AI for Centralized Property Management

Answer a couple of questions and we'll connect you with the right team member.

LISTEN ON

The New Skillset Needed by Multifamily Leaders in 2026 │ Kelsi Cory, Founder & CEO of CORY Executive Recruiting

Summary

Kelsi Cory is the founder and CEO of CORY Executive Recruiting, a boutique real estate executive search firm that places C-suite and senior operators across multifamily and the wider real estate industry. Over eight years, she has become one of the most trusted voices in real estate recruiting. With a cross-company view of how leadership hiring is changing, and through her Leaders On Deck and Fractionals On Deck brands, she also has front-row seat to the rise of fractional leadership. She sits down with host Jacob Kosior to explain why operators have stopped hiring specialists in favor of utility players, what a resume can never tell you about a leader, why the jump from regional to VP is where so many careers stall, and the skills that matter more as AI takes on the busy work. Along the way, they get into how the best leaders treat their teams, why she tells everyone to find their own university, and how AI is creating new roles even as it reshapes old ones.

Companies are getting away from being siloed. What that means for talent is they want utility players, not specialists.

In This Episode

Takeaways

  • Operators want utility players, not specialists. As companies move from silos toward centralization, the leaders in demand have range, able to set strategy and get in the weeds in the same afternoon. Kelsi's career advice follows the same logic: diversify early, find your craft in the middle, then combine both into a true utility player.
  • A resume gets you in the room. Character gets you the role. A resume shows what someone has done, but Kelsi says she can read who a leader is within a five-minute call. There are tells she watches for, including whether they talk about their team as an investment or a cost. At the executive level, indicators like these can matter more than the line items.
  • Your strongest regionals can have the most retention risk. Many regional managers are buried putting out fires with no time to develop, so they stall below the VP level. The best ones leave for companies that give them a real path. It's rarely about money. It's about growth, and the operators who build that runway keep their best people.‍
  • As AI absorbs the busy work, soft skills decide everything. Leading through change, holding people accountable, having the hard conversations: these are the skills Kelsi says will separate the next generation of leaders, precisely because so much of the routine work is being automated.