Kimberlee Carr, Chief Operating Officer of Real Estate and Managing Broker at TAWANI Enterprises, shares how a chance fill-in role sparked a career she’s grown into with grit, curiosity, and a love for challenge. In this conversation, Kimberlee traces her path from on-site property manager to executive leader, explaining why her core values never changed with the title: positivity, accountability, respect, teamwork, integrity, and pride in the work. She describes her “wolf pack” philosophy of leadership—guiding from behind, protecting the team, and lifting one another when someone stumbles.

Kimberlee unpacks the realities of running portfolios that span conventional residential assets and historically significant properties. Preservation, she notes, isn’t about maximizing short-term profit; it’s about stewarding architecture and history for future generations, even when sourcing period-appropriate materials or custom fabrication stretches budgets. She also demystifies scale: whether a single home or a high-rise, the fundamentals (HVAC, plumbing, electrical) are the same—just bigger.

On resident experience and fiscal responsibility, Kimberlee argues that transparency wins. When rents rise, she and her teams explain the “why” (taxes, capital upgrades), and they focus on what residents feel daily: cleanliness, responsiveness, and systems that work—because “it’s their home; we leave, they stay.” She charts the tech journey from Excel and mail merges to platforms like Yardi/MRI that automate notices, payments, and work orders, freeing staff to solve higher-order problems. Looking ahead, she sees promise in AI for service and operations—while urging care for senior residents who may need extra support with new tools.

Community is a throughline. Kimberlee discusses TAWANI’s gifts of the Lang House Chicago and Frank Lloyd Wright’s Emil Bach House to Loyola University Chicago and why placing historic assets with mission-aligned stewards matters. Beyond philanthropy, she highlights hands-on service—school projects, art festivals, backpack drives—and how visible participation builds trust and safer, more vibrant neighborhoods. Sustainability follows the same principle: educate and involve residents (even with small contests) so savings and stewardship compound for everyone.

Kimberlee also reflects on professional growth. Earning IREM’s ARM (Accredited Residential Manager) and CPM (Certified Property Manager) challenged her to deepen financial acumen—from budgets she loves to acquisition math and amortization—so she can better advise owners and coach teams. Mentorship, for her, means grace, accountability, and letting newcomers make (and learn from) mistakes—while also learning from their speed and digital instincts.

About Kimberlee Carr:

- https://tawanienterprises.com/

- https://tawanipropertymanagement.com/

About Federico Ramallo ✨👨‍💻🌎

🚀 Software Engineering Manager | 🛠 Founder of DensityLabs.io & PreVetted.ai | 🤝 Connecting 🇺🇸 U.S. teams with top nearshore 🌎 LATAM engineers

- 💼 https://www.linkedin.com/in/framallo/

- 🌐 https://densitylabs.io

- ✅ https://prevetted.ai

🎙 PreVetted Podcast 🎧📡

- 🎯 https://prevetted.ai/podcast

- 🐦 https://x.com/PrevettedPod

- 🔗 https://www.linkedin.com/company/prevetted-podcast

01:01 Accidental entry into real estate

02:20 Turning points and seizing opportunities

04:42 Transition to COO and unchanging leadership philosophy

07:21 Managing middle management with core values

08:56 Balancing preservation and financial performance

11:54 Operational challenges at scale

13:17 Fiscal responsibility and resident satisfaction

16:13 Evolution of property management technology

21:43 Philanthropy and community

26:24 Property leaders’ community responsibilities

31:07 Profitability versus long-term sustainability

34:22 Impact of ARM and CPM certifications

38:14 Shifting from daily operations to strategic leadership

42:27 Mentoring younger property professionals