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I am seeking a tool that offers the features to
1. export data, using filters, from a legacy organization
2. map that data to a existing or new structures in a new org, example

Leads with set of custom fields
to
Leads with association to custom object containing those legacy fields
or
Legacy Object fields to different fields in the new corresponding Object

  1. Load the data and most importantly, preserve the relationships from the legacy information, example

    Account owners (users) to Accounts (mapping newly created Users)
    Lead/Contact Owners to Users (mapping newly created Users)
    Opportunities to Contacts
    Cases to Accounts
    etc

I envision some wizard-like utility that allows the user to simultaneously log into and access the data/structures of two different orgs, and present a filter for exporting legacy data, and a mapping utility for mapping the fields between legacy and new objects.

Then, once all legacy objects/fields (to be migrated) are mapped, pushing a button to actually move the data, taking into account number of records being transferred, and "chunking" appropriately.

Is this a pipe dream, or does such a thing exist?

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Informatica cloud will be suitable for this use case. You can install trial version for one month from app exchange. It gives features like querying data from multiple tables, defining custom mapping, populating lookups etc. Also there is a process builder, which allows you to get data from multiple sources and do processing like VLOOKUP and load data to target. It also allows to schedule data syncing operation.

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You can go with Either DBSync or Informatica for your requirement.

Both are available in the Salesforce App Exchange. Both these apps provides free trial for one month. You will be able to query from multiple table and provide features to map fields across two platforms. You can provide filters and conditions. To Preserve the Relationship you can use either LINK or TLOOKUPS. You have to create two salesforce Adapters with different names. Assign each adapter for Different Salesforce Orgs and map fields from the Source Org to Target.

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Being with it is definitely not a dream and there are quite a few tools to do or implement what you have described above. They are also available at a great price point. You can choose any of them to implement it depending upon your priority.

Note these points when choosing one among them in market:

  1. It should have a core-engine which lets you choose between multiple applications and use them as your Source and Target connectors.
  2. Once you establish your Source & Target connectors, the schemas of both target and source should be exposed for you to pick and choose fields you want to map.
  3. It should support establishing various relationships like Lookup, Master-Detail which are more specific to Salesforce.
  4. It should be configurable or define direction of the sync as well.
  5. Once all these processes are laid out, it should be able to schedule times and filters for a sync based on your business process.

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