Cheshire, CT

Jason Bestor

Director of System Engineering  ·  Infrastructure & Automation

20+ years leading enterprise infrastructure — translating business needs into resilient, scalable systems across hybrid and cloud environments.

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Background

About

As a systems and infrastructure leader, I translate the operational needs of business stakeholders into environments that connect people, process, and technology. I currently serve as Director of System Engineering at Bankwell — a commercial bank with $3B+ in assets — where I lead all phases of systems engineering projects, manage the Systems Engineering team, and oversee hybrid and cloud infrastructure strategy.

I'm a self-directed IT professional with 20+ years of experience in Windows, virtual, and cloud-based infrastructure design, implementation, and day-to-day management. I have in-depth knowledge of cloud and virtual infrastructures, enterprise monitoring, capacity planning, and networking, with a strong ability to communicate technical solutions in non-technical terms to business stakeholders.

I serve as an approving member of the Change Advisory Board (CAB) and partner closely with Information Security to maintain a strong organizational security posture. I report directly to the CIO.

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Career

Employment History

2025 — Present
Bankwell
Director of System Engineering

Lead all phases of systems engineering projects for a $3B+ commercial bank, managing the Systems Engineering team and reporting directly to the CIO.

  • Oversees hybrid and cloud infrastructure strategy and execution
  • Directs enterprise monitoring, capacity planning, and vendor management
  • Approving member of the Change Advisory Board (CAB)
  • Partners with Information Security to maintain the organization's security posture
2017 — 2025
CentrePoint Industries
Infrastructure Architect / Analyst

Designed and managed enterprise infrastructure for a multi-site manufacturing environment. Led cloud adoption initiatives, infrastructure modernization, and managed vendor relationships across networking, compute, and security domains.

2007 — 2017
Vatti-Manhattan Group
Infrastructure Architect / Manager  ·  Sr System Engineer / Manager

Progressed from Senior Systems Engineer to Infrastructure Architect over a decade. Designed, deployed, and managed enterprise-scale Windows, virtual, and network infrastructure across multiple sites. Built and led the systems engineering function.

Earlier
Earlier Experience
Systems & Infrastructure Engineering
Pyne-Davidson — Systems / Infrastructure Printing Island — Systems / Infrastructure Westcott Press — Systems / Infrastructure
Expertise

Skills

Cloud & IaaS
AWS Azure Hybrid Cloud IaaS Architecture Cloud Migration
Virtualization
VMware vSphere Hyper-V vSAN NSX VDI
Networking
Cisco Routing & Switching SD-WAN Firewalls VPN DNS / DHCP
Security
Change Advisory Board IAM Endpoint Protection Compliance Security Architecture
Windows Server
Active Directory Group Policy IIS SCCM / Intune Exchange
Scripting & Automation
PowerShell Bash Terraform Ansible
Monitoring & Operations
Enterprise Monitoring Capacity Planning ITSM Incident Response DR / BCP
Leadership
Team Management Vendor Management Budget & Planning CIO Reporting Strategic Planning
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