Matteo Masi
GTM Builder | Market Creation & Expansion | Agentic AI, Cloud & SaaS (AWS, UiPath, Cisco)
ex-Amazon Web Services (AWS)Fex-Fragmentalis S.r.l.I'm not really looking for a specific What I've enjoyed most throughout my career is
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Building markets. Building teams. Building new business segments. Helping companies navigate major technology shifts and turn emerging technologies into scalable Over the last 20+ years, I've had the opportunity to do exactly that across Networking, Cloud, SaaS, Automation and now Agentic I started by helping launch and grow the Italian operations of US technology companies such as Blue Coat and Aruba Networks. Later, at AWS, I built the Startup & Digital Native segment in Italy from the ground up, working closely with founders, venture capital firms, accelerators and technology I then moved into Enterprise GTM leadership, leading growth across more than 900 enterprise accounts and a $40M+ consumption-based business. During that time, I helped build one of the fastest-growing segments in the country, combining strategic growth initiatives, complex enterprise sales, ecosystem development and cross-functional Today, I focus on Agentic AI and Intelligent Automation at UiPath, helping large organizations transform how work gets done through next-generation What motivates me most is the early stage of growth: when a market needs to be shaped, when there is no established playbook, and when success depends on creating momentum rather than simply managing Throughout my career, I've worked closely with enterprise executives, founders, venture capital firms, accelerators and Global System Integrators, helping drive adoption of new technology platforms at I enjoy operating at the intersection of strategy and execution — building go-to-market motions, opening doors, creating partnerships, winning customers and helping organizations If you're building something ambitious and looking to expand in Italy or Southern Europe, I'd be happy to Beyond my core role:- Active contributor to the startup and VC ecosystem, with hands-on experience across accelerators and incubators- Board member of Fragmentalis, focused on hyper-secure data communication technologiesOutside of work:- Boxing lover and practitioner- Marathon finisher (New York, Nov 2025), an experience that reflects my mindset: discipline, resilience, and long-term - Passionate about gluten-free cooking and nutrition. By necessity first, by passion now.
GTM Index
- UIPATHJOB
- GTM Leader (AI & Agentic A…2Y 4M
GTM Leader (AI & Agentic Automation) - Energy&Utilities, Manufacturing, Automotive & Telco Segments
UiPath
Leading GTM and expansion strategy across UiPath’s largest and fastest-growing vertical segment, driving automation-led enterprise transformation in complex, multi-stakeholder environments. • Position Agentic Automation as economic transformation • Built ROI-driven business cases linking Agentic to KPIs • Operate in hybrid monetization environment (license + expansion + value realization) • Navigate complex enterprise buying committees (C-level, Operations, IT, Legal, Procurement) • Drive land-and-expand motion anchored in measurable value delivery
- AMAZON WEB SERVICES (AWS)JOB
- Senior Mgr - Head of GTM -…2Y 6M
Senior Manager - Head of GTM - Enterprise
Amazon Web Services (AWS)
Enterprise GTM Leader | $40M Run-Rate | 20-Person Revenue Team | Consumption-Based Cloud/AI/Agentic revenue Model | Land & Expand Strategy Core skills • Consumption-Based Cloud/ML/AI revenue models • Designed Land&Expand strategy for 900+ Enterprise accounts • Maintained forecast accuracy in variable consumption-based revenue business • Usage-based & outcome-based monetization models • Revenue volatility management in consumption environments • Hybrid ARR + variable revenue structuring • CFO-level ROI & infrastructure economics modeling • Forecast discipline in non-linear revenue systems • Territory & coverage design for revenue density optimization • Enterprise & Startup GTM architecture…
- Country Leader - Startup S…3Y 1M
Country Leader - Startup Segment
Amazon Web Services (AWS)
Built and led startup GTM segment from inception, partnering with venture-backed, technology-native companies. • Partnered with founders scaling usage-based infrastructure models • Advised on cost structure, scalability and margin sensitivity • Managed highly variable consumption-driven revenue streams • Designed GTM motion for high-growth digital-native companies • Defined and implemented a Get/Keep/Growth land&expand strategy Part of EMEA Startup Leadership Team with direct report to EMEA Startup Segment Director
- FRAGMENTALIS S.R.L.JOB
- Board member & Mentor1Y 6M
Board member & Mentor
Fragmentalis S.r.l.
