Hi, I'm Nate.
Engineering leader who delivers results-focused products to millions, inventing systems and growing the ownership-driven people that ship and sustain them.
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 teams of
5-30
engineers, managers, product managers, and solutions architects
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.
Passion over experience.
Extreme candor and transparency.
Measurable, TIME-bound goals.
Fail fast, evolve faster.
Experience
-
Since 2025
1+ year
Senior Engineering Manager · Cash App / Block
Leading the Taxes Product and 8-engineer Tax Engine team. Launched 3 AI products, transformed operational excellence (80% reduction in pages and tech debt), and lifted team output ~60% through AI-tool adoption and innovation.
-
2020-2025
5+ years
Software Development Manager · Amazon (AWS · Prime Video)
Led teams of 5 to 14 across three orgs. Launched new RPKI route security system across all AWS routers globally. 0 to 1 creation of Content Experience team, launching new notification platform and A/B testing to 5M+ customers across Mobile, FireTV, and Prime Video devices.
-
2013-2020
7 years
Senior Manager / Principal Lead Engineer · Vistaprint
Lead 30-person Design Tech org, and launched greenfield DIY website builder across 20+ engineers, reversing a 3% signup decline into 5% growth. Founded a 4-year mentorship guild that reached 100+ engineers and growing 8 ICs into managers.
-
2007-2013
6+ years
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 JS UI framework used across Windows, Xbox, and all Microsoft accounts.
Frameworks I've built
06 systems
Original systems I invented while leading engineering teams. Several outlived me at the companies that adopted them.
- Project delivery system
Dependency Graphs
One artifact for realistic estimates, delivery status, scope and resourcing trade-offs, milestone tracking, and rapid prioritization. Used to launch dozens of multi-month projects on time or early.
- Prioritization system
Tributary
Rapid prioritization across 20+ concurrent initiatives covering product, tech debt, on-call, and team work. Engineer-owned with backward-planned dates. Weekly review names what we're working on AND what we're explicitly not, freeing the team from reactive mode.
- Org operating system
Swarms & Colonies
Everyone is in both a Colony (persistent code ownership) AND a Swarm (current workstream). Resources are transparently allocated across project delivery, operational health, and innovation. Monthly rebalances are small allocation shifts instead of large, costly re-orgs.
- Coaching framework
TIME-entific Method
An evolution of SMART goals into career goals in the 1:1 context. Leverages the scientific method to track progress toward evolving goals, habit formation, and the ROI of time spent on career growth.
- High-impact feedback
Sailboat Feedback
Structured, recurring, in-person team exercises for sharing feedback directly with teammates. Replaces written or anonymous 360 surveys with more actionable items, stronger psychological safety, and feedback skills that grow on both sides.
- Engineering principles model
Facets of Growth
A peer-built model defining the behaviors actually critical to a company, like Amazon's Leadership Principles but ground-up rather than handed down. Turns those behaviors into career growth guidelines, feedback vectors, and structured performance evaluation.
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.