Head of IT Strategy and Transformation

ICW Group•San Diego, CA

4d•$171,301 - $306,633•Hybrid

About The Position

The Head of IT Strategy and Transformation (STO) leads an integrated enterprise capability that connects strategy, architecture, investment planning, delivery excellence, organizational change, and executive governance. This role brings Enterprise Architecture, Lean Portfolio Management, Agile Delivery (LACE), Organizational Change Management, and Executive Governance together into one accountable operating model. Through this leadership, the Head of IT Strategy & Transformation ensures technology investments are strategically aligned, architecturally sound, appropriately prioritized, delivery-ready, and supported through adoption. The role connects enterprise strategy to execution by enabling informed decisions, focusing resources on the highest-value work, and improving transparency, consistency, and accountability for transformation outcomes.

Requirements

Bachelor's degree from a four-year college or university required, in Computer Science, Information Systems, Business Administration, or a related field.
Minimum 12 years of progressive experience across enterprise architecture, portfolio management, agile delivery, or IT/business strategy.
Minimum 7 years in a leadership role managing multidisciplinary teams and/or a Strategy, Transformation, PMO, or Enterprise Architecture function.
Demonstrated track record building or leading a Lean Portfolio Management model, Agile Center of Excellence, or comparable transformation function.
SAFe Program Consultant (SPC) or SAFe Agilist required.
Deep working knowledge of enterprise architecture frameworks, Lean Portfolio Management, SAFe or comparable scaled-agile operating models, and executive governance design.
Proven ability to translate enterprise strategy into a funded, architected, and delivery-ready portfolio of initiatives.
Skilled at designing governance forums, decision rights, and operating cadences that hold a large organization accountable without adding bureaucracy.
Strong financial acumen — able to build, defend, and manage a multidisciplinary budget and demonstrate portfolio-level value realization.
Exceptional executive communication and influence skills; able to synthesize complex, cross-functional trade-offs into clear recommendations for senior leadership and the Board.
Experience leading organizational change across historically siloed functions, building one shared operating culture out of separate disciplines.
Hands-on knowledge of organizational change management methodology (e.g., Prosci ADKAR or equivalent) and demonstrated ability to personally sponsor change on high-visibility, enterprise-wide initiatives.
Regularly required to talk or hear.
Frequently will sit, stand, walk, and bend during working hours.
Requires manual and finger dexterity and eye-hand coordination.
May be required to lift light objects.
Requires normal or corrected vision and hearing corrected to a normal range.
Frequent use of computer, telephone, copier, and other standard office equipment.

Nice To Haves

Master's degree (MBA or equivalent) preferred.
SAFe Lean Portfolio Management (LPM) certification preferred.
TOGAF or equivalent enterprise architecture certification preferred.
Prosci Change Management Certification or equivalent OCM credential preferred.
PMP, PgMP, or ITIL certification a plus.

Responsibilities

Leads the Integrated IT Strategy & Transformation Office, setting the strategic agenda and annual operating plan, unifying architecture, portfolio, delivery, and governance activity.
Owns the end-to-end operating model connecting strategy formulation, investment funding, architectural standards, delivery execution, and governance decision rights.
Serves as the single executive point of accountability for whether the organization's technology investments collectively advance its strategic priorities.
Represents the STO to the executive team, the Investment Council, and Board-level committees, translating strategic intent into well-formed, architected, and delivery-ready investment recommendations.
Directs the definition of enterprise architecture standards, technology roadmaps, and reference architectures.
Establishes the architecture governance model, including an Architecture Review Board.
Owns the technology rationalization and modernization roadmap, reducing redundant platforms and technical debt.
Directs enterprise investment planning, aligning funding, capacity, and prioritization with strategic themes and value streams.
Facilitates the Investment Council by preparing prioritized investment recommendations, portfolio trade-off analysis, and capacity/value data.
Owns portfolio-level value realization: tracking benefits, cost, and capacity against plan, and reallocating investment as strategic priorities shift.
Builds and matures enterprise delivery capability through the Lean-Agile Center of Excellence.
Sets delivery standards and operating cadences that give the portfolio a predictable, transparent delivery rhythm.
Establishes delivery KPIs and drives continuous improvement across delivery teams.
Personally designs, chairs, and runs the decision forums and escalation paths that connect strategy, investment, architecture, and execution.
Ensures every major decision is made in the right forum, by the right owner, with the right information.
Publishes and maintains a governance operating calendar and RACI.
Serves as the escalation point of last resort within the STO for unresolved cross-discipline conflicts.
Owns enterprise-level change leadership for the operational and process-related impacts of major initiatives on the business.
Directs the Manager, Organizational Change Management to build and run a repeatable OCM methodology.
Ensures every initiative entering the portfolio carries a change-readiness assessment and a named change plan before it is funded.
Personally sponsors change management for the STO's own operating model.
Partners with HR, Communications, and business-unit leaders to align change plans with broader organizational initiatives.
Establishes adoption and sentiment metrics and reviews them alongside delivery and portfolio KPIs.
Provides strategic, tactical, and day-to-day direction to the architecture, portfolio, delivery, and change management leads.
Builds a cohesive leadership team across historically separate disciplines.
Owns hiring, performance management, coaching, and development planning for direct reports.
Manages the STO's budget, staffing, and vendor/consulting resources.
Acts as an escalation point and thought partner for the organization on complex, cross-functional strategy, architecture, portfolio, or delivery problems.