How Connected Agentic AI Solves Operational Workflow Friction with Sofia Rossato & Jennifer Cashier of Inhabit
September 8, 2026
Sofia Rossato, Executive Vice President of Inhabit’s Short-Term Rental division, and Jennifer Cashier, VP of Product for the Short-Term Rental division, bring two complementary perspectives to the AI conversation: Sofia from the strategic and operational side of technology transformation, and Jennifer from the product side, where customer problems are being translated into practical AI capabilities.
In this episode of The Vacation Rental Show, Lynell sits down with Sofia and Jennifer to explore how agentic AI is beginning to reshape property management software. They discuss why the industry needs to move beyond “AI for AI’s sake,” how Inhabit is using customer feedback to guide product development, where agents can reduce repetitive work, how AEO could affect direct bookings, and why the most valuable AI investments will be the ones tied to real business outcomes rather than another layer of technology.
Sofia Rossato and Jennifer Cashier join Lynell Gordon to discuss what practical AI adoption should look like inside a vacation rental business. Sofia frames the broader challenge: AI adoption is accelerating, but operators risk creating what she calls “workflow slop” if they simply automate existing processes without first questioning whether those processes should exist in the same form at all. Her advice is to start with the business outcome, identify the real friction points, and then work backward into the data, systems, and automation required to solve them.
Jennifer then brings that thinking into the product layer. She explains how Inhabit’s LEO Agentic AI is being built around customer requests rather than generic AI features, with use cases ranging from bulk listing optimization and real-time product support to custom reporting, property insights, and conversational search.
This conversation also looks ahead at how traveler behavior and product development are changing. Sofia and Jennifer discuss the shift from SEO toward AEO as more travelers use tools like ChatGPT, Gemini, and Claude to plan trips, the growing importance of natural-language and voice search, and why property managers need to think strategically about where their listings appear in these new discovery channels.
What you'll learn:
- What Agentic AI means and how it differs from a simple chatbot or standalone AI tool
- Why Sofia believes operators should avoid “workflow slop” and rethink processes before automating them
- How Inhabit is using customer advisory boards, focus groups, and direct feedback to prioritize AI development
- Why listing optimization became one of the first major use cases after customers reported that roughly 60% of listings were out of date
- How AI can generate channel-specific listing descriptions at scale while maintaining a property manager’s brand voice
- How support agents can combine code, knowledge bases, and recently resolved tickets to provide more current product guidance
- How property managers can access their own data through APIs to build custom agents, dashboards, and reporting
- Why AEO is becoming increasingly important as travelers use AI tools to search for and plan trips
- How natural-language and voice search could change the way guests find vacation rentals
- Why AI should be evaluated by its effect on owner retention, bookings, customer experience, and enterprise value
About Sofia Rossato: Sofia Rossato is Executive Vice President of Inhabit’s Short-Term Rental division and a technology executive with more than 25 years of experience growing companies across SaaS, FinTech, PropTech, and communications. Her career includes leadership roles with full P&L responsibility, scaling high-growth businesses, leading product and corporate strategy, and guiding organizations through major periods of transformation. She was named a HousingWire Woman of Influence in 2024, an Inman Best in Finance honoree in 2024, and Most Powerful Woman in FinTech by PROGRESS in Lending Association in 2025.
About Jennifer Cashier: Jennifer Cashier is VP of Product for Inhabit’s Short-Term Rental division, where she leads product vision, strategy, and execution across the portfolio. Her work focuses on aligning customer needs, market opportunities, and business goals while shaping AI-driven products that improve efficiency, customer experience, and growth. Across her career, Jennifer has led product and technology initiatives in healthcare, finance, entertainment, and real estate, with a particular focus on AI/ML, data-driven decision-making, and scalable product innovation.
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Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.
Check out the three most downloaded episodes:
- Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
- Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
- Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty
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