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SENIOR PROGRAM MANAGER - REMOTE CANADA

TSG is seeking a Senior Program Manager to lead execution of a network modernization and franchise enablement initiative. This is a dedicated, full-time delivery role supporting the transition of corporate and franchise locations from a flat, vendor-managed network to a standardized, zero-trust architecture.

The successful candidate will bring strong program execution discipline, stakeholder accountability, and enough technical fluency to understand network and infrastructure work without being responsible for architecture design. This person will manage near-term procurement activities alongside longer-term rollout planning and execution.

What You'll Bring:

• 7+ years of Senior Program Management or Project Management experience
• Experience leading complex, multi-stakeholder technology initiatives independently
• Background managing IT infrastructure, network, retail technology, franchise technology, or similar operational rollouts
• Working technical fluency in networking concepts, including segmentation, zero-trust architecture, vendor coordination, and hardware deployment
• Strong vendor management, stakeholder management, and executive communication skills
• Comfortable operating in ambiguity with evolving scope and competing priorities
• Experience in compliance-driven or regulated environments

Bonus Experience: 

• PCI DSS exposure
• Retail, franchise, or multi-site location rollout experience
• Experience coordinating network modernization or security-related initiatives
• Experience working in a large enterprise environment

What You'll Do: 

• Drive execution across corporate and franchise workstreams
• Hold internal teams, vendors, legal, network/security, and franchise stakeholders accountable to timelines and commitments
• Coordinate parallel workstreams, including a near-term procurement deadline and longer-term rollout phases
• Translate technical progress into clear, concise executive and business updates
• Track milestones, dependencies, risks, scope changes, and cross-team decisions
• Escalate blockers that could affect timeline, delivery, or stakeholder alignment
• Facilitate working sessions and maintain momentum across a fast-moving initiative
• Support continuity between planning, procurement, ordering/fulfillment, and deployment activities

• Execute Cisco Catalyst switch refreshes and network hardware replacement projects.
• Coordinate and participate in planned maintenance windows, cutovers, and migration activities.
• Implement network changes in accordance with established change management procedures.
• Perform configuration, validation, testing, and post-cutover support activities.
• Troubleshoot network issues related to implementation and migration activities.
• Maintain accurate implementation documentation and change records.
• Collaborate with client technical teams and stakeholders to ensure successful project execution.
• Support multiple healthcare facilities and locations throughout the greater Raleigh area.

• 5+ years of enterprise network engineering experience.
• Strong hands-on experience with Cisco Catalyst switching platforms.
• Experience implementing network changes in large enterprise environments.
• Proven ability to independently execute switch replacements, cutovers, and network migrations.
• Strong troubleshooting skills related to Layer 2 and Layer 3 networking.
• Experience following formal change management processes.
• Strong documentation and communication skills.
• Ability to work independently while coordinating with multiple stakeholders.

• Lead enterprise Microsoft 365 migration initiatives including tenant-to-tenant migrations and collaboration modernization programs. 

• Evaluate and improve migration methodologies currently being utilized by third-party vendors. 

• Design migration sequencing, coexistence planning, cutover strategies, rollback procedures, and stabilization planning. 

• Support migration and administration activities across Exchange Online, Microsoft Teams, SharePoint Online, OneDrive, Intune, and Entra ID / Azure AD. 

• Lead technical workshops and migration readiness discussions. 

• Support modern workplace transformation initiatives and endpoint readiness planning. 

• Assist with hybrid Microsoft 365 and Google Workspace coexistence environments where applicable. 

• Coordinate closely with infrastructure, networking, and cybersecurity teams during migration activities. 

• Troubleshoot complex post-migration issues related to identity, mail flow, authentication, and collaboration tools. 

• Support M&A integration efforts involving collaboration platforms, user migrations, endpoint transitions, and tenant alignment. 

• Conduct current-state assessments and migration planning for newly acquired organizations. 

• Assist with user experience standardization and operational transition planning. 

• Serve as a senior escalation point during migration and cutover activities. 

• Mentor junior engineers and support personnel. 

• Partner with project managers to support delivery planning and risk management activities. 

• Assist with documentation, knowledge transfer, and operational handoff activities. 

• 7+ years of enterprise Microsoft infrastructure and migration experience. 

