Managing Director, STS Strategy & Transformation

Your Opportunity

The Managing Director, STS Strategy & Transformation is a senior leadership role responsible for shaping and executing the strategic direction of Schwab Technology Services (STS) and leading a broad portfolio of technology transformation initiatives. This leader is responsible for both strategy and execution – defining technology priorities, translating them into actionable programs driving scale, efficiency, modernization, and business outcomes across STS and its partner organizations. Creates singular clearer accountability for enterprise priorities and transformation outcomes. 

This role is accountable for leading STS’ transformation agenda, including Schwab India Stewardship, Enterprise Agile transformation, operating model evolution, change enablement, value realization, STS data and reporting capabilities, and strategic/ portfolio planning. The organization is responsible for the successful execution of STS transformation (STS Next) and achieving approximately $500M in scale and efficiency benefits by 2029 through a combination of operating model improvements, workforce transformation, global delivery expansion, and productivity enhancements.

The Managing Director serves as a trusted advisor to the STS Senior Management Team, CIO, CTO, and other executive leaders, driving alignment across highly matrixed organizations and ensuring strategic initiatives deliver measurable business outcomes. The role also serves as the senior U.S.-based leader responsible for enabling the continued growth and success of Schwab India, a critical long-term strategic initiative designed to increase organizational capacity, enhance delivery capabilities, and improve operational efficiency.

Measures of Success

• Continued evolution of STS Strategy and transformation agenda
• Successful execution of the STS Next transformation initiatives and achievement of targeted scale and efficiency objectives.
• Delivery of measurable business value through transformation initiatives, operating model improvements, and modernization efforts.
• Effective leadership of Schwab India expansion and realization of associated business case outcomes.
• Increased organizational agility, productivity, and decision-making effectiveness across STS.
• Establishment of scalable governance, metrics, and reporting frameworks that improve visibility and accountability.
• Strong alignment across senior leaders, enterprise and technology partners, and transformation stakeholders.
• Successful adoption of new ways of working and sustained cultural and organizational change.
• Development of a high-performing team that enables technology transformation and strategic execution.
• Strong alignment between strategy development and execution. 

Core Responsibilities

STS Strategy & Enterprise Transformation

• Lead the development, evolution, and execution of the STS strategic roadmap, ensuring alignment with enterprise priorities and long-term business objectives.
• Serve as the central leader responsible for connecting strategy, transformation, and execution across STS.
• Identify and drive strategic opportunities enhancing organizational effectiveness, improving performance, and accelerating modernization efforts.
• Partner with senior leaders to define priorities, evaluate tradeoffs, and align investments to desired business outcomes.
• Translate complex enterprise objectives into actionable initiatives with clear accountability and measurable results.
• Bring external perspectives and competitive updates to inform technology evolution

STS Next Transformation Leadership

• Provide end-to-end leadership for the STS transformation portfolio, ensuring coordinated execution across multiple interconnected initiatives.
• Drive achievement of targeted scale, efficiency, productivity, and modernization outcomes.
• Establish governance, execution disciplines, and operating mechanisms that improve transparency and decision-making.
• Oversee transformation performance, ensuring value realization and benefits tracking are integrated throughout the lifecycle of major initiatives.
• Proactively identify risks, dependencies, and barriers to execution and lead mitigation efforts across stakeholder groups.

Schwab India Strategy & Stewardship

• Serve as the senior U.S.-based executive sponsor responsible for supporting the continued growth and success of Schwab India.
• Partner with leaders across STS and Schwab India to ensure alignment on strategy, operating models, workforce planning, and business objectives.
• Support the successful transition of work, including knowledge transfer, organizational readiness, and change management activities.
• Drive delivery against financial and operational objectives associated with the multi-year business case.
• Strengthen partnership, governance, collaboration, and cultural integration across global teams.

Agile Transformation & Operating Model Enablement

• Lead enterprise Agile transformation efforts to improve organizational effectiveness, delivery speed, and business outcomes.
• Drive adoption and enablement of evolving operating models across STS and partner organizations.
• Establish frameworks, practices, and capabilities that support continuous improvement and organizational agility.
• Partner with technology and business leaders to align operating model changes with strategic objectives and execution priorities.
• Ensure transformation efforts result in sustainable behavioral and operational change.
• Evolve operating models with the development of AI

Data, Metrics & Value Management

• Oversee the development of integrated data, metrics, reporting, and value management capabilities that support executive decision-making.
• Lead the definition and requirements for performance measurement frameworks, including value realization and benefits tracking.
• Establish governance and accountability for data quality, reporting consistency, and actionable insights.
• Ensure leaders have transparent access to meaningful operational, financial, and transformation metrics.
• Leverage data-driven insights to guide strategic decisions and prioritize investments.

Change Leadership & Organizational Effectiveness

• Lead change management and organizational readiness efforts across transformation initiatives.
• Champion adoption of new ways of working, helping leaders and teams navigate ambiguity and organizational change.
• Build alignment across stakeholders through clear communication, engagement, and partnership.
• Foster a culture of continuous improvement, innovation, accountability, and results.
• Develop leadership capabilities and strengthen organizational readiness for future transformation efforts.

Executive Stakeholder Management

• Serve as a trusted advisor to the STS Senior Management Team, STS Operating Council, CIO, CTO, Executive Committee members, and other enterprise leaders.
• Drive alignment across leadership forums and strategic decision-making bodies.
• Lead executive communications related to strategy, transformation progress, outcomes, risks, and opportunities.
• Influence outcomes across highly matrixed organizations through collaboration, credibility, and strong executive presence.
• Build partnerships across Technology, Finance, Human Resources, Corporate Real Estate, and other enterprise functions to deliver strategic objectives.

Required Qualifications

• 15+ years of progressive leadership experience in strategy, transformation, technology, operations, consulting, or related disciplines.
• Demonstrated success leading large-scale enterprise transformations with measurable business outcomes.
• Significant experience operating at the executive level and influencing senior leaders across complex, matrixed organizations.
• Proven ability to develop strategy and translate vision into executable plans and tangible results.
• Strong financial acumen, including business case development, value realization, investment planning, and benefits tracking.
• Experience leading organizational change and driving adoption of new operating models and ways of working.
• Exceptional executive communication, stakeholder management, and presentation skills.
• Demonstrated ability to influence without authority and build alignment across diverse stakeholder groups.
• Strong risk management and strategic decision-making capabilities in ambiguous and evolving environments.
• Experience building, leading, and developing high-performing teams focused on enterprise outcomes.

Preferred Qualifications

• Experience leading enterprise Agile transformations and operating model modernization efforts.
• Experience supporting global delivery organizations and offshore delivery strategy.
• Demonstrated success leading large-scale technology or digital transformation initiatives.
• Experience developing enterprise performance measurement, reporting, and value management frameworks.
• Strong understanding of portfolio management, organizational effectiveness, and transformation governance.
• Experience partnering with technology organizations, software engineering teams, and product delivery functions.
• Consulting, transformation office, strategy, or enterprise program leadership experience preferred.
• Advanced degree in Business, Technology, Organizational Leadership, or a related field preferred.