Let’s look into several common money issues in relation to Shabbat.

Payment for Services Rendered on Shabbat

One may pay a gentile for services rendered on Shabbat, e.g. a waitress, or a taxi-driver (when called for someone who is ill). However, payment should not be made on Shabbat. This rule applies even if you avoid handling the money (which is muktzah, “set aside,” and may not be handled), and merely show the non-Jew from where to take his/her payment. This is because payment is a transaction, an act that is forbidden on Shabbat.1

When it is not possible to delay payment until after Shabbat, payment may be made on Shabbat, as suggested above.2 This allowance (“heter”) applies to a case of medical need. Payment of waiters and similar should be pre-arranged in an acceptable manner, making payment before or after Shabbat.

Conversely, services rendered by a Jew on Shabbat may not be charged for. This is termed as sechar Shabbat (“Shabbat compensation”). This raises the question for paying cantors and similar, whose services are rendered on Shabbat. The classic solution is havla’ah (lit. “absorbed”), whereby the contract includes services rendered before or after Shabbat, and the payment is a lump-sum, and the payment for Shabbat is ‘absorbed’ in the package – which includes non-Shabbat time.3

Babysitters

Some rabbinic authorities permit payment given as a gift.4 Contemporary authorities apply this only in a case where the payment is voluntary, e.g. a visiting cantor. Since cantors may sometimes lead the prayers without payment, the payment given after Shabbat therefore may be viewed as a gratuity (“tip”).5

I see merit in applying this line of reasoning in the case of a babysitter who does so on a casual basis, e.g. a close relative or friend, who would babysit for you as a favor too. Hence, the payment afterwards can be defined as a gift. But a “professional” babysitter would have to make avail of the solution of havla’ah, i.e. to agree on a “package” price for Shabbat and non-Shabbat services. This price should not be calculated rigidly on an hourly rate.

Raffle

On Shabbat, one may not draw a raffle whereby the winner will receive a specific article.6 This is particularly relevant to children’s groups held on Shabbat. But it is permitted to distribute tickets for a raffle that will be drawn after Shabbat.7

Vending Machines

One of the pre-war rabbinic authorities permitted the placement of vending machines in public places, although non-Jews will buy from them on Shabbat. His main argument is that those goods could have equally been bought before or after Shabbat.8

Launderette

Here, there is no “sale of goods.” There is, however, the issue of earning money on Shabbat, and it is therefore not permitted.9

Online Retailers

The majority of contemporary rabbinic authorities rule that sale of goods online should not “happen” on Shabbat, and therefore advise to close the (sales function of the) site for Shabbat.10

Even once one does that, there is an additional concern: that someone in a different time-zone may come to use the site when it is Shabbat for him and not for the owner. This is a lesser problem, but facilities have been set up whereby a website is sensitive to the Shabbat time of the customer too!

Mail Order Delivery

The Shulchan Aruch (Code of Jewish Law)11 discusses the delivery of produce on Shabbat by a non-Jew. Provided that the goods are not yet owned by the Jew, delivery may be made, since the non-Jew is engaging with his goods, not the Jew’s. It follows that the mail order delivery may be accepted on Shabbat. But—as indeed is the minhag with regular mail—we should take heed not to take the item from the hand of the non-Jew. Instead, we should ask him to put it down somewhere inside the house.12

Were a moving van to pull up on Shabbat to deliver furniture belonging to a Jew, the law would differ from the above: Since the driver’s non-Shabbat activities would be done on the Jew’s behalf, that delivery is therefore not permitted.