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Pillow Talk Sessions

Pillow Talk Sessions

De : Jessica Gillingham and Kristian Lupinski
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Pillow Talk Sessions is a podcast about modern hospitality operations and how guest experience is operationally delivered in a tech-enabled world.


Hosted by Jessica Gillingham, author of Tech-Enabled Hospitality, and produced by Abode Worldwide, the show features in-depth conversations with leaders building, operating, and scaling modern hospitality across hotels, short-term rentals, serviced living, and flexible living models.


Each episode explores how hospitality is evolving beyond traditional hotels. From the hotelization of real estate to the rise of platform-driven and automated operations, we unpack how technology, systems, and organizational design are reshaping how stays are designed, delivered, and experienced.


Pillow Talk Sessions goes deep on hospitality operations, technology, and strategy. Topics include new operating models, guest experience delivery, AI and automation, platform ecosystems, and the convergence of hotels, short-term rentals, and serviced living.


This podcast is for hospitality operators, founders, owners, and technology leaders who want to understand the future of hospitality beyond trends, and how modern hospitality actually works on the ground.



About your host


Jessica Gillingham is the author of “Tech-Enabled Hospitality – Strategies to Elevate Guest Experience and Operational Efficiency,” and is also an industry speaker, adviser, and the CEO of Abode Worldwide, a global strategic communications and PR agency for the tech transforming hospitality.



The podcast is brought to you by the team at
Abode Worldwide.

© 2026 Pillow Talk Sessions
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    Épisodes
    • Professionalising Short-Term Rentals with Merilee Karr (UnderTheDoormat)
      Feb 12 2026

      In this episode of Pillow Talk Sessions, Merilee Karr, CEO of UnderTheDoormat Group, explains how short-term rentals have evolved from fragmented, alternative accommodation into a professional, institutional-grade asset class operating at scale across Europe and beyond.

      With short-term rentals now accounting for over 20% of accommodation nights in Europe, the sector is no longer a niche. Merilee outlines how operational infrastructure, technology platforms, and regulatory collaboration are shaping its next phase of growth.

      UnderTheDoormat operates across luxury B2C properties and institutional portfolios in London and Paris, while its technology arm, Hospiria, supports global operators with flexible PMS and reservation systems designed specifically for converging asset classes. Through Trusted Stays, the group has also opened access to government contracts and global distribution systems, accelerating the sector’s professionalisation.

      The conversation explores how short-term rentals intersect with real estate, hospitality, and policy, and what must happen next for the sector to mature sustainably.

      Key themes explored:

      Why short-term rentals have become a core part of Europe’s accommodation landscape
      How the merger of UnderTheDoormat and Veeve strengthened luxury and institutional portfolio management
      The role of Hospiria in enabling flexible, mixed-use rental operations
      How Trusted Stays unlocked government and GDS distribution channels for short-term rentals
      The difference between hotelization and hospitality, and why authenticity still matters
      How the UK Renters Reform Bill is accelerating institutional interest in flexible rental models
      Why tenant-driven subletting models can increase retention without destabilizing buildings
      The scale of opportunity in the Middle East, where short-term rentals represent less than 5% of accommodation nights
      Why legacy PMS systems struggle to manage converged asset classes
      How AI and emerging technology are likely to disrupt flexible rental operations over the next five years

      For leaders across hospitality, real estate, and flexible living, this episode reframes short-term rentals not as disruption, but as convergence. The next competitive advantage will come from professional standards, agile infrastructure, and thoughtful regulatory collaboration.

      Explore related industry analysis and strategic perspectives:
      https://abodeworldwide.com/news-insights/

      Website: https://abodeworldwide.com

      LinkedIn: https://www.linkedin.com/company/abode-worldwide

      #ShortTermRentals #FlexibleLiving #HospitalityInnovation #PropTech #RealEstateTech #LivingSector #DigitalInfrastructure #Professionalisation #PillowTalkSessions

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      44 min
    • Scaling Short-Stay Living with Laurenz Schwarzhappel (Global Living Apartments)
      Jan 29 2026

      In this episode of Pillow Talk Sessions, Laurenz Schwarzhappel, Co-Founder and Co-CEO of Global Living Apartments, explains how the company consistently achieves around 92% occupancy across nine German cities by doing what most hospitality operators avoid. Narrowing the guest segment, rethinking asset use, and automating everything possible.

      Global Living Apartments focuses on families and group travelers, a segment traditional hotels struggle to serve. By converting commercial properties into short-stay apartments and operating with a deeply automated tech stack, the company delivers affordable, high-density stays with a lean team and minimal friction.

      The conversation explores how this model performs not only in major cities, but also in smaller industrial markets where demand is stable and competition is limited.

      Key themes explored:

      • Why targeting families and groups unlocks consistently higher occupancy than hotels
      • How operating in smaller cities like Jena and Chemnitz delivered 90%+ occupancy and exceeded financial expectations
      • The regulatory advantage of converting commercial real estate into short-stay apartments in Germany
      • How AI-driven guest communication saved 800–900 operational hours with a team of five
      • Why automation should precede hiring, not follow it
      • How tech-first operations reduce ADR while improving guest satisfaction
      • What AI-driven booking assistants will change about demand, discovery, and niche positioning
      • Why “if you address all, you address no one” is becoming a survival rule in hospitality
      • Global Living’s expansion into property management services for smaller operators in 2026

      For hospitality, short-stay, and living sector leaders, this episode reframes performance. The competitive edge is not scale alone, but clarity of segment, disciplined automation, and a willingness to operate where others are not looking.

      Explore related industry analysis and strategic perspectives:
      https://abodeworldwide.com/news-insights/

      Website: https://abodeworldwide.com
      LinkedIn: https://www.linkedin.com/company/abode-worldwide

      #ShortStay #HospitalityTech #PropTech #LivingTech #Automation #AIinHospitality #FamilyTravel #AlternativeAccommodation #OperationalStrategy #PillowTalkSessions


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      38 min
    • Hospitality’s Digital Reset with Ulrich Pillau (Apaleo)
      Jan 15 2026

      In this episode of Pillow Talk Sessions, Jessica Gillingham sits down with Ulrich Pillau, Co-founder & CEO of Apaleo, to explore how AI and API-first technology are redefining what modern hospitality looks like behind the scenes and in front of guests.

      Uli explains why the industry is splitting between digital-first operators and legacy brands struggling to adapt, and why simply “moving to the cloud” won’t fix broken guest journeys without a fundamental rethink of operating models.

      💡 In this conversation, you’ll hear about:
      🤖 How AI and LLMs are changing how guests research, book, and interact
      🏨 Why replacing a PMS doesn’t automatically modernise operations
      🔌 How open, API-first platforms enable faster experimentation and innovation
      🔄 The emergence of hybrid models blending hotels, serviced living, and niche lodging
      ⚠️ Why mid-market brands face consolidation pressure without real digital reinvention

      A clear-eyed look at what hospitality must rethink now to stay competitive in an AI-driven world.


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      40 min
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