

Founding Engineer Circle: Roundtable with Jairaj Sethi
What is this? An exclusive monthly roundtable discussion for members of Founding Engineer Circle. This month, we're joined by Jairaj Sethi, Co-founder and CTO of Substack, for an intimate conversation about scaling technical organizations and navigating the unique challenges of building at scale.
Why attend? Members-only access to candid conversations with successful CTOs who've walked the path you're on. No staged presentations or generic advice - just honest dialogue about the real challenges, decisions, and lessons learned from someone who's built and scaled a major platform.
About our guest: Jairaj Sethi Co-founder and CTO at Substack, where he's led the technical vision behind one of the most important publishing platforms of our time. Previously Head of Platform at Kik Interactive and a Y Combinator alum (W18). Jairaj brings deep experience in scaling both technology and teams from startup to scale.
What to expect
Members-only intimate setting - capped at 16 people for quality discussion
Direct Q&A with Jairaj about technical leadership, scaling challenges, and founder dynamics
Peer discussions among founding engineers and early CTOs
Coffee and light breakfast provided
Opportunity to build relationships within the verified Circle community
Format: Roundtable discussion, not a presentation. Come with your questions and challenges.
We'll have breakfast starting at 9:30 AM, roundtable discussion from 10-11:30 AM.
Hosted by Randy Brown, formerly CTO at Jopwell (YC S15) and currently Founder of Scout.