033: The People Side of Buying and Selling a Property Management Business with Dylan Scroggins

In this episode, I’m joined by Dylan Scroggins, founder of the Kalmar Group, a recruiting firm that helps property management companies find high-level leaders in operations, business development, marketing, and more.

When we talk about buying or selling a property management company, it’s easy to focus on the numbers. But the people inside the business can have just as much impact on what happens before, during, and after a transaction.

Dylan and I talk about why recruiting should be a forward-thinking strategy rather than something you only think about when someone leaves, how the right leadership team can create value when you’re preparing to sell, and what buyers should consider about the existing team before and after an acquisition.

We also get into why job titles matter more than most business owners realize, what happens when a company grows beyond the capacity of one of its leaders, and why the team that got you here may not always be the team that gets you where you want to go.

What You’ll Learn in This Episode:
✔️ Why buyers and sellers should evaluate the people side of a business alongside the financials
✔️ How strong leadership can create more confidence and continuity when preparing a business for sale
✔️ Why buyers should plan for potential team changes before an acquisition closes
✔️ Why recruiting reactively can lead to rushed hires and months of lost performance
✔️ Why Dylan believes business owners should always be recruiting, even when they don’t have an immediate opening
✔️ Why job titles matter when recruiting talent and planning for future growth
✔️ Why giving someone a senior title too early can leave less room for future growth
✔️ Why strong candidates may come from outside the property management industry
✔️ Why the capacity of a leader can ultimately become the capacity of the department or business they lead
✔️ How to recognize when someone who helped get your business here may not be the person who can get it there
✔️ Why retaining key employees becomes especially important during an ownership transition

More About Dylan
With over 15 years of experience in the recruiting industry, Dylan Scroggins founded the Kalmar Group to connect great companies with great leaders. Some of Dylan’s first hires were in property management, where he placed multiple leaders at Evernest, then gkhouses.com, including two leaders who are still with the company approximately 10 years later.
Today, Dylan recruits roles including Directors of Operations, Business Development Managers, and Marketing Managers for property management owners across the country who are ready to let go of parts of their business but haven’t found the right caliber of leaders through traditional methods like posting jobs or reaching out to their existing network.

Connect With Dylan
Website: https://www.thekalmargroup.com/pm
LinkedIn: https://www.linkedin.com/in/dylanscroggins/

Connect With Stacey
Website: https://www.staceysalyer.com/
Facebook: https://www.facebook.com/the.stacey.salyer/
Instagram: https://www.instagram.com/stacey.salyer/
LinkedIn: https://www.linkedin.com/in/stacey-salyer-39254012