The Mid-Year Renewal Trap: How to Stop Getting Caught Off Guard

Janine, an office manager at a growing marketing agency, once shared over coffee, “I’m sure we paid for that project management tool twice this year. It just kept renewing!” She wasn’t alone. A survey of 100 small business owners found 42% admitted they lost track of a SaaS renewal in the past year—and it cost them. 

Renewals aren’t always as predictable as the calendar suggests. Many vendors set odd renewal cycles—mid-year, quarterly, or even based on the date you first signed. That means your team could get blindsided when a big contract auto-renews, draining your budget or tying you to a service you no longer use. 

Let’s cut through the noise and get practical. Here’s how to build a bulletproof system for renewals—without fancy tools or a steep learning curve. 

Step 1: Build a Simple Renewal Calendar 

You don't need a big system to start. A spreadsheet will do, or a shared Google Calendar. The key is to list every contract, subscription, and license in one place-along with the exact renewal date, not just "Q2" or "July-ish." 

One ops leader once joked, "Our renewal dates were like a family secret-only our finance director knew them, and she left in April!" Avoid that mess by giving everyone access. 

Add these columns to your calendar: 

• Vendor name
• Contract owner
• Renewal date
• Auto-renewal? Yes/No
• Current cost
• Notes (anything that might affect renewal, like price increases) 

Don't forget annual services that sneak up mid-year-things like insurance, compliance platforms, or niche tools. 

Of course, if you're ready to move beyond spreadsheets, a tool like BetterTracker can make life a lot easier by centralizing your contracts, keeping renewal dates visible, and sending automated reminders-so nothing falls through the cracks. 

Step 2: Set Calendar Alerts that Actually Get Noticed 

A good calendar is only as good as its reminders. Set alerts at least 60 days before the renewal date. This gives you time to review the service, negotiate terms, or cancel if needed. 

Use tools your team already checks daily-like Slack, Microsoft Teams, or email. Some folks swear by using their personal calendar apps for critical reminders. 

One IT director said, "We get flooded with system notifications all day, so I started setting contract alerts as recurring calendar invites-with ALL CAPS and a 15-minute reminder. That way, it pings me right in the middle of my day." 

Find a reminder system that works for your team-whether it's a shared calendar, a simple spreadsheet, or a dedicated solution like BetterTracker that keeps you on top of renewals automatically. 

Step 3: Assign a Real Owner for Every Contract 

If everyone owns a contract, no one does. Make sure every service, software, or subscription has a clear owner—someone responsible for the renewal decision. 

Here’s a simple way to assign owners: 

• IT owns technical tools (security, infrastructure, development platforms)
• Finance owns accounting software, tax tools, and compliance
• Operations owns facilities and office-related services
• Department heads own team-specific tools