Founding Engineer Circle: Managing Up & Out Workshop
What is this?
A case study workshop for founding engineers navigating the dual communication challenge: managing up to non-technical founders while building and communicating with your team. We'll work through real scenarios—unrealistic timelines, technical tradeoffs, team alignment—and develop frameworks you can use immediately.
Why this matters
You know how to build. The hard part? Managing the relationship with your founder when they don't understand technical tradeoffs, promise features on timelines that don't exist, or want to pivot architecture based on what a competitor shipped. Then turning around and translating those decisions to your growing team in a way that builds trust and alignment.
Most founding engineers figure this out through painful trial and error. This workshop compresses that learning curve using real cases from founding engineers at venture-backed startups.
What to expect
Two real scenarios from founding engineers (anonymized):
Case 1: Managing up to non-technical founders (timeline conflicts, technical pivots, resource decisions)
Case 2: Communicating technical decisions to your broader team (explaining tradeoffs, building buy-in, maintaining velocity)
Small group breakouts to workshop approaches and frameworks for each case
Peer discussion of what's worked (and what's failed) in similar situations
Tactical takeaways you can apply to your actual relationships on Monday
Coffee and breakfast provided
Format: Case study workshop with peer discussion. Come ready to engage—this is a working session, not a lecture.
Breakfast at 9:30 AM, workshop from 10-11:30 AM.
Who's in the room
This is an engineers-only gathering limited to 16 founding engineers and early CTOs who've been verified as first-to-fifth technical hires at venture-backed startups. Previous attendees include technical leaders from companies backed by a16z, Sequoia, YC, and other top-tier investors.
Hosted by Randy Brown - Founder of Scout, former CTO at Jopwell (YC S15, a16z-backed), and creator of the Founding Engineer Circle community in San Francisco. Randy brings together technical talent through events, workshops, and a private network that helps engineers thrive in early-stage startups.