Pillow Talk Sessions Podcast By Jessica Gillingham and Kristian Lupinski cover art

Pillow Talk Sessions

Pillow Talk Sessions

By: 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
Economics Management Management & Leadership
Episodes
  • Curated Hospitality with Cathrine Reimann (Landfolk)
    Mar 12 2026

    In this episode of Pillow Talk Sessions with Jessica Gillingham, Cathrine Reimann, Co-Founder of Landfolk, explains why disciplined curation, not scale alone, is the foundation of a successful short-stay marketplace.

    Landfolk has grown from just 33 homes to more than 1,500 handpicked properties across seven markets. But unlike many platforms focused on inventory growth, Landfolk rejects roughly 50% of potential hosts in order to protect quality, brand integrity, and long-term community health.

    This approach has produced unusually strong host loyalty. Nearly 60% of the original hosts who joined the platform five years ago remain active today, demonstrating what Cathrine calls “emotional collateral”, the trust and relationships that develop when hosts feel valued rather than treated as interchangeable supply.

    The conversation explores how Landfolk balances technology with human judgment, using AI to support efficiency while preserving what the company calls “warm hands” in moments where human interaction matters most.

    Key themes explored:

    • Why rejecting 50% of hosts strengthened Landfolk’s growth and brand reputation
    • How host retention became the company’s most important KPI
    • The concept of emotional collateral and why it drives long-term marketplace stability
    • How combining AI with human support improves guest and host experience
    • Why Landfolk built an AI-powered search engine focused on vibe and storytelling rather than filters
    • The importance of high-quality photos, descriptions, and reviews in an AI-driven discovery world
    • How curated onboarding and host referrals maintain consistent inventory quality
    • Landfolk’s pilot expansion into urban rentals in Copenhagen under strict regulatory compliance
    • Why quality, not supply volume, is the company’s most important strategic value

    For leaders across hospitality, short-stay, and living platforms, this episode highlights an important shift. The strongest marketplaces of the future may not be the biggest. They may be the most disciplined, the most curated, and the most trusted by the communities they serve.

    #ShortStay #VacationRentals #HospitalityInnovation #MarketplaceStrategy #LivingSector #CuratedTravel #HospitalityLeadership #PillowTalkSessions

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

    Website: https://www.pillowtalksessions.com/

    LinkedIn: https://www.linkedin.com/company/pillowtalksessionspodcast/

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    33 mins
  • Reinventing Hotel Standards with Adam Tuttle (Yipy)
    Feb 26 2026

    In this episode of Pillow Talk Sessions with Jessica Gillingham, Adam Tuttle, Co-Founder and CEO of Yipy, explains why hospitality’s approach to standards management has remained fundamentally outdated and how digitising standards can transform operational performance, team culture, and guest experience.

    While hotels have embraced digital guest journeys and automation, internal standards often still live in binders, PDFs, or static intranets. Adam argues that without a live, accessible standards system, consistency breaks down, training becomes inconsistent, and decision-making relies too heavily on human bias.

    Yipy transforms standards from passive documents into an active operating system. By defining, distributing, and tracking compliance in real time, the platform gives hotels measurable visibility into performance across teams, properties, and portfolios. This shift unlocks smarter budgeting, more precise training, and stronger operational accountability.

    The conversation explores how standards intersect with culture, data, and emerging AI capabilities, and what must change for hospitality to evolve beyond outdated compliance models.

    Key themes explored:

    • Why traditional standards management systems fail to drive daily performance
    • How digitised standards improve team confidence and operational consistency
    • Replacing tribal knowledge with real-time compliance data
    • How independent hotels can define identity and strengthen brand delivery through structured standards
    • Why vacation rentals must mature standards to improve guest experience and reputation
    • Using performance data to eliminate bias in budgeting and annual reviews
    • How aggregated compliance data supports smarter capital expenditure decisions
    • The role of AI in recommending training plans, budgets, and operational improvements
    • Why transparent standards may eventually influence guest booking decisions
    • How modern standards systems can align staff, management, owners, and guests

    For leaders across hospitality, living, and operations, this episode reframes standards not as administrative paperwork, but as infrastructure. The next competitive advantage will come from measurable clarity, embedded culture, and intelligent data-driven execution.


    #HospitalityOperations #HotelLeadership #StandardsManagement #HospitalityTech #DigitalTransformation #LivingSector #OperationalExcellence #PillowTalkSessions

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

    Website: https://www.pillowtalksessions.com/

    LinkedIn: https://www.linkedin.com/company/pillowtalksessionspodcast/

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    44 mins
  • 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 mins
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