Descriptive data on the state of the U.S. superintendency have been collected approximately every 10 years since 1923; yet no comprehensive data were collected on the characteristics, career paths, recruiting, and retention of ASOS heads between 1993 and 2011. This study gathered current data on the characteristics and career paths of ASOS heads; identified changes that occurred between the 1992-93 and 2010-11 school years; and provided valuable data on factors impacting recruiting and retention. Results from a sample of 157 ASOS heads (80.9% response rate) showed that current heads were older than their 1992-93 counterparts upon becoming an administrator and then head for the first time, and when responding to the survey. They were also more experienced educators upon becoming a head. They spanned a wider range of ages at the time of response and had a wider range of teaching and administrative backgrounds prior to becoming a head. They were more likely to have served as vice principal and less likely to have served as principal. School size and heads' salaries were highly correlated and those with performance related, negotiated salaries earned the most. Though the mean length of stay as a head remained steady, small school heads served significantly fewer years than their medium and large school counterparts. Only 51.6% of the sampled heads reported intent to be serving as head in five years with 22.9% of heads intending to leave the headship but not retire. The results suggested several keys to increasing the pool of ASOS head candidates. They included understanding why heads have obtained a broader range of experiences and thus have waited longer to enter the headship, focusing on mentoring more women into the headship and implementing succession planning, recruiting a broader range of head candidates including former U.S. superintendents, and focusing on increasing the retention of ASOS heads through enhanced board and head training in order to strengthen board-head relationships. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]