A system and method for facilitating annuity transactions between annuity purchasers and providers via an annuities placement program accessible to the purchasers and providers. Purchasers enter quote solicitation information used by the annuity providers to establish a quote for an annuity. Annuity providers enter a quote in response to the quote solicitation information, and the quote is provided to the purchaser via the annuities placement program. The quote is customized to the annuity purchaser's quote solicitation information. Multiple quotes from multiple providers may be presented to the purchaser for ease of quote comparison. To facilitate such transactions, a discretionary group is established to be a contract holder for each participating annuity provider. A master group contract is established for each of the participating providers, each of which is written by a respective one of the participating annuity providers to the discretionary group to allow the discretionary group to be the contract holder for annuities purchased by the annuity purchasers. In response to an annuity purchase, a certificate of participation is issued to the purchaser from the provider under the terms of the master group contract of that annuity provider, which reflects annuity terms customized to the annuity purchaser.