Navigating the Career Labyrinth: From Intern to Director

In this candid and insightful talk, Jeff Sing walks us through his professional journey from entry-level intern to Director of Engineering at a high-growth tech company. Drawing on over a decade of experience in Quality Engineering and Engineering Operations, Jeff shares the hard-won lessons, strategic decisions, and honest missteps that shaped his path upward. Attendees will hear real-world anecdotes about moving through the ranks—what worked, what didn’t, and how he identified the right opportunities, mentors, and mindsets to keep growing.

Beyond just climbing the ladder, Jeff offers a rare dual perspective: both as someone who’s navigated the journey and as a leader who now hires, promotes, and coaches others through theirs. He’ll pull back the curtain on what no one tells you about the expectations at each level, from individual contributor to people manager and beyond. Whether you're just starting out or considering your next big leap, this talk will equip you with practical frameworks, reflective questions, and a healthy dose of reality to help chart your own course through the career maze.

Jeff Sing

Jeff Sing is a Quality Leader who has been in the testing industry for over 15 years. During this time, he has built automation frameworks, test strategies, and executed quality initiatives for fields such as medical devices, infrastructure security, web identification, marketing tech, and experimentation and progressive delivery. Jeff is currently a Director of Engineering at Iterable where he leads the Quality Engineering organization to orchestrate their quality control plan utilizing a combination of automated testing, implementing QA procedures, and acts as Iterable‘s customer experience champion to ensure Iterable remains the world's leading customer engagement platform. He also has built and leads Iterable‘s Engineering Operations Team, which runs the services and programs to systematically improve effectiveness and productivity across the engineering organization as it scales.