Director Portfolio Strategist Jobs (NOW HIRING)

Come join one of America's fastest-growing insurance companies. Since 1848, National Life Group has aimed to keep our promises, providing families with stability in good times and in bad. Throughout that history, we have provided peace of mind to those families as they plan their futures.
Our mission extends beyond the insurance and annuities policies that we offer. We strive to make the world a better place through our grants from our charitable foundation, paid volunteer time for our employees, environmentally sustainable and healthy workplaces, and events that promote the work of nonprofits in our own backyard.
We foster a collaborative environment with opportunities for growth and encourage our associates to live our values: Do good. Be good. Make good.
Please note that we do not offer visa sponsorship for this position.
Role Summary
The Director, Portfolio Management serves as a principal portfolio advisor responsible for leading integrated portfolio planning, demand flow, roadmap transparency, capacity visibility, and prioritization support within an assigned business technology domain. This role translates strategic objectives into executable short-term portfolio plans, ensuring the organization has a clear, fact-based view of requested work, committed work, available capacity, dependencies, execution constraints, and tradeoffs required to deliver meaningful business and technology impact.
This role partners closely with technology domain leadership, business owners, delivery leaders, Project Managers, enterprise portfolio partners, and governance forums to ensure the domain is focused on the highest-value work at the right time. The Director owns the integrated domain portfolio plan, connecting domain demand, roadmap priorities, committed initiatives, delivery milestones, dependencies, capacity assumptions, deferred work, reprioritization impacts, and decision rationale.
The ideal candidate is an experienced portfolio leader who can navigate complex and ambiguous business and technology environments, shape portfolio practices, influence senior stakeholders, guide tradeoff conversations, and create transparency across departments. Success requires the ability to connect strategy to executable work, identify constraints early, drive alignment across stakeholders, and improve portfolio flow while supporting measurable organizational impact.
This position currently offers an onsite work schedule, with the expectation that you will be in the office four (4) days per week during onsite core days. Our current onsite core days are Monday, Tuesday, Wednesday, and Thursday. The work schedule type and core days are subject to change with advance notification and manager discretion.
Essential Duties and Responsibilities

• Lead and maintain the integrated domain portfolio plan, including committed initiatives, emerging demand, roadmap sequencing, delivery milestones, dependencies, capacity assumptions, deferred work, risks, and decision rationale.
• Translate strategic business and technology objectives into short-term executable portfolio priorities, sequencing recommendations, and roadmap plans for the assigned domain.
• Serve as a principal advisor to domain technology leadership, business owners, enterprise portfolio partners, and governance forums on portfolio health, prioritization tradeoffs, delivery risk, capacity constraints, and execution feasibility.
• Partner with technology domain leadership and business owners to ensure the domain roadmap is executable, transparent, and aligned to enterprise priorities.
• Shape and continuously improve portfolio planning, demand management, roadmap transparency, prioritization, and governance practices within the assigned domain.
• Provide visibility into work in progress, deferred work, risks, constraints, dependencies, and tradeoffs required when priorities shift.
• Maintain roadmap transparency so stakeholders understand sequencing, timing, dependencies, and the impact of portfolio changes.
• Lead the process for domain intake and demand management in partnership with business owners and technology domain leadership.
• Ensure incoming demand is clearly defined, connected to business priorities, sized appropriately, assessed for delivery and operational readiness, and evaluated against capacity, value, dependencies, technical constraints, and enterprise priorities.
• Develop prioritization recommendations that consider business value, strategic alignment, customer and agent impact, operational impact, regulatory needs, delivery risk, technical complexity, supplier constraints, and cross-domain dependencies.
• Serve as the domain's central source of portfolio insight by maintaining a current view of demand, delivery capacity, project status, dependency risks, supplier constraints, resource bottlenecks, and sequencing conflicts.
• Provide executive-ready, fact-based decision support to technology domain leadership, business owners, enterprise portfolio partners, and governance forums.
• Surface capacity and execution data early so senior leaders understand whether decisions are executable before commitments are made.
• Identify the consequences of new or urgent work, including what must move, pause, be descoped, be resequenced, or be escalated.
• Prepare clear options and tradeoff views that show value, timing, capacity impact, delivery risk, dependency impact, operational impact, and deferred-work implications.
• Maintain transparency into portfolio health, value realization progress, delivery confidence, capacity utilization, and emerging risks.
• Provide domain-level direction and portfolio context to Project Managers assigned to the domain through a dotted-line alignment for roadmap sequencing, dependency visibility, planning assumptions, capacity impacts, and portfolio reporting.
• Partner with Project Managers to ensure initiative-level integrated project plans align to domain priorities, sequencing decisions, capacity realities, delivery readiness, and dependency constraints.
• Ensure Project Managers have clear visibility into business context, prioritization rationale, committed outcomes, sequencing logic, and tradeoff decisions.
• Consolidate project-level plans, milestones, risks, dependencies, and delivery impacts into an integrated domain portfolio view.
• Identify bottlenecks, dependency risks, resource conflicts, supplier constraints, and sequencing issues that may affect delivery commitments or require reprioritization.
• Coordinate with peer Portfolio Management leaders and enterprise portfolio partners to identify cross-domain dependencies, shared capacity needs, sequencing conflicts, and enterprise impacts.
• Maintain visibility into how domain decisions affect other technology domains, enterprise capacity, supplier capacity, and business operations.
• Support enterprise prioritization conversations by providing domain-specific facts, constraints, capacity data, value assumptions, and tradeoff implications.
• Ensure emerging work, capacity constraints, and dependency risks are visible before they become execution issues.
• Communicate portfolio changes clearly and consistently across affected stakeholders.
• Partner with business owners, technology domain leadership, and delivery teams to connect roadmap items to intended business value, operational impact, adoption measures, and success indicators.
• Track whether delivered capabilities are producing the intended impact and surface where benefits, adoption, or operational improvements are not materializing.
• Identify work that is consuming capacity without clear value, measurable impact, or alignment to domain and enterprise priorities.
• Use portfolio insights, delivery data, and value indicators to continuously improve demand shaping, sequencing, investment focus, and execution confidence.
• Lead structured reassessment when new demand emerges, urgent business needs arise, operational issues disrupt planned work, delivery risks materialize, supplier performance creates risk, or capacity assumptions change.
• Provide rapid visibility into available capacity, impacted committed work, created risks, and required decisions.
• Guide senior stakeholder discussions on reprioritization decisions, tradeoffs, deferred work, assumptions, and impacts.
• All other duties as assigned.

