Director of Information Technology

Destination Cleveland•Cleveland, OH

2d•Onsite

About The Position

The Director of Information Technology serves as Destination Cleveland’s senior technology leader, responsible for translating the organization’s technology vision into disciplined execution, reliable operations, and measurable progress. Reporting to the Chief People & Business Operations Officer, this role leads the implementation of the technology roadmap while ensuring secure, resilient, cost-effective, and service-oriented technology operations. The Chief People & Business Operations Officer provides executive-level strategic vision and enterprise alignment for technology, data, AI, and business operations. The Director converts that vision into actionable plans, governance practices, implementation roadmaps, vendor and managed services provider accountability, and cross-functional execution. The Director works closely with executive leadership, departments, managed service providers, and strategic technology partners to clarify ownership, guide implementation decisions, strengthen accountability, and ensure technology enables organizational priorities. A key expectation of this role is to bring structure and clarity to how internal IT, marketing technology, business-owned platforms, managed service providers, and external partners work together. The Director leads a blended technology operating model that maintains strong internal expertise in infrastructure, cybersecurity, business systems, integrations, and technology governance while leveraging managed service providers and specialized partners for scalable or specialized technical expertise, including Microsoft 365 administration and end-user support.

Requirements

Exceptional written, verbal, and interpersonal communication skills, including the ability to communicate technical priorities and risks to non-technical audiences.
Strong business acumen with the ability to translate organizational strategy and executive vision into technology priorities, implementation plans, and operational practices.
Demonstrated ability to build trusted partnerships, influence decision-making, clarify ownership, and lead cross-functional initiatives.
Excellent judgment in balancing business needs, technology investments, cybersecurity, vendor performance, organizational risk, and competing priorities.
Experience leading enterprise technology modernization, digital transformation, systems implementation, governance, and operational stabilization initiatives.
Broad working knowledge of enterprise applications, cloud technologies, systems integration, cybersecurity, infrastructure, identity and access management, and modern technology architecture.
Experience managing enterprise technology vendors, managed service providers, consultants, contracts, statements of work, service expectations, and performance outcomes.
Experience supporting technology, data, cybersecurity, application, vendor, or AI governance frameworks.
Commitment to continuous improvement, documentation, customer service, practical problem-solving, and collaborative leadership in a lean, fast-paced environment.
Bachelor’s degree in information technology, computer science, business, operations, or a related field; equivalent experience may be considered.
Minimum of seven years of progressively responsible technology, IT operations, or enterprise systems experience.
Minimum of three years of leadership experience managing people, vendors, managed service providers, consultants, or cross-functional technology initiatives.
Experience working in a lean or mid-sized organization where the role requires both strategic implementation and hands-on operational leadership.
Experience supporting executive leadership, cross-functional business partners, and non-technical stakeholders through technology change, risk management, and implementation planning.

Responsibilities

Translate the technology vision and enterprise priorities set with the Chief People & Business Operations Officer and Executive leaders into roadmaps, implementation plans, sequencing, and measurable outcomes.
Lead delivery of approved priorities, managing dependencies, risks, resourcing, and decision points.
Advise leadership on investments, emerging technology, architecture, and modernization, weighing value, risk, capacity, and cost.
Lead change and adoption, and communicate priorities, risks, and trade-offs clearly to non-technical audiences.
Establish and mature governance for technology, data, AI, applications, security, and vendors, defining ownership, prioritization, decision rights, escalation, and accountability.
Develop and evolve clear business and technical ownership for every platform. Business owners and super-users own requirements, priorities, basic configuration, adoption, and outcomes. IT owns system administration, integration, security, architecture, and platform stability across all applications.
Chair cross-functional governance forums for technology, data, AI, and risk.
Lead the lifecycle of core business applications: implementation, administration, integration, optimization, and simplification, including the CRM.
Enable the organization's data strategy in partnership with the Director of Research & Analytics, and execute the enterprise AI strategy with attention to responsible use, privacy, security, cost, and adoption.
Keep enterprise and business-owned platforms secure, integrated, reliable, documented, and not dependent on any single person's knowledge or access.
Provide operational leadership for infrastructure, applications, cloud services, endpoints, identity, and end-user technology.
Own security guardrails and incident response across systems, administrative access, data movement, and integrations, directing internal staff and external security partners for monitoring and remediation.
Strengthen IT service management: intake and escalation, documentation, onboarding and offboarding support, and recurring-issue analysis.
Manage the managed service provider and specialized partners: scope, service levels, statements of work, performance, escalation, and value.
Lead and develop internal staff while leveraging partners, building a sustainable operating model.
Own the annual technology budget across managed services, software, hardware, licensing, security, and strategic investments.