Role Overview & Key Responsibilities

Oakline is hiring a Portfolio Operations Specialist to get the platform's enterprise initiatives deployed and adopted, both at the corporate level and across Oakline's property management partners. These are the cross-platform programs that scale how Oakline operates: enterprise technology and systems, process standardization, and workflow optimization. This is a high-ownership individual-contributor role reporting to the VP of Integration, with real runway to shape how Oakline deploys and scales initiatives as the platform continues to grow. The person in this seat program-manages initiatives end to end, building the plan, sequencing the work, training the teams, driving adoption on the ground, and making sure changes hold well after go-live. When a newly acquired partner reaches stabilization after close, this role carries it the rest of the way onto Oakline's platform. Throughout, the leader keeps dashboards clean enough that leadership and the board can read them directly, and after each rollout captures what worked and what did not, turning it into the templates, checklists, sequencing, and standard communications that make the next deployment faster, then ensures those updates actually get used.

Running the Oakline operating rhythm is the second half of the job. The leader owns the regular operating cadence with partner companies - the rhythm that keeps everyone aligned, surfaces where help is needed and gives each deployment a place to land. The leader runs these sessions with tight agendas, clear notes, and action items that each carry an owner, a date, and real follow-through.

Because Oakline operates a decentralized set of partner companies, the role gets things done through coordination and credibility rather than direct authority, earning trust with VPs and senior leaders quickly and flagging risks early with a fix already in mind. The leader uses the operating cadence as the channel back to the business, taking what surfaces in partner reviews (needs, blockers, dependencies) and routing it to the right functional leaders across Finance, HR, Technology, and Procurement so they can act.
Success in the Role

By 3 months: The leader is up to speed on Oakline's systems and operating model and already running point on a live deployment and the operating cadence.

By 6 months: The leader is independently leading enterprise deployments across multiple partners, owning assigned standard rollouts end to end, and is the person the organization goes to for where each deployment stands. The operating cadence runs reliably across all partners, with blockers surfaced early and routed to the right functional leaders.

By 12 months: The deployment playbook is sharper and repeatable, rollouts scale cleanly to new partners as they come onto the platform, and the work shows up in the numbers, with standards adopted across the portfolio, the operating cadence running reliably, and procurement and process gains landing in NOI and platform EBITDA, reportable to the board.
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

• 4-8 years in operations, operational excellence, transformation, or program management, in roles where you owned execution, not just the plan
• Track record rolling out operational changes or enterprise initiatives end to end across multiple sites or business units, with adoption and results you can point to
• Hands-on experience deploying enterprise systems or platforms (HRIS, ERP, PMS, travel and expense, procurement tooling, or similar) and driving the adoption that makes them stick
• Strong program management capability: can run several enterprise rollouts across different partners at once, including the operating reviews that keep them on track, without dropping the thread
• Experience owning a recurring operating cadence or PMO rhythm with tight agendas, action tracking, and follow-through
• Gets things done through people who do not report to you, and earns trust with VPs and senior leaders quickly
• Comfortable taking full ownership and moving forward with incomplete information
• Multifamily, property management, or real estate operations experience preferred but not required
• Exposure to procurement, sourcing, or process-optimization work a plus
• Bachelor's degree required; advanced degree a plus