Minimum Qualifications

• Bachelor's degree or equivalent related work experience.
• 14 or more years of related experience in portfolio management, program management, product-oriented delivery, business strategy, value stream leadership, enterprise transformation, business analysis, or technology-enabled business change within complex environments.
• Strong Life and Annuity industry experience with demonstrated expertise in the assigned domain.
• Proven ability to translate business and technology strategy into executable portfolio plans, roadmap priorities, sequencing options, prioritization recommendations, and measurable capability improvements.
• Demonstrated experience leading complex portfolio planning across business, technology, delivery, operational, supplier, and enterprise stakeholder groups.
• Strong experience with intake management, demand shaping, roadmap sequencing, capacity planning, prioritization analysis, tradeoff structuring, dependency management, dynamic reprioritization, and value realization tracking.
• Proven ability to serve as a trusted advisor to senior business and technology leaders by clarifying tradeoffs, surfacing execution constraints, and creating alignment in complex, highly matrixed environments.
• Demonstrated ability to influence portfolio practices, governance conversations, roadmap decisions, and prioritization outcomes across departments or business technology domains.
• Strong analytical capability with the ability to synthesize portfolio data, capacity information, delivery health, dependency impacts, and value indicators into clear executive-ready recommendations.
• Strong systems-thinking capability with the ability to balance domain priorities with enterprise alignment, customer and advisor impact, operational sustainability, and execution feasibility.
• Strong communication, facilitation, and stakeholder management skills with the ability to reduce ambiguity, create transparency, and maintain confidence across senior business and technology stakeholders.

Preferred Qualifications

• Advanced degree in business, technology, operations, or a related field.
• Experience supporting technology-enabled transformation within a complex financial services or insurance environment.
• Experience advising senior leaders in portfolio governance, prioritization, enterprise planning, or strategic execution forums.
• Domain-specific Life and Annuity experience, such as New Business, Underwriting, Distribution, Finance, Actuarial, Financial Controls, In-Force, Service, policy administration, claims, or customer operations.
• Experience shaping portfolio management practices, governance routines, roadmap planning discipline, or value realization frameworks.
• Experience providing dotted-line direction, portfolio context, or planning guidance to Project Managers, delivery teams, or cross-functional execution partners.

AI Proficiency Expectations
At National Life Group, we view AI as an enabler of human potential. We use AI to help us work smarter, serve more clients, and keep our promises, while remaining a relationship-driven business where our people are our greatest strength.
All applicants are expected to:

• Leverage approved AI tools, where appropriate, to improve the efficiency, quality, and impact of their work.
• Stay curious and open to new AI-enabled ways of working.
• Exercise sound judgment by reviewing and validating AI-generated content.
• Maintain accountability for the accuracy, quality, fairness, and integrity of work products by adhering to National Life's AI guiding principles.
• Use AI responsibly and in accordance with company policies related to confidentiality, data privacy, security, compliance, retention and intellectual property.

Benefits

• Your benefits start day one and are flexible and customizable to your and your family's specific needs. Check out the BENEFITS of a Career at National Life!

Base Pay Range. The base pay range for this position is the range National Life reasonably and in good faith expects to pay for the position taking into account the wide variety of factors, including: prior experience and job-related knowledge; education, training and certificates; current business needs; and market factors. The final salary or hourly wages offered may be outside of this range based on other reasons and individual circumstances.
Additional Compensation and Benefits. The total compensation package for this position may also include a full range of medical, financial, and/or other benefits (including 401(k) eligibility and various paid time off benefits, such as vacation, sick time, and parental leave), dependent on the position offered. The successful candidate may also be eligible to participate in National Life's discretionary annual incentive programs, subject to the rules governing such programs. If hired, the employee will be in an "at-will position" and National Life reserves the right to modify base salary (as well as any other discretionary payment or compensation or benefit program) at any time, including for reasons related to individual performance, company or individual department/team performance, and market factors.
National Life is accepting applications for this role on an ongoing basis and the role remains open until filled.
Salary Pay Range
$127,500-$187,000 USD
National Life Group® is a trade name of National Life Insurance Company, Montpelier, VT - founded in 1848, Life Insurance Company of the Southwest, Addison, TX - chartered in 1955, and their affiliates. Each company of National Life Group is solely responsible for its own financial condition and contractual obligations. Life Insurance Company of the Southwest is not an authorized insurer in New York and does not conduct insurance business i