It started with a simple idea from James Tyack: “What if we hosted a hackathon at ELC Annual?” The result was a unique experiment where 14 senior engineering leaders stepped away from strategy to build and ship functioning apps in one weekend, unlocking new insights on AI-native workflows, "vibe coding," and the future of engineering. In this episode, we deconstruct the entire hackathon operational playbook, sharing lessons on everything from “best failure awards” and async collaboration structures to structuring ideation periods for maximum business alignment. Beyond the logistics, we explore how getting hands-on helped these leaders overcome imposter syndrome and why "rolling up your sleeves" is now a prerequisite for leading effective engineering teams. Plus, James shares how he plans to evolve the hackathon format at ELC and beyond. If you’ve been curious about leveraging hackathons to drive innovation, expose your team to new tools, or evolve how your org builds, this episode provides the blueprint for successful implementation.

James is an engineering manager with a passion for people, technology, and learning. He's built and led distributed, diverse teams of engineers across locations and timezones for 10 years. James believes strongly in the value of diversity and championing a sense of belonging for everyone, from day 1. He's well versed in growth strategy, chaos engineering, major incident response, and blameless practice, and culture grounded by trust and psychological safety. He leads the Growth Acquisition team at Coursera where he's proud to be part of an organization that's transforming lives through learning. Previously, James enjoyed building and leading the Growth and Integrations engineering teams at PagerDuty.

Span is the AI-native developer intelligence platform bringing clarity to engineering organizations with a holistic, human-centered approach to developer productivity.

If you want a complete picture of your engineering impact and health, drive high performance, and make smarter business decisions…

• The results of ELC’s first-ever hackathon: 14 leaders shipping fully functional apps (2:21)
• The “Scrappy” beginning: Extending the invitation and early community engagement (4:50)
• The most surprising insights: Problem solving for “life outside of work” and micromanaging AI agents (5:42)
• Navigating the shifting boundaries between product, engineering, and management roles (8:43)
• James’ personal journey: Building 5 apps in 5 hours to stay relevant and relatable (10:05)
• Deconstructing the Hackathon structure: The “Take-Home Assignment” approach (16:16)
• The Hall of Fame: Creating artifacts to recognize contribution (18:00)
• Iterating on the format: Pivots made for the next hackathon iteration at Coursera (18:47)
• The importance of a 2-week ideation period for alignment (20:59)
• A recap of the playbook: Seeding ideas, easy tooling, and safe deployment (22:15)
• The future of hackathons: Cross-functional participation beyond engineering (26:46)
• Rapid Fire Questions (28:15)

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This is a special episode, highlighting a session from ELC Annual 2025! Bill Coughran (Partner @ Sequoia Capital & former SVP of Engineering @ Google) and Bret Reckard (Talent Partner @ The General Partnership) deconstruct the evolving role of engineering leadership in an era dominated by AI hype. Bill is a legendary leader who joined Google right after the .com bubble and has seen every major industry shift since. Drawing on his experience scaling Google and advising world-class startups, Bill shares why the best leaders are "catastrophic thinkers," how to balance servant leadership with the need for decisive action, and why AI is forcing every leader to return to their technical roots. Plus they cover enduring companies and real value capture in the AI era, the nuances of organizational design, the "apprentice model" for mentorship and the dangers of over-layered hierarchies that stifle speed. Bill also provides a candid look at leadership transitions, offering a tactical guide for those moving from Big Tech to early-stage startups.

Bill Coughran works as a founders' coach and partner at Sequoia Capital to help build spectacular technology-centric companies. Previously, Bill was Senior Vice President of Engineering at Google with oversight of Chrome, YouTube, maps, google.com, underlying infrastructure systems, and security.

Bret Reckard is Talent Partner at The General Partnership (TheGP), a hands-on venture firm working alongside ambitious founders in talent, engineering, go-to-market, and product. He leads TheGP’s Talent vertical, matching foundational leaders, early engineers, and key specialists across the portfolio. Before this role, Bret spent over a decade at Sequoia Capital leading Talent and Network, where he helped hundreds of founders at companies like Stripe, Confluent, Retool and DoorDash build their early teams.

Span is the AI-native developer intelligence platform bringing clarity to engineering organizations with a holistic, human-centered approach to developer productivity.

If you want a complete picture of your engineering impact and health, drive high performance, and make smarter business decisions…

• Introduction and Bill Coughran's background at Sequoia and Google (1:36)
• Hiring pitfalls and the biggest mistakes made as a leader (3:49)
• Managing crises: Acting as a dictator during the 2010 Google hack (5:25)
• Building for the AI world without chasing "shiny objects" (7:09)
• Developing context: How to learn AI without relying on LLM summaries (9:02)
• Identifying enduring companies and real value capture in the AI era (10:53)
• The debate on coding assistants and the future of junior engineering talent (13:23)
• Transitions: Making the leap from large organizations to early-stage startups (15:59)
• Staying curious and finding excitement in the next professional challenge (18:23)

• Link to the video for this session
• Link to all ELC Annual 2025 sessions

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.