Director, Portfolio Management - Contract to Hire (Remote)

Do you have a passion for children and education? Would you like to positively impact families in need of help? We want to speak with you! Step Up For Students empowers families to pursue and engage in the most appropriate learning options for their children. Step Up For Students empowers families to pursue the most appropriate learning options for their children. We unite communities to provide scholarships that open doors to a stronger future. With this support, students can choose the right learning environment and access resources to reach their full potential. Our culture is rooted in two core values: Everyone is an asset Every event is an improvement opportunity These values guide how we work together and continuously improve. We expect every team member to bring these principles to life in their daily work. The Director of Portfolio Management provides enterprise-level leadership to ensure strategic initiatives and investments are aligned with the organization’s mission, long-term objectives, and operational priorities. This role is responsible for architecting and leading a comprehensive portfolio governance framework that enables data-driven decision-making, value realization, and effective resource allocation across the enterprise. Reporting into senior leadership, the Director oversees portfolio planning, prioritization, governance, performance management, risk oversight, and benefits realization, bringing transparency and rigor to how initiatives are selected, funded, and delivered. As a trusted advisor and key liaison between executive leadership and delivery teams, this leader facilitates informed investment decisions, resolves cross-portfolio trade-offs, and ensures enterprise capacity and resources are optimally aligned to drive outcomes and maximize portfolio value. Location: Remote (United States) Key Responsibilities: Architect and lead enterprise-wide governance frameworks that drive alignment of strategic investments with corporate objectives and long-range plans. Facilitate C-suite portfolio governance forums, enabling high-quality decision-making through advanced scenario planning, trade-off modeling, and strategic risk assessment. Maintain enterprise visibility of the full strategic initiative portfolio, ensuring optimal balance between near-term operational demands and long-term growth objectives. Provide executive oversight and mentorship to the portfolio team, ensuring consistent application of governance standards, project assurance practices, and audit. Design and evolve governance protocols, including scoring models and prioritization criteria, based on organizational performance analytics and strategic shifts. Own and evolve enterprise portfolio management policies, including stage-gate, intake, scoring, and selection procedures. Ensure continuous improvement of governance practices based on performance metrics, stakeholder feedback, and benchmarking. Lead enterprise-level governance committees and facilitate decision-making at the executive level. Represent the EPMO as a trusted advisor in senior leadership forums, providing enterprise portfolio performance reporting and recommending strategic adjustments through informed data driven decision making. Direct the intake, evaluation, and strategic prioritization of enterprise-wide initiatives, ensuring investment decisions are aligned with business objectives and resource constraints. Develop and maintain an integrated, multi-year strategic roadmap that aligns investment timing with corporate business planning and opportunities. Serve as the escalation point for enterprise prioritization conflicts, resolving trade-offs with executive sponsors to maximize portfolio value. Support the annual planning process with scenario-based portfolio modeling and capital/resource forecasting. Act as the enterprise integrator for strategic initiatives, ensuring clarity of dependencies, sequencing, and benefit realization across portfolios. Own the enterprise benefits realization lifecycle, tracking value delivery and ensuring measurable outcomes from strategic investments. Establish and manage enterprise metrics and KPIs to measure portfolio health, strategic contribution, and realized business value. Drive continuous assessment of initiative performance, making recommendations for continuation, acceleration, or termination. Hold formal portfolio reviews and benefits assessments, ensuring transparent reporting to executive stakeholders. Proactively identify systemic and cross-portfolio risks; develop enterprise-level mitigation plans to protect strategic investments. Govern enterprise resource allocation and capacity management to ensure successful delivery of strategic initiatives. Partner to align with budgeting and staffing strategies and evolving portfolio needs. Lead a portfolio team fostering development and retention. Own EPMO quality oversight, ensuring project compliance, alignment with standards, and audit assessment across portfolios. Collaborate with senior leaders across business units to align strategies and resolve portfolio level conflicts. Champion portfolio management as a discipline, promoting a culture of transparency, accountability, and continuous improvement. The above is not an all-inclusive list of all duties performed by this job title, only a representative summary of the primary duties and responsibilities. Incumbent may be required to perform other additional duties as assigned. Qualifications: Demonstrated success and a proven track record in professional/life experience in specific job functions, projects, or industries. Military service can substitute for professional experience and/or formal education requirements. Master’s degree in Business Administration (MBA), Project Management, Engineering, or a related field. In lieu of a master’s degree, a minimum of 12+ years of progressive project management experience, including 5+ years in a portfolio management role, may be considered overseeing enterprise-wide projects. 