Head of IT Strategy and Transformation

Are you looking to make an impactful difference in your work, yourself, and your community? Why settle for just a job when you can land a career? At ICW Group, we are hiring team members who are ready to use their skills, curiosity, and drive to be part of our journey as we strive to transform the insurance carrier space. We're proud to be in business for over 50 years, and its change agents like yourself that will help us continue to deliver our mission to create the best insurance experience possible.

Headquartered in San Diego with regional offices located throughout the United States, ICW Group has been named for the twelfth consecutive year in a row and for the 20th time overall as a Top 50 performing P&C organization offering the stability of a large, profitable and growing company combined with a focus on all things people. It's our team members who make us an employer of choice and the vibrant company we are today. We strive to make both our internal and external communities better everyday! Learn more about why you want to be here!

PURPOSE OF THE JOB 

Head of the IT Strategy and Transformation Office (STO) leads an integrated enterprise capability that connects strategy, architecture, investment planning, delivery excellence, organizational change, and executive governance. The 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. 

ESSENTIAL DUTIES AND RESPONSIBILITIES 

Leads the Integrated IT Strategy & Transformation Office 

• Sets the strategic agenda and annual operating plan for the STO, unifying architecture, portfolio, delivery, and governance activity behind one coherent enterprise strategy. 

• 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 — through the quality of the recommendations, architecture, and delivery readiness the STO brings forward, not through unilateral funding authority. 

• 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 for those bodies to decide. 

 

Enterprise Architecture 

• Directs the definition of enterprise architecture standards, technology roadmaps, and reference architectures that ensure every investment advances one coherent strategy. 

• Establishes the architecture governance model — including an Architecture Review Board that evaluates major initiatives for strategic fit, technical risk, and reuse before funding is committed — and delegates day-to-day chairmanship of the Board to the Principal Architect. 

• Owns the technology rationalization and modernization roadmap, reducing redundant platforms and technical debt over time. 

 

Lean Portfolio Management 

• Directs enterprise investment planning, aligning funding, capacity, and prioritization with strategic themes and value streams. 

• Facilitates the Investment Council — a standing committee of executive leaders who hold formal decision-making authority over funding, sequencing, and re-prioritization of major initiatives — by preparing prioritized investment recommendations, portfolio trade-off analysis, and capacity/value data for the committee's decisions. The Head of IT Strategy & Transformation does not hold personal or unilateral funding decision rights. 

• Owns portfolio-level value realization: tracking benefits, cost, and capacity against plan, and reallocating investment as strategic priorities shift. 

 

Agile Delivery (LACE) 

• Builds and matures enterprise delivery capability through the Lean-Agile Center of Excellence — coaching, engineering practices, and operating model maturity across delivery teams. 

• Scope note: LACE owns the ways of working and delivery-team practices used to build initiatives; it does not own business-side adoption of the resulting process or operational changes — that responsibility sits with Organizational Change Management, below. 

• Sets delivery standards and operating cadences (e.g., Program Increment planning, Scrum of Scrums) that give the portfolio a predictable, transparent delivery rhythm. 

• Establishes delivery KPIs (predictability, flow, quality, cycle time) and drives continuous improvement across delivery teams. 

 

Executive Governance 

• Personally designs, chairs, and runs the decision forums and escalation paths that connect strategy, investment, architecture, and execution — including cadence, membership, and decision rights for each forum. This is not delegated to a direct-report manager; the Head of IT Strategy & Transformation is the accountable owner of governance. 

• Ensures every major decision (funding, architecture exception, delivery risk) is made in the right forum, by the right owner, with the right information, and personally facilitates the highest-stakes / executive-level sessions. 

• Publishes and maintains a governance operating calendar and RACI so accountability is explicit at every level of the model; may be supported by governance/PMO analysts for administration and reporting, but retains direct ownership of the function. 

• Serves as the escalation point of last resort within the STO for unresolved cross-discipline conflicts (e.g., architecture vs. delivery timeline, portfolio priority disputes). 

 

Organizational Change Management 

Owns enterprise-level change leadership for the operational and process-related impacts of major initiatives on the business — how work gets done, roles change, and processes are re-designed — as distinct from LACE's focus on delivery-team ways of working. 

