The millennial generation comprise 47.1% of the Philippine workforce in 2020 and this number will shoot up to 75% by 2030. In the Philippines, millennials make up 1/3 of its total population and they occupy a significant part of the workforce already, thus shaping the direction of the country’s economy. It has been cited in many surveys which included Filipino participants that “millennials don’t mind job-hopping.” The average is that 6 out of 10 will leave their current job in the next four years. As a growing concern, it is incumbent to look into how these changing interests and expectations of incoming generation of millennial employees can be met and satisfied with focus on adapting the company’s employee engagement and career development programs toward a more effective and responsive retention program. With Structural Equation Modeling (SEM) approach and a survey conducted in selected industries,  results showed that management initiatives and working conditions have the most significant direct effect on millennials’ engagement and job satisfaction which in turn were directly influenced by career expectations, and all together significantly related to meaningful work and fulfillment for employees and goal achievement and organizational efficiency for the company – a win-win strategy desired by employers.