Kate Simer

Background

About Kate Simer

Company founder, licensed property manager, and entrepreneur with 25+ years of experience leading businesses at the intersection of hospitality, real estate, and values-driven operations. As CEO of Descansa, I oversee a Portland-based property management company that blends thoughtful guest care with long-term partnerships built on trust. My general manager leads the day-to-day; I focus on vision, strategy, and ensuring our systems and people are set up to thrive. I spend part of the year in Portugal and lead remotely — scaling the business with care, trust, and strong systems that reflect both my Montessori background and 25+ years building values-driven ventures. My approach is deeply influenced by my background in Montessori education (AMI-trained) and lifelong passion for learning and community-building. I believe great businesses function like great classrooms: structured but flexible, grounded in respect, and always evolving with the people in them. We contribute monthly to local organizations, prioritize inclusivity in our partnerships, and make decisions that support long-term health — not just short-term wins. What I bring: • Strategic leadership & sustainable growth • Hospitality-rooted property management • Empowered teams & collaborative culture • Cross-cultural connection & remote operations • A Montessori-informed approach to business and life Let’s connect — especially if you’re a homeowner, founder, or creative partner building something thoughtful, ambitious, and rooted in real values.