Chief of Staff/ Senior Director of Investments (Washington)

Investment Strategy and Business Case Development Director (Government Contracting)

This role is 3-4x per week in their DC area office.

We are looking for a finance leader who can develop investment theses and build repeatable, high-quality business cases for enterprise and strategic investments. This role will help shape decisions on capability-led offerings, capital investments, real estate and other active investment opportunities, capital structure, and enterprise cash deployment. The ideal candidate combines strong corporate finance capability with curiosity about government contracting , thrives in ambiguity, builds relationships easily, and has the persistence to carry ideas from early concept through investment thesis, decision, and execution. This person should be comfortable working directly with the CFO, engaging senior leaders and the Board, and translating complex mission, operating, and financial realities into clear, decision-ready recommendations.

Strategic Investment, Capital Planning, and Business Case Development

• Lead decision-ready business cases for strategic and enterprise investments including capability development, service centers, AI and digital infrastructure, facilities, and other mission-enabling capital initiatives.
• Build repeatable business case frameworks
• Develop investment theses grounded in mission relevance, sponsor demand, enterprise strategy, financial sustainability, operational feasibility, and institutional resilience.
• Turn ambiguous ideas into structured analyses that clarify opportunities, frame decisions, surface data gaps, and support action.
• Partner with enterprise leaders, operations, finance, and technical teams to develop credible assumptions around costs, benefits, dependencies, risks, and implementation requirements.
• Assess opportunities related to capability-led offerings, service centers, enterprise platforms, AI-enabled operating models, data and cyber capabilities, real estate, and other institutional investments that strengthen long-term self-financing capacity.
• Develop clear executive- and board-ready recommendations that synthesize strategic rationale, economics, operating implications, risk, and capital needs.

Corporate Finance, Capital Structure, and Opportunity Assessment

• Build robust financial models for strategic and enterprise initiatives, including demand scenarios, cost structure, margin and cash flow implications, capital requirements, returns, downside cases, and sensitivities.
• Analyze opportunities through both a cost-recovery and enterprise economic lens, with curiosity about value creation in a predominantly cost-plus environment and where greater P&L-like discipline can improve decisions.
• Support capital structure strategy by assessing liquidity needs, balance sheet resilience, investment capacity, and tradeoffs among cash, debt, real estate, and other sources of financial flexibility that is required for the investment strategy.
• Partner on enterprise cash forecasting and long-range financial planning tied to investment pacing, liquidity preservation, and multi-year strategic choices.
• Evaluate build, partner, invest, or internally develop options for strategic capabilities and infrastructure, with a clear view of execution risk, affordability, and institutional fit.
• Conduct benchmarking, market scans, peer analysis, and comparable economic assessments to inform decisions, particularly in government contracting, mission technology, and institutional capital planning.
• Improve capital allocation discipline by bringing greater consistency, transparency, and follow-through to how opportunities are assessed, compared, tracked, and revisited.

Leadership Profile

• Strong business case builder with a repeatable, structured approach.
• Persistent in tracking assumptions, milestones, dependencies, and outcomes through the full decision cycle.
• Skilled at pulling useful information out of leaders, operators, and technical experts.
• Strong corporate finance judgment and comfort operating across strategy, finance, operations, and mission.
• Curious about government contracting
• Strong PowerPoint and visual storytelling skills, with the ability to turn complex ideas into polished, decision-ready materials for executives and the Board.
• Executive presence and strong communication skills.