Pillow Talk Sessions

Jessica Gillingham
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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.

  1. Redefining Resi: From short lets to branded living with Maxine Leufroy-Murat (Sejour Living)

    18 juin

    Redefining Resi: From short lets to branded living with Maxine Leufroy-Murat (Sejour Living)

    Like many entrepreneurs entering the short-term rental space, Maxime Leufroy-Murat started out believing growth was a function of acquiring more properties and scaling operations. After more than a decade in the industry, he has reached very different conclusions. Maxime Leufroy-Murat has spent over a decade inside the short-term rental industry — building City Relay, one of London's most established lettings management platforms, and Opago, a tech-enabled operations business now managing around 5,000 units across London and Paris. When growth hit a ceiling, he built sideways — into a new venture called Sejour Living, a design-led branded living concept in the heart of London targeting the part of the private rented sector that institutional capital is just beginning to take seriously. His central argument is that growth alone is not a strategy. Businesses that have survived the last decade in STR have done so by constantly reading the market and evolving ahead of it, not by holding their position and hoping the fundamentals stayed the same. In this episode, Maxime traces the journey from short lets to branded residential, and makes the case that the skills hospitality operators have spent years developing — speed, service culture, owner relationships — are exactly what the PRS has been missing. The conversation gets into: Why the short let model in London was always a tool, not a strategy — and what the operators who survived worked out earlyThe gap Sejour is targeting: a BTR-style guest experience, without the BTR price tag or the amenities arms raceHow hospitality instincts translate into a long let product — and where the translation breaks downWhy community in residential doesn't require a rooftop terrace or a co-working spaceWhat it takes to build a brand in a sector where most landlords have never thought about brand at allThe role of institutional capital in the PRS — and where Sejour fits in a market that is starting to consolidateMaxime runs four interconnected businesses that together form a vertically integrated stack: investment, development, operations, lettings, and brand. That structure shapes everything about how he thinks — and it's what makes this conversation worth paying attention to. 🎧 Listen to the full episode to hear how Maxime Leufroy-Murat is applying a decade of short let experience to the biggest and most underbranded slice of the rental market. #Hospitality #ShortTermRentals #BrandedLiving #PillowTalkSessions Explore related industry analysis and strategic perspectives: https://abodeworldwide.com/news-insights/ Pillow Talk Sessions: https://www.pillowtalksessions.com/ LinkedIn: https://www.linkedin.com/company/pillowtalksessionspodcast/ Tech-Enabled Hospitality: https://techenabledhospitality.com/ Maxime's LinkedIn: https://www.linkedin.com/in/maxime-leufroy-murat/  City Relay: http://cityrelay.com/  Opago: https://www.opago.co/  Leufroy: http://leufroy.com  Séjour Living: https://sejour.living/ Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    44 min
  2. We Grew Too Fast and Nearly Lost Everything - With Njål Elliasson, Proptonomy & Heimby

    4 juin

    We Grew Too Fast and Nearly Lost Everything - With Njål Elliasson, Proptonomy & Heimby

    When Njål Elliasson co-founded his Norwegian-based short-term rental property management company, Heimby, in 2022, he was over the moon as it quickly grew in size and profit. But before he knew it, his company started crumbling, going from a $100k profit in year one to a $200k loss by the end of year two.  By the end of 2023, Njål was forced to start over, prioritizing quality of product over profit and growth. He got rid of all of his team, downsized to just the 20 best homes, hired at CTO and spent a year working on a tech product that would help him scale, but this time better. He is now also the founder of Proptonomy, an AI-driven operations platform built to solve the challenges he encountered while scaling and his property management company is doing better than ever.  In this episode of the Pillow Talk Sessions Podcast, Njål's shares his story. This is not a straightforward success story, and in today's interview, he shares all the lessons he learned from starting, failing, and restarting Heimby, going from catastrophic failure to building a completely different, AI-driven approach to hospitality. The conversation explores: • Why so many short-term rental operators hit a ceiling when they try to scale • The operational mistakes that nearly brought Heimby down • Why quality and process matter more than chasing margins • The lessons learned from rebuilding a company from the ground up • How AI is being used to streamline maintenance, onboarding, and day-to-day operations • Why technology can become a competitive moat in property management • The changing relationship between operators and property owners Njål challenges some of the industry's assumptions. While many operators view relationships as their primary competitive advantage, Njål argues that technology and operational excellence may ultimately prove more scalable. He also makes the case that owners should take greater responsibility for the performance of their own assets, rather than relying on operators to absorb every problem. What emerges throughout the conversation is a picture of an industry wrestling with complexity. Short-term rentals have often been built on hospitality principles, but as portfolios grow, logistics, systems and operational discipline become increasingly important. Looking ahead, Njål's focus is on helping other operators avoid the mistakes he made. Through both Heimby and Proptonomy, he is exploring how technology, process, and accountability can help property managers scale without sacrificing quality. 🎧 Listen to the full episode to hear how Njål Eliasson went from rapid growth to operational collapse and back again — and what his experience reveals about the future of short-term rental management. Njål Elliasson LinkedIn: https://www.linkedin.com/in/njaleliasson/?locale=en_US Heimby LI: https://www.linkedin.com/company/heimby-no/ Heimby website: https://www.heimby.no/ Proptonomy LI: https://www.linkedin.com/company/proptonomy/ Poptonomy website: https://proptonomy.ai/ Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    36 min
  3. How Mollie's is Running Hospitality Like a High Street Retailer - With Matt Bell, Mollie's Motels

