In response to receiving a request from a querying entity, such as a seller of goods or services, embodiments of a service engine present to a client computing device of the querying entity a set of queries about goods or services sold by the querying entity and other characteristics of the business of the querying entity. The service engine may intelligently determine which queries to present based on responses to preceding queries. The service engine may then compare the entries in response to the queries against stored rules for a one or more of a plurality of tax jurisdictions, the stored rules being about establishing nexus for purposes of remitting transaction tax in the certain tax jurisdiction. The service engine may then determine information regarding potential lack of tax compliance of the querying entity based on the comparison, and notify accordingly.