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 we’ve built over time. In everything that we do, we know that delivering a friendly and helpful interaction makes for a better experience for everyone involved. That’s 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 individual’s 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 $140,800 - $201,410, 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 years. In addition, the Group is consistently recognized as a Ward’s 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.