Yes they did. It is inaccurate to depict the Medinan society of the Prophet (saw) as one where the men worked and the women were exclusively supported by them. This was the general pattern but women also worked as employees or business owners.
Al-Rabī bint Muawwadh and al-Ḥawlā used to make perfumes in Madīnah and sell them. (Ibn Sa'd in al-Ṭabaqāt and Ibn Ḥajar in al-Iṣābah respectively)
The Prophet's wife Zaynab (ra) used to sew and embroider things for sale and give from her earnings in charity. (Muslim)
The Prophet (saw) entered the date farm of Umm Bishr al-Anṣāriyyah. (Muslim)
Umm Sulayṭ used to make leather water skins. (al-Bukhāri)
Umm Shurayk used to own and run a guesthouse. (Ibn Abdul-Barr in al-Istī'āb)
The Prophet's (saw) minbar was made by a woman's carpentry business. (Muslim)
Ibn Masūd's wife used to work and support him. (Aḥmad)
Jābir narrates, "My aunt was divorced and she wanted to go out to collect the dates from her farm. A man told her to go back to her home. She went to the Prophet
(saw) and he said, "No, go collect your dates. Perhaps you may give in charity or do something good with them.""(Muslim)
There are guidelines that should be adhered to that are detailed in the books of fiqh:
1.The work must be permissible in its nature.
2.It will not cause fitnah.
3.It does not conflict with the rights of others like the husband and children.
4.The permission of the wali is taken.