Jonathan Masland brings over a decade of coaching, advising, and career leadership experience to his work with undergraduate students at Fortuna. His work focuses on helping students tell their story in a compelling, authentic way – one that deepens self-understanding and clearly resonates with admissions committees.

As Executive Director of Career Services at the Tuck School of Business at Dartmouth, Jonathan worked closely with admissions and coached hundreds of students pursuing careers across finance, consulting, technology, healthcare, energy, and entrepreneurship. This experience informs his approach to undergraduate advising: helping students connect their interests, experiences, and aspirations into a coherent narrative with real-world grounding.

Jonathan began his coaching journey as a collegiate squash coach at Harvard, his alma mater. While earning a dual MBA/MA through the Wharton–Lauder Program, he served as a resident advisor for first-year undergraduate students, gaining firsthand insight into the academic and personal transitions that define the early college years.

His professional background includes investment banking and healthcare M&A, as well as entrepreneurship. He has co-founded a fintech startup in San Francisco, built and operates a food-truck leasing business, helped develop rural broadband infrastructure, and works closely with an education startup in India alongside a Dartmouth alumnus.

Today, Jonathan coaches both undergraduate and MBA applicants, collaborates on educational programs in India, and pursues entrepreneurial ventures. He lives near Dartmouth with his family and enjoys skiing and hiking in the mountains and running on the trails around campus.