Secure associate ordering and transaction methods and systems. An order for an alternative device different from a baseline device is received at an order processing platform. The alternative device is available for purchase by the associate at a cost differential between the alternative and baseline devices. The cost differential is based on a predetermined enterprise discount. A message including a secure link associated with the order is sent to the associate. Payment information associated with the cost differential is received by a secure payment (SP) platform from the associate via a secure website using the secure link. The payment information is submitted to a payment institution. The order processing platform receives a transaction confirmation from the SP platform when the payment information is accepted and adds at least features of the alternative device associated with the baseline device to a service account of the enterprise customer for the service provider.