Hi @KyleRisi,
I have several custom properties on my Contact/Company view in HubSpot. Some of these I use for renewal dates.
You could have, for example, Annual Subscription Renewal Date property and 3-Month Subscription Renewal Date. Set values for these, then use Active Lists to list all companies where e.g. Annual Subscription Renewal Date is in the next 2 months.
You can even select all these contacts and add them to a task queue (or bulk enrol in a sequence - e.g. “Annual Subscription due in 2 months”).
Hope this helps. May not be the best method, but it works for me. I’m not sure if there’s smarter things that can be done using functionality I don’t have access to (Workflows, for example) - always keen to hear ideas from the community on how I can further improve my processes!