Director, Portfolio Execution

Blue Cross Blue Shield Association•Chicago, IL

5d•$140,560 - $190,087•Hybrid

About The Position

The Portfolio Execution function is responsible for strengthening how strategic initiatives are operationalized, tracked, and executed across Operations. The leader in this role will be responsible for building the CoE, including execution methodology, portfolio reporting, risk management, and ensuring business-IT coordination. This leader will establish the standards and management frameworks that bring structure and visibility to Business Operations' portfolio of strategic initiatives. Through disciplined execution practices, executive-ready reporting, and proactive issue resolution, this role ensures Operations leadership has the insights needed to make timely, informed decisions and that strategic priorities translate into measurable outcomes.

Requirements

Required BS ; or equivalent experience
10+ Years progressive experience in leading strategy execution, program management or related fields within complex organizations
Deep understanding of how to translate strategic objectives into executable work—including decomposition of goals, workstream design, and accountability frameworks
Ability to see across organizational boundaries and identify dependencies, conflicts, and optimization opportunities
Strategic thinking combined with operational pragmatism—knows when to design the perfect solution vs. when to ship the minimum viable process
Understanding of Business Operations in healthcare/insurance context (national programs, government markets, inter-plan systems, regulatory environment)
Financial acumen including budget management, forecasting, business case development
Proven ability to design and implement performance management systems (dashboards, scorecards, reporting cadences)
Experience with portfolio management tools and methodologies (Workboard, Clarity, Smartsheet, PowerBI, etc.)
Strong project and program management skills with ability to lead complex, cross-functional initiatives
Risk management expertise—identifying, quantifying, mitigating, and escalating risks appropriately
Process design and optimization skills—can diagnose execution breakdowns and design sustainable solutions
Comfort with technology concepts and ability to translate between technical and business language
Experience working at the business-IT interface; understands how to ensure IT delivery serves business outcomes
Data literacy—can interpret dashboards, analyze trends, and derive actionable insights
Familiarity with enterprise tools (Microsoft 365, SharePoint, collaboration tools)
Interest in AI/automation applications for execution and performance management
Consultative skills and experience partnering with and influencing senior executives (VP, EVP, C-suite levels)
Ability to operate with authority without formal authority—influences through expertise, relationships, and value delivery
Strong stakeholder and relationship management skills across diverse functional areas and organizational levels
Comfort navigating ambiguity, complexity, and organizational politics with professionalism and integrity
Change leadership—can drive adoption of new ways of working with empathy and persistence
Exceptional written and verbal communication skills—can distill complexity into clear, compelling narratives for executive audiences
Executive presence and gravitas—comfort presenting to COO and senior leadership
Strong facilitation skills—can lead productive meetings, drive decisions, and manage group dynamics
Impactful storytelling—translates data and status into strategic insights and actionable recommendations
Ability to adapt communication style to different audiences (technical teams, business owners, executive leaders)
Systems thinker who sees patterns, connections, and unintended consequences
Intellectually curious with a continuous learning orientation
Detail-oriented with strong follow-through while maintaining strategic perspective
Comfortable with ambiguity and adept at applying novel solutions to complex problems
High integrity, discretion, and judgment—handles sensitive information and difficult situations professionally
Bias toward action—moves quickly from analysis to decision to implementation
Collaborative team player who builds capability in others and shares credit generously

Nice To Haves

Preferred MS or related advanced degree
Certified Project Management Professional (PMP) - PMI
PgMP - Program Management Professional - PMI
Certified Scrum Master - Scrum Alliance
Certified Change Management Professional - CCMP

Responsibilities

Leads the Portfolio Execution team, translating strategic initiatives into clear execution methodology, standards, and management process frameworks for Business Operations.
Ensures strategic objectives are translated into structured execution plans with defined workplans, workstream ownership, team assignments, RACI accountability, and performance metrics.
Convenes cross-functional stakeholders to ensure alignment, drive progress, and resolve dependencies.
Provides hands-on execution leadership for highest-priority or highest-risk initiatives.
Designs and maintains the Executive Operations Portfolio dashboards and reports, providing clear visibility into initiative health and risk exposure.
Delivers executive-ready insights that connect project execution to business outcomes, OKRs, and enterprise priorities.
Conducts portfolio-level analysis to identify trends and optimization opportunities.
Supports Quarterly Business Reviews, Portfolio Review meetings, ELT meetings as required, and strategic planning with data, insights, and facilitation.
Establishes early warning systems and leading indicators that identify risks before they escalate to drive to timely resolution of blockers and escalations through structured problem-solving.
Serves as strategic liaison between Business Operations and Enterprise Information Technology (IT), ensuring IT delivery aligns to business priorities and technical execution translates into business outcomes.
Partners with Tech Operations to jointly identify standards, reporting, and alignment with IT to deliver on core technology-enabled initiatives.
Synthesizes technical status into business-focused reporting that enables executive decision-making.
Facilitates business-IT alignment on priorities, sequencing, and resource allocation.
Develops training, playbooks, and self-service resources that build execution excellence across Business Operations.
Conducts retrospectives and lessons-learned sessions.
Provides execution and quality oversight of external consulting partners who are staffed on enterprise priority programs to ensure value delivery and alignment with BCBSA project execution standards.
Fosters a culture of disciplined execution, transparency, and accountability.
Leads a team of business execution managers and subject matter experts to drive effective performance, foster professional growth, and create a positive work environment.
Develops talent through coaching and mentoring.
Builds team capability in strategic execution, performance management, business-IT integration, and stakeholder engagement.