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VP of Technology Operations & Support (Boston)

VP of Technology Operations & Support (Boston)

The Stepping Stones Group, LLCBoston, MA, US
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Stepping Stones Group and its affiliated companies is seeking a Vice President of Technology Operations & Support. This person is responsible for driving the strategic vision, execution, and operational excellence of the enterprise technology environment. This includes leadership of cloud platforms, infrastructure services, unified communications, networking, end-user computing, and technology support.

This role will ensure the stability, scalability, and security of Stepping Stones Groups Microsoft technology ecosystem, including Azure cloud services, Microsoft 365, the Power Platform, Teams, SharePoint, Intune, and Entra ID (Azure Active Directory). In addition, the VP will oversee the companys telecommunications platforms (8x8 UCaaS) and physical network infrastructure (Cisco Meraki LAN / WAN, Wi-Fi, security appliances, and switches).

The VP will be accountable for technology governance, compliance, vendor partnerships, service delivery, and the modernization of IT operations to meet evolving business needs. The successful candidate will be a transformational leader, guiding cross-functional teams and managed service providers to deliver secure, reliable, and innovative technology services that enable organizational growth and efficiency.

Primary Responsibilities :

Strategic Leadership

  • Partner with the CIO and business leaders to align technology operations with organizational priorities.
  • Define and execute enterprise strategies for cloud, infrastructure, networking, and unified communications.
  • Champion modernization and digital transformation initiatives leveraging the Microsoft technology stack.

Microsoft Cloud & Platform Management

  • Oversee administration, governance, and optimization of Microsoft 365 tenants including Teams, SharePoint, OneDrive, Exchange Online, Intune, and Defender.
  • Direct management of Azure infrastructure services including virtual networks, compute, storage, backup, and disaster recovery.
  • Guide adoption and innovation using the Microsoft Power Platform (Power Apps, Power Automate, Power BI).

    • Networking & Physical Infrastructure

  • Oversee enterprise LAN / WAN, wireless, and security infrastructure, with a focus on Cisco Meraki platforms (switching, firewalls, Wi-Fi, SD-WAN).
  • Ensure availability, scalability, and redundancy of core networking services.
  • Lead infrastructure modernization initiatives including network segmentation, Zero Trust, and secure connectivity.

    • Security & Compliance

  • Ensure robust cybersecurity practices leveraging Microsoft Defender, Entra ID (Azure AD), conditional access policies, MFA, and threat intelligence.
  • Lead compliance initiatives across M365 security and compliance center, including data governance, retention, and eDiscovery.
  • Partner with InfoSec to monitor, assess, and mitigate technology risks.

    • Operations, Telecom & Support

  • Establish IT service management practices and performance metrics aligned to ITIL and modern DevOps / SRE principles.
  • Oversee support delivery (internal team and managed service providers) for end-user experience, collaboration tools, and business-critical systems.
  • Manage unified communications platforms including 8x8 UCaaS VoIP and Microsoft Teams Phone.

    • Vendor & Financial Management

  • Lead vendor negotiations, contract management, and performance reviews for cloud, telecom, networking, and managed services providers.
  • Develop and manage budgets, forecasts, and cost optimization strategies across cloud, telecom, and network infrastructure.

    • Essential Qualifications :

  • Deep expertise with Microsoft cloud technologies, including Azure IaaS / PaaS, Microsoft 365, Intune, Defender, and Entra ID.
  • Proven track record in enterprise IT operations, networking, unified communications, and support leadership in mid- to large-scale environments.
  • Strong knowledge of cybersecurity, compliance frameworks, and identity governance.
  • Hands-on experience managing telecommunications platforms, specifically 8x8 UCaaS VoIP systems.
  • Direct experience with physical networking and Cisco Meraki infrastructure (LAN / WAN, Wi-Fi, switches, firewalls, and SD-WAN).
  • Demonstrated success in building high-performing teams and managing managed service providers.
  • Excellent leadership, communication, and stakeholder engagement skills.
  • Ability to operate strategically and tactically, balancing innovation with operational excellence.

    • Experience / Education :

  • Bachelors degree in Computer Science, Information Systems, or related field (Masters preferred).
  • 10+ years of progressive IT leadership experience, including at least 5 years in senior technology operations leadership.
  • Hands-on experience in Microsoft 365 administration, Azure cloud management, and modern endpoint management.
  • Direct experience managing 8x8 UCaaS VoIP or comparable enterprise-class UCaaS / telecom systems.
  • Strong working knowledge of Cisco Meraki infrastructure and enterprise networking.
  • Familiarity with automation tools, scripting (e.g., PowerShell), and DevOps practices.

    • Supervision Exercised :

    Direct leadership of IT operations, support, and network infrastructure staff, along with direct oversight of managed service providers.

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