    21 mai

    How Mollie's is Running Hospitality Like a High Street Retailer - With Matt Bell, Mollie's Motels

    What does it take to build a hospitality brand that delivers genuine quality at a budget price point? Matt Bell is the Managing Director of Mollie's, a design-led motel and diner concept with properties in Oxford, Bristol, and Manchester. With nearly two decades in independent hospitality, Matt brings a rare mix of operational rigour and brand instinct to everything Mollie's does. In this episode, Matt breaks down the philosophy behind the brand — why budget doesn't have to mean boring, and how Mollie's is building what he calls a value-lux proposition. Great design, thoughtful food, and a deeply human guest experience, all at an accessible price point.exclusive to the luxury end of the hospitality chain.  The conversation gets into: What it means to run a hospitality brand like a retailer — and where that analogy breaksWhy technology should remove friction without replacing warmth, and how Mollie's walks that lineThe three-part test every decision at Mollie's gets held against: guest satisfaction, financial viability, and team performanceWhy Mollie's embraces failure, iterates fast, and doesn't wait for perfectHow a young brand thinks about scale — and the discipline required to get thereWhat makes Mollie's worth paying attention to is the clarity of thinking and deliberation. In a sector where budget often means transactional and the bare minimum, Matt and his team are making a deliberate case that the guest experience and the price point don't have to trade off against each other. The design, the diner, the technology, the people — each one is chosen to pull in the same direction. Matt is also clear about what technology should and shouldn't do. At Mollie's, it's an enabler — centralising expertise, reducing friction, and freeing up the floor team to focus entirely on the guest in front of them. The human side of the experience is non-negotiable, and the technology is there to protect it, not replace it. Looking ahead, Matt sees Mollie's growing through discipline. A standardised, refined product that can scale quickly, into locations with the right blend of corporate and leisure demand. The goal is a brand guests actively seek out — not just somewhere reliable to stop, but somewhere they actually want to be. 🎧 Listen to the full episode to hear how Matt Bell and the team at Mollie's are building a hospitality brand where great design, smart operations, and genuine warmth are designed to work together, not compete. #Hospitality #HospitalityTech #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/ Tech-Enabled Hospitality: https://techenabledhospitality.com/  Matt Bell: https://www.linkedin.com/in/matthewcrbell/ Mollie’s Motels: https://www.linkedin.com/company/mollies/  Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    40 min
  4. How CitizenM Mastered Hospitality Automation with Mike Rawson (Formerly CitizenM)

    7 mai

    How CitizenM Mastered Hospitality Automation with Mike Rawson (Formerly CitizenM)

    Mike Rawson spent seven years as CIO of CitizenM, one of the most tech-forward hotel brands in the world. His biggest lesson? Technology comes last. In the latest episode of Pillow Talk Sessions, Mike joins me to break down what most hotels are getting wrong about automation and how CitizenM built an NPS score good enough to catch Marriott's attention. His belief: you shouldn't reach for technology until you understand the real requirement, the business value it will bring, and most fundamentally, the people around it. In this episode, Mike shares with me: Why the speed of AI innovation is making decision-making so difficult for operators right nowHow most operators are currently stuck between paralysis and poor decisionsThe compliance, governance and control conversation nobody in hospitality is having — and why that's going to hurtHow AI, done right, frees people for the moments that actually move NPSWhat Mike's ideal hotel would look like if he were starting from scratch in 2026#HospitalityTech #CitizenM #HotelTech #PillowTalkSessions Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    43 min
  5. The Rise of Agentic AI in Hospitality with Tim Major (Operto)

    23 avr.

