Director, Program Strategy, Retirement Plan Services Modernization Initiatives (PL)

Charles Schwab Corporation; Lone Tree (CO); On-site; USD 180,000 - 270,000; Full time

Job summary

Charles Schwab Corporation seeks a Director to lead Retirement Plan Services modernization initiatives, guiding cross-functional teams through planning, execution, and readiness activities. The role requires translating strategic objectives into actionable implementation plans while ensuring business readiness and regulatory alignment in a complex, regulated environment.

The position is on-site in Colorado, reporting to senior leadership, with significant stakeholder engagement.

Qualifications

• 10+ years leading large-scale transformation programs in financial services.
• Ability to navigate ambiguity and manage multiple priorities.
• Proven track record in risk, issues, and blockers resolution.
• Experience unifying business, operations, technology, risk, and compliance.
• Exceptional stakeholder management and influencing skills.
• Strong experience turning strategy into actionable roadmaps and outcomes.
• Experience leading organizational readiness and change initiatives.
• Strong governance, planning, dependency management, and execution oversight.
• Excellent executive communication, with presentations and status materials.
• Bachelor's degree or equivalent.

Responsibilities

• Lead planning and execution for Retirement Plan Services modernization initiatives.
• Coordinate with business, operations, product, technology, risk, and HR teams.
• Translate modernization objectives into actionable plans with clear ownership and timelines.
• Lead change and readiness activities including communications and training.
• Identify and manage risks, dependencies and resource constraints.
• Develop and maintain integrated project plans across workstreams.
• Support governance with executive updates and risk assessments.

Skills

Leadership

Strategic Program Management

Stakeholder Management

Risk Management

Change Management

Cross-functional Collaboration

Communication

Ambiguity Navigation

Execution Excellence

Executive Influence

Education

Bachelor's degree or equivalent

Tools

PMP Certification

Agile/Scrum

Job description

Your Opportunity

We believe in the importance of in-office collaboration and fully intend for the selected candidate for this role to work on site in the specified location(s).

At Schwab, you’re empowered to make an impact on your career. Here, innovative thought meets creative problem solving, helping us “challenge the status quo” and transform the finance industry together.

The Director, Retirement Plan Services Modernization Initiatives will lead critical components of a multi-year modernization program focused on transforming Retirement Plan Services recordkeeping capabilities, strengthening operational infrastructure, and enabling business readiness for future-state platform and service delivery models.

This leader will drive planning, governance, execution, and readiness activities across complex, cross-functional initiatives with significant business, operational, technology, risk, and client implications. Success in this role requires strong program leadership, the ability to navigate ambiguity, influence stakeholders across a matrixed environment, and deliver results through disciplined execution and collaboration.

Key Outcomes

• Lead planning and execution for key Retirement Plan Services modernization initiatives, including implementation and business readiness activities.
• Partner with business, operations, product, technology, risk, communications, human resources, and client-facing teams to coordinate execution and prepare teams for upcoming changes.
• Translate modernization objectives into actionable implementation plans with clear ownership, timelines, deliverables, and success measures.
• Lead change and business readiness activities, including stakeholder engagement, process changes, communications, training, operational preparedness, and implementation planning.
• Help leaders and teams understand what is changing, why it matters, and what they need to do differently as modernization capabilities are implemented.
• Identify and manage program risks, dependencies, resource constraints, and adoption issues that could impact implementation or business readiness.
• Develop and maintain integrated project plans, milestones, dependencies, risks, and readiness activities across impacted workstreams.
• Facilitate alignment across stakeholders to resolve competing priorities, address implementation issues, and maintain progress against key modernization milestones.
• Support governance through executive updates, decision materials, risk assessments, program status reporting, and readiness updates.
• Support conversion and implementation readiness through planning, coordination operational readiness assessments, and stakeholder preparation.
• Reinforce new processes and ways of working to support implementation to help changes become embedded in day-to-day operations.
• Contribute to measurable improvements in execution, organizational readiness, operational effectiveness, and the client and participant experience

What you have

Required Experience

• 10+ years of experience leading large-scale transformation, modernization, strategic initiatives, or complex business change programs within financial services or similarly regulated industries.
• Proven ability to lead through ambiguity and navigate complex, fast-moving environments with multiple priorities, stakeholders, and dependencies.
• Demonstrated success identifying, escalating, and resolving program risks, issues, and roadblocks while maintaining momentum against critical business objectives.
• Strong track record serving as an integrator across business, operations, technology, risk, compliance, and other enterprise functions to drive alignment and execution.
• Exceptional stakeholder management and influencing skills, with the ability to build consensus, resolve competing priorities, and drive decisions without direct authority.
• Experience translating strategic objectives into actionable plans, execution roadmaps, and measurable business outcomes.
• Proven ability to lead organizational readiness and change initiatives, including stakeholder engagement, communications, adoption planning, training, and implementation support.
• Strong program leadership capabilities, including governance, integrated planning, dependency management, risk mitigation, and execution oversight.
• Demonstrated ability to foster accountability, collaboration, and a solutions-oriented mindset across cross-functional teams during periods of significant change.
• Strong executive communication skills, including experience preparing presentations, status reporting, decision materials, and recommendations for senior leadership.
• Bachelor's degree or equivalent combination of education and related experience.

Preferred Experience

• Project Management Professional (PMP), Agile, Scrum, or related program management certifications.