Director, Chief of Staff – Individual Markets

This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Director, Chief of Staff – Individual Markets based in the United States. We are seeking a strategic and execution-focused Chief of Staff to partner with the senior leadership of a growing individual insurance business. In this high-impact role, you will translate strategic priorities into actionable plans, drive cross-functional initiatives, and ensure leadership decisions translate into measurable business results. You will operate at the intersection of strategy, business operations, financial planning, and executive communications, working closely with leaders across distribution, product, technology, risk, finance, and operations. From preparing executive-level presentations to establishing performance dashboards and managing complex transformation programs, you will help maintain alignment and momentum across the organization. This opportunity is suited to a commercially minded leader who combines analytical rigor with strong stakeholder management and sound judgment. You will play a pivotal role in advancing a multi-year growth strategy while supporting operational excellence, organizational effectiveness, and a high-performance culture.

Serve as the primary strategic execution partner to the Co-Heads of Individual Markets, translating leadership priorities into structured plans, milestones, and measurable outcomes. Own the business operating cadence, including leadership meetings, business reviews, staff meetings, offsites, and town halls, ensuring decisions are documented and commitments are followed through. Drive execution of the business's strategic agenda by coordinating cross-functional teams, tracking progress, identifying dependencies, resolving obstacles, and escalating risks when necessary. Prepare and coordinate executive communications and presentation materials, including board updates, investor-related updates, quarterly business reviews, executive leadership presentations, and internal or external talking points. Synthesize complex financial, operational, and strategic information into clear, concise, decision-ready narratives for senior leadership and other key stakeholders. Partner with Finance and Strategy on annual business planning, budgeting, and long-range planning, ensuring strategic priorities align with resource allocation, business objectives, and measurable key performance indicators. Establish and maintain performance management processes, including KPIs, dashboards, reporting frameworks, and execution reviews that provide leadership with timely insights into business performance. Build alignment across Distribution, Product, Operations, Technology, Risk, Human Capital, Legal, and Finance, helping stakeholders resolve issues and move important decisions to completion. Lead or co-lead strategic initiatives from initial scoping through implementation, including new capability launches, operating model changes, integration projects, and business transformation workstreams. Represent senior leadership in selected internal forums and working groups, ensuring priorities remain clear and decisions progress effectively across the organization. Serve as a trusted thought partner on organizational design, talent development, team effectiveness, and culture initiatives. Identify opportunities to improve productivity and business processes through AI-enabled solutions, balancing efficiency gains with appropriate governance, controls, and risk management. Maintain a strong understanding of business performance, economics, competitive dynamics, and execution risks to support informed decision-making and sustained growth. Requirements: 10+ years of professional experience in strategy, management consulting, business operations, program management, or a Chief of Staff role, with meaningful exposure to insurance, asset management, or financial services. A bachelor's degree is required; an MBA or other advanced degree is preferred. Demonstrated success leading complex, cross-functional initiatives from strategic planning through execution within a matrixed organization. Strong executive presence and communication skills, with the ability to prepare and deliver compelling presentations and written materials for C-suite leaders, boards, and other senior audiences. Excellent analytical, quantitative, and structured problem-solving capabilities, with the ability to move confidently between high-level strategic questions and operational details. Strong business acumen and the ability to understand financial performance, business economics, KPIs, market dynamics, and strategic growth opportunities. Familiarity with annuity, life insurance, retirement products, and individual insurance distribution channels is strongly preferred. Proven ability to influence stakeholders and build trust across functions without relying on direct reporting authority. Exceptional organizational skills and program management capabilities, including prioritization, milestone tracking, risk identification, and accountability for outcomes. High emotional intelligence, discretion, and sound judgment when managing confidential information, sensitive business matters, and complex stakeholder relationships. Experience identifying and implementing AI-enabled process improvements across cross-functional teams, with appropriate attention to governance, compliance, and risk. Proficiency with executive-level PowerPoint and Excel, as well as modern collaboration and business productivity tools. A proactive, results-oriented mindset, with the ability to operate effectively in ambiguous, fast-moving environments and maintain a high standard of quality. Strong interpersonal skills and a collaborative leadership style that supports organizational alignment, talent development, and a high-performance culture. Benefits: Annual base salary: $225,000–$300,000 USD for positions based in New York, Pennsylvania, or Iowa. Eligibility for a discretionary bonus, depending on individual and team performance. Compensation within the stated range may vary based on experience, skills, qualifications, and the location of the position. A senior leadership opportunity with significant exposure to strategic decision-making and enterprise-wide initiatives. The opportunity to work closely with executive leadership and influence business strategy, operational performance, and organizational effectiveness. A role spanning strategy, financial planning, transformation, and cross-functional leadership within the individual insurance and retirement products sector.