Background The advancement of surgical science relies on educating new generations of surgeon-scientists. Career development awards (K Awards) from the National Institutes of Health, often considered a marker of early academic success, are one way physician-scientists may foster skills through a mentored research experience. This study aimed to develop a conceptual framework to understand institutional support and other factors leading to a K Award. Methods A national, qualitative study was conducted with academic surgeons. Participants included 15 K Awardees and 12 surgery department Chairs. Purposive sampling ensured a diverse range of experiences. Semistructured, in-depth telephone interviews were conducted. Interviews were audio recorded and transcribed verbatim, and 2 reviewers analyzed the transcripts using Grounded Theory methodology. Results Participants described individual and institutional factors contributing to success. K Awardees cited personal factors such as perseverance and team leadership skills. Chairs described the K Awardee as an institutional “investment” requiring protected time for research, financial support, and mentorship. Both K Awardees and Chairs identified a number of challenges unique to the surgeon-scientist, including financial strains and competing clinical demands. Conclusion Institutional support for surgeons pursuing K Awards is a complex investment with significant initial costs to the department. Chairs act as stewards of institutional resources and support those surgeon-scientists most likely to be successful. Although the K Award pathway is one way to develop surgeon-scientists, financial burdens and challenges may limit its usefulness. These findings, however, may better prepare young surgeons to develop career plans and identify new mechanisms for academic productivity.