Director of Information Technology (Director as a Service)

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.

• 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.

Pioneer Technology is a nationwide Managed Services Provider with a strong focus on healthcare and enterprise customers. We deliver secure, scalable IT solutions across cloud, networking, systems, and security. Our mission is to help organizations modernize their technology environments while protecting them against evolving cyber threats., Pioneer Technology is a nationwide Managed Services Provider with a strong focus on healthcare and\nenterprise customers. We deliver secure, scalable IT solutions across cloud, networking, systems, and\nsecurity. Our mission is to help organizations modernize their technology environments while protecting\nthem against evolving cyber threats.