Tim Prugar is the Head of Product and Engineering at fileAI, a Series A company solving the challenge of extracting insights and automating processes from unstructured data. With extensive experience in product development, engineering leadership, and strategic growth, Tim has played a crucial role in scaling technology-driven businesses. His expertise spans operational leadership and technical strategy, making him a trusted advisor to entrepreneurs and product leaders.

A Proven Track Record in Product and Engineering Leadership

Before joining fileAI, Tim was VP of Operations and Product Owner at Next Caller (YC14). As a key leadership team member, he helped grow the company and guided it through a successful acquisition by Pindrop Security in 2021. After the acquisition, he transitioned into the role of Chief of Staff to the CTO at Pindrop, implementing scalable processes to enhance the company’s product and engineering capabilities.

At Pindrop, Tim streamlined engineering workflows, improved collaboration between product and technical teams, and ensured the company’s technology roadmap was aligned with strategic goals. His deep understanding of team leadership, operational scaling, and product ownership made him a pivotal figure in the company’s post-acquisition growth.

Expanding Global Presence and Technical Leadership

In 2022, Tim relocated to Singapore to establish Pindrop’s Asia-Pacific and Japan office, serving as the lead technical resource for the region. His expertise in navigating global markets and managing cross-functional teams positioned Pindrop for successful expansion.

Setting up operations in a new region required adapting to local market conditions, engaging with partners and customers, and ensuring that Pindrop’s offerings met regulatory and business requirements. His experience in building international teams, identifying business opportunities, and structuring technical partnerships helped drive Pindrop’s strategic growth across APAC.

A Unique Journey from Education to Technology

Tim’s career journey is unconventional—he began as a middle school teacher, Dean of Students, and wrestling coach before transitioning into tech. His background in education developed his leadership, mentorship, and communication skills, which have been instrumental in his success in the technology sector.

His early experiences shaped his team-building philosophy, equipping him with the ability to nurture high-performing teams and guide them in solving complex challenges with confidence. This approach has been a critical factor in his leadership success.

Guiding Businesses Through Growth and Transformation

-          With extensive experience in high-growth environments, Tim provides valuable guidance in several key areas:

-          Building and Scaling Product and Engineering Teams – Creating effective teams, fostering collaboration, and implementing best practices for sustainable growth.

-          Partner Selection and Alignment – Ensuring businesses choose the right partners and drive mutual success.

-          Investor Relations and Management – Investor expectations and stakeholder relationships.

-          Mergers and Acquisitions (M&A) – Leading businesses through acquisitions, integrations, and post-M&A transitions.

A Mentor Committed to Sharing Hard-Earned Wisdom

Tim firmly believes in the power of experience to shape good judgment. As his mother wisely said, “Good judgment comes from experience, and experience comes from poor judgment.”

Having learned from his own journey, Tim is passionate about mentoring and advising others. He provides start-up founders, product leaders, and engineers with the insights, frameworks, and strategies they need to accelerate growth and avoid common pitfalls.

His hands-on leadership and mentorship approach ensures that the individuals and teams he supports receive practical, real-world guidance tailored to their unique challenges. He actively fosters a culture of learning, collaboration, and experimentation, creating environments where innovation flourishes.

Driving the Future of Product and Engineering

Tim continues to push the boundaries of product development, engineering leadership, and business strategy. His ability to bridge technical and business challenges makes him an invaluable resource for companies looking to scale, innovate, and build resilient product and engineering teams.

As Head of Product and Engineering at fileAI, Tim remains committed to empowering start-ups, scale-ups, and enterprises with cutting-edge technology solutions. His leadership, combined with his deep expertise in mentorship, strategy, and technical innovation, ensures that the businesses he supports are set up for long-term success.

Whether guiding teams through high-growth phases, helping organisations align business and technology objectives, or mentoring the next generation of product and engineering leaders, Tim remains a trusted advisor, strategist, and mentor. His unique blend of experience, technical expertise, and leadership skills positions him as a valuable partner for any organisation looking to thrive in an increasingly digital world.