Director of Information Technology

Position Overview

Pioneer Technology seeks a Director of Information Technology to serve as an embedded technology leader under our Director as a Service model. The role oversees daily incidents, requests, and projects across all client locations while leading the cloud roadmap, technology budget, and network, systems, and security standards.

The Director is the client’s principal technology decision-maker below the executive sponsor and primary owner of key application, security, and infrastructure vendor relationships. The successful candidate can resolve technical issues, present capital requests, and develop internal IT staff while representing Pioneer Technology and remaining accountable to both organizations.

Engagement Model: Director as a Service. The Director is employed and supported by Pioneer Technology while dedicated to the assigned client. The role leads modernization across a regulated, multi-site environment spanning on-premises and cloud services to strengthen resilience, security, and scalability.

Responsibilities

• Own daily IT operations across the client’s locations, prioritizing incidents and requests, assigning work across the client’s team, Pioneer Technology, and outside partners, and ensuring timely resolution with appropriate executive escalation.
• Oversee server and storage health, backup and recovery operations, identity and access administration, endpoint and print services, telephony, and support for core business and site applications.
• Lead technology modernization and migration to cloud and hosted services, including Microsoft 365 consolidation, legacy server retirement, cloud-managed printing, and evaluation of hosted storage, backup, and disaster recovery solutions.
• Manage technology projects from planning through cutover and post-implementation review, establishing schedules, coordinating vendors and internal testers, and reporting progress and risks to client leadership and Pioneer Technology.
• Partner with executive and finance leadership to manage annual technology operating and capital budgets, including equipment refreshes, recurring services, and project spending.
• Maintain a multi-year technology roadmap aligned with growth objectives, regulatory obligations, and asset lifecycles, anticipating storage, bandwidth, licensing, and staffing needs before they affect service.
• Present the technology roadmap and funding requirements to senior management and, when requested, the client’s board or technology committee.
• Define and enforce network, systems, and security architecture standards across headquarters, remote sites, and the disaster recovery location.
• Govern network segmentation, firewall policy, secure remote access, multifactor authentication, endpoint protection, patch management, and identity and privileged access.
• Maintain documented backup and recovery targets and current, securely managed credential and configuration records.
• Support internal and external audits, penetration tests, and regulatory examinations, and own remediation of resulting findings.
• Establish repeatable processes for opening, relocating, and renovating sites, onboarding staff, and integrating systems acquired through expansion.
• Serve as the day-to-day relationship owner for core application, managed security, network, hardware, and software providers, managing service levels and escalations and holding partners accountable for committed dates and deliverables.
• Review vendor contracts and renewals for cost, terms, and service fit; maintain required third-party risk documentation; and preserve the client’s ability to transition providers when needed.
• Supervise, coach, and develop the client’s IT specialists, setting clear priorities and expectations and providing hands-on technical guidance.
• Build individual development plans and team coverage that strengthen cloud administration, security operations, and project delivery skills as the organization grows.

Required Qualifications

• Bachelor’s degree in information technology, computer science, or a related field, or equivalent professional experience.
• Seven or more years in information technology, including at least three years leading a team, a function, or a portfolio of projects.
• Demonstrated experience planning and executing cloud or hosted migrations, including cutover planning, testing, and user communication.
• Working command of Windows Server, virtualization, enterprise storage, backup and recovery, Active Directory, and Microsoft 365 administration.
• Practical network and security knowledge: routing and segmentation, enterprise firewalls, VPN and multifactor authentication, and endpoint protection.
• Experience owning a technology budget and presenting spending and roadmap decisions to senior management.
• Experience managing vendors and service providers, including contracts, service levels, and escalations.

Preferred Qualifications

• Prior experience in banking, financial services, healthcare, or another regulated industry, including familiarity with the audit and examination processes.
• Familiarity with a core line-of-business platform and the network and connectivity requirements that support it.
• Experience working alongside outsourced security operations or managed services provider.
• Certifications such as Microsoft Azure or Microsoft 365 administration, CISSP, Security , or a recognized project management credential.
• Experience supporting a multi-site environment with a separate disaster recovery location.
• Prior consulting, managed services, virtual CIO, or fractional IT leadership experience working inside client environments.