Sr Dir Dig Enblmt Portfo Mgmt

Job Summary

The Senior Director of Systems & Tools Portfolio Management is a strategic leadership role responsible for supporting the planning and execution of the company's key technology investments to modernize our frontline tools and processes. 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 help oversee the Systems & Tools portfolio in partnership with Finance, CPTO (IT), and key business stakeholders, and will lead implementation of priority technology initiatives including the migration of the company to a new billing platform as well as the consolidation and optimization of Optimum’s frontline tools.  This position requires deep experience leading complex, cross-functional technology transformations at scale. 

Responsibilities

1. Technology Strategy & Portfolio Governance

• Partner with CPTO, Finance, and key Business Stakeholders to develop and maintain the frontline tool strategy, ensuring alignment with enterprise priorities and budget.
• Support aggregation of business cases across IT and Operations, partnering with Finance on cost/benefit modeling.
• Track and report on expected vs. realized benefits and savings against defined targets as initiatives are deployed.

2. Program Leadership & Execution

• Lead the cross-functional planning and execution of strategic technology investments aimed at modernizing frontline tools and processes.
• Oversee the end-to-end execution of initiatives, including scope, timeline, resourcing, budget, and risk management.
• Ensure thorough end-to-end testing plans across both technology and business teams along with stand-up of go/no-go criteria and checkpoints for any pilot expansion and full deployment.
• Establish governance cadences, including steering committees and working team status reviews, to track progress, surface risks, and drive timely decisions.

3. Change Management & Frontline Enablement

• Partner with Operations, Communications, and HR teams to ensure frontline employees are supported through tool transitions, including training, communication, and feedback loops.
• Champion a people-first approach to technology rollouts, ensuring the frontline user experience as well as the customer experience is a central input to design and sequencing decisions.
• Monitor adoption and performance metrics post-launch, driving continuous improvement of new platforms and processes.

4. Cross-Functional Alignment & Executive Reporting

• Serve as the central point of coordination across Technology, Operations, Finance, Communications, and HR to ensure on-time, on-budget delivery.
• Develop and maintain executive-ready reporting on technology initiative status, including roadmap progress, spend versus budget, risks, and key decisions required.
• Facilitate senior leadership discussions on prioritization, trade-offs, and resourcing across the technology investment portfolio as-needed.

5. Governance & Continuous Improvement

• Establish and continuously refine governance practices for technology initiatives including planning frameworks, execution/deployment status monitoring, and post-implementation reviews.
• Partner with the CPTO PMO and broader enterprise program team to align technology initiative governance with overall portfolio management best practices.
• Work 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, Information Technology, or a related field.
• 10+ years of experience in technology strategy, program management, or business/IT transformation, including significant experience leading large-scale platform implementations.
• Demonstrated experience partnering with product/technology leadership and Finance on technology investment planning and prioritization.
• Proven track record leading complex, cross-functional technology initiatives (e.g., platform migrations, new system rollouts) from planning through adoption.
• Strong executive communication skills, with the ability to translate technical strategy into clear, actionable narratives for senior leadership.
• Strong analytical and financial acumen, including experience building business cases and tracking ROI on technology investments.
• Comfortable operating in highly cross-functional environments spanning technology, operations, customer support, and finance.

Preferred

• Master's degree or MBA.
• Experience with customer support and/or billing systems and operations, including platform migrations or consolidations.
• Experience in telecommunications, cable, or a related consumer services industry.
• PMP or equivalent program management certification.
• Background in change management or organizational effectiveness.