Top Hiring Challenges in Commercial Real Estate Leadership Roles

In the fast-evolving world of commercial real estate (CRE), leadership talent is the engine that drives performance, profitability, and growth. Yet finding and keeping the right leaders—especially in property management—has never been harder. The competition for skilled executives is fierce, the skill sets are shifting, and the stakes are higher than ever.

This is where working with a Property Management Recruitment Firm specializing in permanent placement property management can make the difference between organizational stagnation and long-term success.

📊 Real Data: The Current CRE Leadership Landscape

Here’s what the latest industry data reveals:

• 🏢 CRE Companies Are Hiring More—and Paying More In 2025, CRE firms planning to grow headcount outnumbered those downsizing by 3.5-to-1. Executive compensation is also trending upward, with projected increases between 3.2% and 3.4%.

• ⚖ Staffing & Recruitment Are Top Challenges In a national survey, 74% of property managers ranked HR, staffing, and recruitment as a top-three challenge, and 50% ranked it as their #1 issue. Turnover has hovered at 33%—well above the national average for other industries.

• 📉 Entry-Level Roles Are Shrinking Job postings for roles requiring 0–2 years of experience fell 17% in 2023 and another 9% in 2024. Although 2025 has seen a modest 7% rebound, openings are still 19% below 2021 peaks—impacting the future leadership pipeline.

• 🤖 AI Skills Are Now a Leadership Priority Among 440 surveyed CRE executives, 49% identified AI as their top strategic opportunity over the next 12 months—ranking ahead of property systems, automation, and even sustainability initiatives.

🚨 Signs Your CRE Property Management Team May Be Struggling

😓 Over-reliance on Interim or Temporary Leadership

Short-term hires may keep operations running, but without strategic alignment, you risk inconsistent management, unclear priorities, and long-term inefficiencies.

📉 Falling Behind in Tech & Data Adoption

If your senior property managers aren’t comfortable with analytics tools, AI-powered systems, or proptech, your portfolio’s performance could lag behind competitors.

🚪 Weak Entry-Level Pipeline

With fewer junior hires entering the industry, your ability to develop and promote future leaders is severely limited—leaving your succession plan vulnerable.

🕵️‍♂️ Missing Passive Talent

The best candidates often aren’t actively applying for jobs. Without a Property Management Recruitment Firm that can identify and engage these leaders, they’ll join your competitors instead.

🛠 How to Tackle CRE Leadership Hiring Challenges

1️⃣ Conduct a Leadership Audit

Evaluate your org chart and ask:

• Do we have leaders in place who can adapt to technology-driven changes?

• Are succession plans clearly documented for all key roles?

• Are there markets or asset classes where leadership coverage is thin?

2️⃣ Strengthen Internal Leadership Development

Build rotational programs, mentorship structures, and cross-training initiatives. This not only improves retention but ensures your leadership bench is ready for expansion or transitions.

3️⃣ Update Job Requirements to Match Modern Demands

Today’s leaders must combine traditional property management expertise with skills in AI, sustainability, data analytics, and automation. Ensure your job descriptions reflect this reality.

4️⃣ Partner with a Specialist for Permanent Placement

A Property Management Recruitment Firm skilled in permanent placement property management offers:

• 🎯 Direct access to top-tier, passive executive talent

• 🤝 Better cultural alignment and market-specific expertise

• ⏱ Faster, more efficient searches with higher retention rates

💼 Why CRE Firms Choose Executive Property Staffing, LLC

At Executive Property Staffing, LLC, we focus solely on CRE and property management leadership recruitment.

Here’s why firms trust us:

• Specialization – 100% dedicated to commercial real estate and property management leadership roles.

• Permanent Placement Expertise – We deliver long-term hires who drive performance and stability.

• Passive Talent Access – We tap into networks beyond job boards, connecting you with leaders you won’t find publicly.

• Confidential Searches – Ideal for replacing or upgrading leadership without market disruption.

❓ Questions to Ask Your Team Today

• Are our current leaders equipped to adopt AI, sustainability practices, and advanced analytics?

• Do we have a backup plan if a regional director or head of property management exits tomorrow?

• Is our leadership structure scalable as we expand into new markets or asset classes?

• Could a Property Management Recruitment Firm help us secure the talent we’ve been missing?

🔑 Final Thoughts: The Right Leaders Drive the Right Outcomes

In the competitive CRE space, leadership quality directly impacts operational efficiency, tenant satisfaction, and portfolio returns. The wrong hire—or a vacant seat—can cost millions in lost opportunities.

By working with a Property Management Recruitment Firm that specializes in permanent placement property management, you ensure every leadership hire is not just a quick fix but a long-term strategic asset.

At Executive Property Staffing, LLC, our mission is to help CRE firms secure the leaders they need to innovate, adapt, and thrive.