Senior Director, Chief of Staff – Office of the CTO

Early Warning® • San Francisco, CA

1d • $226,000 - $310,000 • Hybrid

About The Position

The Senior Director, Chief of Staff serves as a strategy and operations leader within the CTO Office, partnering closely with the Chief Technology Officer, Technology Chief Operating Officer, and technology leadership team to connect technology vision and strategy to disciplined execution. This role translates strategic priorities into actionable plans, operating mechanisms, investment priorities, and measurable outcomes while maintaining alignment across technology, product, risk, operations, finance, and other enterprise functions. The Senior Director brings structure to complex and ambiguous priorities, identifies and resolves barriers to execution, and strengthens the operating model and governance required to deliver technology objectives. The role requires strong technology and financial-services acumen and the ability to connect technology investments and capabilities to business value, client needs, operational resilience, risk management, and the evolving banking and payments ecosystem.

Requirements

• Typically has 15 years of experience or demonstrated portfolio consistent with experience required of the role.
• Demonstrated leadership experience in technology strategy, business operations, enterprise transformation, portfolio management, or enablement within a CTO, CIO, financial services, management consulting, or comparable technology organization.
• Experience partnering directly with a CTO, Technology COO, CIO, or other senior technology executives.
• Demonstrated experience leading complex, cross-functional initiatives and translating strategic objectives into executable roadmaps, operating plans, governance mechanisms, and measurable outcomes.
• Experience operating within or closely supporting a complex technology organization, with sufficient technical fluency to engage effectively with leaders across software engineering, architecture, cloud, data, cybersecurity, reliability, APIs, artificial intelligence, and platform modernization.
• Experience with strategic planning, technology investment or portfolio planning, prioritization, governance, performance management, and executive decision support.
• Demonstrated understanding of how technology strategy and investment decisions connect to product priorities, business and client value, operational resilience, organizational capacity, and enterprise risk.
• Strong analytical and financial acumen with demonstrated ability to evaluate complex information, develop business cases, identify implications and tradeoffs, and formulate actionable recommendations.
• Demonstrated ability to communicate complex technical and business topics clearly to executive and nontechnical audiences and to influence decisions and align stakeholders across functions.
• Demonstrated ability to lead through ambiguity, manage competing priorities and dependencies, establish scalable operating mechanisms, and drive accountability and follow-through across teams.
• Experience working within or closely with financial institutions, payment companies, fintech organizations, financial infrastructure providers, regulated technology organizations, or comparable environments.
• Bachelor’s degree in computer science, engineering, business, finance, a related field, or equivalent practical experience.

Nice To Haves

• Knowledge of financial-services regulation, technology controls, third-party risk, and operational resilience.
• Experience developing organizational capabilities, leading change, or building and developing technology strategy, operations, transformation, or program enablement teams.
• MBA, technical graduate degree, or other relevant advanced qualification.

Responsibilities

• Partner with the CTO and Technology COO to maintain alignment among technology vision, enterprise priorities, investment decisions, organizational objectives, and execution.
• Translate technology strategy into multiyear roadmaps, annual priorities, operating plans, governance mechanisms, and measurable outcomes; identify gaps between strategy and execution and drive cross-functional resolution.
• Lead strategic planning and analysis using business and organizational data, financial information, technology and market trends, and relevant developments across banking, payments, financial services, and the broader technology landscape.
• Connect enterprise, product, client, operational, and risk priorities to required technology capabilities and investments, including considerations related to artificial intelligence, cloud, cybersecurity, data, digital identity, fraud prevention, payments, and platform modernization.
• Establish scalable mechanisms for prioritizing, governing, and monitoring strategic technology initiatives, including clear outcomes, ownership, milestones, dependencies, risks, investment considerations, and performance measures.
• Partner across Technology, Product, Finance, Risk, Operations, and other functions to support portfolio planning, resource alignment, funding decisions, and prioritization based on strategic alignment, business and client value, operational resilience, risk, and delivery capacity.
• Strengthen the technology operating model by improving decision rights, accountability mechanisms, escalation paths, planning processes, leadership forums, operating reviews, and cross-functional coordination.
• Lead cross-functional initiatives and change efforts that improve organizational effectiveness, execution discipline, technology capabilities, and ways of working; anticipate delivery risks, remove barriers, and ensure sustained follow-through.
• Partner with technology leadership and Human Resources on organizational design, workforce and capability planning, talent priorities, and change-management strategies required to support the technology strategy.
• Develop executive-level strategy documents, business cases, presentations, operating reviews, and decision materials that translate complex technology, operational, and financial information into clear narratives and actionable recommendations.
• Represent the CTO Office in enterprise initiatives and leadership forums, building alignment across senior stakeholders and influencing decisions without relying solely on formal authority.
• Lead and develop team members, as applicable, by establishing clear expectations, enabling strong performance, developing future capabilities and leaders, and reinforcing accountability for results.

Benefits

• Competitive medical (PPO/HDHP), dental, and vision plans as well as company contributions to your Health Savings Account (HSA) or pre-tax savings through flexible spending accounts (FSA) for commuting, health & dependent care expenses.
• 100% Company Safe Harbor Match on your first 6% deferral immediately upon eligibility for the 401(k) Retirement Plan.
• Flexible Time Off for Exempt (salaried) employees, as well as generous PTO for Non-Exempt (hourly) employees, plus 11 paid company holidays and a paid volunteer day.
• 12 weeks of Paid Parental Leave
• Maven Family Planning – provides support through your Parenting journey including egg freezing, fertility, adoption, surrogacy, pregnancy, postpartum, early pediatrics, and returning to work.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior