Olga A. Schupak
Enterprise Cloud & AI Transformation @ Microsoft | Strategy, Adoption, Scale | Advisor to AI & B2B Startups
I work at the intersection of enterprise technology, AI adoption, and organizational transformation. At Microsoft, I help organizations move from strategic ambition to scalable execution across cloud, data, and AI.
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My work often sits where technology decisions become organizational decisions — involving operating models, governance, stakeholder alignment, investment priorities, and long-term adoption. Over the years, I’ve worked across engineering, delivery, pre-sales, strategy, and transformation roles. That combination gives me a practical understanding of how organizations evaluate change, where momentum slows down, and what it takes to move initiatives from experimentation to operational reality. I’m particularly interested in: • Enterprise AI adoption and transformation • Scalable operating and adoption models • Technology strategy in complex environments • The intersection of AI, product, and organizational change • Turning emerging technology into sustainable organizational value Alongside my enterprise work, I mentor startups and founders on navigating the transition from early traction to enterprise adoption — helping them refine positioning, challenge scaling assumptions, and better understand the realities of complex European environments where technology alone is rarely enough to drive change. Open to selected advisory conversations and ecosystem collaborations.
GTM Index
- MICROSOFTJOB
- Enterprise Cloud & AI Tran…1Y 1M
Enterprise Cloud & AI Transformation Lead - Public Sector
Microsoft
Leading enterprise Cloud & AI transformation initiatives across central government environments, with a focus on turning long-term technology priorities into executable and scalable adoption paths. Work spans highly regulated and institutionally complex organizations where Cloud & AI decisions involve governance, architecture, funding, security, operational risk, and multi-stakeholder alignment. Key focus areas include: • Shaping Cloud & AI transformation strategies ahead of major investment decisions • Translating strategic priorities into executable adoption approaches • Aligning business, architecture, delivery, and governance stakeholders • Designing repeatable transformation models…
- Enterprise Application Inn…1Y 11M
Enterprise Application Innovation Lead - Public Sector
Microsoft
Focused on moving cloud-native and AI-driven initiatives from early-stage exploration into committed execution within enterprise public sector environments. Worked across customers, partners, architects, and account teams to assess adoption readiness, shape scalable modernization approaches, and identify initiatives with long-term operational potential beyond isolated pilots. Key contributions included: • Turning early-stage innovation initiatives into executable transformation paths • Identifying scalable modernization opportunities across complex environments • Establishing repeatable adoption approaches rather than one-off implementations • Helping organizations move from experimentat…
- Enterprise Application Mod…3Y 5M
Enterprise Application Modernization Lead - Retail
Microsoft
Partnered with enterprise retail organizations on large-scale application modernization and cloud transformation initiatives, with a focus on scalable adoption approaches rather than isolated implementations. This role laid the foundation for later work in enterprise transformation, adoption strategy, and repeatable modernization models across complex organizations.
- KOPPERHEAD BVJOB
- Independent Advisor - AI,…6Y 7M
Independent Advisor - AI, Cloud & GTM Strategy
Kopperhead BV
Advising selected startups and scaleups on enterprise technology strategy, cloud adoption, go-to-market alignment, and scaling from experimentation to operational execution. Areas of focus include: • Enterprise AI and cloud strategy • GTM and enterprise positioning • Product and platform feedback from enterprise perspective • Scaling adoption in complex organizations • Bridging startup execution with enterprise realities Working across both startup and enterprise environments has provided a practical perspective on how emerging technology moves from innovation to scalable business value.
- GTM & European Expansion S…2Y 5M
Go-to-Market & European Expansion Strategist
Kopperhead BV
Advised startups and scaleups on European market-entry strategy, go-to-market positioning, and commercialization approaches across diverse technology and digital business models. Worked closely with founders to validate expansion assumptions, refine positioning, prioritize market opportunities, and shape scalable growth approaches suited for complex European markets. Focus areas included: * European market-entry strategy * Go-to-market validation and positioning * Commercial scaling assumptions * Partner and ecosystem strategy * Early-stage growth prioritization
- SPHINX-PROJECTJOB
- Advisory Board Member2Y 11M
Advisory Board Member – European Commission Horizon 2020 Initiative
sphinx-project
Served on the advisory board of a European Commission Horizon 2020 initiative focused on cybersecurity and resilience across healthcare and care ecosystems. Provided independent strategic perspective on technology direction, execution feasibility, risk assumptions, and adoption considerations in highly regulated environments. Contributed to discussions spanning: * cybersecurity strategy, * institutional risk, * operational feasibility, * ecosystem coordination, * and long-term implementation considerations.
- PERFECTOJOB
- Enterprise Solution Consul…2Y
Enterprise Solution Consultant – SaaS & Transformation
Perfecto
Supported enterprise SaaS sales by qualifying complex opportunities, shaping business cases, and winning technical decisions with Fortune 500 customers.
