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

The Agile Coach Podcast

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.

4. Mindset Shifts and Dealing with Imposter Syndrome

Haley and Sid discuss the emotional journey, moving from self-doubt and imposter syndrome to confidence and self-advocacy.

They encourage listeners to "lean into discomfort," ask questions, and recognize that growth happens outside the comfort zone.

5. Practical Job Search Strategies

The guests share actionable tactics: rigorous interview prep, building detailed Q&A documents, practicing with mentors, and making themselves available for opportunities at any time.

Paulo and Sid note the importance of being proactive, applying to many positions, and not being discouraged by rejections, especially as international candidates.

6. Transitioning and Thriving in Tech Roles

Once in their roles, guests focused on continuous learning, building relationships with team members, and seeking feedback.

Darian Riley, now a senior agile leader, describes how coaching and servant leadership skills from sports directly informed his agile practice, team empowerment, and ability to drive business value.

7. Embracing Remote Work and Flexibility

Haley and Paulo reflect on the benefits and adjustments of remote work, including the freedom to travel and the need for self-discipline and asynchronous communication.

8. The Role of AI and Continuous Upskilling

The panel discusses how AI tools are transforming learning and productivity, making it easier to upskill and adapt to new challenges in tech.

KEY TAKEAWAYS:

Persistence Pays Off: Breaking into tech, especially as an international student or career changer, requires resilience, relentless application, and a willingness to stand out.

Soft Skills Matter: Communication, leadership, and adaptability often outweigh technical skills, especially in agile roles.

Mentorship Accelerates Growth: Seek out mentors, practice interviews, and leverage community resources.

Mindset is Everything: Overcoming self-doubt and embracing discomfort are crucial for growth.

Be Proactive and Prepared: Prepare extensively for interviews, make yourself available, and treat every opportunity as potentially life-changing.

Continuous Learning: Invest in your own growth, leverage AI tools, and never stop improving.