Although they can be difficult to implement, employee-friendly workplaces, with generous compensation, schedule flexibility, and perks, foster more satisfied and productive employees than traditional work environments. Transforming a work environment from conventional to more liberal, and likely more satisfying, takes a certain type of leader. This study seeks to understand in what ways the “100 Best Companies to Work For” CEOs differ from traditionally successful, Fortune 500 CEOs. Using political affiliation as a proxy for openness to change, we test our hypothesis that Best Company CEOs are more open to change, and therefore, more left-leaning than Fortune 500 CEOs. We use campaign contributions of CEOs from the top 100 Fortune 500 companies and the “100 Best Companies to Work For” to discern whether executive receptiveness to change differs between these two groups. Our OLS probit model provides strong evidence that companies in Republican industries (i.e. aerospace, defense, petroleum, etc.) and companies with right-leaning CEOs are unlikely to be Best Companies. We also find that being identified as a Best Company in the short-term is best achieved through inexpensive perks, while being identified as a Best Company in the long-term requires strong compensation, sabbatical options, and vacation time.