Hi, I'm Nate.
19 years in software. 9+ as an EM. Cash App, Amazon, Vistaprint, Microsoft. Exploring Senior EM and Director roles.
Senior EM at Cash App
Tax Server / Engine team
Since Apr 2025
Open to
Senior EM
Director of Engineering
Consumer tech, marketplaces, or developer platforms. Remote-first preferred.
Tenure
19y
software, 9+ as EM
Led up to
30
engineers, Design Tech at Vistaprint
Reach
50M+
customers on Prime Video with Ads
Mentored
150+
engineers across a multi-year guild
Find me on
What I believe
Lead with empathy.
Fail fast, evolve faster.
Extreme candor & transparency.
Trust is a motivator.
Better requires change.
Experience
Since 2025
Leading the Tax Server / Engine team. Shipped three AI product launches, transformed operational excellence (about 80% reduction in pages and tech debt), and lifted team output ~60% through team-wide adoption of AI-assisted development.
2020-2025
Led teams of 4 to 14 across three orgs. Launched RPKI route security across all AWS routers globally, built Freevee's notification platform from zero to 5M+ customers, and delivered Prime Video with Ads in 4 months with a 14-engineer tiger team, unblocking launch to 50M+ customers.
2013-2020
Built the DIY website builder (Tower) from greenfield to launch with 20+ engineers, reversing a 3% signup decline into 5% growth. Formed a 30-person Design Tech org. Founded a 4-year mentorship guild that reached 100+ engineers and converted 8 ICs into managers.
2007-2013
Designed Microsoft Account's two-factor authentication system (500M+ users). Built the enterprise authentication client presented at Microsoft PDC 2008, and authored a JS UI framework used across Windows and Xbox.
Frameworks I've built
06 systems
Original systems I invented while leading engineering teams. Several outlived me at the companies that adopted them.
An in-person session that replaces 360 surveys. 95% attendance and 10 to 20 actions per person across the teams I've run it on.
A peer-built career framework derived from the qualities of respected ICs. Evolved into an org-wide evaluation and coaching system at Vistaprint.
Visual scoping that surfaces hidden risk before commitment. Predicted a 4-month launch estimate for Prime Video with Ads to the day.
Self-organizing team structure that turned multi-month reorgs into days. 8 to 10 rebalances in 10 months without losing people.
A successor to SMART goals built for the 1:1 coaching context. Tracks habit formation and the ROI of time spent.
Owner-driven status board that replaced project meetings. 20+ initiatives visible in a 30-minute weekly review.
Writing
Essays on leadership, coaching, and team building, published on Medium.
Talks
Elsewhere
Things I build outside of work. Some are businesses, some are art, all of them are how I stay sharp.
Get in touch
Reach me on LinkedIn. That's the best place to start a conversation. I'm especially open to Senior EM and Director conversations right now.