Tech-Enabled Hospitality: Jessica Gillingham on what really moves the needle for STRs

Jessica Gillingham shared a host of enlightening takeaways from her new book – Tech-Enabled Hospitality – during her appearance on the Host Planet Podcast.

Even tech leaders say the human experience matters more than the tools. Yet many property managers use only a fraction of their systems – frustrating vendors who, as Jessica notes, must also improve client education.

Here are some key takeaways from the episode, which is available now on our website, YouTube, Spotify, or Apple.

Tech changes everything – but mindset changes results

Jessica’s research across hotels and STR operators found a clear split: leaders who treat technology as a strategic investment outperform those who see it as a one-off cost or band-aid. The difference isn’t budget; it’s mindset – a vision for how tech will improve operations and the guest journey.

Crucially, every leader she interviewed – even the most tech-forward – said the human experience remains the core of hospitality. Automation can reduce friction and staffing needs, but the goal is still to make people feel looked after. Tech is the enabler; hospitality is the product.

Democratisation, not just disruption

For independent hosts and boutique managers, the good news is that modern tools level the playing field. With a small portfolio, you can now run professional-grade operations – pricing, IoT access, communications, and marketing – at a standard that used to require big-brand resources. That’s tech’s greatest gift to STRs: democratisation.

At the same time, operators told Jessica they value stability over novelty. Shiny start-ups are exciting, but managers want vendors who can stick around, scale with them, and act like partners – not just software suppliers.

Key takeaway from Tech-Enabled Hospitality: operators are failing to use 80% of utility

One uncomfortable finding: many companies use only about 20% of their tools’ capabilities. Some of that’s on vendors (onboarding and education), but part of it is internal – teams chasing the next tool before fully deploying the one they have. Jessica’s advice: diagnose the real problem first, then sandbox and trial solutions before rolling them out.

The future: personalisation, attributes, and lifetime value

AI is pushing hospitality towards true personalisation – not just name-merge emails, but context-aware experiences across operations and guest comms. We’re not fully there yet, but the trajectory is clear. For STRs, that pairs with two commercial shifts Jessica highlights: attribute-based selling (charging for what guests value within a stay) and thinking in terms of lifetime value, not just one-off bookings. Loyalty in STRs won’t look like hotels’ points programmes; it will be relationship-led – recognition, relevance, and reasons to return.

PR matters more in the age of LLMs like ChatGPT

As large language models like ChatGPT surface answers from “trusted” sources, earned media – credible press, reputable industry sites, and consistent thought leadership – matters more than ever. If you want AI (and humans) to “find” your brand, you need visibility beyond your own website. That’s where disciplined PR and positioning pay off.

What great brands do differently

From Jessica’s vantage point advising many of the sector’s standout companies, the differentiator is leadership: clarity of vision, willingness to take calculated risks, commitment to consistency, and a product that puts customers at the centre. You can’t PR your way past a weak experience – but if your product is strong, strategic communications can accelerate trust and adoption.

Tech-Enabled Hospitality is out now, and Jessica is active on LinkedIn if you want to continue the conversation. For STR operators wondering where to focus next, her message is refreshingly clear: keep hospitality human, make technology intentional, and communicate your value – consistently.