Matt Schenkman – IT Leader

Matt Schenkman

IT Leader | Mentor | Agile Operations Expert

Trumbull, CT | Email Me | LinkedIn

About Me

With over 18 years of experience in IT leadership, I’ve built and led teams, optimized processes, and fostered a culture of continuous learning. My leadership approach is centered on developing strong top-down support from leadership and empowering ground-up initiatives from my teams. I believe that measurable outcomes are the key to meaningful improvement, and I strive to create environments where everyone is aligned and motivated to deliver exceptional results.

What I Offer

  • Agile Leadership: Expertise in guiding teams through agile transformations, ensuring flexibility and responsiveness to change.
  • Mentorship: Committed to developing talent through active listening, thoughtful questioning, and supportive leadership.
  • Process Improvement: Proven ability to streamline operations, reduce costs, and enhance performance across departments.
  • Strategic IT Management: Skilled in aligning IT initiatives with business goals, managing budgets, and driving innovation.
  • Learning & Development: Developer of effective Learning Management Systems that promote ongoing education and professional growth.
  • Holistic Team Support: Focused on building a strong foundation of top-down support from leadership and fostering ground-up engagement from team members.

Professional Experience

MSP/MSSP/MCP Managed IT Services Organization | Operations Director

Led operations to enhance efficiency across departments, managed a budget to maximize ROI, improved automation | process | compliance, and mentored a diverse team to achieve their full potential. Developed strong top-down support while encouraging ground-up innovation to drive success.

MSP/MSSP/MCP Organization with CMMC specialization | Customer Success Manager

Focused on client satisfaction and successful onboarding, while leading a technical team in developing strategic security and compliance initiatives. Built collaborative relationships with leadership and teams to ensure project alignment.

Automotive E-Commerce Forbes Fast 500 Organization | Director of IT

Directed IT services for a growing e-commerce organization, managed an IT budget of 250k annually, established KPIs, developed disaster recovery plans, and implemented a custom Learning Management System. Fostered a culture of support from both leadership and the team, driving operational excellence.

MSP Organization | Senior Manager of Service Delivery | vCIO | Operations Leadership

Led Technical Account Management and service delivery for over 30 clients, optimizing operations during M&A activities and reducing costs. Consistently developed top-down leadership alignment and team-based initiatives for sustained growth.

Technical Skills

Systems: Windows, OS X, Linux, Active Directory, Virtualization, Multi-Factor Authentication.
Networking: Firewalls, VPNs, Zero Trust, DNS/DHCP, Group Policy, Network Storage.
Applications: Office 365, Azure, Microsoft Sentinel, Microsoft Defender, Jira, Confluence, Google Workspace.
Security: Endpoint Detection, SIEM, Compliance (HIPAA, GDPR, CMMC).

Certifications & Awards

Certified Scrum Master | ITIL v3 Foundations | Six Sigma Lean Professional

MCSA Messaging | CompTIA A+ | CompTIA Net+

Fujitsu MVC Award

Let’s Connect and Collaborate

References available upon request.