Senior Director of Operations (Greater Chicago Area)

Landmark Property Management is looking for a decisive, organized leader who is relentless about results. As Senior Director of Operations, you will oversee the day-to-day operations of the business and report directly to the owner, backed by an incredible team of high performers. You will lead three department heads (property management, operations, and business development) and own the execution, accountability, and scorecard for the success of the company as a whole.

This is a leadership role where success comes from leading the team to deliver, not from doing the work personally. The right person likes to organize and run the business, has a motor that doesn't quit, and moves fast from decision to implementation.

The Mandate

You will be personally responsible for the final results of the following priorities:

• Significantly reduce owner churn.
• Deliver net door growth, meaning doors signed minus doors lost, which requires managing sales and operations together.
• Reduce operational complexity by installing a weekly scorecard and meeting rhythm, clarifying ownership, and taking day-to-day escalations off the owner.
• Own the handoff between sales and operations so promises made at signing are kept after onboarding.

Experience Required

You have managed managers across multiple departments in a field-service business of similar size and are ready to do it again.

• Managed managers: has led leaders who run their own teams, across more than one department.
• P&L ownership: has owned a P&L, not just a budget line.
• Has already done this job: scaled a field-service company 2 to 3 times with a recurring-revenue model. If you've grown a membership or service-agreement program in HVAC, plumbing, electrical, or landscaping and owned retention and renewal rates, we want to talk to you.
• Property management knowledge is not required : our Director of Property Management will bring you up to speed on owner relations, trust accounting, leasing, and the Chicago RLTO. You'll need to learn it fast.
• Right-sized background: has worked at companies roughly 2 to 5 times Landmark's size, not large corporations with deep support staff.
• Accountability system: EOS Integrator experience preferred, or a comparable system.
• Sales leadership exposure: enough to manage a BDM and coach a pipeline.
• Data-driven decision maker: logical and objective; deciphers data, spots trends, and makes informed decisions quickly.

Why Landmark

You'll run the business, not just a department. The role is hybrid, so you can split your time between home, the field, and our office as it comes online. You'll have real autonomy, a direct line to the owner, and the backing to make changes stick. You'll lead a team of high performers who asked for this role, so you'll be walking into support, not resistance. At our size, every system you build shows up in the numbers quarter to quarter. And you'll help build what's next, including the opportunity to take our turn team beyond our own portfolio and serve other property management companies. Success in this seat opens the door to future opportunities, including COO and potential equity.

Core Values

You'll need to share Landmark's core values to lead the business effectively.

• Hard work
• Growth oriented
• Integrity
• Dependable
• Have fun, be happy
• All In

Ranked #1 in Chicago and #6 in the country by PropertyManagement.com, Landmark has a foundation of excellence and positive momentum to build something special. We are looking for a practical, structured leader with a natural head for business to take us into this next stage of growth. We're in pursuit of excellence, and great isn't good enough. We want a leader who won't settle until Landmark is the best in the business.