Objective Examine the characteristics of recent head and neck oncology (H&N) fellowship graduates and assess their current perceptions of career alignment and satisfaction. Methods H&N fellowship graduates from American Head & Neck Society (AHNS)-accredited programs between 2015 to 2020 were surveyed. Two-sample t-tests and analysis of variance tests were used to determine the effect of respondents’ demographics, fellowship characteristics, career preferences, and current practice on their degree of career alignment with expectations and overall job satisfaction. Results Fifty-eight fellowship graduates completed the cross-sectional survey. Fifty-two of all respondents (89.7%) primarily preferred an academic job, of whom 5 (9.6%) went into private practice. Respondents in private practice, those treating general Otolaryngology patients, or those who do not work with residents demonstrated significantly poorer job alignment and career satisfaction compared to those in academic medicine, those only treating H&N patients, or those working with residents, respectively. Discussion The number of desirable academic positions each year may be insufficient for graduating fellows. By setting realistic career expectations, planning for a mixed scope of practice, and integrating resident involvement into private practice groups, H&N providers may ultimately find more fulfillment in their work. These findings could be valuable to fellowship programs in designing training and to future H&N fellows in their career planning. Further studies with higher power would be warranted to identify other indicators of H&N career satisfaction and ways to reduce physician burnout.