Director, Technology Strategy & Portfolio Management

Who are we

Western National Insurance Group is a private mutual insurance company with over 120 years of experience serving customers property-and-casualty insurance needs in the Midwestern Northwestern and Southwestern United States. Known as The Relationship Company we define success as a measure of the relationships weve built over everything that we do we know that delivering a friendly and helpful interaction makes for a better experience for everyone involved. Thats the power of nice. At Western National nice is something we work to bring to every person and organization with whom we partner and serve.

Does this opportunity interest you

Western National is seeking a Director Technology Strategy & Portfolio Management to join our team!

The individual in this role will have the opportunity to ensure that technology investments are aligned with enterprise strategy sequenced appropriately transparently governed and communicated clearly across the organization. This individuals work will enable high-quality decisions effective delivery timely conflict resolution and well-articulated tradeoffs that minimize delays and promote predictable outcomes.

This individual will own the development of enterprise technology prioritization recommendations and portfolio tradeoff analyses framing decisions for executive approval. While delivery accountability remains with engineering and IT leaders this role ensures that prioritization decisions are transparent data-informed and aligned with enterprise strategy.

What are the responsibilities and opportunities of this role

• Partners with executive leadership to translate enterprise strategy into a clear multi-year technology roadmap and explicit investment themes (e.g. modernization AI risk reduction).
• Maintains a rolling 12- to 36-month view of strategic initiatives.
• Owns the enterprise technology portfolio across applications infrastructure data and AI and security.
• Establishes and runs a standardized demand intake and prioritization process.
• Facilitates prioritization and tradeoffs across business domains (e.g. Claims Underwriting Operations Finance).
• Partners with the Finance Team to align funding capacity and delivery expectations enabling transparent decision-making.
• Defines success metrics for major initiatives (business outcomes not just milestones) and tracks benefit realization at the portfolio level.
• Highlights underperforming or misaligned initiatives early.
• Supports executive and board-level reporting with clear outcome-focused insights.
• Designs and facilitates technology governance forums as needed.
• Ensures decisions are documented communicated and revised when assumptions change.
• Serves as a broker between delivery engineering security and business leaders.
• Owns the enterprise communication strategy for the technology roadmap and prioritization efforts.
• Translates portfolio decisions sequencing and tradeoffs into clear consistent messaging for the IT organization.
• Ensures technology teams understand how priorities align to enterprise strategy business outcomes and investment themes.
• Establishes regular communication cadences and standard artifacts to reinforce alignment manage expectations and reduce delivery conflicts.
• Partners with IT and engineering leaders to ensure shared understanding of priorities and commitments.
• Guides prioritization and trade-off decisions across initiatives ensuring alignment with organizational strategy available resources and desired outcomes.
• Supports leadership decision-making by establishing clear processes providing relevant insights and ensuring decisions are documented communicated and aligned across stakeholders.
• Ensures initiatives and priorities are aligned for delivering meaningful value and improved experiences for internal and external customers.
• Incorporates feedback performance data and stakeholder input to identify pain points and continuously enhance customer outcomes.

What are the must-have qualifications for a candidate

• At least ten years of progressive experience in technology strategy portfolio management enterprise IT or related roles within a complex organization.
• Demonstrated experience translating enterprise or business strategy into multi-year technology roadmaps and investment priorities.
• Strong background in portfolio demand and prioritization management including trade-off decisions across competing initiatives.
• Ability to frame complex technology decisions for executive audiences with data-informed recommendations.
• Strong executive-level communication skills including articulating priorities sequencing and rationale to diverse stakeholders.
• Strong critical thinking and judgment in managing trade-offs risks and changing assumptions.
• Ability to operate effectively within governance and decision-making forums.
• Experience with enterprise portfolio and demand management frameworks and processes.
• Experience in technology strategy and roadmap development.
• Knowledge of financial alignment concepts including funding capacity planning and investment prioritization.
• Familiarity with governance models and decision-support frameworks.
• Degree in information technology business or a related field is preferred.

What will our ideal candidate have

• Experience partnering closely with a finance team to align funding capacity and delivery expectations.
• Ability to build credibility and influence across business and technology stakeholders (e.g. engineering infrastructure data security and business functions) without direct authority.

Compensation overview

The targeted hiring range for this role is $140800 - $201410 annually. However the base pay offered may vary depending on the job-related knowledge skills credentials and experience of each candidate as well as other factors such as the scope and location of the role. Candidates looking for compensation outside of the posted range are encouraged to apply and will be considered based on their individual qualifications and / or may be considered for other positions.

Culture and Total Rewards

Western National has long been known as The Relationship Company and caring for our employees is part of that relationship commitment. We value connectiveness empowerment and accountability and we believe that our employees are our biggest asset.

Currently ranked as the 41st largest private company by revenue in Minnesota (Minneapolis/St. Paul Business Journal) Western National has earned accolades year-over-year as an employer of choice and garnered multiple awards for wellness in the workplace. Western National has also been named a Top Workplace by the Star Tribune for consecutive addition the Group is consistently recognized as a Wards 50 property-and-casualty insurance company for its outstanding financial results.

Western National offers full-time employees a significant Total Rewards Package including:

• Medical insurance plan options and other standard employee benefits including dental insurance vision benefits life insurance disability insurance and more!
• Health Savings Accounts (HSA) and Flexible Spending Accounts (FSA)
• 401(k) Plan (participants are eligible for 100% matching on the first 6% of their contributions)
• Wellbeing Program including onsite fitness studio
• Paid Time Off including holiday vacation and volunteer
• 100% company-paid tuition reimbursement for approved job-relevant coursework and access to The Institutes (Risk and insurance education)
• Paid parental leave
• Bonus opportunities

Western National believes in supporting balance between work and life by providing a flexible work environment which includes a variety of hybrid and remote work arrangements designed to balance individual job department and company needs.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.

Western National provides employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race color religion age sex national origin disability status genetics protected veteran status sexual orientation gender identity or expression or any other characteristic protected by federal state or local laws.