Nathan Toups
1,215 min coached
26 followers
Studied at Georgia Institute of Technology
Worked at rojoroboto
Successful clients at
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About Nathan
I've spent my career helping engineers and teams do their best work and enjoy it. My path wasn't conventional: I started with a theatre degree, taught myself to code, and eventually earned my Master's in Computer Science from Georgia Tech. I've worked in Staff Platform Engineer and Software Architect roles, and as a CTO, and I've consulted with over 100 companies along the way. What I learned is that the human side of engineering, how people work together and whether they're growing, is what makes or breaks a team. What I care about most is helping the people around me grow and thrive. That's what I've done as a mentor and a leader, and it's why I co-host Book Overflow, where each week we read a book and talk craft with people like Kent Beck, Martin Fowler, and Brian Kernighan. I believe the work that lasts comes from going deep on things you care about, with people you love working with. These days I do that from Costa Rica, building a working life around what actually matters.
Why do I coach?
Sixteen years ago, someone took a chance on a theatre major who wanted to break into tech. That bet changed my life, and I've been paying it forward ever since. Helping the people around me grow has been the most rewarding part of my career, more than any title or launch. I coach because I've seen what actually makes people happy in this work: doing something meaningful, going deep enough to be good at it, and doing it with people you trust. Prestige rarely does it. I've watched talented engineers lose their spark to the wrong environment, and I've watched them get it back. I'd like to help you find yours.
Work Experience
Owner
rojoroboto
October 2025 - Present
I started rojoroboto in 2010 and operated it continuously until 2020. After a 5-year hiatus working in the startup world, I'm back to running rojorboto full-time, focusing on contract and consulting work.
Software Architect
All In Bits
October 2024 - November 2025
Software Architect at All In Bits, where I lead blockchain innovation across two chains. I run a small Innovation Lab exploring the bleeding edge of UX/DX for blockchain, while architecting solutions that touch every engineering team. I report directly to the CEO, bridging technical innovation with strategic vision.
Co-founder + Co-host
Book Overflow
June 2024 - Present
A weekly podcast where two software engineers read the books you've been meaning to get to. We dive deep into technical books, career development, and timeless wisdom—then bring on authors and industry leaders to share their perspectives. Your engineering book club, delivered weekly.
Sr Staff Platform Engineer
Flyr
July 2023 - September 2024
I work closely with Product and Engineer to build a happy and productive engineering culture. I've led initiatives related to Developer Experience, integrating acquisitions into our larger culture of shipping code, and cloud migration initiatives from AWS to GCP. I'm a tech lead who shares IC and management responsibilities and I work hard to provide operational excellence while meeting our business needs. I also work closely with our security team, leading "shift left" initiatives in the organization. I work multi-cloud. I have a deep knowledge in SOC 2 Type2 compliance, AWS and GCP, FinOps, and IDP. Platform engineering, DevOps and +3 skills
Chief Cloud Architect
Clairity, Inc
April 2022 - July 2023
I work cross functionally with product and engineering to design, build, and maintain our cloud infrastructure. This includes designing cloud infrastructure to meet our needs for our Software as a Medical Device (SaMD) and provide a centralized design philosophy for our ML, Analytics, and production engineering teams. As part of this, I've championed AWS Multi account Organizations with Control Tower for streamlined compliance tools. I also work closely with our engineering team to ensure that our security and reliability goals are being met while we build our systems. This includes "supply chain" software management, internal artifact management, security scanning, and low-trust and zero trust patterns for CICD and engineering development flows. Our core tooling is heavily "serverless", so designing highly available, horizontally scalable infrastructure is a core component in my work. This includes tools such as s3, docker, lambda, step functions, DynamoDB and carefully scoped private subnet VPCs to meet HIPAA and FDA medical device requirements.
CTO
Key.co
January 2015 - March 2017
I was the third person hired at Key (and first technical hire) after consulting on the early project. I helped raise seed funding through Series A. I was fortunate enough to have the opportunity build an product and engineering team from scratch, which had grown to a team of eight before I left. While CTO, we developed an automated CI/CD toolset for our application that included Hashicorp Vault, CircleCI, and Docker container orchestration that allowed our small engineering team to safely push code and work productively and predictably form local dev with predictable and reliable translations to deployments. I eventually left to pursue contract and consulting work generally, at which time, I helped hire a new CTO and I stayed on at KEY as a contractor through the end of 2017.
Owner
rojoroboto
January 2010 - March 2020
I help organizations build internal platforms that make the right thing easy and the wrong thing hard, whether that's developers shipping code or analysts using AI tools. For over a decade, this meant Platform Engineering: CI/CD optimization, developer experience, Team Topologies-based org design. I founded rojoroboto in 2010, consulted with 100+ companies, and eventually stepped away to solve these problems full-time. I've worked as a CTO, Chief Cloud Architect, and Staff Platform Engineer at a series of startups. That experience taught me what actually works in production, not just in architecture diagrams. Now the problem has expanded. LLMs are putting automation capabilities in the hands of every knowledge worker, and organizations need the same golden paths, guardrails, and observability they built for developers. The Internal Developer Platform was the answer for engineering. The same pattern applies organization-wide. My approach: start local and low-friction, validate what's already working, then operationalize it into something sustainable and governed. Find the value, prove it, scale it. Services: Fractional platform leadership, fixed-scope projects (IDP, AI enablement, Team Topologies redesign), and executive advisory for technical leaders navigating this shift.
Education
Georgia Institute of Technology
Master's degree, Computer Science
2021 - 2024
Specialization: Computing Systems
Louisiana State University
Bachelor of Arts - BA, Theatre/Theater
2002 - 2006
Focus: Design and Technology
18 Reviews
Overall Rating
5.0
Knowledge
5.0
Value
5.0
Responsiveness
5.0
Supportiveness
5.0
Nathan has helped clients get into these companies: