The leadership obligations nobody taught you
A newsletter for mid-career product professionals on the human work of leading teams.
What you'll get
Focused writing on the human side of leading product teams.
- Practical frameworks drawn from 20+ years leading teams
- Honest takes on conflict, trust, and difficult conversations
- The discipline of becoming the leader your team deserves
- Systems thinking for people who build products and lead people
What it looks like in your inbox
The most recent issue · July 11, 2026
I worked 80-hour weeks. Now I keep the Sabbath.
Why trust me
I'm Matthew Stublefield. I've spent 20+ years leading product and engineering teams – from scaling CoinDesk through a crypto winter to directing an 80-person team at Stride to running a pilot program at a Big Four firm that touched 20,000 employees.
My background is unconventional for tech. I studied Religious Studies and Poetry in college – not because I couldn't do the technical work, but because I wanted to understand people. That foundation taught me to ask “why” until I reach root causes, and to listen for what's not being said. Later, I became a Certified Grief Counselor to better understand how loss and change impact teams under pressure.
I'm the founder of Fieldway, LLC, where I help software teams figure out the next right thing to build (and what not to), and I'm currently writing What a Leader Owes Their Team – a book about the obligation-based leadership framework I've developed over two decades of practice.