While TripIt does not offer phone support (with two exceptions), our help pages combined with our email support work very well to answer and solve user questions and issues.
If you cannot find the information you need on our help pages please contact us using http://www.tripit.com/uhp/feedback. (To avoid the captcha sign in to your account prior to using the feedback form.) Our support team is here to assist you Monday - Friday.
All support email is permanently housed in our tracking system allowing TripIt and you to keep a record of all interactions as well as providing a detailed report for TripIt on all user issues and enhancement requests
If you are a TripIt Pro subscriber be sure to select 'TripIt Pro Members (premium account)' as your category in the 'Type of Feedback' dropdown menu. This will prioritize your question to our premium user queue (after we verify your's is a Pro account).
Billing: We do offer a phone number if you have a billing question on your TripIt Pro subscription or TripIt for Teams account. Information on contacting TripIt with billing/credit card charge questions can be found at http://help.tripit.com/entries/20408623