Senior Manager, Strategy

Your Opportunity

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 Digital Retail team is responsible for delivering world-class client experiences across Schwab.com, the Schwab Mobile app, and digital messaging. In Digital Retail, we empower investors to Own Their Tomorrow by delivering industry-leading digital experiences at scale. 

Role Summary

We are seeking a Senior Manager, Digital Retail Strategy to join our Strategic Planning & Insights team. This is a high-ownership strategist-operator role responsible for turning complex inputs into clear strategic direction, leadership narratives, and decision-ready recommendations. This role requires someone who can operate effectively in gray space, bring structure to incomplete or conflicting inputs, and maintain a high bar for precision, accuracy, and follow-through in leadership-facing work. You will partner closely with data, product, and technology to translate outputs into executive-level implications, strategic choices, and actionable direction for Digital Retail. Success in this role requires strong strategic thinking, executive presence, stakeholder influence, and the ability to move from ambiguity to practical solutions. This person must be comfortable challenging assumptions, driving alignment across senior stakeholders, and connecting strategy to execution through better planning, clearer narratives, and smarter ways of working. 

Key Responsibilities

Executive Storytelling & Leadership Influence

• Lead development of executive-ready narratives, presentations, readouts, and strategic recommendations for senior Digital Retail and Retail leadership forums. 

• Pressure-test materials for gaps, inconsistencies, unclear logic, and unsupported claims before they reach senior leadership. 

• Translate complex business, product, technology, market, and performance inputs into clear, concise, decision-oriented stories that articulate what matters, why it matters, and what leaders should do next. 

• Shape leadership conversations proactively by surfacing risks, trade-offs, and implications before they become escalations. 

• Drive cross-functional alignment across Product, Technology, Data, Portfolio Management, Retail Strategy, and partner teams. 

• Ensure executive materials are not just polished, but recommendation-based, actionable, and tied to business outcomes. 

• Maintain a high standard for accuracy, consistency, and detail in executive-facing materials, ensuring data, messages, recommendations, and follow-ups are clear, credible, and aligned. 

Strategic Planning & Alignment

• Lead high-value strategic planning work for Digital Retail, including annual planning inputs, long-range strategy development, OKR narrative development, and executive planning materials. 

• Translate enterprise and portfolio priorities into a coherent Digital Retail strategy narrative that can guide leadership decisions and execution planning. 

• Identify gaps, trade-offs, and inconsistencies across planning inputs and turn them into strategic recommendations and follow-up actions. 

• Improve the clarity, effectiveness, and repeatability of planning artifacts, templates, and strategic operating mechanisms that support leadership decision-making. 

• Partner closely with teams that own execution to ensure leadership is seeing the right signals and that plans are communicated credibly and consistently. 

Insights Translation & Strategic Recommendation

• Partner closely with Data, Competitive Intelligence, Voice of Client, and related teams to define the business questions that matter most for leadership decisions. 

• Ensure executive narratives and strategic planning materials are grounded in the right evidence, while maintaining clear separation from the teams that own the underlying analysis. 

• Identify missing information or weak logic early and drive the right follow-up with partner teams so that leadership decisions are informed by the strongest possible inputs. 

• Bring together disparate inputs into a cohesive strategic view that supports prioritization of leadership attention, clearer communication, and stronger decisions. 

Problem Solving & Strategic Solutioning

• Operate effectively in gray space by identifying the core problem, clarifying what is known versus unknown, and creating a practical path forward when direction, ownership, or data is incomplete. 

• Balance strategic framing with hands-on work, including building working models, shaping templates, improving routines, and solving workflow friction that slows decision-making. 

• Act as a force multiplier for the Strategic Planning & Insights team by improving how strategy work gets done, not just what is delivered. 

• Bring discipline to ambiguous work by defining the decision needed, the inputs required, the accountable owners, and the next steps to move from uncertainty to action. 

• Anticipate where ambiguity may create misalignment, dropped balls, or rework, and proactively establish clarity across stakeholders. 

AI & Automation

• Identify, prioritize, and drive AI and automation use cases that improve strategy development, executive storytelling, knowledge discovery, recurring reporting, and workflow efficiency. 

• Use approved AI tools, including Copilot-style tools, hands-on to accelerate research, synthesis, drafting, summarization, and material creation while validating outputs with sound judgment. 

• Partner with AI / process, data, product, and technology teams to pilot and implement workflow improvements and automation use cases, without owning model development or core AI platform engineering. 

• Develop repeatable prompts, templates, and workflows that improve consistency, reduce manual effort, and help the team move faster with higher quality. 

• Define measurable success criteria for AI and automation efforts, including time saved, reduced manual work, improved consistency, or improved decision speed / quality. 

• Operate with appropriate discipline for a regulated environment, including validation of outputs, strong judgment on data handling, and adherence to governance and control expectations. 

What Success Looks Like

• Leadership receives clearer, faster, and more decision-oriented strategic guidance. 

• Executive materials consistently demonstrate strong judgment, accuracy, and attention to detail, reducing rework and increasing leadership confidence. 

• Strategy materials consistently connect insights to implications, recommendations, and action. 

• Cross-functional stakeholders view this role as a credible thought partner who can align, challenge, and move work forward. 

• The team is better able to translate complex inputs into strategy without over-relying on informal coordination. 

• Stakeholders trust this role to catch gaps, pressure-test assumptions, and create clarity before issues escalate. 

• AI and automation use cases move from ideas to measurable improvements in how strategic work, reporting, and executive storytelling are done

What you have

Required Qualifications

• 8–10+ years of experience in digital strategy, product strategy, management consulting, corporate strategy, product operations, or related roles within financial services or other regulated industries 

• Exceptional attention to detail, with a proven ability to produce accurate, leadership-ready materials that withstand executive scrutiny. 

• Demonstrated ability to operate in ambiguous environments, bring structure to unclear problems, and drive work forward with limited direction. 

• Proven ability to influence cross-functional leaders and drive alignment without direct authority 

• Strong executive communication and storytelling skills, with experience creating materials that inform leadership decisions 

• Ability to move beyond synthesis to develop implications, recommendations, and action-oriented points of view 

• Strong data fluency, including comfort interpreting dashboards, performance metrics, and business analyses, and translating them into strategic decisions 

• Comfort using AI-powered tools, including Copilot-style tools, to accelerate strategic work products and workflow efficiency 

• Experience identifying and driving automation, AI, or process improvement use cases with measurable outcomes 

• Bachelor’s degree 

Preferred Qualifications

• Experience supporting annual planning, OKRs, executive reporting, or portfolio-level strategy development 

• Experience supporting senior leadership in complex, fast-moving environments where priorities, ownership, or decision rights are not always clearly defined. 

• Experience partnering closely with analytics, research, or competitive intelligence teams and translating their work into executive recommendations 

• Experience improving planning, reporting, or leadership workflows through automation, templates, or operating mechanism redesign 

• Demonstrated ability to challenge constructively and influence senior leaders in high-stakes or ambiguous settings 

• Curiosity about emerging technologies and practical judgment on how to apply them in a business setting 

• Experience operating in environments with strong governance, compliance, or risk constraints