The high turnover among chief digital officers (CDOs) can be attributed to the challenging nature of data-driven digital transformation, which is more like a metamorphosis than a simple transformation. CDOs often face unrealistic expectations, lack of support from leadership, and resistance from employees due to skepticism about data analytics or inertia. To overcome these challenges, newly hired CDOs should start small and scale fast by targeting less ambitious but important business goals and promoting their successes internally. Employing the modern data stack (MDS) can help eliminate in-house building chores and lay a foundation for an efficient and reliable data and analytics strategy that improves future business outcomes and spurs innovation.