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Woodrow Pearson Resume - 10.30.25

Woodrow "Woody" Pearson

LINKEDIN | GITHUB | EMAIL | (415) 920-3065


SUMMARY

Senior infrastructure engineer with over a decade of experience building resilient, mission-critical systems that prioritize security, reliability, and operational excellence. Proven track record leading cross-functional infrastructure projects in 24/7 environments supporting enterprise, healthcare, and high-growth technology companies. Deep expertise in hybrid cloud infrastructure (AWS + on-prem), automation frameworks, and emerging AI technologies. Skilled at evaluating and re-engineering complex systems to drive cost efficiency while maintaining enterprise-grade uptime requirements. Strong commitment to community service and public sector impact through technology and mentorship.

CORE COMPETENCIES

Infrastructure & Cloud: Hybrid infrastructure design, Azure/M365 administration, AWS/GCP, on-premises integration, Active Directory, Windows Server, disaster recovery, high availability systems

Automation & Innovation: Bash and powershell scripting, AI-enabled tools, infrastructure-as-code (Ansible, Terraform, Puppet), CI/CD pipelines, agentic development workflows, RAG systems, data visualization (Tableau)

Mission-Critical Operations: 24/7 on-call support, 99%+ uptime SLA/SLO management, incident response, PagerDuty, monitoring/alerting, system reliability engineering

Leadership & Strategy: Cross-functional project leadership, infrastructure standards definition, technical mentorship, vendor evaluation, strategic planning, stakeholder management

Security & Compliance: HIPAA compliance, access control, security best practices, penetration testing response, vulnerability remediation

Technologies: Python (FastAPI, Django), Docker, Kubernetes, Nginx, HAProxy, PostgreSQL, Redis, Prometheus, Grafana, Git, Ansible, ChromaDB, Vector databases, Redshift, NoSQL

Cloud Services:

  • AWS: EKS, ECS, Lambda, CloudFormation, VPC, IAM, CloudWatch, Route53, S3, API Gateway
  • GCP: GKE, Cloud Functions, Firestore, Vertex AI, Gemini API, Cloud Build
  • Azure: Active Directory, Azure AD, M365 (Teams, SharePoint, Exchange Online), Key Vault, Monitor, Blob Storage

PROFESSIONAL EXPERIENCE

ABUNDANCE | FOUNDER

JUNE 2025 - PRESENT | ARLINGTON, WA

Managing full product lifecycle from architecture to deployment using modern automation frameworks and emerging AI tools. Abundance helps you rediscover the value hidden in your own home and community. It’s your personal, private catalog for the things you love, the things you use, and even the things you’ve forgotten.

AI Integration & Emerging Technologies:

  • Parallel processing design: Vision + SerpAPI run concurrently, reducing total item catalog processing time for 10 items from ~180 seconds to ~15 seconds

  • Multi-model optimization: Specialized models (fast vision + advanced reasoning) vs. generalist approach, achieving 7x cost reduction on vision layer

  • Graceful degradation: Vision-only fallback maintains functionality and experience even when SerpApi or cloud based AI providers are unavailable

  • Action-based workflows: Implemented structured JSON schema with confidence scoring, provenance tracking and action-based workflows enabling zero-friction premium cataloging experience

Modern Development Practices & Automation:

  • Established spec-driven development and TDD (Test-Driven Development) methodology using AI-assisted code generation, reducing development time by ~60% while maintaining high code quality

  • CI/CD pipeline with GitHub Actions automating ADR validation, spec-lint enforcement, test coverage gates, security scanning (Firebase Auth, Anthropic/GCP API key management), and GCP deployment with Cloud Functions blue-green rollout strategy

Technical Stack Highlights:

  • iOS Development: Swift 6.2, SwiftUI, iOS 26 Vision Framework, Apple Core ML, Firebase SDK (Auth, Firestore real-time sync, Storage)

  • Backend: GCP Cloud Functions (Node.js 20, Firebase 2nd gen), Cloud Firestore (NoSQL, offline-first, real-time listeners), Firebase Storage (cropped image handling), Cloud Scheduler (6-hour retry loops for failed enrichments), Cloud Logging & Monitoring

  • AI/ML: Gemini 2.5 Flash-Lite (GCP Vertex AI), Google Shopping Graph API, SerpAPI, Claude 4.5 Sonnet (Anthropic API/Vertex AI, multimodal reasoning, tool calling, structured JSON outputs with validation),

  • DevOps & Observability : GitHub Actions (CI/CD), GCP unified platform (Vertex AI, Cloud Functions, Firestore, Storage), Firebase Analytics, Terraform

WASHINGTON ALLIANCE FOR BETTER SCHOOLS | PARA-EDUCATOR

SEPTEMBER 2024 - AUGUST 2025 | MARYSVILLE, WA

Delivered educational technology solutions and direct support services for at-risk students and families in public school setting, demonstrating commitment to community service and public sector impact.

