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 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.

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.

• 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.

Requirements

• At least ten years of progressive experience in technology strategy, portfolio management, enterprise IT, or related…