Rolando was born in Manila and raised in Daly City, California. He was the first in his family to attend and graduate from college, which shapes his commitment to helping young people through the college process. He studied politics and pre-law at Dominican, planning to attend law school, but a work-study job as an admissions student ambassador led him to a career in college admissions and counseling.

After nine years in college admissions at universities in the Bay Area and Honolulu, he "decided to switch to the other side of the desk" and moved to college counseling at independent schools. Before joining Sonoma Academy, he was Director of College Counseling at Woodside Priory, a boarding school in Portola Valley, California.

Rolando aims to celebrate each student's individuality while encouraging them to think big. He mentors new college counselors and volunteers with first-generation students at local public high schools and community organizations. Outside work, he enjoys travel and Wine Country with his wife, a Montessori teacher. He also spends time with his nieces and nephews and watches his father's band, Good Reasons, perform locally.