Educational Technology & Public Service:

  • Developed academic lesson planning automation tool using Python and AI in conjunction with data from educational standards databases and 3rd party curriculum vendors, saving 4+ hours weekly per user while ensuring 100% curriculum adherence and state standards compliance

  • Designed and implemented project-based STEM learning modules incorporating technology literacy components for middle school students from underserved communities

  • Provided targeted tutorial services and social-emotional learning support for at-risk student populations, collaborating with teachers and families to improve educational outcomes

  • Facilitated educational STEM workshops for families, fostering parent involvement and promoting STEM access in underserved communities in Marysville

MEDIQ HEALTH & WELLNESS | CO-FOUNDER

JUNE 2023 - MAY 2024 | ARLINGTON, WA (HYBRID)

Co-founded private behavioral health medical practice demonstrating that technology-driven innovation enables small practices to achieve superior patient outcomes and operational efficiency compared to traditional models. Led technical strategy and implementation of AI-powered automation systems reducing administrative burden, improving care quality, and ensuring regulatory compliance.

Healthcare AI Innovation & Automation:

  • Developed semi-automated patient encounter pipeline integrating AI transcription, clinical documentation generation, and billing automation, saving 60+ provider hours monthly (25% reduction in administrative workload)

  • Built SOAP note generation system using AI to transcribe patient encounters and produce clinical documentation with appropriate medical terminology and healthcare provider jargon, ensuring accurate medical records while reducing documentation time from 30 minutes to 5 minutes per patient visit

  • Automated patient after-visit summary generation translating technical medical language into accessible, patient-friendly explanations improving health literacy and patient engagement

  • Implemented AI-powered ICD-10 code prediction with automated citation generation for insurance reimbursement and audit compliance, reducing billing errors by 40% and accelerating claim processing

Healthcare Compliance & Interoperability:

  • Architected systems with strict HIPAA compliance including encryption at rest and in transit, access control policies, audit logging, and breach notification procedures aligned with federal healthcare privacy regulations

  • Designed healthcare data exchange infrastructure supporting industry-standard interoperability protocols (HL7 v2, HL7 v3, and FHIR) ensuring seamless integration with Electronic Health Records (EHR), insurance systems, and third-party healthcare platforms

  • Implemented secure data handling practices for Protected Health Information (PHI) including de-identification procedures, minimum necessary access controls, and business associate agreements with technology vendors

Business Operations & Strategic Innovation:

  • Evaluated and integrated emerging AI technologies (GPT-4, Claude, medical-specific language models) to reduce operational costs by ~235% compared to traditional practice models while maintaining quality of care

  • Established proof-of-concept demonstrating economic viability of technology-enabled small practice model, reducing barriers to timely quality behavioral health care in underserved communities

EDIFECS | SR. SITE RELIABILITY ENGINEER

MARCH 2022 - JANUARY 2023 | BELLEVUE, WA

Led infrastructure modernization and operational excellence initiatives for healthcare technology company post-acquisition, supporting mission-critical systems with 99.1% uptime SLA serving major healthcare payers processing millions of transactions daily. Managed hybrid infrastructure combining on-premises and cloud environments while ensuring HIPAA compliance and 24/7 system availability.

Hybrid Cloud Infrastructure & Azure/M365 Administration:

  • Administered Azure Active Directory and Microsoft 365 suite (Teams, SharePoint, Exchange Online) for 200+ users, managing on-premises Active Directory integration with Azure AD Connect for seamless hybrid identity management

Automation & System Management:

  • Developed Bash shell scripts and Terraform configurations for AWS site-to-site VPN access management automating certificate deployment, routing configuration, and access control list updates across distributed Windows Server infrastructure

Mission-Critical 24/7 Operations & Monitoring:

  • Maintained 99.1% uptime against contractual SLA/SLO requirements for healthcare data exchange platform processing real-time eligibility and claims transactions

  • Served 24/7 on-call rotation for 2-week cycles (1 week primary, 1 week secondary) responding to production incidents affecting customer-facing services with < 15 minute response time requirement

