Senior Director of IT Operations & Infrastructure Transformation

Nicholas
Stoddard

15+ years driving infrastructure modernization, cloud transformation, and operational excellence across enterprise and multi-site environments.

15+ Years in Enterprise IT
3,200+ Endpoints Modernized
30% Infrastructure Cost Reduction
10 Days Healthcare Outage — Zero Downtime

Executive Summary

I'm a technology executive with 15+ years of progressive leadership experience building and transforming enterprise IT operations — from hands-on infrastructure deployments to directing multi-state technology strategy and standing up a Managed Services practice from the ground up.

I specialize in infrastructure modernization, cloud transformation, operational excellence, and cybersecurity governance across complex, multi-site environments spanning healthcare, financial services, legal, nonprofit, manufacturing, and distribution organizations.

My focus is on making technology a genuine business advantage — creating repeatable operational frameworks, integrating disparate systems, leveraging AI-driven automation, and aligning technology strategy with executive business objectives. I bring both technical depth and business fluency, and am most effective bridging the two.

Areas of Expertise

Infrastructure & Cloud Architecture
Hybrid-cloud design spanning Azure, AWS, and VMware. Multi-site network modernization with SD-WAN, fiber redundancy, and high-availability switching.
Cybersecurity & Governance
End-to-end security programs including Zero Trust architecture, MFA enforcement, EDR deployment, IAM redesign, and DR/BC documentation.
Unified Communications
Enterprise VoIP and UCaaS deployments at scale. Avaya ACIS/ACSS certified with deep expertise in SIP, SBC, QoS design, and CRM/ERP integration.
AI & Automation Integration
Led enterprise adoption of ML-based alerting and predictive maintenance, cutting incident response times by 40% and mean time to resolution by 45%.
IT Strategy & Executive Leadership
Long-range technology roadmapping, multi-year capital planning, vendor strategy, and building multi-location technical teams with clear development paths.
Data & Business Intelligence
CRM/ERP integrations, Power BI dashboards, SQL-based analytics, and real-time KPI tracking to drive data-informed decisions across sales and operations.

Professional Experience

CommPath
2021 – Present
IT Director | Head of Technology & Managed Services
Executive leadership for technology operations, infrastructure strategy, cybersecurity, managed services delivery, cloud platforms, and communications infrastructure across a multi-state organization.
  • Built and scaled the Managed Services practice from concept to production — establishing service delivery standards, escalation frameworks, KPI reporting, and customer success methodologies
  • Directed enterprise technology modernization supporting more than 3,200 endpoints across financial services, healthcare, legal, nonprofit, and commercial organizations
  • Led the migration of 500+ users across NY, NJ, CT, and FL for David Lerner Associates, modernizing infrastructure while maintaining uninterrupted business operations
  • Directed migration of 600+ digital, analog, and IP endpoints across five Manhattan Beer Distributors locations, including a mission-critical customer service call center
  • Led 400+ endpoint migration for Cullen and Dykman LLP, ensuring full continuity for legal operations, attorneys, and client-facing services
  • Managed operational continuity during a major healthcare network outage affecting 100+ locations and nearly 2,000 endpoints — maintaining uninterrupted communications for more than ten days
  • Led hybrid-cloud transformation (Microsoft 365, Entra ID, AWS EC2/S3, VMware ESXi, Linux) reducing operating costs by 30%
  • Implemented AI-assisted monitoring and predictive alerting, reducing incident response times by 40% and MTTR by 45%
  • Established executive dashboards using SQL, Power BI, and Crystal Reports for real-time visibility into service delivery, infrastructure health, and KPIs
CommPath
2017 – 2020
Installation & Service Technician
Enterprise-scale infrastructure, networking, cloud, and communications deployments across healthcare, financial services, legal, nonprofit, government, and commercial organizations.
  • Designed and implemented highly available communications environments utilizing SIP, VoIP, QoS, Session Border Controllers, VPN, and resilient network architectures
  • Authored deployment standards, implementation methodologies, and documentation frameworks that improved consistency and reduced post-deployment incidents
  • Earned Avaya ACIS and ACSS certifications
CommPath
2013 – 2016
Call Center Manager
Led technology-enabled sales operations, CRM administration, reporting, workforce management, KPI development, and operational process improvement.
  • Designed and developed an internally managed CRM platform integrating telephony, SQL databases, and real-time operational dashboards
  • Built KPI reporting infrastructure and sales process frameworks that improved rep performance and operational visibility

Project Highlights

Cloud
30%
Hybrid-Cloud Modernization
Led adoption of Microsoft 365, Entra ID, AWS EC2/S3, and VMware hybrid infrastructure across multi-state environments, cutting operating costs by 30%.
Infrastructure
3,200+
Enterprise Endpoint Modernization
Directed technology transformation initiatives across 3,200+ endpoints spanning financial services, healthcare, legal, nonprofit, and commercial clients — including David Lerner Associates, Manhattan Beer Distributors, and Cullen & Dykman LLP.
Business Continuity
10 Days
Healthcare Network Outage Response
Maintained uninterrupted telecommunications services during a major network outage affecting 100+ locations and nearly 2,000 endpoints for more than ten consecutive days.
AI / Automation
45%
AI-Driven Operations
Deployed ML-based alerting, predictive maintenance, and automation workflows that reduced MTTR by 45% and cut incident response times by 40%.

Technology Stack

Infrastructure
Windows Server Active Directory VMware ESXi Hyper-V Linux Ansible
Cloud
Microsoft 365 Entra ID AWS EC2 / S3 Azure Hybrid-Cloud Design
Security
Zero Trust IAM MFA EDR Vulnerability Management DR/BC Planning
Operations
ITSM Incident Management Change Management Root Cause Analysis Service Delivery
Automation
Python PowerShell API Integrations Workflow Orchestration
Networking
LAN / WAN SD-WAN VPN VoIP / SIP Unified Communications Session Border Controller
Data & BI
Power BI SQL Crystal Reports CRM / ERP Integration

Education & Certifications

University of Miami
Bachelor of Arts, Business Administration
Coral Gables, FL · 2009
AWS
Certified Solutions Architect
Amazon Web Services
Avaya ACIS
Avaya Certified Implementation Specialist
Avaya
Avaya ACSS
Avaya Certified Support Specialist
Avaya

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