Jobs at Oakline Properties (Now Hiring) — 3 open

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 & Key Responsibilities

Oakline is hiring a Senior Manager, Strategic Procurement to lead procurement as a platform-wide value-creation function. This is a high-ownership, high-visibility role reporting to the VP of Integration, with direct impact on operating performance across every Oakline partner organization. The person in this seat owns the design and execution of Oakline's sourcing strategy: the vendor programs, category frameworks, governance, and procurement infrastructure that convert scale into measurable, durable savings. 

Procurement at Oakline is a core value driver, not a back-office function. Vendor costs spanning maintenance and facilities, make-ready and unit turns, MRO supply, landscaping, waste, utilities, insurance and employee benefits, and enterprise technology flow directly through to asset-level NOI and EBITDA across the portfolio.  

The role operates at two levels. At the platform level, it sets the standards, tools, and governance that define how Oakline sources and manages vendors, including the vendor taxonomy, RFx process, bid analysis, supplier scorecards, and savings-tracking methodology. At the partner level, it engages directly with property-management operators across the portfolio to drive adoption, close compliance gaps, and turn preferred-vendor agreements into realized savings. Because Oakline operates a decentralized set of partner companies, this role succeeds through influence and credibility rather than positional authority. 

Reporting into Integration, the leader treats procurement as a value creation lever: each newly acquired partner represents a fresh surface of spend, contracts, and vendor relationships to be assessed, onboarded, and brought under enterprise standards on a predictable timeline. Day to day, the leader owns category management end-to-end, running sourcing initiatives across priority categories from supplier selection through contract negotiation and ongoing performance management, and building category-level spend visibility and cost-reduction roadmaps. They stand up the preferred-vendor program category by category, including the governance model that holds pricing compliance and contract adherence across the portfolio, and establish a benefits-tracking methodology spanning hard savings, cost avoidance, and rebates, reporting outcomes in the language operators understand: cost-per-unit and annual spend reduction. 

Success in the Role

By 3 months: The vendor taxonomy is complete, an addressable-spend baseline is established across partner organizations, and categories have been prioritized. At least two priority categories are in active sourcing or renegotiation, and the leader has built working relationships with partner operators and a clear read on where the largest, most capturable savings sit. 

By 6 months: The preferred-vendor program is live in at least one category with documented savings, the savings-tracking framework is operational, and a partner engagement cadence is running with early compliance and adoption metrics visible. The platform insurance and benefits workstream is structured in partnership with Finance. 

By 12 months: Procurement operates across all priority categories, quantifiable cost-per-unit savings are delivered and reportable to the board, and Oakline's sourcing playbook is documented and ready to apply to incoming acquisitions so newly integrated spend comes under enterprise standards on a repeatable timeline.

Location

Location is flexible, with a preference for Chicago or New York City. Occasional travel to partner operating markets is expected. This role requires on-the-ground engagement to drive adoption across decentralized teams, not just platform-level oversight. 

Candidate Requirements

• 8+ years in strategic sourcing, procurement, or category management, with demonstrated end-to-end ownership of sourcing cycles and measurable savings delivered
• Experience standing up or substantially building a procurement function in a high-growth, multi-entity, or platform environment, rather than operating within an established, mature function
• Track record managing categories at scale (preferably $100M+ in managed or influenced spend) across maintenance and facilities, MRO, technology, or professional services
• Proven ability to drive adoption and compliance across decentralized operating teams through influence rather than authority
• Strong analytical capability, comfortable building spend baselines, TCO models, and savings reporting from raw, imperfect data 
• Experience leading or building a small team (3+ reports), or clear readiness to do so as the function scales 
• Familiarity with procurement technology (e-sourcing platforms, contract lifecycle management, ERP integration); multifamily, real estate, or property management experience preferred 
• Exposure to indirect categories such as insurance, employee benefits, or facilities sourcing a plus, given the platform insurance and benefits mandate 
• Comfortable operating with limited infrastructure and motivated to build; energized by significant runway to shape and grow the function 
• Bachelor's degree required; advanced degree or procurement certification (e.g., CPSM, CIPS) preferred 

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.