Massimiliano Grosso
IT Delivery Lead - Senior Manager - CRM - Microsoft Technologies - AI @ Avanade
About
I turn technological complexity into business value—something I’ve been doing for over 25 years.I lead complex IT transformation programs, turning legacy-driven technological environments into scalable, business-oriented platforms. With over 25 years of experience, I specialize in enterprise transformation initiatives — including mainframe modernization, cloud adoption, and AI-driven evolution — operating at the intersection of IT strategy, execution, and business value. In recent years, I have successfully led large-scale transformation programs, reducing execution time by 20% in critical M&A migrations and delivering measurable improvements in operating efficiency and scalability. My focus is not just on delivery, but on redesigning IT operating models — ensuring that technology becomes a growth enabler rather than a constraint, especially in complex and highly regulated environments. I work across global, multi-vendor ecosystems, leading cross-functional teams in EMEA and APAC, and engaging with senior stakeholders from Board-level discussions down to execution. Today, my ambition is to drive the next wave of enterprise transformation, leveraging Generative AI and modern IT architectures to unlock new value for organizations.If you're seeking a transformative approach to manage your IT department, let’s connect and explore how we can work together to drive your business
Italy
Milan
Information Technology & Services
IT Strategy, Strategic Planning, Cost Optimization (OPEX/CAPEX), Technology Leadership, IT Governance, Cloud Applications, Microfocus, Digital Transformation, Artificial Intelligence (AI), Business Strategy, Lavoro di squadra, Team leadership, Project Portfolio Management, Strategia IT, Prendere decisioni, It leadership, Product Management, Stakeholder Management, Innovation Management, Change Management
Experience

IT Delivery Lead - Senior Manager - CRM - Microsoft Technologies - AI
Milan
Responsible for digital transformation projects with an average volume of some million euros per year, in Italy and abroad, managing relationships with top-level executives (CEO, CTO, CFO, Commercial Directors), various project teams, and increasing the profitability of contracts Responsible for significant annual budget IT projects in Italy and abroad. Skilled in managing relationships with top-level executives (CEO, CTO, CFO, Commercial Directors) , diverse project teams and in increasing the profitability of contracts. Global Results: Achieved a Gross Operating Margin that surpassed expectations through innovative strategies and effective management. Consistently exceeded software quality expectations, demonstrating a commitment to excellence. Key IT Projects: Major Insurance Company: Project for Mainframe Porting to the Cloud (Microfocus - DB2 LUW) Mergers and Acquisitions Project: Led a complex IT project involving mergers and acquisitions. Significantly improved migration timelines and reduced costs through effective application convergence, portfolio migration, and accounting and tax data management. Worked closely with sales teams to understand and meet project requirements, establishing long-term relationships with executive-level stakeholders. Sales Catalog and Customer Management Automation: Identified and implemented an innovative solution for data integration and adjustment, optimizing data management and convergence procedures. Digital Transformation in Insurance Sector: Directed a team of 20, completing the project with significant savings in both time and cost. Sales Force Automation Projects on Dynamics 365 CRM: Completed a sales force automation project within 6 months, showcasing agility and efficiency.

IT Delivery Manager - Software Factory Manager - Microsoft Technologies
Milan Area, Italy
Managed the Milan IT Factory as Technology officer, coordinating a team of 50 resources and managing projects worth million euros Global Results and Achievements: Team Management and Project Leadership: Oversaw the operations of the Milan IT Factory, coordinating a dynamic team of 50 professionals. Expertly managed multiple projects, demonstrating strong leadership and organizational skills. Successfully supervised a large team, ensuring the company's success both technically and operationally. Founded and managed a research, development, and innovation unit, leading to significant advancements in technology and process improvement. This initiative garnered recognition and support, exemplifying commitment to innovation and growth. Enhanced the efficiency of the software development processes and elevated software quality by adopting and implementing the DevOps model, showcasing adaptability and a forward-thinking approach Spearheaded an innovative IT project that significantly streamlined the sales process. This was achieved by implementing a comprehensive ERP system on tablets in a paperless mode, which markedly improved efficiency and customer experience in the retail environment. Led the development of a critical software management project. This project played a key role in enhancing the operational capabilities of the organization, demonstrating expertise in software development and project management. Successfully delivered a license management software project within a tight timeframe, achieving full customer satisfaction. The project involved close collaboration with the client to understand their needs, resulting in a solution that automated processes and enhanced profitability.

Project Leader IT - CRM - Microsoft Technologies
Directed the launch phase of an international software factory, focusing on the development of software for acquisition and reservation processes. This role involved ensuring efficient development costs, improving profitability, and accelerating sales processes. Key responsibilities included: Nearshore Software Factory Project: Established operational methods and resource engagement for a new software factory, achieving operational status within a short timeframe and significantly reducing software development costs. CRM Project Management: Led a small team in optimizing sales process management within a retail environment. Successfully implemented paperless sales processes, leading to enhanced sales efficiency. Demonstrated rapid team assembly and adept adoption of Agile methodologies. Software Acquisition Process Management Project: Successfully managed project costs while adhering to strict timelines, exemplifying strategic cost containment and timely delivery. Track Management Software Development: Oversaw the development of a specialized management software project, significantly enhancing its market appeal and preemptively addressing end-user needs. This project demonstrated innovative thinking and market foresight in software development. Ecatalogue Project Leadership: Quickly assembled a new development team and implemented Agile methodologies. Delivered innovative graphical solutions and proposed business improvements that notably enhanced productivity.

Team Project Leader - Vodafone Project
I grew up professionally becoming a Project Leader on major projects for Vodafone Managed the allocation of resources, project planning, performance metrics control, and client relations. Effectively managed the allocation of resources, project planning, performance metrics, information management and client relations. Key accomplishments in this role included: Dealer Station Project: Innovated within a major project by integrating electronic payments and paperless management, securing a substantial competitive edge. Led a team of 16, enhancing software security and increasing the productivity of hardware infrastructure. Sales Channel Software Development Project: Spearheaded the development of software for a new sales channel. Successfully contained infrastructure and hardware adjustment costs. Pioneered a new communication method between Web Servers and the Back End, focusing on cost containment and IT security. Implemented innovative solutions that significantly improved IT security and efficiency.

Analyst- Software developer
Oversaw the software analysis and development phase, demonstrating strong project management, strategic vision and technical skills. Key accomplishments included: Telecommunications Project: Successfully completed the development of complex reports in Business Object 5.1, well ahead of the scheduled deadline. This project showcased expertise in handling intricate data layouts and delivering timely results. Aerospace Software Development Project: Developed innovative software for the management of helicopter fleets. This project was recognized for its quality by an external military entity, highlighting a commitment to high standards and innovative solutions in software development for critical applications.

C.I.T, TUTOR
CEPU Srl
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