• Deep expertise across Microsoft 365 technologies and migration tooling. 

• Strong experience with Exchange Online, Teams, SharePoint Online, OneDrive, Intune, and Entra ID / Azure AD. 

• Experience supporting large-scale migration and integration initiatives. 

• Strong troubleshooting and escalation management capabilities. 

• Experience operating in enterprise or consulting-based delivery environments. 

Desktop Support Engineer

Location: Louisville, CO OR Boulder, CO
Work Model: Primarily Onsite 

Overview

We are seeking customer-focused Desktop Support Engineers to support a large-scale Microsoft 365 modernization initiative while providing day-to-day desktop support for end users in a corporate environment.

This role will serve as the primary onsite IT support presence for one office location, assisting users with Microsoft 365 applications, endpoint support, account access issues, device deployments, and general technical troubleshooting. The ideal candidate is comfortable working directly with end users, providing white-glove support, and operating in a fast-paced environment where customer service is just as important as technical ability.

Responsibilities

• Provide onsite desktop support for end users in a corporate environment

• Troubleshoot Microsoft 365 applications including Outlook, Teams, OneDrive, SharePoint, and Exchange Online

• Support user authentication issues including password resets, MFA enrollment, account unlocks, and access requests

• Troubleshoot Windows 10/11 operating system, hardware, software, and connectivity issues

• Deploy, configure, and support laptops, desktops, monitors, docking stations, printers, and peripherals

• Assist with user onboarding and offboarding activities

• Support conference room technology and collaboration tools

• Provide hands-on support during Microsoft 365 migration and modernization activities

• Assist users with post-migration questions, troubleshooting, and adoption support

• Document issues, resolutions, and support activities within ticketing systems

• Escalate advanced infrastructure, networking, or identity-related issues when appropriate

• Deliver high-touch support to business users and leadership teams

• Partner closely with project managers, engineers, and infrastructure teams during key project milestones

Required Qualifications

• 2+ years of desktop support, deskside support, or IT support experience

• Experience supporting Microsoft 365 applications including Outlook, Teams, OneDrive, and SharePoint

• Strong troubleshooting experience in Windows 10/11 environments

• Experience supporting Active Directory user accounts, password resets, permissions, and group memberships

• Familiarity with MFA, authentication, and account access troubleshooting

• Experience supporting laptops, desktops, printers, docking stations, and related hardware

• Strong customer service and communication skills

• Ability to work onsite and provide hands-on support to end users

Preferred Qualifications

• Experience supporting Microsoft 365 migration, deployment, or modernization initiatives

• Familiarity with Entra ID (Azure AD)

• Experience with Intune or endpoint management platforms

• Experience supporting executive or VIP users

• Experience working in enterprise corporate environments

• Prior consulting or managed services experience

Nice to Have

• PowerShell experience

• Experience with Okta or other identity management platforms

• Exposure to device imaging, provisioning, or deployment tools

If you enjoy working directly with end users, solving technical problems, and supporting modern workplace technologies in a hands-on environment, we'd love to hear from you.

TSG is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. #LI-AL3

Desktop Support Engineer

Location: College Park, MD
Work Model: Onsite 

Overview

We are seeking customer-focused Desktop Support Engineers to support a large-scale Microsoft 365 modernization initiative while providing day-to-day desktop support for end users in a corporate environment.

This role will serve as the primary onsite IT support presence for one office location, assisting users with Microsoft 365 applications, endpoint support, account access issues, device deployments, and general technical troubleshooting. The ideal candidate is comfortable working directly with end users, providing white-glove support, and operating in a fast-paced environment where customer service is just as important as technical ability.

