Background/Objectives: The influence of surgeon expertise on patients' outcomes after repair of acute type A aortic dissection (ATAAD) is not well established. The aim of this paper is to report the results of ATAAD repair performed by expert (ES) and not expert aortic surgeons (NES) in our center. Methods: We have retrospectively divided 199 patients into two groups according to the first surgeon experience (ES = 138 patients and NES = 61 patients), all being members of the aortic team. We evaluated and compared early and long-term outcomes. Results: Although the two groups were comparable in terms of clinical presentation and intraoperative setting, ES performed more aortic arch repairs (40% vs. 26%, p = 0.06) and frozen elephant trunk procedures (15% vs. 3%, p = 0.02), albeit with similar intraoperative times (median cardiopulmonary bypass time of 203 min in ES vs. 201 min in NES, respectively, p = 0.88). The 30-day mortality was the same in the two groups (8%, p = 1), and the postoperative course was similar except for a shorter in-hospital stay in the NES group (10 vs. 17 days, p = 0.04). Conclusions: In our experience, repair of ATAAD could be achieved with similar results between ES and NES. However, NES performed less technically demanding repairs. With standardization of pre-, intra-, and post-operative management, NES can be expected to increase their technical skills and be progressively involved in more complex ATAAD repairs without adversely affecting surgical results.