Sr. Portfolio Enablement Lead

Senior Portfolio Enablement Lead
Brooksource
Fortune 50 Health Insurance Client
Overview
The Senior Portfolio Enablement Lead is a strategic transformation leader responsible for shaping and enabling portfolio operations, Agile Release Train (ART) design, organizational ways of working, and large-scale business transformation initiatives. This role serves as a trusted advisor to senior executives and portfolio leaders, translating transformation strategies into scalable execution models that improve alignment, delivery predictability, operational excellence, and business outcomes.
The ideal candidate brings deep expertise in Lean Portfolio Management, Agile methodologies at scale, organizational design, and change management. This position focuses on enterprise enablement and continuous improvement rather than traditional project or delivery management.
Key Responsibilities
Portfolio Transformation & Strategy

• Partner with business and technology leaders to develop and enable portfolio operating models aligned with strategic objectives.
• Guide portfolio transformation efforts through organizational design, process optimization, and operating model improvements.
• Build and manage transformation roadmaps that drive executive alignment and stakeholder engagement.
• Conduct qualitative and quantitative assessments, including stakeholder analyses and change impact evaluations, to inform transformation strategies.
• Facilitate executive decision-making sessions and advise leadership on delivery challenges, value-stream optimization, and organizational effectiveness.

Agile & Lean Enablement

• Provide expertise in Lean Portfolio Management, Agile at Scale, and Agile Release Train (ART) design.
• Mentor and develop Release Train Engineers, Scrum Masters, Product Leaders, and other key stakeholders.
• Support adoption and continuous improvement of portfolio and team-level ways of working.
• Facilitate value stream identification and value stream mapping activities to improve flow efficiency and value delivery.
• Promote enterprise-wide best practices and scalable approaches to portfolio operations.

Organizational Change Leadership

• Drive enterprise transformation initiatives and organizational change programs.
• Develop and execute change management strategies to improve adoption and business outcomes.
• Measure effectiveness of transformation efforts using defined metrics and continuously refine approaches.
• Foster a culture of continuous learning, experimentation, innovation, and operational excellence.
• Lead training, coaching, and mentoring initiatives related to Lean, Agile, and continuous improvement methodologies.

Continuous Improvement & Operational Excellence

• Identify opportunities to improve business processes, systems, and organizational performance.
• Partner with leaders across functions to establish and achieve continuous improvement goals.
• Facilitate problem-solving workshops, process improvement initiatives, and operational excellence programs.
• Monitor portfolio health, identify risks and issues, and proactively recommend solutions.
• Drive data-informed decision-making through effective use of metrics and performance indicators.

Required Qualifications

• 8+ years of experience enabling business and technology portfolios in complex organizations.
• Experience advising senior executives and organizational leaders on transformation initiatives.
• Strong expertise in Lean Portfolio Management and Agile methodologies at scale.
• Demonstrated success leading organizational change and transformation initiatives.
• Experience supporting execution across value streams and complex enterprise programs.
• Proven ability to facilitate Value Stream Identification and Value Stream Mapping activities.
• Excellent communication, facilitation, coaching, and mentoring skills.
• Strong emotional intelligence and stakeholder management capabilities.
• Passion for continuous improvement and enhancing customer and employee experiences.
• Active SAFe certification (SPC preferred or ability to obtain within six months).

Preferred Qualifications

• Bachelor's degree in Business, Information Technology, Organizational Leadership, or a related field.
• SAFe Program Consultant (SPC) certification.
• Prosci Change Management certification.
• Experience with Agile lifecycle management tools such as Jira Align and Azure DevOps.
• Experience in highly regulated industries.
• Understanding of Software Development Lifecycle (SDLC) and Product Development Lifecycle (PDLC).
• Experience mentoring Product Management, Program Management, and Technology leadership teams.
• Background working within large enterprise organizations.

Desired Skills & Competencies

• Executive presence and ability to influence senior leadership.
• Strategic thinking and analytical problem-solving skills.
• Strong facilitation, coaching, and leadership abilities.
• Excellent written and verbal communication skills.
• Ability to work independently in fast-paced and ambiguous environments.
• Exceptional organizational and prioritization skills.
• Collaborative mindset with a focus on building strong relationships.
• Experience driving sustainable enterprise-wide change.
• Commitment to operational excellence and continuous improvement.