Engineering Leadership
Leading engineering teams through delivery planning, technical decision-making, prioritization, and organizational change while maintaining clarity across both technical and business stakeholders.
Software Development Leader · Security Program Builder · Technical Strategist
Engineering leadership for secure systems.
I build engineering organizations and security programs in environments where customer data, service reliability, and organizational scale are tightly connected.
Over 20 years across enterprise cybersecurity, cloud infrastructure, and high-scale platforms, with a consistent pattern: identify systemic risk, convert it into funded programs, deliver measurable outcomes.
me@padenclayton.com- Engineering Leadership
- Security Governance
- Distributed Systems
Professional Snapshot
Twenty years of engineering leadership where security, architecture, and execution have to work as one system.
Most of my work has centered on environments where technical decisions, security posture, and organizational coordination have to function together at scale. I lead engineering teams, build security programs, and architect the operating systems that let both endure.
Security Strategy
Building security programs that integrate team ownership, risk identification, architectural review, and engineering accountability into existing development environments.
Software Architecture
Working across distributed systems, service integrations, cloud infrastructure, and modernization efforts where architectural decisions directly influence service stability and long-term maintainability.
Execution Discipline
Improving delivery mechanisms, system visibility, governance processes, and technical coordination across environments where reliability and execution consistency matter.
Career Timeline
Leading high-trust work where engineering quality and security matter.
Amazon (Woot) · June 2022 to Present
Senior Software Development Manager
Leading engineering and security strategy across a subsidiary environment where customer data protection, platform modernization, and organizational scaling have to operate together.
- Designed and operationalized Woot’s enterprise security program from zero, scaling the Security Guardians model across 3 engineering teams, reducing uncertified applications by 74%, and remediating 3,169 risks.
- Directed a Critical-rated DST Business Security Review requiring VP escalation, authoring the executive business case with an 824:1 cost-benefit ratio that secured a 3 to 5 year roadmap and prevented $4.45M in projected security exposure.
- Managed a $2.96M Professional Services engagement end-to-end, delivering all contracted objectives at $987K, 67% under budget, and saving 704 dev-weeks through a strategic deprecation decision.
- Led the Shopify platform migration affecting 60% of services, committing 9 engineers across 12+ project areas and 7 milestones spanning Q3 2025 to Q1 2027.
- Built people systems adopted org-wide: promotion frameworks, 60% to 85% success, SDE onboarding, 8 to 5 weeks, and Talent Review tooling, 8 to 3 hours of prep per manager.
Monkedia · March 2018 to May 2022
Lead Full Stack Developer
Owned cloud infrastructure, platform modernization, and engineering operations across a multi-stack environment serving enterprise marketing and analytics clients.
- Managed a 326-resource AWS environment spanning EC2, Redshift, RDS, Lambda, S3, and CloudFront, with full ownership over cost, reliability, and scalability.
- Led 6 to 8 month platform overhauls modernizing the stack through ES6 and React, standardizing practices across Vanilla JS, PHP, and React teams.
- Architected a unified analytics framework consolidating 5 vendor reporting systems, Facebook, Google, Amazon, Shopify, and Klaviyo, into the primary decision-making platform for the business.
Nusani Inc · March 2011 to March 2018
Technology Director
Directed technology strategy and infrastructure for a hosting operation serving 2,400+ websites, with full ownership over availability, security monitoring, and recovery.
- Built a deployment platform that increased deployment velocity by 734%, enabling scaling from dozens to thousands of managed sites.
- Led a major platform modernization initiative, optimizing performance and security across the entire hosting infrastructure.
- Built and maintained custom enterprise applications supporting hosting operations and internal workflows, while managing outsourcing relationships and concurrent project delivery.
Suddenlink Media · March 2006 to July 2011
IT Administrator
Led a technical team responsible for network infrastructure, vendor coordination, and end-user operations across a media business where uptime directly affected production and revenue.
- Owned network and infrastructure modernization initiatives that improved security posture, capacity, and reliability across business-critical operations.
- Managed vendor relationships and outage response across the infrastructure portfolio, establishing the operational coordination patterns that would scale into later director and management roles.
Selected Work
Programs I’ve built and outcomes I’ve delivered.
Building an Enterprise Security Program from Zero
Woot had no formal security program and a 9:1 apps-per-engineer ratio that made traditional certification economically impossible. I designed the Security Guardians model to distribute security ownership across engineering teams, scaled it across 3 teams with 4 trained certifiers, and made the strategic call to deprecate 159 applications rather than certify all of them. The program reduced uncertified applications by 74%, remediated 3,169 risks, and saved 704 dev-weeks of engineering effort.
Securing VP Sponsorship for a Multi-Year Security Roadmap
A Critical-rated DST Business Security Review required VP-level escalation and a defensible long-term plan. I orchestrated 3 parallel workstreams across 7 organizations and authored the executive business case at an 824:1 cost-benefit ratio. The plan secured VP approval for a 3 to 5 year roadmap, 5 dedicated contractors, and OWASP SAMM maturity progression across 10 practices, preventing $4.45M in projected security exposure.
Rebuilding the Team Operating Model
The team was operating under a Scrum cadence that was costing predictability and morale. I redesigned the operating model around cross-training, rotating leadership, and capacity-based sprint planning, raising Work-Life Balance scores from 2.7 to 4.0 while holding a 95% initiative success rate. A controlled 4-sprint Kanban vs. Scrum experiment then reduced cycle time by 33%, increased velocity by 38%, and raised Delivery Predictability from 3.0 to 5.0.
Perspective
Depth that converts into speed across the full stack of eras.
I have been working with computers since the early DOS era and professionally in technology since 2004, which means I have operated across the full arc of modern computing: pre-internet desktop systems, the rise of the web, the consolidation of cloud, and the current generation of AI-augmented platforms.
What that history has produced is range. I can analyze a complex issue, understand its impact, identify root cause, and articulate a path forward quickly enough to keep pace with senior engineers in the room, and I can do that whether the system in question is 20 years old or shipped last quarter.
That same fluency lets me shift between the boardroom and the engineering frontlines without losing context in either direction: partnering with engineers as a peer when the work calls for it, and translating the same problem into executive language when the decision moves upstairs.
Credentials
- AWS Certified Database Specialty
- AWS Solutions Architect Associate
- Graph Developer Professional
- Graph Developer Associate
- Professional Scrum Master I
- Project+
- MBA Information Technology Management
- PhD Information Systems Security, in progress
Personal Philosophy
Build with enough clarity that others can carry the work forward.
I’m drawn to systems that endure: resilient technical organizations, well-designed software, disciplined engineering practices, and historical structures that survived because their foundations were carefully considered.
My approach is heavily influenced by systems thinking, long-term maintainability, and the organizational structures required to support complex technical environments over time. Understand the foundations, respect the real-world constraints, and build systems clearly enough that other people can sustain and extend them over time.