Director of AI Enablement and Implementation

Location: Milan, Italy (Remote-friendly or Hybrid)

Seniority: 8 - 15 years of relevant experience

About Shop Circle

We are one of Europe’s fastest growing AI-driven software groups, on a mission to power the infrastructure of modern enterprises.

Backed by more than $150M in funding, we have completed 16 acquisitions in just four years, building a portfolio of mission-critical software that is redefining how businesses work, scale, and stay ahead.

At Shop Circle, we embed AI-powered tools into the core of business operations, making work faster, smarter, and truly future-ready. Today, more than 140,000 companies, from lean SMBs to global enterprises, rely on us to run their most essential operations every day.

Role Overview

We’re hiring a Director of AI Enablement and Implementation to lead the company-wide adoption and integration of AI-powered tools. This is not a research or AI modeling role. It’s about taking an already AI-friendly organization to the next level: identifying high-impact use cases, deploying the right tools, embedding them into functional workflows, and ensuring strong adoption with measurable ROI.

You will be a cross-functional change agent, ensuring that every team is leveraging AI to work smarter, reduce manual work, and free up time for higher-value activities. You’ll be the driving force behind our AI-first strategy, embedding AI across the company as a core enabler of speed, scale, and efficiency.

What You’ll Do

• Define and lead the AI enablement roadmap across all departments
• Translate business needs into concrete, AI-powered solutions using tools like OpenAI, Writer, Jasper, Glean, LangChain, Zapier , etc.
• Collaborate with Engineering, Product, and Operations to integrate tools via APIs, webhooks, or low-code platforms
• Build quick proof-of-concepts and pilots to validate use cases
• Own onboarding, enablement, and internal training to drive AI adoption
• Track and report on usage, adoption metrics , and business impact
• Ensure every function is using the best-fit tools for their specific workflows
• Manage vendor selection, pricing negotiations, and procurement
• Shape the operational rollout of Shop Circle’s AI-first vision
• Help implement and scale intelligent agents (e.g., autonomous financial assistants, workflow bots) across our software portfolio

What We’re Looking For

• 8–15 years in solution engineering , internal tools , technical consulting , or AI/automation delivery
• Proven success in rolling out tools across departments in fast-paced environments
• Strong business acumen and the ability to tie automation to real-world outcomes
• Technically fluent, hands-on, and pragmatic
• Excellent communicator with both technical and non-technical teams
• Fluent in English and based in Italy
• Background in consulting, system integration , or internal innovation teams is a plus

Bonus Experience (Tools & Platforms)

• Writing & Content : Jasper, Writer, Copy.ai
• Productivity & Coding : GitHub Copilot, Cursor
• Knowledge Management : Glean, Dashworks, Hebbia
• Automation Frameworks : Zapier, LangChain, Crew AI
• CX Enablement : Intercom Fin, Cohere, Forethought
• Note-taking & Research : Notion AI, Rewind, Claude
• Finance & FP&A : Pigment, DataRails, Cube
• M&A & Strategy : Tegus, AlphaSense, Cascade, Revi

Why Join Us

• Strategic role reporting directly to senior leadership
• High-visibility opportunity to shape the AI foundation of a next-gen software group
• Empower teams to work faster, smarter, and better
• Entrepreneurial culture with ownership and autonomy
• Competitive compensation and the chance to drive real transformation

Ready to join us?

Apply now and help shape the future of AI-driven enterprise software at Shop Circle!