Director, Head of Residential Whole Loan Investments

About the role

Obra Capital is a credit-focused investment manager with a growing platform across private credit, insurance lending, and structured products. We are building a dedicated residential whole loan investment capability and are seeking a Managing Director to lead this effort — from platform construction and acquisition strategy through trading, portfolio management, and capital markets execution across residential whole loan investments.

Responsibilities

• Define and execute the strategic roadmap for Obra's whole loan platform
• Establish and maintain sourcing relationships with originators, correspondent lenders, brokers, aggregators, and direct sellers across residential mortgage, consumer, ABF, and small-balance commercial segments
• Build the infrastructure required to support the platform: underwriting guidelines, credit policy, hedging policy, rate sheet/pricing framework, due diligence workflow, custodial and servicing arrangements, data and analytics, and operational processes
• Work directly with existing and prospective insurance company clients to understand investment objectives, risk appetite, liability profiles, and regulatory constraints
• Leverage whole loan investments to effectively match opportunities to client objectives — including liability duration, convexity, credit risk tolerance, and FHLB requirements
• Identify investment opportunities tailored to each client's liability profile, capital structure, and risk tolerance; develop bespoke solutions that optimize risk-adjusted returns within insurance regulatory frameworks
• Lead whole loan acquisition activities across flow and bulk executions, including sourcing, structuring, bid management, and trade settlement
• Evaluate bid packages and pools across asset classes; conduct credit and collateral due diligence; structure purchases to optimize risk-adjusted returns
• Determine best-execution strategies — whole loan holds versus securitization alternatives — to optimize deployment efficiency and portfolio P&L
• Manage daily pricing, rate sheets, position risk, and inventory across the whole loan book, including margin targets and counterparty exposure
• Develop, implement and maintain whole loan hedging policy which is consistent with Obra’s whole loan investment strategy
• Oversee pipeline management and bid flow to ensure consistent, disciplined capital deployment in line with portfolio construction targets
• Partner with structuring, legal, and rating agencies to execute securitization transactions as the platform scales
• Optimize warehouse facility utilization and advance rates across the funding stack; manage lender relationships and facility renewals
• Engage institutional investors and broker-dealers to develop the investor base for Obra's whole loan and structured credit securities
• Evaluate and execute forward flow agreements, co-investment structures, and other capital-efficient sourcing and funding arrangements
• Oversee ongoing portfolio monitoring including prepayment, delinquency, default, and loss analytics across all asset classes; maintain a real-time view of portfolio credit quality and duration risk
• Develop and maintain portfolio-level stress testing, scenario analysis, and loss projection models
• Manage servicer relationships and oversee servicing performance, loss mitigation, and REO or charge-off disposition
• Present portfolio performance and risk metrics to senior leadership and investors on a regular cadence
• Identify, develop, and cultivate relationships with insurance company clients and prospects; provide market insights and excellent client service across the whole loan and ABF investment universe
• Develop and maintain strong relationships with whole loan investors, broker-dealers, aggregation desks, warehouse lenders, and securitization counterparties
• Represent the firm in all buy-side and sell-side trading interactions, negotiations, and market discussions across asset classes
• Serve as the firm's whole loan thought leader — represent Obra externally at industry conferences, with counterparties, and in investor meetings
• Support fundraising and investor relations efforts as a subject matter expert for whole loan and insurance asset management strategies

Requirements

• 8+ years of experience in investment management, with meaningful tenure in whole loan investing at a REIT, asset manager, insurance company, or specialty finance firm
• Deep knowledge of residential whole loans; specifically Non-QM
• Strong understanding of insurance company investment needs, risk appetite, and regulatory requirements across various regimes
• Advanced expertise in secondary market whole loan trading economics, including best-execution analysis, bid-ask dynamics, and seller counterparty management
• Hands-on securitization experience — either as a principal structuring transactions or as a senior participant overseeing the process end to end
• Strong relationships with originators, servicers, aggregators, warehouse lenders, and capital markets counterparties across relevant asset classes
• Demonstrated ability to hire, develop, and retain high-performing investment and operations professionals
• Strong written and verbal communication skills with internal and external stakeholders; ability to develop and manage relationships with prospective and existing clients
• Proficiency in Excel and financial modeling; working knowledge of Python, VBA, or SQL preferred
• CFA, MBA, or equivalent; strong quantitative and credit analytical foundation
• Prior involvement in investor relations or capital raising for a whole loan or structured credit strategy
• Entrepreneurial track record — demonstrated ability to build systems, teams, and processes in an environment that did not previously have them
• Exposure to adjacent asset classes: Residential Transition Loans (Fix and Flip) and Second Liens

Preferred

• Familiarity with regulatory frameworks relevant to consumer lending, mortgage origination across multiple insurance regimes
• Exposure to both performing and non-performing or special servicing loan portfolios across multiple asset classes
• Prior involvement in investor relations or capital raising for a whole loan or structured credit strategy
• Entrepreneurial track record — demonstrated ability to build systems, teams, and processes in an environment that did not previously have them
• Exposure to adjacent asset classes: Residential Transition Loans (Fix and Flip) and Second Liens

Benefits

In addition to the base salary, total compensation may include a discretionary bonus based on performance. This range given is a best faith estimate which reflects a variety of factors, including years of relevant experience, education, location and other qualifications pertinent to the position. Base salary does not include any other performance based compensation such as year end cash bonus. The firm also offers robust Benefits offerings which include Comprehensive Medical/Rx, Dental and Vision plans; 401(k) program with company match; Flexible Savings Accounts (FSA); Healthcare Savings Accounts (HSA) with company contribution; Basic and Voluntary Life Insurance; Long-Term Disability (LTD) and Short-Term Disability (STD) insurance; and Commuter Benefits plan for parking and transit. In addition all employees of Obra are provided with a daily lunch stipend.