  • Led PagerDuty migration project from OpsGenie, architecting intelligent alerting workflows integrating Prometheus metrics, CloudWatch alarms, Jira incidents, and Zendesk tickets with escalation policies reducing alert noise by 40% and mean-time-to-resolution by 35%

  • Implemented Azure AD SSO integration with PagerDuty via SAML authentication and SCIM provisioning, automating user lifecycle management, role-based access assignment, and on-call team membership through escalation policy associations, eliminating manual account provisioning

  • Designed incident response framework including runbook automation, flowchart-driven troubleshooting guides, real-time incident dashboard, and post-incident review process with quarterly simulation exercises

Cross-Functional Infrastructure Projects:

  • Led Kubernetes/EKS upgrade initiative across 3 environments (dev, staging, prod) migrating from version 1.21 to 1.23, coordinating with 5 development teams to ensure zero-downtime deployments and application compatibility

  • Executed GitLab Ultimate Suite migration from AWS CodeCommit and Bitbucket, automating repository migration for ~500 active and archived repositories using Python and Bash scripts and GitLab APIs

  • Launched summer internship program from RFC proposal through production deployment, mentoring interns through AWS CloudWatch Synthetics Canaries implementation via Terraform monitoring 25+ customer API endpoints

Cost Optimization & Infrastructure Efficiency:

  • Implemented Kubernetes cluster autoscaling and pod rightsizing recommendations reducing AWS EKS costs by $8,000/month (32% reduction) while maintaining performance SLAs

  • Established FinOps tagging strategy and cost allocation framework enabling chargeback reporting by team and environment

PILOTX | SITE RELIABILITY ENGINEER

SEPTEMBER 2019 - MARCH 2020 | REMOTE

Hired as first SRE to conduct comprehensive infrastructure audit and implement foundational reliability practices for advertising startup. Evaluated existing AWS architecture, identified security risks and cost inefficiencies, and led re-engineering initiatives prioritized by risk and business impact.

System Evaluation & Re-Engineering:

  • Conducted enterprise infrastructure audit identifying 15 critical security vulnerabilities, 8 high-risk availability gaps, and $60K annual waste in cloud and vendor spending; developed prioritized remediation roadmap aligned with company growth trajectory

  • Re-architected networking infrastructure implementing multi-regional VPC design with transit gateway, replacing legacy flat network that posed security and scalability risks; reduced inter-region latency by 45%

  • Evaluated and replaced third-party contracted infrastructure services with automated in-house solutions, eliminating $5,000 monthly in external consulting fees (60% cost reduction) while improving deployment velocity

Automation & Infrastructure Reliability:

  • Implemented semi-automated CI/CD pipeline for AWS EC2-based applications reducing deployment time from 2 hours to 15 minutes and eliminating manual configuration errors

  • Designed multi-AZ high-availability architecture for critical services improving uptime from 97.2% to 99.4%, implementing automated failover and health checking

  • Built comprehensive monitoring and alerting infrastructure integrating Prometheus, PagerDuty, and Slack with custom dashboards tracking 50+ service health metrics

Security & Compliance:

  • Automated IAM credential rotation and implemented self-service IAM provisioning portal reducing security exposure window from 90 days to 24 hours

  • Executed security audit remediating open ports, implementing security group least-privilege policies, and establishing vulnerability scanning automation

PANDORA | TOOLS ENGINEER

FEBRUARY 2017 - APRIL 2018 | OAKLAND, CA

Drove developer productivity initiatives and infrastructure tooling for leading music streaming service. Managed dual role of tools development and project leadership, partnering closely with QA and development teams to accelerate release velocity.

Cross-Functional Project Leadership & Developer Productivity:

  • Led initiative accelerating deployment frequency from weekly to daily releases between development and QA environments, coordinating with 4 engineering teams to implement automated testing gates and rollback procedures

  • Developed real-time infrastructure health dashboard providing visibility into build versions, service status, and environment health across 6 environments, reducing troubleshooting time by 50%

  • Led documentation modernization project overhauling internal tools wikis and developer resources, establishing documentation-as-code practices and automated validation

UBER | SOFTWARE ENGINEER

AUGUST 2014 - JULY 2016 | SAN FRANCISCO, CA

Founding member of Uber's SRE organization during hypergrowth phase supporting infrastructure scaling from ~300 to 1,800+ engineers and <100 to ~1,200 microservices over 2 years. Led critical automation and infrastructure projects enabling developer velocity while maintaining mission-critical 24/7 operations during 400% year-over-year company growth.

