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
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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.
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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.
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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.
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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.
Used at Microsoft · Vistaprint · AWS · Prime Video · Cash App - 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.
Used at AWS · Prime Video · Cash App - 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.
Used at Vistaprint Design Tech - 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.
Used at Vistaprint · Amazon · Cash App - 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.
Used at Vistaprint · AWS · Prime Video · Cash App - 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.
Used at Vistaprint Design Tech
Writing
Essays on leadership, coaching, and team building.
- Fueling Flames: My 3 Rules for World-Changing Delegation Medium ↗
- The TIME-entific Method: A New System for Accomplishing Your Long-Term Goals Medium ↗
- A Career Coach, a Manager, and a Mentor Walk Into A Bar… Medium ↗
- Avoid Those Large, Lousy Meetings By Asking One Simple Question Medium ↗
- TIME Goals: A Scientific Approach to Success Medium ↗
- Stop Being Nice, Start Being Kind Medium ↗
Talks
Open-Source Development
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The #1 WYSIWYG Editor on Github
Digital Tech Days
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medium-editor: An Open Source Story
DevCon 2018
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Semantic Versioning
Lunch & Learn
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medium-editor: An Introduction
Lunch & Learn
Front-End Development
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How We React
Digital Tech Days
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I Read The UI Events Spec
Lunch & Learn
Authentication
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Digital SSO-my-god?!
Digital Tech Days
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Digital Authentication
Lunch & Learn
Career Coaching
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Coaching 101: Why Coaching Is Worth Trying
Vistaprint Coaching Program
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Coaching 101: Getting Started
Vistaprint Coaching Program
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Coaching 101: Creating Goals
Vistaprint Coaching Program
Blockchain
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D is for Dogecoin: An Intro to Blockchain & Consensus
DevCon 2019
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From Bitcoin to DogeCoin
Lunch & Learn
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An Intro to Bitcoin & Blockchain
Lunch & Learn
Elsewhere
My creative outlets. Some are art, some are music, some are product, all of them keep me sharp.
Proof of Thought LLC. Umbrella for my side ventures.
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.