Aaron Sims

A distinguished career in the Medicare industry, beginning with the establishment of a boutique agency in Topeka, Kansas. Through strategic growth and operational excellence, the firm achieved $5 million in annual premium volume prior to a successful acquisition.

Subsequently founded Oracle Marketing, scaling the enterprise to exceed $70 million in Medicare Supplement premium annually—a testament to sustained leadership in a highly competitive sector.

Throughout this trajectory, demonstrated a commitment to industry innovation by pioneering automated underwriting technology through ebbie.ai and orchestrating the launch of the first direct-to-consumer Medicare Supplement plan in partnership with Aetna and SilverScript in 2019.

Having established a proven record of building and scaling successful Medicare enterprises, a critical insight emerged: consumers required education, not sales tactics. This conviction led to the creation of EnrollMedicare.com—now the largest privately held Medicare education resource in the nation. The platform remains entirely free of charge, a permanent commitment to empowering beneficiaries with the knowledge they need to make informed decisions.