Sr. Director, CTO Portfolio

CoverMyMeds' Technology organization is seeking a Sr. Director, CTO Portfolioto serve as a strategic and operational partner to the CTO leadership team. This role owns endtoend portfolio health across Technology and Data, bringing structure, clarity, and maturity to how work is planned, governed, measured, and communicated.

This role translates strategy into actionable roadmaps, establishes executiveready reporting, and ensures the organization is investing in the right work at the right time. Our ideal candidate brings deep experience building and leading mature technology portfolio organizations.

** Our ideal candidate will reside in the Columbus, OH area to support a hybrid work schedule. We may consider a highly qualified candidate in the remote hub areas of Atlanta, GA or Irving, TX.

*This position requires current, unrestricted authorization to work in the United States that is not time-limited or dependent on a future change in status. We are unable to consider or sponsor candidates on temporary work authorization, including F1 OPT, STEM OPT, CPT, or any status requiring employer sponsorship now or in the future.

What You'll Do:

• Own theendtoend technology portfolio lifecycle, including annual planning, longrange planning, investment governance, and ongoing portfolio health management

• Translate enterprise and CoverMyMeds strategy intointegrated, multiyear roadmapswith clear milestones, dependencies, and outcomes

• Establish and deliverstandardized executive reporting and dashboardsthat provide clear insight into progress, risk, capacity, and value realization

• Build and evolve amature portfolio operating modelacross Technology and Data & Analytics, balancing "run the business" and strategic initiatives

• Lead and develop a team of portfolio leaders and managers, including building organizational structure, capability, and succession plans

• Partner closely with Technology Program Delivery, Product, Finance, Operations and Mckesson Enterprise Technology teams to align priorities and execution

• Champion and embed SAFe portfolio practies, enabling transparency, prioritization, and iterative delivery at scale

• Monitor the evolvingAI landscape, identify opportunities to apply AI within portfolio and planning processes, and model AIenabled ways of working

• Act as a trusted advisor to senior leaders, driving timely decisions, resolving blockers, and maintaining alignment across a complex stakeholder environment

Basic Requirements:

• Degree or equivalent experience, and typically requires13+ years of relative experience, including6+ years of diversified leadership, planning, communication, organization and people motivation skills (or equivalent experience)

• Demonstrated experience leading largescaletechnology portfolio managementwithin a complex enterprise environment

• Proven ability to design and implementexecutivelevel reporting, dashboards, and portfolio governance

• Strong technology fluency, with the ability to engage credibly on topics such as cloud platforms, data, and modern delivery models

Preferred Skills & Experience:

• Background working withintechnologyled or SaaS organizations

• Experience operating inSAFe or largescale Agile environmentsat the portfolio level

• Demonstrated success building or maturing portfolio organizations that were previously understructured

• Strong financial acumen, including investment management, forecasting, and capacity planning

• Exposure toAIenabled tools or practicesand curiosity to apply AI to improve efficiency and decisionmaking

• Exceptional communication skills, with the ability to influence senior executives and diverse stakeholder groups