Directs the Manager, Organizational Change Management to build and run a repeatable OCM methodology (stakeholder analysis, change impact assessment, communication planning, training, and adoption measurement) applied consistently across major initiatives. 

Ensures every initiative entering the portfolio carries a change-readiness assessment and a named change plan before it is funded, closing a common gap where technical delivery outpaces organizational readiness. 

Personally sponsors change management for the STO's own operating model — leading the organization through the shift to a unified strategy, architecture, portfolio, and governance function, including communication, training, and adoption of new decision rights and cadences. 

Partners with HR, Communications, and business-unit leaders to align change plans with broader organizational initiatives and to manage change fatigue across concurrent transformations. 

Establishes adoption and sentiment metrics (e.g., stakeholder readiness scores, training completion, adoption rates) and reviews them alongside delivery and portfolio KPIs so change outcomes are tracked with the same rigor as cost and schedule. 

 

Team Leadership and Development 

Provides strategic, tactical, and day-to-day direction to the architecture, portfolio, delivery, and change management leads who report into the STO. 

Builds a cohesive leadership team across historically separate disciplines, establishing shared metrics, cadence, and a common operating language — while personally modeling the governance standard the team is held to, since the Head of IT Strategy & Transformation owns that discipline directly. 

Owns hiring, performance management, coaching, and development planning for direct reports; holds them accountable for the same standard across their functions. 

Manages the STO's budget, staffing, and vendor/consulting resources, and ensures adherence to company policy and compliance requirements. 

Acts as an escalation point and thought partner for the organization on complex, cross-functional strategy, architecture, portfolio, or delivery problems. 

 

SUPERVISORY RESPONSIBILITIES 

Directly supervises the leaders of Enterprise Architecture, Lean Portfolio Management, Agile Delivery (LACE), and Organizational Change Management, and carries out supervisory responsibilities in accordance with company policies and applicable laws. Executive Governance is run by the Head of IT Strategy & Transformation directly and has no dedicated manager. Supervisory responsibilities include interviewing, hiring, and training team members; planning, assigning, and directing work; conducting performance and salary reviews; rewarding and disciplining staff; addressing complaints and resolving problems; coaching, mentoring, and developing direct reports and their teams; creating and monitoring development plans; setting performance expectations and goals; forecasting staffing needs across the STO; and enforcing department policies and procedures. 

EDUCATION AND EXPERIENCE 

• Bachelor's degree from a four-year college or university required, in Computer Science, Information Systems, Business Administration, or a related field; Master's degree (MBA or equivalent) preferred. 

• 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. 

 

CERTIFICATES AND LICENSES 

SAFe Program Consultant (SPC) or SAFe Agilist required; 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. 

KNOWLEDGE AND SKILLS 

• 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. 

 

PHYSICAL REQUIREMENTS 

This job operates in a professional office environment. While performing the duties of this job, the employee is regularly required to talk or hear. The employee 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. 

WORK ENVIRONMENT 

This position operates in an office environment and requires the frequent use of computer, telephone, copier, and other standard office equipment. 

This description is a general statement of essential job functions and responsibilities. The position may include other duties as assigned. 

We are currently not offering employment sponsorship for this opportunity.

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The current range for this position is

$171,301.18 - $306,632.68

This range is exclusive of fringe benefits and potential bonuses. If hired at ICW Group, your final base salary compensation will be determined by factors unique to each candidate, including experience, education and the location of the role and considers employees performing substantially similar work.

WHY JOIN ICW GROUP?

• Challenging work and the ability to make a difference
• You will have a voice and feel a sense of belonging
• We offer a competitive benefits package, with generous medical, dental, and vision plans as well as 401K retirement plans and company match
• Bonus potential for all positions
• Paid Time Off
• Paid holidays throughout the calendar year
• Want to continue learning? We’ll support you 100% 

ICW Group is committed to creating a diverse environment and is proud to be an Equal Opportunity Employer. ICW Group will not discriminate against an applicant or employee on the basis of race, color, religion, national origin, ancestry, sex/gender, age, physical or mental disability, military or veteran status, genetic information, sexual orientation, gender identity, gender expression, marital status, or any other characteristic protected by applicable federal, state or local law.

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Job Category

IT