Why Key Collective Management left, then returned, to Guesty

Key Collective Management operates a growing portfolio of 22 vacation rentals. Founded by Emily Wade, the business manages properties across Tennessee and Georgia, having expanded significantly during the pandemic as remote work trends drove demand for longer stays. Today, the company focuses on delivering high-quality guest experiences while maintaining efficient operations in a competitive market.

After using Guesty successfully for four years, Key Collective Management decided to switch to a competitor, Journey, lured by promises of advanced AI guest communication. However, the move quickly exposed critical operational gaps that threatened the stability of the business. The most immediate source of friction was the unreliability of “nesting rules” (smart calendar rules). Despite assurances that settings were correct, the system failed to block dates accurately, forcing the team to constantly monitor the calendar manually to prevent double bookings.

Beyond calendar anxiety, the promised owner portal never materialized, leaving property owners without visibility into their data. The accounting features were equally rigid; Wade could not customize commission formulas to deduct fees correctly before the split, nor could she apply different commission rates for specific owners. This forced her team back into manual workflows, requiring them to build end-of-month owner statements by hand — a time-consuming process that stifled scalability.

Wade chose to return to Guesty because she needed a partner, not just a platform. The decision was driven by the maturity of Guesty’s product, particularly the robust accounting and owner management features that the competitor lacked.

With the return to Guesty, the team restored confidence in their operations. The reliable multi-calendar eliminated the fear of double bookings, removing the need for constant manual verification. Furthermore, leveraging Guesty’s customizable accounting features meant the team no longer had to calculate commissions manually or generate owner statements outside the system.

Now fully migrated back, the Key Collective Management team — including an operations manager and guest communication lead — is utilizing Guesty’s automation to its full potential. They are consolidating their tech stack by replacing third-party tools like Breezeway and Turno with Guesty’s native Tasks feature, streamlining operations into a single dashboard.

With the basics automated, they have set up detailed workflows to handle guest inquiries instantly and are rolling out the Owner Portal to give clients transparency and the ability to block dates for personal use.

With their operations stabilized, Wade plans to shift her focus from crisis management back to growth. The immediate goal is to expand the portfolio by onboarding new properties in the Tennessee and Georgia markets. Additionally, the team plans to leverage their guest data for targeted email marketing campaigns to drive repeat business — a strategy that was previously impossible while they were bogged down by manual administrative tasks.