Senior Vice President of Technology

About the role

This role is the company's senior technology executive, accountable for IT strategy, infrastructure, cybersecurity, ERP and data across headquarters, the multi-state offices, and Azure. The role reports to executive leadership (CFO) and partners closely with the COO, Finance, Sales, Design and Production.

The role combines strategic leadership with the technical depth to direct managed service providers and specialist vendors, judge their work, and make sound architecture decisions. Hands-on skill is valued, but day-to-day execution can be shared with partners.

Key responsibilities:

Strategy and leadership

• Own the multi-year IT roadmap and budget, tied to company goals for growths.
• Present cost, value and risk of IT initiatives to the executive team; build business cases and TCO models.
• Lead and develop IT staff and managed service partners; set policies, standards and protocols.
• Track technology and AI developments and drive practical, governed adoption across the business.

Infrastructure and cloud

• Run the hybrid environment: on-prem virtualization, Microsoft Azure and Microsoft 365.
• Own network and site connectivity across the offices and Azure, including firewalls and site-to-site VPN.
• Own backup, disaster recovery and business continuity, with tested restores.
• Lead platform migrations and modernization (virtualization, telephony, storage).

Cybersecurity and compliance

• Own the security program end to end: identity and Conditional Access, EDR/MDR, email security, SIEM monitoring and incident response.
• Run security awareness training and phishing simulations.
• Maintain compliance obligations, including CTPAT cybersecurity requirements and PCI for payment processing.
• Manage privileged access and periodic access reviews across all systems.

ERP and business systems

• Own the BlueCherry ERP (CGS) and integrated systems such as Elastic Suite B2B, working with in-house ERP SMEs and the vendor.
• Diagnose and resolve ERP data, allocation and integration issues; manage vendor support cases.
• Support business processes with partners such as CIT (factoring) and licensors' data feeds.

Vendors and budget

• Negotiate and manage contracts and renewals with IT vendors, MSPs, resellers and SaaS providers.
• Control licensing and cloud spend; challenge renewal increases and right-size subscriptions.

IT operations

• Ensure reliable end-user support, device lifecycle and onboarding/offboarding for roughly 250 users.
• Maintain current documentation of systems, access and vendor relationships.

Qualifications:

Required

• 10+ years in IT, including 3+ years leading IT for a small or mid-sized company with a lean team.
• Bachelor's degree in computer science, information systems, engineering or equivalent experience.
• Hands-on depth in Microsoft 365, Entra ID and Azure administration, including Conditional Access.
• Hands-on experience with virtualization (VMware and/or Hyper-V), Windows Server, networking and firewalls.
• Working knowledge of a security stack: EDR, email security, SIEM, identity protection and incident response.
• Experience owning an ERP environment and working with the vendor on data and integration issues.
• Proven vendor negotiation and budget management; able to build TCO and ROI cases for executives.
• Clear communicator with non-technical leaders and end users.

Preferred

• Apparel, fashion or wholesale/distribution industry experience; BlueCherry or a similar apparel ERP.
• Business intelligence and data pipeline experience.
• UCaaS migration experience, ideally Teams Phone.
• Familiarity with CTPAT, PCI or similar compliance programs.
• Practical experience deploying AI tools with governance.
• Certifications such as Microsoft Azure/M365, CISSP or CISM.