In this episode of The Unchecked-In Podcast, Bobby Marhamat sits down with Jacob Messina, CEO of Stayntouch, a cloud-native PMS helping hotels streamline operations and deliver exceptional guest experiences.

Jacob shares insights from his journey across hospitality—from working in restaurants as a teen, to leading operations at Lowe’s Hotels and MCR Hotels, to now driving innovation in hotel technology. He dives into the real challenges hotel operators face with tech adoption, why independent hotels often outperform big brands in flexibility and guest experience, and how AI and automation can enhance—but not replace—the human touch in hospitality.

What you’ll learn in this episode:

• How to approach hotel technology without fear of choosing the “wrong” system
• The balance between automation, AI, and personalized guest experiences
• Key operational processes that drive the biggest impact on staff and guest satisfaction
• Lessons learned from mistakes early in Jacob’s career and how they shaped his leadership
• The philosophy behind roadmap planning, prioritizing customer requests, and standardization
• Insights on change management and making technology actually work for your team

Links:
Jacob on LinkedIn: https://www.linkedin.com/in/jacob-messina-b6361311

Company Website: https://www.stayntouch.com/

Connect with Bobby Marhamat:
Website: https://bobbymarhamat.com/
Facebook: https://www.facebook.com/bobbymarhamat/
LinkedIn: https://www.linkedin.com/in/bobbymarhamat/
Instagram: https://www.instagram.com/bobbyhabanero

AI Hotel Revenue Management Software | TakeUp
TakeUp: https://takeup.ai/
LinkedIn: https://www.linkedin.com/company/takeup-ai/
Instagram: https://www.instagram.com/takeupforhospitality
Facebook: https://www.facebook.com/takeupforhospitality
YouTube: https://www.youtube.com/@TakeUp-for-hospitality

Heather Shannon runs Speckled Hen Inn with a pricing strategy that contradicts what most revenue management systems recommend: she ignores competitor rates completely. After nine years of building a working farm operation with 35+ organic crops integrated into daily service, her approach centers on creating experiences competitors can't replicate—guests return years later naming the specific lambs they bottle-fed, not comparing room rates.

Her operational framework came from expensive failures. An emergency renovation during peak season cost 45 days of revenue and nearly broke the business, leading to a specific capital reserve formula she now considers non-negotiable. Year three brought an operational crisis when dietary restrictions exploded—handling five simultaneous special diets for 10-12 guests at one table forced a complete service model redesign from traditional single-plate breakfast to menu-based operations. The contractor relationships that saved the business during the renovation crisis were built through a simple daily feeding program that converted transactional vendors into long-term partners offering emergency discounts.

Topics discussed:

• Capital reserve calculation using 30 days of highest room rate revenue as emergency fund baseline
• Single-plate to menu-based breakfast transition for handling gluten-free, dairy-free, keto, vegetarian, and vegan simultaneously without separate prep
• Daily contractor feeding program that converts vendor relationships into partnership discounts
• Rate-setting approach that eliminates competitive comparison in favor of unique value positioning
• Operating 35+ organic crop farm-to-table model without additional kitchen staff
• Succession planning realities for aging owner-operators without exit buyers

Meredith Garrett operates Nashville party properties and remote Smoky Mountains resorts including 45-foot treehouses and glamping domes. She reveals why 8 units isn't enough to make remote hospitality profitable, the specific staffing math that changes at scale, and how to price experiences where no traditional comps exist, plus the misalignment between marketing and service delivery that most operators miss when occupancy drops.

From navigating spiral staircases with guest luggage to managing expectation gaps between luxury glamping and actual camping, Garrett shares the operational frameworks that determine when to deploy staff versus recalibrate guests remotely. She also breaks down her crowdfunding launch strategy that created founding members at permanent discount rates who now bring full-price friends, solving both launch revenue and repeat business simultaneously.

Topics Discussed:

• Why 10-12 units is the minimum threshold for remote property profitability
• Consecutive 12-hour on-site shifts versus dispatch-based staffing economics
• Pricing unique properties through market learning when direct comps don't exist
• The service delivery-ADR alignment framework for diagnosing booking problems
• Deploying staff after-hours versus remote expectation recalibration decision matrix
• Crowdfunding founding members at permanent discount rates who bring full-price guests
• Builder inexperience costs on unique products requiring larger financial buffers
• Operational complexity creating ADR floors regardless of occupancy pressure