This dissertation explores three areas where managerial discretion can impact firm outcomes. The in the first essay examines how CEOs with a career background in sales and marketing, “Sales CEOs”, impact operating outcomes at the firm. We find that firms with a Sales CEO control larger market shares, increase market shares when a Sales CEO is hired, and during industry sales downturns experience lower decreases in sales and market value. We also explore outside perception of Sales CEOs firms. We find that firms with Sales CEOs exhibit increases in institutional ownership when the Sales CEO is hired. We also find that Sales CEOs meet or beat analyst expectations more frequently than their non-sales and marketing peers. The second essay focuses on the market’s perception of uncertainty about a firm when Sales CEOs are present. We document larger decreases in uncertainty when Sales CEOs are hired and when Sales CEOs release earnings announcements, relative to their non-sales and marketing peers. We hypothesize and find that our set of Sales CEOs communicate more frequently with investors, and that communication tends to be more readable and positive. The third essay focuses on managerial discretion when estimating bad debt expense around hospital bond issuance. We hypothesize and find that managers under report bad debt expense prior to bond issuance. Further, we find that hospitals that significantly underreport bad debt expense experience significantly lower cost of debt when issuing bonds. Finally, we identify discretionary charity care as one channel that hospitals may misclassify bad debt expense as charity care.