Breaking Into Tech: Journeys of Sid Sachdeva, Paulo Carini, Haley Prestwood, and Darian Riley

In this special episode of The Agile Coach Podcast, we bring together four inspiring guests: Sid Sachdeva, Paulo Carini, Haley Prestwood, and Darian Riley, each sharing their unique path into the tech industry.

From international students navigating visa challenges to career changers leveraging non-technical backgrounds, this episode is packed with practical advice, candid reflections, and actionable strategies for anyone aspiring to break into tech roles like Product Manager, Scrum Master, or Agile Coach.

Key Topics & Insights

1. Overcoming Barriers as International Students

Sid Sachdeva and Paulo Carini recount their experiences moving to the U.S. for education, facing uncertainties, and navigating the additional hurdles of visa sponsorship and limited interview opportunities.

They emphasize the importance of persistence, networking, and standing out by being resourceful and indispensable to their teams.

2. Leveraging Non-Traditional Backgrounds

Haley Prestwood and Darian Riley highlight how skills from unrelated fields, such as philosophy, politics, law, and even Division I basketball coaching, can translate into tech roles.

Both stress the value of soft skills: communication, facilitation, and leadership, which are often more critical than technical expertise for roles like Scrum Master and Product Manager.

3. The Power of Mentorship and Community

All guests credit mentorship, peer support, and structured bootcamps (like the Agile Coach Program) as pivotal in their transitions.

Mock interviews, feedback from experienced practitioners, and ongoing community support helped them build confidence and refine their approach to job applications and interviews.