AI Learning Strategist

talentgarden; Milano; Hybrid; EUR 45,000 - 55,000; Full time

Benefits offered by this job

Hybrid work environment

Coworking spaces access across Europe

Master courses access

Meal vouchers €1,000 welfare budget

Mum&Dad policy with remote options

Additional 6 vacation days

Holidays: Dec 24 & 31

MacBook provided

Discounts & events at co-working spots

Pet-friendly

Job summary

Talent Garden in Italy is seeking an AI Learning Strategist to join our Strategy team within the B2B Corporate Transformation unit. You will identify high‑impact AI opportunities with corporate clients, shape practical AI‑enabled solutions through discovery and rapid prototyping, and translate them into structured transformation programs and learning pathways ready for delivery.

You will lead workshops with C‑suite executives, design AI transformation initiatives, build proofs of concept using

Qualifications

• 4+ years in consulting, system integration, IT, innovation, digital transformation, or capability-building environments.
• At least 1 year building production-grade or client-facing AI workflows.
• Strong AI literacy; able to explain AI concepts clearly to clients and lead discovery workshops.
• GenAI ecosystem mastery; Microsoft Copilot certification is a plus.
• Native Italian; professional English.
• Based in Milan or Rome, or willing to travel regularly.

Responsibilities

• Conduct discovery workshops with C-level stakeholders to identify AI use cases.
• Design AI-enabled transformation initiatives and learning programs.
• Build rapid proofs of concept and prototypes using GenAI tools, prompt engineering, and automation platforms.
• Analyze AS-IS processes and design TO-BE AI-augmented processes to unlock automation and productivity gains.
• Translate AI capabilities into clear business outcomes and connect technologies to operational impact.
• Structure proposals, adoption roadmaps, and solution architectures for AI-enabled transformations.
• Define guardrails for responsible AI adoption, addressing privacy, security, and compliance.
• Craft narratives and learning pathways to move leaders and employees from experimentation to adoption.
• Collaborate with Strategy, Client, and Delivery teams as a subject matter expert on AI transformation.

Skills

Stakeholder engagement

AI workflow development

GenAI expertise

Bilingual Italian/English

Travel willingness

Tools

Claude

Gemini

OpenAI APIs

n8n

Make

Microsoft Copilot

Job description

About us

Talent Garden is a leading AI Transformation school in Europe, empowering individuals and organizations to thrive in the innovation ecosystem through diverse learning experiences. With online, offline, and hybrid courses, corporate programs and work and events spaces we offer an unparalleled vision to combine work life and learning.

Founded in Italy in 2011, Talent Garden has trained over 25,000 professionals in digital skills and business innovation, developed tailored corporate education programs for Fortune 500 companies, and built a network of 7 campuses in 3 countries, hosting over 4,500 innovators from startups, corporate labs, investors, and SMEs.

Today, our focus is on helping organizations adopt AI as a driver of business transformation, combining strategic advisory with hands‑on implementation.

The role

We are on the lookout for an AI Learning Strategist to join our Strategy team within the B2B Corporate Transformation business unit.

In this role, your mission will be to identify high-impact AI opportunities with our corporate clients, shape practical AI-enabled solutions through discovery and rapid prototyping, and translate them into structured transformation programs and learning pathways ready for delivery.

Responsibilities

• Conduct discovery workshops with C-level stakeholders to identify business pain points and prioritize high-impact AI use cases.
• Design AI-enabled transformation initiatives and learning programs, translating strategic objectives into structured adoption paths.
• Build rapid proofs of concept and prototypes using GenAI tools, prompt engineering, and automation platforms (e.g. Microsoft Copilot, Claude, Google Gemini, OpenAI APIs, n8n, Make or similar tools).
• Analyze AS-IS process and workflows and design TO-BE AI-augmented processes to unlock automation, productivity gains, and improved operating models.
• Translate AI capabilities into clear business outcomes, connecting technologies such as LLMs, embeddings, or automation workflows to operational impact.
• Structure proposals, adoption roadmaps, and solution architectures to support AI-enabled transformation initiatives.
• Define guardrails for responsible AI adoption, addressing data privacy, security, compliance, and the management of “Shadow AI”.
• Craft narratives and learning pathways that help leaders, HR teams, and employees move from experimentation to structured AI adoption.
• Collaborate with the Strategy team and act as a subject matter expert on AI transformation across projects.

About you

Ideally, you are a strategist with a builder mindset, comfortable engaging with executive stakeholders while also experimenting hands‑on with AI tools to turn ideas into tangible solutions.

On top of this, you:

• Bring 4+ years of experience in consulting, system integration, IT, innovation, digital transformation, or capability-building environments, working at the intersection of strategy, technology, and organizational change.
• Have at least 1+ year building production‑grade or client‑facing AI workflows, not just personal experimentation using tools such as Claude, Gemini, OpenAI APIs, n8n, Make, or similar platforms.
• Demonstrate strong AI and tech literacy, with the ability to explain AI concepts clearly, facilitate AI discovery workshops with clients, and identify high‑impact automation or AI adoption opportunities.
• Demonstrate strong mastery of the GenAI ecosystem, including LLM architectures, emerging capabilities, and practical applications of AI tools in business contexts; certification of Microsoft Copilot / Microsoft ecosystem is considered a plus.
• Interact confidently with senior stakeholders, navigating complex organizational dynamics and challenging assumptions when needed.
• Work effectively both independently and as part of the Strategy team, collaborating closely with the Client and Delivery teams to shape impactful AI-enabled solutions.
• Speak Italian at a native level and English at a professional level.
• Are based in Milan or Rome, or able to travel regularly to these locations.

Perks and benefits

• Hybrid work environment, combining remote flexibility with regular on‑site collaboration across our campuses
• Access to all our co‑working spaces across Europe
• Free access to all our Master courses
• Meal vouchers and a €1,000 welfare budget to spend as you like (available only in Italy)
• Mum&Dad policy offering (even more) flexible remote work options for expecting parents, a €1,000 bonus, and additional leave for dads to bond with their child
• An extra 6 working days of vacation each year, on top of local regulations
• December 24 and 31 automatically become holidays when they fall on weekdays
• Company‑provided MacBook
• Access to discounts, events, and networking opportunities at our co‑working spaces
• P.S. We’re pet‑friendly, so you’re welcome to bring your furry friend to work!

Salary

The salary/salary range for the role is 45.000,00/55.000,00€ gross per year based on the experiences and expertise of the candidate.

At Talent Garden, diversity is our strength. We're committed to a safe, inclusive environment, welcoming applicants regardless of background. While we set high standards, we encourage individuals, especially women, not to let the fear of not being a perfect fit hold them back. We prioritize talent over traditional qualifications and invite passionate individuals to apply. Your unique strengths could make a valuable contribution to our team! You can read our privacy policy here.