It may seem like the answer is really “never”, but the best time is “now”. Staff should not have to manage day to day with an inadequate property management system guessing their way through reports and constantly backtracking guest information. Independent hotels should not fear the transition, Skyware provides personalized onboarding and hands-on training, ensuring your team feels confident and prepared. Switching to a new PMS at the perfect time should help turn the transition into a strategic opportunity rather than a disruption.

Top Factors To Consider When Deciding The Best Time To Switch Your Property Management Software

• Shoulder Season: With fewer guests and lower occupancy, your staff can focus on learning the new system without being overwhelmed by day-to-day demands.
• Before Major Seasonal Peaks: For resorts with strong seasonality (ski, beach, summer, etc.), aim to complete the switch well before your busiest season starts.
• After Budget Planning / Fiscal Year Start: Many resorts align tech investments with their fiscal year. Starting right after budget approval ensures you’ve got financial backing and strategic clarity.
• When You’re Undergoing Other Tech or Operational Updates: If you’re already upgrading your POS, CRS, or CRM, it can be efficient to integrate a new PMS at the same time.

Picking the right time is never obvious! Unlike big hotel chains with full IT teams, independent resorts often rely on a small group of staff wearing many hats, which can make the transition to a new system feel overwhelming. The key to success is dedicating focused time for training and choosing the right partner who will guide you every step of the way. Be cautious of vendors offering only limited training hours! Consistent, personalized support makes all the difference. No matter when the decision is made to switch your PMS, Skyware will provide personalized training and hands-on support with your team.

If your independent hotel or resort is ready to upgrade to Skyware’s simply better all-in-one property management software, don’t wait any longer to contact us by calling 877-759-9329, emailing [email protected] or by completing our Contact Us form.