The Opportunity

This role is designed for a high‑trajectory early‑career professional who wants to grow inside a fast‑moving investment platform. Oakdale is consolidating several fractional functions (underwriting, asset management, analysis) into a single full‑time utility player who can support both acquisitions and asset management while taking true ownership of deals.

You will work directly with the VP of Acquisitions, Head of Construction, and the firm's Founding Partners, gaining exposure to the full lifecycle of multifamily investing-from sourcing through underwriting, closing, business‑plan execution, and ongoing performance management.

This is not a narrow analyst role. It's a chance to be part of a lean, entrepreneurial team where your work directly impacts deal flow, investor outcomes, and the firm's growth trajectory.

Key Responsibilities

Acquisitions (Primary Focus)

• Deal Underwriting - Build and refine financial models for value‑add multifamily acquisitions using Excel and/or modeling templates.

• Market Research - Analyze submarkets, rent comps, demographic trends, and supply/demand dynamics across the Midwest and Southeast.

• Investment Committee Materials - Prepare memos, underwriting summaries, and presentation materials for internal and external stakeholders.

• Due Diligence Support - Assist with lease audits, financial reviews, CapEx scoping, and third‑party coordination.

• Deal Process Management - Help shepherd deals from LOI through closing, working closely with lenders, brokers, and consultants.

Asset Management (Secondary but Growing Focus)

• Portfolio Monitoring - Track performance of existing assets, including occupancy, rent growth, expenses, and variance analysis.

• Business Plan Execution - Support CapEx planning, renovation tracking, and operational improvements alongside the Head of Construction.

• Reporting - Assist in preparing monthly and quarterly reporting for internal leadership and investors.

• Ownership Mentality - Act as a true steward of the assets, thinking like an owner rather than a task executor.

Cross‑Functional / Strategic

• Work closely with leadership on investor relations, capital raising materials, and organizational build‑out as the firm scales.

• Help streamline and eventually replace several fractional support roles by becoming a centralized, full‑time resource for underwriting and asset management.

• Contribute to internal systems, processes, and templates as Oakdale builds its long‑term operating foundation.

Who You Are

• 1-3 years of experience in real estate acquisitions, asset management, valuations, investment banking, or related analytical roles.

• Multifamily experience strongly preferred; value‑add exposure is a major plus.

• Strong financial modeling skills and comfort with underwriting fundamentals.

• Ability to work independently in a fully remote environment. As company grows, the plan is to have headquarters in Chicago, but still with the flexibility of remote.

• A "utility player" mindset-comfortable wearing multiple hats and stepping into whatever the business needs.

• Entrepreneurial, resourceful, and excited by the pace of a high‑growth emerging sponsor.

• Strong communication skills and the ability to interface with senior leadership, lenders, and investors.

Compensation

• Base salary: Targeting $80,000-$100,000, depending on experience.

• Bonus: Deal‑based bonus structure tied to transaction activity and performance.

• Upside: Significant exposure to deal flow and long‑term platform growth.