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

Technology leader with 20+ years of experience designing and managing enterprise infrastructure across Windows, virtual, and cloud environments. I currently serve as Director of System Engineering at Bankwell — a commercial bank with $3B+ in assets — where I lead the Systems Engineering team, own hybrid and cloud infrastructure strategy, and report directly to the CIO.

My focus is translating business needs into resilient, scalable systems. Over my career I've built and managed infrastructure for organizations ranging from multi-site software firms to regulated financial institutions — including virtualization platforms, identity and access management, backup and disaster recovery, and increasingly, workflow automation and AI tooling.

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. Outside of infrastructure, I'm actively expanding into Power Platform, Okta Workflows, and AI-assisted automation using tools like Microsoft Copilot and Claude.

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Career

Employment History

2017 — Present
Bankwell
Director of System Engineering, VP May 2025 – Present

Lead all phases of systems engineering projects for a $3B+ commercial bank, managing the Systems Engineering team and reporting directly to the CIO. Own hybrid and cloud infrastructure strategy, enterprise security posture, and the organization's backup and disaster recovery programs. Approving member of the Change Advisory Board (CAB).

IT Engineering Manager, VP Oct 2022 – May 2025

Managed the IT Engineering team across Systems, Networking, and Service Desk. Deployed GoAnywhere MFT for secure file automation, built Power Apps and Power Automate workflows for business process automation, and implemented immutable backup and DR strategy using Rubrik and Zerto.

Sr System Engineer / Lead Nov 2017 – Oct 2022

Acting lead engineer and architect for bank infrastructure including VMware clusters, Windows Servers, and SaaS/Cloud applications. Implemented Okta SSO/IDaaS, Atlassian Jira and Confluence, and ManageEngine for security reporting.

2017
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 Jun 2010 – Jul 2017

Reduced data center costs 25% through VMware virtual infrastructure design and management. Sustained 99.9% availability for a 2,000-user SaaS application. Maintained SOC2 compliance, disaster recovery, and business continuity as a principal member of the security council. Advised COO on cloud platforms (AWS, Azure) and vendor negotiations.

Sr System Engineer / Manager Mar 2007 – Jun 2010

Led System Administrators supporting 5 domains across 6 US and India locations. Reduced development environment overhead 35% with VMware ESXi and HP P4500 VSA SAN. Maintained Microsoft enterprise stack: Windows Server, AD, Exchange, SharePoint.

2001 — 2006
Printing Industry
Various roles across printing & production

Account Executive  ·  Print Assistant  ·  Production Coordinator

Expertise

Skills

Cloud & Virtualization
AWS / IaaS VMware VPC Azure
Identity & Security
Okta Falcon Shield IDP PAM Active Directory Group Policy SOC2 Domain Security VPN (IPSEC/SSL)
Automation & Integration
PowerShell RPA Workflow Automation API GoAnywhere MFT Power Platform Copilot Claude
Windows & Productivity
Windows Server Office 365 Exchange SharePoint RDP / VDI Terminal Services Visio Lucidchart
Backup, Recovery & BCP
Rubrik Zerto Disaster Recovery Business Continuity
Storage & Monitoring
FC / iSCSI / NAS Pure Storage Cloud Storage PRTG SQL Server
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