NB: It appears that the recent versions of Quicken for Mac aren't able to export the transactions in a supported file format.
To start, you need to export your transactions for each account from Quicken, see this article from Quicken for details about exporting from Quicken. Once you have exported all of your accounts from Quicken, you can then import them into PocketSmith using the express migration tool.
There are 2 ways to reach the express migration tool, one if you have a new PocketSmith account and another if you already have a PocketSmith account. Details on how to find the express migration tool are below or go directly there by going to my.pocketsmith.com/setup/quicken
New PocketSmith account
If you are starting with a new PocketSmith account, select Migrate your accounts when you login into PocketSmith and the express migration tool will open
Existing PocketSmith account
If you already have a PocketSmith accounts, with other accounts, go to the Accounts menu and select Account Summary
On the Account Summary page, go to New offline account in the toolbar and select Express migration tool
Express migration tool
When the express migration tool is open, select Quicken
You can then either select the files you have exported from Quicken and drag and drop them onto the page or select the Quicken files by clicking the Choose Files button
When you have added your Quicken files, they will be uploaded to PocketSmith and will then show in the express migration tool
Click Choose/create account for each file and either select an existing account or create a new account by typing the new account name and clicking Create account: [account name]
Click Choose/create bank to choose the institution, either select an existing institution or create a new institution by typing the new institution name and clicking Create institution: [institution name]
Enter the current balance of the account
Once all Quicken files have account, institution names and a current balance click the Start import button
The Quicken files will then be imported into your PocketSmith account, once the import is complete, you can view the imported transactions by clicking on the Categorize [number] transactions button
You have now migrated from Quicken to PocketSmith.
You may now want to connect your accounts to a Live Feed, so that they are updated with new transactions. To connect the newly imported accounts to a Live Feed, see the article: Setting up a Live Feed