- BINCKBANKJOB
- Platform Transformation &…3Y 7M
Platform Transformation & Automation Lead
BinckBank
- EBAYJOB
- Senior Automation Eng1Y 11M
Senior Automation Engineer – DevOps & Microservices
eBay
- COMPARE GROUPJOB
- Mobile Web Innovation Lead1Y 3M
Mobile Web Innovation Lead
Compare Group
- T-MOBILE NEDERLANDJOB
- eCommerce Delivery & Autom…1Y 3M
eCommerce Delivery & Automation Lead
T-Mobile Nederland
- THOMSON REUTERSJOB
- Release Orchestration Lead1Y 3M
Release Orchestration Lead
Thomson Reuters
- TOIS TEAMJOB
- Projects Coordinator & Bid…1Y 11M
Projects Coordinator & Bid Strategist
TOIS Team
- Job: Microsoft — Enterprise Cloud & AI Transformation Lead - Public Sector · 2025-07 – present — Leading enterprise Cloud & AI transformation initiatives across central government environments, with a focus on turning long-term technology priorities into executable and scalable adoption paths. Work spans highly regulated and institutionally complex organizations where Cloud & AI decisions involve governance, architecture, funding, security, operational risk, and multi-stakeholder alignment. Key focus areas include: • Shaping Cloud & AI transformation strategies ahead of major investment decisions • Translating strategic priorities into executable adoption approaches • Aligning business, architecture, delivery, and governance stakeholders • Designing repeatable transformation models…
- Job: Microsoft — Enterprise Application Innovation Lead - Public Sector · 2023-07 – 2025-06 — Focused on moving cloud-native and AI-driven initiatives from early-stage exploration into committed execution within enterprise public sector environments. Worked across customers, partners, architects, and account teams to assess adoption readiness, shape scalable modernization approaches, and identify initiatives with long-term operational potential beyond isolated pilots. Key contributions included: • Turning early-stage innovation initiatives into executable transformation paths • Identifying scalable modernization opportunities across complex environments • Establishing repeatable adoption approaches rather than one-off implementations • Helping organizations move from experimentat…
- Job: Microsoft — Enterprise Application Modernization Lead - Retail · 2020-01 – 2023-06 — Partnered with enterprise retail organizations on large-scale application modernization and cloud transformation initiatives, with a focus on scalable adoption approaches rather than isolated implementations. This role laid the foundation for later work in enterprise transformation, adoption strategy, and repeatable modernization models across complex organizations.
- Job: Kopperhead BV — Independent Advisor - AI, Cloud & GTM Strategy · 2020-01 – present — Advising selected startups and scaleups on enterprise technology strategy, cloud adoption, go-to-market alignment, and scaling from experimentation to operational execution. Areas of focus include: • Enterprise AI and cloud strategy • GTM and enterprise positioning • Product and platform feedback from enterprise perspective • Scaling adoption in complex organizations • Bridging startup execution with enterprise realities Working across both startup and enterprise environments has provided a practical perspective on how emerging technology moves from innovation to scalable business value.
- Job: Kopperhead BV — Go-to-Market & European Expansion Strategist · 2017-07 – 2019-12 — Advised startups and scaleups on European market-entry strategy, go-to-market positioning, and commercialization approaches across diverse technology and digital business models. Worked closely with founders to validate expansion assumptions, refine positioning, prioritize market opportunities, and shape scalable growth approaches suited for complex European markets. Focus areas included: * European market-entry strategy * Go-to-market validation and positioning * Commercial scaling assumptions * Partner and ecosystem strategy * Early-stage growth prioritization
- Job: sphinx-project — Advisory Board Member – European Commission Horizon 2020 Initiative · 2019-01 – 2021-12 — Served on the advisory board of a European Commission Horizon 2020 initiative focused on cybersecurity and resilience across healthcare and care ecosystems. Provided independent strategic perspective on technology direction, execution feasibility, risk assumptions, and adoption considerations in highly regulated environments. Contributed to discussions spanning: * cybersecurity strategy, * institutional risk, * operational feasibility, * ecosystem coordination, * and long-term implementation considerations.
- Job: Perfecto — Enterprise Solution Consultant – SaaS & Transformation · 2015-06 – 2017-06 — Supported enterprise SaaS sales by qualifying complex opportunities, shaping business cases, and winning technical decisions with Fortune 500 customers.
- Job: BinckBank — Platform Transformation & Automation Lead · 2011-10 – 2015-05
- Job: eBay — Senior Automation Engineer – DevOps & Microservices · 2009-10 – 2011-09
- Job: Compare Group — Mobile Web Innovation Lead · 2008-06 – 2009-09
- Job: T-Mobile Nederland — eCommerce Delivery & Automation Lead · 2007-01 – 2008-04
- Job: Thomson Reuters — Release Orchestration Lead · 2005-09 – 2006-12
- Job: TOIS Team — Projects Coordinator & Bid Strategist · 2003-09 – 2005-08
- School: INSEAD — Executive Education Certificate, Negotiation & Strategic Influence
- School: Universitatea de Stat din Moldova — Master of Science (M.Sc.), Computer Science
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