Director, IT Strategy & Implementations

Insurance Office of America

1d•Remote

About The Position

The Director, IT, Strategy & Implementations is responsible for translating enterprise technology strategy into actionable roadmaps and ensuring disciplined execution across major IT initiatives. This role serves as a strategic partner to business and technology leaders, driving prioritization, governance, and delivery of high‑impact programs aligned to company objectives. The Director also maintains accountability for IT vendor and financial management, ensuring technology investments deliver measurable business value.

Requirements

5+ years of progressive experience in IT strategy, program delivery, or technology leadership, with a demonstrated ability to translate enterprise strategy into executable initiatives
Proven experience managing complex, cross‑functional technology programs with a strong record of on‑time, on‑budget delivery
Demonstrated expertise in IT vendor management, contract negotiation, service level agreements, and technology budget oversight
Strong financial acumen, including experience managing large operating and capital technology budgets
Excellent executive communication, stakeholder management, and influence skills across technical and non‑technical audiences
Strong analytical, problem‑solving, and decision‑making capabilities
Flexible, pragmatic leadership style with the ability to adapt to evolving business priorities and change

Responsibilities

Partner with the CIO and senior technology leaders to define enterprise IT strategy, multi‑year roadmaps, and execution priorities.
Translate enterprise strategies into clearly defined, executable programs with aligned scope, dependencies, outcomes, and success metrics.
Establish and lead governance models for initiative intake, prioritization, funding, and delivery oversight.
Oversee delivery of cross‑functional IT initiatives, ensuring timely, cost‑effective execution aligned with business outcomes.
Provide executive‑level visibility into portfolio health, risks, milestones, and value realization.
Continuously improve delivery methodologies, tools, and standards across the IT portfolio.
Oversee strategic IT vendor relationships to ensure service quality, cost efficiency, and alignment with objectives.
Lead vendor contract negotiations, renewals, and SLA management in partnership with Legal, Security, and Procurement.
Conduct vendor performance reviews and implement corrective or optimization actions as needed.
Oversee IT operating and capital budgets, including forecasting, spend tracking, and variance management.
Develop technology spend transparency models, identifying optimization and rationalization opportunities.
Ensure accurate documentation of contracts, renewals, financial commitments, and compliance requirements.