- CISCOJOB
- Industry 4.0 & Smart Manuf…2Y 10M
Industry 4.0 & Smart Manufacturing practice Lead
Cisco
- Sales & BD Mgr South Europ…4Y 5M
Sales & Business Development Manager South Europe - Data Center & Cloud, Networking, Security
Cisco
- CONFINDUSTRIA DIGITALEJOB
- Member of Steering Committ…2Y 10M
Member of Steering Committees "EU Digitization, AI and Data” and ”SME Digitization”
Confindustria Digitale
- ARUBA, A HEWLETT PACKARD ENTERPRISE COMPANYJOB
- Senior Presale & Channel Mgr2Y 5M
Senior Presale & Channel Manager
Aruba, a Hewlett Packard Enterprise company
Opened the Italian Branch of startup, led sales for North of Italy and created the partner channel network, leading a growth of 100% YoY
- BLUE COAT SYSTEMSJOB
- Security System Eng - Sout…2Y 6M
Security System Engineer - South Europe
Blue Coat Systems
- ACANTHOJOB
- Presale Mgr & Project Mgr5Y 11M
Presale Manager & Project Manager
Acantho
- Job: UiPath — GTM Leader (AI & Agentic Automation) - Energy&Utilities, Manufacturing, Automotive & Telco Segments · 2024-06 – present · 2y 2mo — Leading GTM and expansion strategy across UiPath’s largest and fastest-growing vertical segment, driving automation-led enterprise transformation in complex, multi-stakeholder environments. • Position Agentic Automation as economic transformation • Built ROI-driven business cases linking Agentic to KPIs • Operate in hybrid monetization environment (license + expansion + value realization) • Navigate complex enterprise buying committees (C-level, Operations, IT, Legal, Procurement) • Drive land-and-expand motion anchored in measurable value delivery
- Job: Amazon Web Services (AWS) — Senior Manager - Head of GTM - Enterprise (Head of GTM Engineering) · 2021-12 – 2024-06 · 2y 6mo — Enterprise GTM Leader | $40M Run-Rate | 20-Person Revenue Team | Consumption-Based Cloud/AI/Agentic revenue Model | Land & Expand Strategy Core skills • Consumption-Based Cloud/ML/AI revenue models • Designed Land&Expand strategy for 900+ Enterprise accounts • Maintained forecast accuracy in variable consumption-based revenue business • Usage-based & outcome-based monetization models • Revenue volatility management in consumption environments • Hybrid ARR + variable revenue structuring • CFO-level ROI & infrastructure economics modeling • Forecast discipline in non-linear revenue systems • Territory & coverage design for revenue density optimization • Enterprise & Startup GTM architecture…
- Job: Amazon Web Services (AWS) — Country Leader - Startup Segment · 2018-11 – 2021-12 · 3y 1mo — Built and led startup GTM segment from inception, partnering with venture-backed, technology-native companies. • Partnered with founders scaling usage-based infrastructure models • Advised on cost structure, scalability and margin sensitivity • Managed highly variable consumption-driven revenue streams • Designed GTM motion for high-growth digital-native companies • Defined and implemented a Get/Keep/Growth land&expand strategy Part of EMEA Startup Leadership Team with direct report to EMEA Startup Segment Director
- Job: Fragmentalis S.r.l. — Board member & Mentor · 2022-06 – 2023-12 · 1y 6mo
- Job: Cisco — Industry 4.0 & Smart Manufacturing practice Lead · 2016-01 – 2018-11 · 2y 10mo
- Job: Cisco — Sales & Business Development Manager South Europe - Data Center & Cloud, Networking, Security · 2011-07 – 2015-12 · 4y 5mo
- Job: Confindustria Digitale — Member of Steering Committees "EU Digitization, AI and Data” and ”SME Digitization” · 2016-01 – 2018-11 · 2y 10mo
- Job: Aruba, a Hewlett Packard Enterprise company — Senior Presale & Channel Manager · 2009-02 – 2011-07 · 2y 5mo — Opened the Italian Branch of startup, led sales for North of Italy and created the partner channel network, leading a growth of 100% YoY
- Job: Blue Coat Systems — Security System Engineer - South Europe · 2006-08 – 2009-02 · 2y 6mo
- Job: Acantho — Presale Manager & Project Manager · 2000-09 – 2006-08 · 5y 11mo
- School: Università di Bologna — Telecommunications Engineering, Telecommunications Management
Skills
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