Director of Strategic Advisory & Investments

Reporting to the Senior Vice President of Real Estate Investments & Strategy, the Director of Strategic Advisory & Investments leads client-facing facilities advisory engagements, supports underwriting and transaction analysis for real estate investments and development, and contributes to portfolio-level asset strategy.

This is a cross-functional leadership role operating across advisory, real estate development and investments, and asset management, coordinating work from project origination through execution and stabilization. The role connects internal teams and external partners to advance high-impact, mission-aligned projects.

This new hire with 22Beacon can be fully remote within the US or work on a hybrid basis with our office in Hanover, MD or New York, NY.

Responsibilities

Strategic Facilities Advisory & Client Engagement

Leads client-facing strategic advisory engagements, guiding schools through early facilities planning, feasibility analysis, and pathways to implementation.

• Lead intake, scoping, and execution of Strategic Advisory (SA) engagements, including application review, client discovery, and project definition across advisory, development, and lending pathways
• Structure and negotiate advisory agreements, including scope, timeline, pricing, and invoicing
• Partner with client schools to assess facility needs, enrollment growth plans, affordability constraints, and programmatic requirements
• Develop high-level financial models, affordability assessments, and feasibility analyses to inform school decision-making and advisory recommendations
• Coordinate initial property diligence, including engagement of brokers and third-party consultants, and review of legal, financial, and technical diligence materials
• Identify viable properties and overall feasibility, including key risk factors and potential mitigants, and present recommendations to client partners
• Prepare client-facing materials and presentations summarizing project strategies, options, and recommendations
• Guide clients from advisory services into implementation pathways, including transition to Fee Developer or Turnkey Development projects, in partnership with internal teams
• Maintain SA-related pipeline and engagement tracking in Salesforce, in coordination with shared pipeline ownership

Pipeline Management, Investment Screening & Deal Advancement

Oversees early-stage pipeline screening, prioritization, and internal coordination to advance mission-aligned opportunities.

• Lead early-stage screening and prioritization of prospective projects, assessing mission alignment, feasibility, and strategic fit
• Manage active pipeline reporting and communication, including preparation for weekly pipeline and school review meetings
• Partner with senior leadership to shape pipeline strategy, balancing advisory, development, and investment priorities
• Support pipeline development through targeted relationship cultivation and repeat engagements, in coordination with Business Development efforts

Real Estate Development, Underwriting & Structuring

Leads underwriting, financial analysis, and transaction structuring to support informed investment and development decisions.

• Lead underwriting and transaction analysis for real estate development and investment opportunities, from initial structuring through investment approval
• Develop and refine project-level and portfolio-level financial models, including cash flow projections, capital structures, and sensitivity analyses
• Conduct market research and competitive analysis to inform investment and development recommendations
• Coordinate underwriting processes internally and with external consultants, including defining scope, assumptions, and deliverables
• Engage directly with school operators to validate underwriting assumptions, including enrollment, operating budgets, governance strength, and educational demand
• Translate underwriting outputs into clear investment recommendations, supporting deal structuring and decision-making
• Prepare investment memos, credit analyses, and materials for senior leadership, board members, and external partners
• Serve as a liaison between school clients, underwriting partners, and transaction counterparts to ensure timely and accurate information flow

Asset Management & Leasing Strategy

Provides strategic oversight and analytical support for leasing, asset performance, and portfolio-level decision-making.

• Provide strategic oversight and manage leasing and asset performance across active assets, including input on new and renewal lease strategies
• Analyze rent levels, operating performance, and debt service to inform lease decisions, hold/sell evaluations, and portfolio-level strategy
• Partner with development, construction, and asset management resources on tenant improvements, capital projects, and portfolio initiatives
• Support strategy development for underperforming or distressed assets, contributing to value-maximization and risk-mitigation plans
• Participate in negotiation of LOIs, lease amendments, and sale agreements, in collaboration with asset management and legal partners

Business Development & Stakeholder Engagement

Cultivates strategic relationships and represents the organization externally to support long-term pipeline strength.

• Build and maintain strategic relationships with key partners and referral sources aligned with organizational markets and growth priorities
• Serve as a senior relationship lead for select school and partner engagements, guiding stakeholders through feasibility and transaction milestones
• Identify and cultivate new partnership opportunities that support long-term pipeline strength
• Represent the organization externally at conferences and industry events, supporting visibility and relationship-building in priority markets

Requirements

• Bachelor’s degree in finance, business, real estate, economics, or a related field.
• Minimum of eight years of experience in commercial real estate, including acquisitions, investment sales, asset management, capital markets, investment banking, or a related role.
• Direct experience in assessing commercial real estate investments preferred
• Advanced financial modeling and credit analysis skills, including expert Excel capability
• Excellent written and verbal communication skills, with the ability to draft clear and compelling credit memos.
• Knowledge of charter school or similar nonprofit finance, real estate development, and real estate finance is highly preferred.
• Strong project management skills, with the ability to manage multiple transactions simultaneously and meet deadlines.
• Proficiency in Microsoft Word and Excel-based financial modeling, with experience in CRM systems.
• Excellent relationship-building and problem-solving skills
• Passion for community development and a commitment to supporting public charter schools in underserved communities.