Executive Director · Engineering Support & IT Operations · Financial Services
Executive Snapshot
Jason Bossmin translates complex technology needs into practical operating models — strengthening execution discipline and aligning engineering support with business, product, risk, and operational priorities. His leadership spans global team management, incident management, platform reliability, $40M+ budget ownership, and resilience-first operational thinking. A Certified Chaos Engineering Practitioner with continuing education in Generative AI, Responsible AI, AI fundamentals, prompt engineering, and AI-enabled business transformation.
Best-Fit Role Themes
Executive technology leadership overseeing engineering support, IT operations, and platform stability
Product and platform leadership with budget ownership, stakeholder alignment, and delivery coordination
Financial services and banking technology — resiliency, DR, regulatory awareness, and SLA ownership
Globally distributed teams, operating model improvement, major incident management, cross-functional delivery
Chaos Engineering, AI-enabled transformation, operational excellence, Agile delivery modernization
Core Differentiators
Leads global teams, develops people, communicates with executive stakeholders, and creates structured routines for decision-making and delivery follow-through.
Drives production stability, incident/problem/change management, disaster recovery, business continuity, Chaos Engineering, risk mitigation, and audit-aware controls.
Supports product governance, platform planning, HPE NonStop operations, infrastructure management, production support, monitoring, and operational readiness.
Owns $40M+ annual product budget, P&L accountability, software licensing, vendor relationships, cost optimization, and financial planning alignment.
Actively pursuing AI literacy — certified in Generative AI and AI Fundamentals — and applying AI-enabled process improvement thinking to modern engineering support and operational modernization.
Experience Portfolio
Capability Matrix
Certifications
Core & Platform
AI & Emerging Technology
Portfolio AI Q&A