Advances in the health IT sector have had a profound positive impact on the economy, to include demands for a skilled IT workforce. Yet, findings from the HIMSS’s December 2015 Compensation Survey and the 27th Annual HIMSS Leadership Survey raise questions surrounding the efficacy of the sector’s IT staff recruitment and retention practices. Evidence from the Compensation Survey, for example, suggest female health IT workers are being marginalized in this sector of the economy. Analyzed several different ways, women consistently earn less than their male counterparts. The findings also suggest females are under-represented in IT-related executive and senior management roles in the health sector. Our questions regarding recruitment/retention practices extend to the emerging clinical IT executive role. With data from the Leadership Survey strongly suggesting clinical IT executives have a notable impact on a healthcare organization’s orientation toward IT, healthcare organizations are encouraged to review their efforts to ensure clinical IT executives have a “voice” within their organization.