Director, Technology Strategy & Portfolio Management

Western National Group & Umialik Insurance•Edina, MN

1h•Hybrid

About The Position

Western National is seeking a Director, Technology Strategy & Portfolio Management to join their team. The individual in this role will ensure that technology investments are aligned with enterprise strategy, sequenced appropriately, transparently governed, and communicated clearly across the organization. This role will enable high-quality decisions, effective delivery, timely conflict resolution, and well-articulated tradeoffs that minimize delays and promote predictable outcomes. The 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.

Requirements

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.
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.

Nice To Haves

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.

Responsibilities

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.

Benefits

Medical insurance plan options
Dental insurance
Vision benefits
Life insurance
Disability insurance
Health Savings Accounts (HSA)
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
Access to The Institutes (Risk and insurance education)
Paid parental leave
Bonus opportunities
Flexible work environment
Hybrid work arrangements
Remote work arrangements