Healthcare Rotational Analyst

Job Description

Job Description

Description

Dwight Securities Management (“DSM”) is an actively managed real estate investment trust specializing in the origination and financing of commercial mortgages across a range of real estate asset classes. DSM works in conjunction with affiliate firm Dwight Capital to source and evaluate lending opportunities nationwide. Within Healthcare Bridge & A/R Financing, DSM manages a multi-billion book of skilled nursing and Seniors Housing healthcare real estate bridge and working capital revolving loans nationwide.

The Healthcare Rotational Analyst Program is DSM’s structured entry point into the Healthcare Bridge & A/R Financing team. Across three phases, analysts rotate through deal sizing, asset management, and underwriting, building the full skill set needed to progress into either the Portfolio/Asset Management or Underwriting track. Progression through each phase is earned through demonstrated competence, not tenure. Each phase can take up to one year, making the full rotational program typically between two to three years. Participants in the program are vital contributors and have increasing responsibility and agency over their work while learning and participating in all aspects of the healthcare business.

Role & Responsibilities

Phase I — Rotational Analyst I | Sizing
• Works closely with the Healthcare Managing Director(s) and Originators to screen new deals and size loan requests across Bridge, HUD, and A/R Financing products
• Presents deal summaries at Greenlight / Investment Committee
• Tracks the healthcare pipeline and supports data analytics in iLevel across the deal lifecycle
• Builds foundational knowledge of Dwight’s sizing model, deal structuring, and healthcare credit culture

Phase II — Rotational Analyst II | Portfolio/Asset Management
• Works closely with the Healthcare MD and Healthcare Credit Officer, managing a portfolio of up to 15 investments across Bridge, HUD, and A/R Financing
• Owns modifications, covenant tracking, monthly financial spreads and analysis, and borrower / counsel / investor coordination for the assigned book
• Prepares recurring and ad hoc portfolio reporting
• Communicates portfolio performance and post-closing item tracking clearly and consistently to senior management
• Moves from supporting to independently completing a range of modifications — maturity extensions, covenant waivers and resets, and HUD collateral bifurcation / release - building working knowledge of Dwight’s debt structures and loan documents

Phase III — Rotational Analyst III | Asset Management & Underwriting
• Supports the Senior Underwriter on new originations — managing third-party reports, guarantor financial review, clinical and capex analysis, cash flow charts, and credit committee submissions
• Independently manages an asset management book of up to 10 loans, including material modifications, structuring, legal review, and memo preparation
• Prepares loan transition memos and diligence checklists bridging underwriting to asset management
• Demonstrates readiness to graduate from the Rotational Analyst Program into either the Asset Management or Underwriting track

Required Experience & Skill Sets

• Professional Experience: 1 to 3 years of experience; open to recent graduates
• Sector Focus: Prior experience in healthcare real estate, AR Financing, or cash flow lending; or prior experience at nationally recognized accounting firm in either audit or consulting
• Technical Skills: Strong Excel skills; strong understanding of financial statement analysis
• Analytical Precision: High attention to detail with financial data, loan covenants, and borrowing base mechanics
• Communication: Ability to present clearly to senior management and at Investment Committee as well as over email with originators and clients
• Autonomous Execution: Comfort navigating ambiguity and managing multiple workstreams in a fast-paced, high-volume environment
• Growth Mindset: Willingness to rotate across sizing, asset management, and underwriting functions and to be evaluated on demonstrated competence rather than tenure