Hi Andrea,
Have a look at our application _PTO Management _>> http://www.clarizen.com/appsmarketplace/item/pto_management.html that should meet your requirements.
If you would like to add additional functionality to this app, this would require customization/custom development and is out of scope via this support channel.
Let me suggest the following options:
We will be happy to build it for you. For that we would need to understand the requirement better to provide with a professional services quote for this. The best approach is to contact your account executive to request a quote from our professional services team for this.
Alternatively, you can also join our free interactive Advanced Q&A sessions ( http://www.clarizen.com/live-demo.html#second). These are great resources for customization consulting with our experts and visual answers to your questions. One of our Customer Success Manager will be able to demo some examples for you and give you guidelines how to build it yourself.
All the best,
Diana