M&A Associate

Oakline Properties acquires and grows leading property management businesses across the U.S. and Canada, partnering with founders to preserve what makes their teams special while building something bigger together. Focused on people, operational excellence, and long-term stewardship, Oakline provides a lasting home where great businesses and careers continue to thrive. Oakline’s values are: Unwavering Stewardship : We believe honoring the legacy of founders, residents, and our teammates is a privilege. We strive to do the right thing — especially when it’s hard — and act like owners every step of the way. Excellence in Action : We hold ourselves to the highest standards — not just to win, but to grow. We show up prepared, invest in our people, and raise the bar every day so that everyone has the chance to get better, go further, and build a career they’re proud of. Built for Belonging : We’re proud of the culture we’ve built — one that’s caring, connected, and genuinely fun to be part of. We support each other, celebrate together, and create space to grow. It’s a place where people feel valued, challenged, and excited to build a meaningful, long-term career. Empowered and Accountable : We trust each other to lead and deliver. We operate with speed, teamwork, and ownership to get the job done. Honesty, clarity, and respect are core to how we operate. Play to Win : We’re building a best-in-class platform — and we’re here to compete. We act with urgency, celebrate the journey, and take pride in what we’re building together. Oakline is backed by Alpine Investors, an investment firm committed to building enduring businesses by investing in and developing exceptional people. Role Overview We are hiring an M&A Associate to support the President and Sr. Associate of M&A in rapidly scaling Oakline via acquisitions. This is a high-rep role for a deal athlete who wants significant exposure to underwriting, diligence, and transaction execution in a high-volume environment, while building an operator’s mindset. This role is designed for rapid growth: 2 months: Fully onboarded; understands Oakline’s M&A process, tools, and modeling standards. Owning core underwriting and diligence deliverables for an active deal. 6 months: Running key diligence workstreams and producing IC-ready models/materials across multiple concurrent deals. 12 months: Trusted execution partner on deals; can quarterback the analytical and process cadence from IOI/LOI through close with minimal oversight. 18–24 months: Expanded ownership—supporting higher deal volume, mentoring more junior support, and taking on broader responsibility in the deal process. Key Responsibilities Deal Execution & Underwriting: Build and own detailed financial models (operating build, transaction mechanics, sensitivities, returns with multiple cases) with clear documentation and auditability Develop and own concise, decision-ready analyses and materials for internal stakeholders (e.g., IC / Board prep support) Drive key diligence workstreams post-LOI, including data requests, analysis, and risk tracking Process & Cross-Functional Coordination: Maintain trackers and timelines to keep deals moving quickly from LOI to close Coordinate with Sourcing, Integration, and functional leaders to ensure a clean handoff from diligence into operations Solicit feedback from integration and functional leaders to continuously improve diligence and underwriting quality Coordinate with Sourcing, Integration and functional leaders to ensure smooth transition from due diligence to operations: Support management calls and seller-facing workstreams with high EQ, responsiveness, and professionalism Work effectively with external advisors (legal, accounting, QoE) to keep diligence efficient and thorough Location Location is in-office in NYC. Travel is required and can be expected as much as weekly for periods of time. Candidate Requirements 2–4 years of experience in private equity, investment banking, corporate M&A / corporate development, consulting or a similarly high-intensity / analytical transaction roles Very strong financial modeling skills (Excel-based operating / transaction / LBO modeling; experience analyzing data sets, comfort with sensitivities and returns) High IQ / High EQ with strong ownership, communication, speed, and attention to detail Experience supporting live deal processes preferred; high-velocity M&A exposure a plus Equal Opportunity Hiring Policy Oakline is an equal opportunity employer and values diversity at every level of the organization. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender identity or expression, sexual orientation, national origin, disability status, protected veteran status, or any other characteristic protected by law. #J-18808-Ljbffr