Hi, I'm Nate.
Engineering leader who builds the teams behind the products, and the systems and culture that make shipping repeatable.
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
Tenure
19y
software, 9+ as EM
Led up to
30
engineers, Design Tech at Vistaprint
Mentored
150+
engineers, managers, and product managers
Open to
Senior EM
Director of Engineering
Consumer tech, marketplaces, or developer platforms. Remote-first preferred.
Find me on
What I believe
Lead with empathy.
Fail fast, evolve faster.
Extreme candor & transparency.
Trust is a motivator.
Passion over experience.
Experience
-
Since 2025
Senior Engineering Manager · Cash App / Block
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.
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2020-2025
Engineering Manager · Amazon (AWS · Freevee · Prime Video)
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.
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2013-2020
Senior Manager / Principal Lead Engineer · Vistaprint
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.
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2007-2013
Senior Software Engineer · Microsoft
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.
- Feedback ritual
Sailboat Feedback
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.
- Engineering growth model
Facets of Growth
A peer-built career framework derived from the qualities of respected ICs. Evolved into an org-wide evaluation and coaching system at Vistaprint.
- Project estimation
Dependency Graphs
Visual scoping that surfaces hidden risk before commitment. Predicted a 4-month launch estimate for Prime Video with Ads to the day.
- Team rebalancing
Swarms & Colonies
Self-organizing team structure that turned multi-month reorgs into days. 8 to 10 rebalances in 10 months without losing people.
- Coaching framework
TIME-entific Method
A successor to SMART goals built for the 1:1 coaching context. Tracks habit formation and the ROI of time spent.
- Initiative tracker
Tributary
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
- Facets of Growth Engineering career framework
- SSO at Vistaprint Conference talk
- medium-editor OSS retrospective
- SemVer in Practice Conference talk
- DOM Events Deep Dive Conference talk
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.