Sr. Director- Strategic Initiatives

Job Summary

The Senior Director of Strategic Initiatives Portfolio Management is a senior leadership role responsible for leading priority initiatives across the enterprise to support achievement of broadband subscriber adds and other key company financial targets. This role will serve as part of our enterprise-wide strategic planning and program lifecycle team at Optimum, reporting directly to the VP of Finance Strategy and Integration.

This role will lead planning and execution of key initiatives in Optimum’s plan of record to support achievement of organizational goals. They are a champion for aligning operational priorities with clear execution plans, ensuring the company's most important initiatives are resourced, tracked, and delivered to meet targets.

Responsibilities

Strategic Initiative Portfolio Governance

• Manage the portfolio of strategic initiatives supporting both broadband subscribers and financial targets as part of Optimum’s plan of record.
• Partner with leadership across Finance, Technology and the Business to ensure alignment on business cases and roll-up to company-wide goals and forecast.
• Track and report on expected vs. realized benefits and savings against defined targets as initiatives are deployed.

Program Leadership & Execution

• Lead the cross-functional planning and execution of strategic operational initiatives aimed at transforming performance across the business.
• Oversee the end-to-end execution of initiatives, including scope, timeline, resourcing, budget, and risk management.
• Establish governance cadences, including steering committees and working team status reviews, to track progress, surface risks, and drive timely decisions.

Change Management & Customer Experience

• Partner with Operations, Communications, and HR teams to ensure both customers and employees are supported throughout the rollout of initiatives including training, communication, and feedback loops.
• Champion a people-first approach to operation changes, ensuring both the frontline teams and customers are considered throughout the process.
• Monitor adoption and performance metrics post-initiative launch, driving continuous improvement of new processes for both customers and employees.
• Design feedback and engagement mechanisms to ensure initiatives remain aligned with customer and employee needs throughout execution.

Cross-Functional Alignment & Executive Reporting

• Serve as the central coordination point across Technology, Operations, Finance, Communications, and HR to ensure enterprise strategic initiatives are aligned and progressing.
• Develop and maintain executive-ready dashboards and status reporting, including portfolio pipeline and initiative overview; progress against investment priorities, with gap analysis and forward outlook; and key risks, decisions required, and trade-offs.
• Facilitate senior leadership discussions on prioritization, trade-offs, and resourcing across the technology investment portfolio as-needed.

Governance & Continuous Improvement

• Conduct post-initiative retrospectives to capture lessons learned and continuously improve portfolio and program management practices across the operations.
• Partner with the team to continue to standardize and optimize governance practices including project playbooks, timelines, RACI structures, and communication templates to ensure consistent and repeatable execution across projects.

Qualifications

Required

• Bachelor's degree in Business Administration or a related field.
• 10+ years of experience in enterprise strategy, program management, or corporate strategy/transformation roles.
• Demonstrated experience managing large, complex, cross-functional enterprise portfolios or programs in matrixed organizations.
• Proven ability to engage credibly with senior executives and the executive team, translating complex strategic and financial information into clear narratives.
• Strong analytical mindset with the ability to interpret financial and operational data, model scenarios, and evaluate investment trade-offs.
• Experience developing governance frameworks, prioritization criteria, and executive reporting for enterprise-level initiatives.
• Comfortable operating in a highly cross-functional environment spanning technology, finance, operations, and customer-facing business units.

Preferred

• Master's degree or MBA.
• Prior experience in a Chief of Staff, corporate strategy, or enterprise PMO leadership role.
• PMP or equivalent professional certification.
• Experience in telecommunications, cable, or a related consumer services industry.
• Background in change management or organizational effectiveness.