Pillow Talk Sessions

Jessica Gillingham and Kristian Lupinski
  • 0.0 (0)
  • MANAGEMENT
  • UPDATED SEMIWEEKLY

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.

  1. Professionalising Short-Term Rentals with Merilee Karr (UnderTheDoormat)

    3D AGO

    Professionalising Short-Term Rentals with Merilee Karr (UnderTheDoormat)

    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

    44 min
  2. Scaling Short-Stay Living with Laurenz Schwarzhappel (Global Living Apartments)

    JAN 29

    Scaling Short-Stay Living with Laurenz Schwarzhappel (Global Living Apartments)

    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 hotelsHow operating in smaller cities like Jena and Chemnitz delivered 90%+ occupancy and exceeded financial expectationsThe regulatory advantage of converting commercial real estate into short-stay apartments in GermanyHow AI-driven guest communication saved 800–900 operational hours with a team of fiveWhy automation should precede hiring, not follow itHow tech-first operations reduce ADR while improving guest satisfactionWhat AI-driven booking assistants will change about demand, discovery, and niche positioningWhy “if you address all, you address no one” is becoming a survival rule in hospitalityGlobal Living’s expansion into property management services for smaller operators in 2026For 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

    38 min
  3. Hospitality’s Digital Reset with Ulrich Pillau (Apaleo)

    JAN 15

    Hospitality’s Digital Reset with Ulrich Pillau (Apaleo)

    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.

    40 min
  4. Scaling Hospitality Through Automation with Alexander Limpert (RentalReady / GuestReady)

    12/04/2025

    Scaling Hospitality Through Automation with Alexander Limpert (RentalReady / GuestReady)

    In this week’s Pillow Talk Sessions, Jessica Gillingham and Kristian Lupinski speak with Alexander Limpert, the founder behind RentalReady and GuestReady, to unpack how automation, data, and AI are transforming operational efficiency in short-term rentals. 💡 Highlights include:  🤖 How RentalReady became the first PMS to integrate OpenAI, now powering a third-gen AI assistant  💬 Why AI replies to “confident messages” but escalates complex ones to humans  🏗️ Why GuestReady is shifting toward entire building management to strengthen revenue stability  🌍 How geographic diversification helps manage regulatory volatility  🛏️ Why GuestReady blends local authenticity with hotel-like standards for a differentiated stay  📜 The case for reasonable, balanced STR regulation that protects housing and enables innovation Alex makes the case for a future where smarter tools empower operators, improve guest experience, and support sustainable growth across the sector. 🌐 pillowtalksessions.com

    39 min
  5. Rethinking UK Housing with Jason Hardman (CBRE)

    11/20/2025

    Rethinking UK Housing with Jason Hardman (CBRE)

    In this week’s Pillow Talk Sessions, Jessica Gillingham and Kristian Lupinski sit down with Jason Hardman, Head of UK Living at CBRE, to explore how policy, planning, and private capital are reshaping the UK’s housing future. 💡 Highlights include:  🏡 Why housing models must evolve to reflect modern lifestyles and longer life spans  🏘️ How institutional investment is fueling growth in single-family rental  📊 The UK’s 1.5 million homes target—and how to balance quality, speed, and sustainability  🤝 How the Renters Reform Bill is changing landlord-tenant relationships  ⚙️ Why tech-led service delivery is the key to happier renters and efficient operations Jason offers a grounded, data-informed perspective on how the UK living sector can innovate without losing sight of long-term value, community, and trust.

    37 min
  6. The Future of Casual Living with Asli Kutlucan (TFE Hotels)

    11/06/2025

    The Future of Casual Living with Asli Kutlucan (TFE Hotels)

    In this week’s Pillow Talk Sessions, Jessica Gillingham and co-host Kristian Lupinski sit down with Asli Kutlucan, CEO Europe at TFE Hotels, to explore how the company is bridging the gap between hotels and homes with its fast-growing Adina and  MM:MT (Moment) brands. In this episode, Asli shares:  🏨 Why casual living is the next evolution of modern hospitality  🏗️ How adaptive reuse is unlocking new value from underused city buildings  🤖 How the new GXP platform is transforming guest experience and staff operations  🌍 Why flexible, service-led living is resonating with a generation on the move  💬 How to balance tech-driven efficiency with authentic hospitality From Berlin to Cambridge, Hamburg to Glasgow, TFE is leading a new era of living that’s flexible, connected, and human-centered.

    50 min
  7. Community, Affordability & Long-Term Value with Stephanie Smith (Muse)

    10/23/2025

    Community, Affordability & Long-Term Value with Stephanie Smith (Muse)

    In this week’s Pillow Talk Sessions, Jessica Gillingham and Kristian Lupinski sit down with Stephanie Smith, Head of Residential at Muse, to unpack how thoughtful design, data, and collaboration are shaping the next era of residential living in the UK. 💡 Highlights include:  🏡 Why responsive service and maintenance matter more than flashy amenities  🌍 How early engagement with residents and local schools drives better design and safety  📊 Why “tech for tech’s sake” is out — and data-driven benchmarking is in  🌿 The financial and environmental benefits of Passive House design  🏘️ How Muse balances regeneration and affordability without triggering gentrification Stephanie’s insights offer a refreshing, pragmatic view on how to create homes that genuinely support communities — not just markets.

    40 min
  8. Global Student Housing Trends with Joe Persechino (Yugo)

    10/09/2025

    Global Student Housing Trends with Joe Persechino (Yugo)

    In this week’s Pillow Talk Sessions, Jessica Gillingham and Kristian Lupinski sit down with Joe Persechino, COO of Yugo, to unpack the global growth trajectory of student accommodation and the strategies needed to meet demand. 💡 Highlights from the conversation:  🌍 Why student numbers are rising from 240M to 400M by 2050  📊 Why markets like the UK are 30% penetrated while Italy lags at only 5%  🏢 How Yugo blends global brand consistency with local market nuance  🤝 Why partnerships with universities and parents are critical for trust and growth  🌱 How Gen Z expectations around sustainability and wellbeing are reshaping the student experience Joe explains why PBSA is no longer a niche “alternative” but a core asset class attracting global institutional capital — and how Yugo is leading the way.

    50 min
See All (35)

Trailer

About

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.

Information

  • Creator
    Jessica Gillingham and Kristian Lupinski
  • Years Active
    2024 - 2026
  • Episodes
    35
  • Rating
    Clean
  • Copyright
    © 2026 Pillow Talk Sessions
  • Show Website
    Pillow Talk Sessions