Responsibilities

• Provide onsite desktop support for end users in a corporate environment

• Troubleshoot Microsoft 365 applications including Outlook, Teams, OneDrive, SharePoint, and Exchange Online

• Support user authentication issues including password resets, MFA enrollment, account unlocks, and access requests

• Troubleshoot Windows 10/11 operating system, hardware, software, and connectivity issues

• Deploy, configure, and support laptops, desktops, monitors, docking stations, printers, and peripherals

• Assist with user onboarding and offboarding activities

• Support conference room technology and collaboration tools

• Provide hands-on support during Microsoft 365 migration and modernization activities

• Assist users with post-migration questions, troubleshooting, and adoption support

• Document issues, resolutions, and support activities within ticketing systems

• Escalate advanced infrastructure, networking, or identity-related issues when appropriate

• Deliver high-touch support to business users and leadership teams

• Partner closely with project managers, engineers, and infrastructure teams during key project milestones

Required Qualifications

• 2+ years of desktop support, deskside support, or IT support experience

• Experience supporting Microsoft 365 applications including Outlook, Teams, OneDrive, and SharePoint

• Strong troubleshooting experience in Windows 10/11 environments

• Experience supporting Active Directory user accounts, password resets, permissions, and group memberships

• Familiarity with MFA, authentication, and account access troubleshooting

• Experience supporting laptops, desktops, printers, docking stations, and related hardware

• Strong customer service and communication skills

• Ability to work onsite and provide hands-on support to end users

Preferred Qualifications

• Experience supporting Microsoft 365 migration, deployment, or modernization initiatives

• Familiarity with Entra ID (Azure AD)

• Experience with Intune or endpoint management platforms

• Experience supporting executive or VIP users

• Experience working in enterprise corporate environments

• Prior consulting or managed services experience

Nice to Have

• PowerShell experience

• Experience with Okta or other identity management platforms

• Exposure to device imaging, provisioning, or deployment tools

If you enjoy working directly with end users, solving technical problems, and supporting modern workplace technologies in a hands-on environment, we'd love to hear from you.

TSG is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. #ES1

Desktop Support Engineer

Location: Centennial, CO OR Louisville, CO OR Boulder, CO
Work Model: Primarily Onsite 

Overview

We are seeking customer-focused Desktop Support Engineers to support a large-scale Microsoft 365 modernization initiative while providing day-to-day desktop support for end users in a corporate environment.

This role will serve as the primary onsite IT support presence for one office location, assisting users with Microsoft 365 applications, endpoint support, account access issues, device deployments, and general technical troubleshooting. The ideal candidate is comfortable working directly with end users, providing white-glove support, and operating in a fast-paced environment where customer service is just as important as technical ability.

Responsibilities

• Provide onsite desktop support for end users in a corporate environment

• Troubleshoot Microsoft 365 applications including Outlook, Teams, OneDrive, SharePoint, and Exchange Online

• Support user authentication issues including password resets, MFA enrollment, account unlocks, and access requests

• Troubleshoot Windows 10/11 operating system, hardware, software, and connectivity issues

• Deploy, configure, and support laptops, desktops, monitors, docking stations, printers, and peripherals

• Assist with user onboarding and offboarding activities

• Support conference room technology and collaboration tools

• Provide hands-on support during Microsoft 365 migration and modernization activities

• Assist users with post-migration questions, troubleshooting, and adoption support

• Document issues, resolutions, and support activities within ticketing systems

• Escalate advanced infrastructure, networking, or identity-related issues when appropriate

• Deliver high-touch support to business users and leadership teams

• Partner closely with project managers, engineers, and infrastructure teams during key project milestones

Required Qualifications

• 3+ years of desktop support, deskside support, or IT support experience

• Experience supporting Microsoft 365 applications including Outlook, Teams, OneDrive, and SharePoint

• Strong troubleshooting experience in Windows 10/11 environments

• Experience supporting Active Directory user accounts, password resets, permissions, and group memberships

• Familiarity with MFA, authentication, and account access troubleshooting

• Experience supporting laptops, desktops, printers, docking stations, and related hardware

• Strong customer service and communication skills

• Ability to work onsite and provide hands-on support to end users

Preferred Qualifications

• Experience supporting Microsoft 365 migration, deployment, or modernization initiatives

• Familiarity with Entra ID (Azure AD)

• Experience with Intune or endpoint management platforms

• Experience supporting executive or VIP users

• Experience working in enterprise corporate environments

• Prior consulting or managed services experience

Nice to Have

• PowerShell experience

• Experience with Okta or other identity management platforms

• Exposure to device imaging, provisioning, or deployment tools

If you enjoy working directly with end users, solving technical problems, and supporting modern workplace technologies in a hands-on environment, we'd love to hear from you.

TSG is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. #LI-AL3