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

Charles Schwab; Lone Tree (CO); On-site; USD 180,000 - 280,000; Full time

Benefits offered by this job

401(k) with company match

Employee stock purchase plan

Paid time off

Sabbatical after five years of service

Parental leave

Job summary

Charles Schwab is seeking a Director to lead Retirement Plan Services modernization initiatives, driving strategic execution, governance, and readiness across complex cross-functional teams.

The role requires extensive experience in large-scale transformation within financial services, with a focus on stakeholder management, risk mitigation, and delivering measurable business outcomes.

Qualifications

• 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.

Responsibilities

• Lead planning and execution for key Retirement Plan Services modernization initiatives, including implementation and business readiness activities.
• Coordinate with business, operations, product, technology, risk, communications, human resources, and client-facing teams to align execution and prepare teams for 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 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 issues, and maintain progress against milestones.
• Support governance through executive updates, decision materials, risk assessments, program status reporting, and readiness updates.
• Support conversion and implementation readiness through planning, coordination of operational readiness assessments, and stakeholder preparation.
• Reinforce new processes and ways of working to embed changes in day-to-day operations.

Skills

Program management

Stakeholder management

Change management

Leadership

Strategic planning

Risk management

Cross-functional collaboration

Executive communication

Education

Bachelor's degree or equivalent

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.

What’s in it for you

At Schwab, you’re empowered to shape your future. We champion your growth through meaningful work, continuous learning, and a culture of trust and collaboration—so you can build the skills to make a lasting impact. Our Hybrid Work and Flexibility approach balances our ongoing commitment to workplace flexibility, serving our clients, and our strong belief in the value of being together in person on a regular basis.

We offer a competitive benefits package that takes care of the whole you – both today and in the future:

• 401(k) with company match and Employee stock purchase plan
• Paid time for vacation, volunteering, and 28-day sabbatical after every 5 years of service for eligible positions
• Paid parental leave and family building benefits
• Tuition reimbursementHealth, dental, and vision insurance