Portfolio Operations Specialist

Oakline Properties•Chicago, IL

19h•Hybrid

About The Position

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 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.

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
Bachelor's degree required

Nice To Haves

Multifamily, property management, or real estate operations experience preferred but not required
Exposure to procurement, sourcing, or process-optimization work a plus
advanced degree a plus

Responsibilities

Program-manage 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.
Carry newly acquired partners onto Oakline's platform after stabilization.
Keep dashboards clean for leadership and the board.
Capture lessons learned from each rollout to improve future deployments.
Own the regular operating cadence with partner companies to ensure alignment and surface needs.
Run operating cadence sessions with tight agendas, clear notes, and actionable follow-through.
Get things done through coordination and credibility rather than direct authority.
Earn trust with VPs and senior leaders quickly.
Flag risks early with a proposed solution.
Route surfaced needs, blockers, and dependencies from partner reviews to the appropriate functional leaders (Finance, HR, Technology, Procurement).