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Robert Stayner

@robertstayner

vCIO at Core Managed who developed multi-year technology roadmaps and built a client-intelligence platform for meeting preparation.

United States

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At Core Managed, I served as a vCIO and strategic technology advisor, developing multi-year roadmaps that connected clients’ business priorities with infrastructure lifecycle, risk, continuity planning, and growth.

I led quarterly technology business reviews and advanced initiatives through discovery, preliminary scoping, and client approval, staying the client-facing communicator while engineering and project teams handled delivery. I also supported strategic onboarding for four new managed-services clients.

I built an initial client-intelligence platform to help the vCIO team prepare for meetings and reviews and surface opportunities. Teammates extended and tested it with their own clients, and I used AI-assisted workflows to support research and meeting preparation while retaining human ownership of recommendations.

Earlier, at Penske Logistics, I migrated more than 150 users to Windows 10 and Microsoft 365 and contributed to infrastructure and workflow changes. My experience also includes restaurant systems at Steak 'n Shake Enterprises and technology deployments across more than 200 stores at Finish Line.

Experience

Work history, roles, and key accomplishments

vCIO

Core Managed

Aug 2022 - Jul 2026 (3 years 11 months)

Served as strategic technology advisor for a portfolio of managed-services clients, leading quarterly technology business reviews and developing multi-year technology roadmaps. Managed lifecycle planning, cloud/hybrid strategy, and disaster recovery readiness while supporting client onboarding and AI governance discussions.

VCIO TBR QBR technology roadmap Executive Advisory Client Discovery Disaster Recovery Business Continuity Infrastructure Lifecycle Cloud Strategy Hybrid Strategy Microsoft 365 AI Governance Client Intelligence

Junior System Administrator

Weaver Popcorn Bulk

Aug 2021 - Dec 2021 (4 months)

Supported user provisioning, endpoint and peripheral deployment, workstation/printer/network staging, infrastructure operations, environmental and safety systems, documentation, and end-user training.

User Provisioning End User Device Deployments Infrastructure Operations Documentation End User Training

Senior PC Technician

Penske Logistics

Oct 2018 - Jul 2021 (2 years 9 months)

Migrated more than 150 users to Windows 10 and Microsoft 365 and supported technology changes required for remote work. Contributed to network hardware refreshes, server migrations, onboarding/account workflow improvements, help-desk portal implementation, and recruiting/training technology.

Windows 10 Microsoft 365 Network Hardware Server Migration Onboarding Help Desk Project Coordination

Systems Analyst, Restaurant Systems

Steak 'n Shake Enterprises

Aug 2015 - Oct 2018 (3 years 2 months)

Provided Level 2/3 support and deployment leadership for restaurant POS and store systems, including Windows and SQL environments, payment devices, menu/pricing releases, online/mobile ordering testing, QA standards, automation, and vendor evaluation.

POS systems Windows SQL Payment Terminals QA Automation Vendor Evaluation

Store Staging and Deployment Specialist

Finish Line

May 2013 - May 2015 (2 years)

Coordinated technology deployment for more than 200 stores, including successful staging and national deployment of 435 workstations. Supported configuration, inventory, lifecycle testing, Active Directory, wireless, VoIP, mobile devices, and deployment scripting.

Deployment Staging Active Directory Wireless VoIP Mobile Devices Scripting