How to Recruit Top Talent in Property Management - with Dylan Scroggins

Property Management Success

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What separates thriving property management companies from those merely surviving? According to recruiting expert Dylan Scroggins, it often comes down to how strategically they build their teams.
Dylan draws a powerful distinction between simply hiring (a reactive process) and true recruiting (a proactive strategy). Too many property management entrepreneurs wait until they're drowning in work before scrambling to find help, only to hire someone who ends up drowning alongside them. The championship approach? Build your bench before you need it.
Through his work with industry leaders like Evernest (formerly GKHouses), Dylan has observed how the most successful property management companies maintain ongoing relationships with potential talent. They're constantly connecting with impressive professionals both inside and outside the industry who might become future team members. This proactive approach transforms how companies handle underperformance and creates the confidence to make necessary changes.
For property management companies approaching growth milestones (300, 500, or 1,000 doors), strategic role planning becomes crucial. Dylan cautions against common pitfalls like title inflation and instead advocates for an output-focused approach to defining positions. Rather than automatically creating director-level roles, smart companies first identify exactly what outcomes they need, then determine the most effective structure to achieve those results.
Perhaps most challenging for property management entrepreneurs is learning to let go. Many founders have built their identity around being the hero who solves every crisis. Yet as discussed, "Every time you solve a problem for your team that they could have solved themselves, you do damage." True leadership means defining clear policies, then stepping back to give your team the autonomy to develop their own processes and solutions.
The most compelling property management companies don't just offer jobs—they present meaningful challenges tied to an exciting vision. Beyond compensation, top talent seeks purpose and the opportunity to contribute to something significant. By clearly articulating both your company's trajectory and the meaningful impact of providing homes while building wealth for investors, you position your company to attract people who want to join your championship team.

Join fellow property management entrepreneurs and 6 expert coaches in a small, private high level event at a mansion style venue with a private chef and personally selected attendees to maximize the value you receive while at the event.
Join the waitlist for additional information here: https://ONYXwaitlist.com
Save the dates! July 13th - 16th, 2025

visit pmsuccess.com for more value packed property management related information or to hire Tony as your property management coach.

Chapters

1. Introduction to Dylan Scroggins (00:00:00)

2. Recruiting vs. Hiring Mindset (00:07:05)

3. Building Your First Team Members (00:15:02)

4. Strategic Title and Role Planning (00:23:05)

5. Culture of Excellence vs. Mediocrity (00:30:45)

6. Letting Go as a Business Owner (00:37:37)

7. Final Thoughts on Property Management Recruiting (00:49:35)