    The Rise of Agentic AI in Hospitality with Tim Major (Operto)

    In this episode of Pillow Talk Sessions, Tim Major, CEO of Operto, joins host Jessica Gillingham to explain how agentic AI is shifting hospitality from automation to autonomous execution. Through Operto One, Operto is building an AI workforce capable of performing operational and marketing tasks, optimizing performance, and driving outcomes across hotel systems. The conversation explores what this shift means for hotel teams, guest experience, and business performance. While AI offers significant potential, most hotels face a fundamental challenge. Data readiness. Without structured, accurate content, AI systems struggle to deliver reliable results. Tim outlines how hotels can begin adopting AI in a controlled, practical way, focusing on high-impact areas like direct bookings and operational efficiency. Key themes explored: What agentic AI means for hospitality operations Why direct booking optimization is a key AI opportunity How hotel teams will evolve into hybrid human-AI workforces The importance of ethical, consent-based data use Why structured data is critical for AI performance How hotels can approach AI adoption without falling into hype For hospitality leaders, this episode provides a clear view of what AI will actually change, and what foundations must be in place to make it work. #HospitalityTech #AIinHospitality #AgenticAI #FutureOfWork #HotelTech #PillowTalkSessions Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    45 min
  6. Privacy, Safety & the Future of Rentals with Nils Mattisson (Minut)

    9 avr.

    Privacy, Safety & the Future of Rentals with Nils Mattisson (Minut)

    In this episode of Pillow Talk Sessions, Nils Mattisson, CEO & Co-Founder of Minut, explains how privacy-first technology is solving one of hospitality’s most complex challenges. Balancing guest privacy with host security. Minut developed a system that detects events such as noise, overcrowding, and smoking without recording or storing audio. This approach builds trust while enabling operators to maintain control over their assets. The conversation expands into broader industry shifts, including the convergence of short-term rentals, student housing, and senior living, all of which are adopting similar technologies and service expectations. At the same time, upcoming EU and UK regulations are expected to reshape supply, pricing, and operational strategies across the market. Key themes explored: How privacy-first monitoring builds trust between hosts and guests Why asset classes are converging across hospitality and living sectors The impact of new EU and UK short-term rental regulations How AI and automation are transforming guest experience and operations Why guest safety remains an underdeveloped area in hospitality The future of building-level monitoring and operational intelligence For hospitality and real estate leaders, this episode highlights a critical shift. The next generation of operations will be defined by how well technology balances privacy, safety, and efficiency. #HospitalityTech #PropTech #ShortStay #DigitalTransformation #GuestSafety #PillowTalkSessions Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    37 min
  7. Building Sustainable Hospitality with Marc Laros (The Usual Hotels)

    26 mars

    Building Sustainable Hospitality with Marc Laros (The Usual Hotels)

    In this episode of Pillow Talk Sessions, Marc Laros, CTO of The Usual Hotels, explains how sustainability, technology, and guest experience can be designed as one integrated operating system. The Usual Hotels is building toward becoming Europe’s most sustainable hotel brand, targeting 20 hotels in five years. Rather than treating sustainability as a layer, the company embeds it into how hotels are built, operated, and measured. At the same time, a flexible, API-driven tech stack and growing use of AI are transforming operations. From frictionless check-in to automated backend workflows, technology is used to remove complexity and allow staff to focus on delivering meaningful guest experiences. The conversation explores how hospitality can evolve by aligning sustainability, automation, and human service into one coherent model. Key themes explored: Why sustainability must be embedded into operations How transparent reporting builds trust and accountability Using AI across guest communication and operational workflows Why automation should enhance staff roles, not replace them How frictionless journeys improve both efficiency and experience The importance of flexible, API-driven infrastructure Why community engagement is central to modern hospitality brands For hospitality and technology leaders, this episode highlights a clear shift. The future of hospitality will not be defined by sustainability or technology alone, but by how effectively they are integrated. #SustainableHospitality #HotelTech #AIinHospitality #DigitalTransformation #GuestExperience #PillowTalkSessions Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    34 min
  8. Curated Hospitality with Cathrine Reimann (Landfolk)

    12 mars

    Curated Hospitality with Cathrine Reimann (Landfolk)

    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 reputationHow host retention became the company’s most important KPI The concept of emotional collateral and why it drives long-term marketplace stabilityHow combining AI with human support improves guest and host experienceWhy Landfolk built an AI-powered search engine focused on vibe and storytelling rather than filtersThe importance of high-quality photos, descriptions, and reviews in an AI-driven discovery worldHow curated onboarding and host referrals maintain consistent inventory qualityLandfolk’s pilot expansion into urban rentals in Copenhagen under strict regulatory complianceWhy quality, not supply volume, is the company’s most important strategic valueFor 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 Meet the host of Pillow Talk Sessions Jessica Gillingham is the Founder and CEO of Abode Worldwide, a strategic public relations agency dedicated to elevating the profile of transformative technology solutions in global hospitality, lodging, and rental living. An established industry thought leader, Jessica is a frequent conference speaker and author of Tech-Enabled Hospitality, a new book exploring the innovations shaping the sector.

    33 min
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À propos

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.

Informations

  • Création
    Jessica Gillingham
  • Années d’activité
    2024 - 2026
  • Épisodes
    44
  • Classification
    Contenu explicite
  • Copyright
    © 2026 Pillow Talk Sessions
  • Site web de l’émission
    Pillow Talk Sessions