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Jason Sipula
Executive Technology Leader & Strategic Architect specializing in cloud-native platforms
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About
Technology leader with experience driving multi-year transformations at Jewelry Supply, including migrating a legacy custom e-commerce platform to SaaS and leading a 3-year ERP program from requirements through implementation and training. Also led a major architecture shift from self-hosted virtualized infrastructure to cloud Kubernetes with a strong DevOps/DevEx focus, emphasizing stakeholder buy-in and scalable processes for distributed engineering teams.
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Key Strengths
- Led multi-year technology roadmap aligning infrastructure modernization to business growth
- Executed e-commerce migration from custom platform to turnkey SaaS to reduce technical debt and increase agility
- Drove 3-year ERP transformation end-to-end (requirements, vendor selection, contract negotiation, implementation)
- Strong cross-functional stakeholder buy-in and change management for disruptive system transitions
- Implemented DevOps practices (CI/CD, dependency management) to improve delivery reliability and speed
- Led architectural shift from self-hosted virtualized workloads to cloud Kubernetes for scalability, security, and velocity
- Pragmatic migration strategy (phased rollout starting with low-criticality services) and team upskilling via training/workshops
- Built processes and culture for distributed teams (open communication, feedback loops, innovation days/hackathons)
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