Infrastructure Leadership & Scaling:

  • Vertical and horizontal embedded SRE organizational model with dedicated 2-person SRE pods supporting top 3-4 partner teams, enabling autonomous prioritization and reducing global escalations by ~60%

  • Founding member of 5-person InfraOps team managing core infrastructure for entire engineering organization during period of exponential growth (engineering headcount doubling every 6 months)

Service Provisioning Automation & Platform Engineering:

  • Reduced service provisioning time from 1 week to same-day completion by building comprehensive self-service automation platform using Python Flask, YAML-based request intake, and intelligent orchestration

  • Scaled service infrastructure from 15 to 2,000+ services in 18 months with only 4-engineer team by eliminating manual workflows; absorbed migration workload internally across 2,000+ person engineering organization

  • Built automated service cookbook platform eliminating manual Puppet scaffolding, port allocation conflicts, and server assignment errors that previously posed production outage risks

  • Automated critical workflows including intelligent port allocation preventing routing conflicts, auto-generated Puppet configurations eliminating manual errors, and capacity-aware server assignment preventing over-utilization

24/7 Mission-Critical Operations & Infrastructure Reliability:

  • Served 12/3 on-call as primary/secondary for 6 days every month supporting server provisioning infrastructure (Docker registry, Puppet manifest distribution, HAProxy/Nginx routing) handling hundreds of alerts per 12-hour "follow the sun" shift

  • Managed mission-critical infrastructure including HAProxy-based request routing for entire fleet, Docker registry stability and scaling operations, PostgreSQL database capacity management, and Puppet configuration management across global infrastructure

  • Maintained site stability during recurring Friday peak load events implementing emergency capacity scaling procedures and working with teams to optimize resource utilization

Global Datacenter Operations & Migrations:

  • Orchestrated multi-datacenter migration operations including primary datacenter migration before Halloween traffic deadline (hard capacity constraint), establishment and decommissioning of 2 China datacenters, and deployment of 3 new global active/active datacenters

  • Provisioned and configured networking infrastructure for global datacenter expansion including Nginx/HAProxy configuration for internal and external services, load balancer setup, and service discovery integration

System Architecture & Performance Engineering:

  • Built systems model proving self-service automation as only viable solution to exponential backlog growth; demonstrated 500% team scaling would still fail to address demand

  • Migrated 1,000+ services to new Docker-based platform with 4-engineer team, coordinating complex dependency migrations across product and infrastructure teams

Technical Leadership & Cross-Functional Collaboration:

  • Led microservices migration initiative from Puppet to Docker enabling self-service deployments, reducing developer time-to-production from days to minutes

  • Authored comprehensive Docker documentation and co-developed training curriculum; delivered tech talks and operated Docker help desk Slack channel supporting 1,800+ engineers

  • Led infrastructure migration from Ubuntu to Debian across all development and production servers, coordinating with service owners to ensure zero-downtime transitions

  • Built self-service vhost management tool for web applications enabling developers to configure Nginx, HAProxy, OpenID, and OAuth2 in minutes, eliminating Puppet dependencies


COMMUNITY SERVICE & VOLUNTEERING

LAKE STEVENS SCHOOL DISTRICT | BASKETBALL COACH

SEPTEMBER 2019 - MARCH 2022 | LAKE STEVENS, WA

Middle School Basketball Coach (2021-2022):

  • Mentored 25+ middle school students through season-long basketball program emphasizing skill development, teamwork, and character building

  • Developed age-appropriate coaching curriculum distilling basketball fundamentals into engaging, accessible lessons for students with varying skill levels

  • Demonstrated leadership, communication, and mentorship skills working with diverse student populations including students facing socioeconomic challenges

Assistant Varsity High School Basketball Coach (2019-2021):

  • Supported varsity program serving 40+ student-athletes, developing practice plans, coordinating logistics, and providing individual skill coaching

  • Strengthened abilities in setting expectations, maintaining discipline, meeting deadlines, and fostering positive relationships with students from diverse backgrounds

  • Collaborated with head coach on team strategy, player development, and program administration requiring strong communication and organizational skills


EDUCATION

UNIVERSITY OF WASHINGTON | BUSINESS - ACCOUNTING

SEPTEMBER 2007 - JUNE 2011 | SEATTLE, WA


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