5+ years in a portfolio management role. Deep knowledge of PMI’s Standard for Portfolio Management and portfolio governance best practices. Strong analytical and decision-making skills, with the ability to synthesize complex data into actionable insights. Proven ability to influence executive leadership and drive alignment across diverse stakeholders. Project Management Professional (PMP) certification. Skilled in using Clarity PPM to deliver real-time portfolio insights, support executive decision making, and enforce governance standards. You’ll Stand Out If You Have: Demonstrated experience using a PPM system such as Clarity (preferred) or another PPM tool for resource allocation, forecasting, capacity planning, and project tracking/ reporting of risks, issues, changes and budgets. Portfolio Management Professional (PfMP) certification. 8+ years of progressive PMO experience. Key Competencies: Demonstrates critical Transformation and Leadership skills and abilities: True Collaboration; Focusing on Outcomes: Owning and effectively solving problems for today and the future; Empathetic Leadership; Adaptability and Resilience; Emotional Intelligence/CEM skills and Continuous Development/Continuous Improvement Mindsets. Proven ability to lead and scale enterprise portfolio management capabilities across complex organizations. Strategic thinker with expertise in aligning investment decisions with business objectives. Strong analytical and problem-solving capabilities, with the ability to synthesize complex data into actionable insights and strategic decisions. Mastery of portfolio and project management methodologies; able to tailor approaches to organizational maturity and complexity. Strong understanding of enterprise operations and cross-functional interdependencies. Mastery of project and portfolio management methodologies. Proven ability to impactfully communicate and engage C-level executives and senior stakeholders through insights, executive-level reporting, and data-driven recommendations. Exceptional written and verbal communication skills, with the ability to tailor messaging to technical and non-technical audiences across all organizational levels. Highly adaptable and resilient in fast-paced, evolving environments, with a continuous improvement mindset. Operates independently with minimal oversight, demonstrating sound judgment and accountability. Demonstrated success in leading high-performing teams with a focus on accountability, development, and delivery excellence. Strong written and verbal communication skills, with the ability to tailor messaging to varied audiences. Self-directed and highly organized, able to operate independently and make sound decisions with limited oversight. Continuously seeks process improvements and fosters a culture of learning and innovation. Strong written and verbal communication skills. Interview Process: Veriff Identity Verification Recruiter Video Interview DiSC Assessment Executive Coaching Session Video Interview with Chief Executive Officer Why you’ll love working here: Award-Winning Culture: We’ve been named one of the Best Companies to Work For four years in a row by Florida Trend and Workforce Research Group and honored as one of the Healthiest Companies by Florida’s First Coast Worksite Wellness Council. Fast Company recognized us as one of the Best Workplaces for Innovators—proof that we foster an environment where big ideas and bold thinking are encouraged. Comprehensive Benefits: Enjoy medical, dental, and vision coverage, plus HSA, FSA, and Lifestyle Spending Accounts. We also offer a competitive 401(k) with company match to help you plan for the future. Flexibility & Work-Life Harmony: Remote work options and unique time-off programs—including 14 paid holidays, Care and Parental Leave, and our Flexible Leave policy. Growth & Development: From mentorship programs to management training and professional development opportunities, we invest in your career journey every step of the way. Supportive Professional Environment: Our dedicated coaching team is here to help you succeed, and employee-led committees give you a voice in shaping our workplace. Collaboration isn’t just encouraged, it’s how we work. Working Conditions and Equipment Use: Work is performed indoors in a typical office environment - not substantially exposed to adverse environmental conditions. Valid driver license with proof of insurance. Must be able to lift up to fifteen (15) pounds. Frequent use of office machines to include telephone, computer, and printer. Step Up For Students is an equal opportunity employer committed to diversity & inclusion in the workplace. Apply To This Job