordance with the principles of diversity, equity, and inclusion.

📌 AI Literacy (Italia)
🏢 Digital Attitude - Digital360 Advisory
📍 Italia