Olivia Wilcox

Co-Founder

West Palm Beach, Florida, United States25 yrs 1 mo experience

Highly Stable

Key Highlights

20+ years of engineering experience across diverse organizations.
Expert in mentoring engineers for career advancement.
Proven track record in cloud consulting and DevOps transformation.

Stackforce AI infers this person is a SaaS and DevOps expert with extensive experience in cloud infrastructure and mentoring.

Contact

Skills

Core Skills

Site Reliability EngineeringDevopsSoftware EngineeringMentoring

Other Skills

Infrastructure as code (IaC)Continuous Integration and Continuous Delivery (CI/CD)Amazon Web Services (AWS)Cloud ComputingTerraformKubernetesMicrosoft AzureSoftware ObservabilityMicroservicesAutomationArchitectureScalabilityHigh Availability (HA)LeadershipPython

About

I'm a working engineer with 20+ years of experience across startups, mid-size companies, and Fortune 100 organizations like American Express. I've reached senior twice, first as a Senior Software Engineer and then as a Senior Site Reliability Engineer, and I know exactly how disorienting the gap between doing senior-level work and actually getting recognized for it can be. That's what I work on with engineers. Not just the technical bar, but the professional operating skills that determine whether you clear it. How you communicate across teams, how you build trust with the people evaluating you, how you make yourself visible without being performative. The stuff nobody teaches you and most people figure out too late. I also work with companies. AI-assisted development training, cloud consulting, DevOps transformation, and platform engineering. One client put it best: "She's not some consultant, she's your team member." That's the goal every time. If you're an engineer trying to level up or a team trying to ship faster, DM me or visit learnwithoj.com. We'll figure out the right next step together.

Experience

25 yrs 1 mo

Total Experience

4 yrs 6 mos

Average Tenure

6 mos

Current Experience

Learn with o.j.

Founder & Senior SRE

Oct 2025 – Present · 6 mos · Remote

Design, deploy, and maintain a cloud-native edtech platform on AWS/EKS with Terraform and GitHub Actions to run production-style labs.
Build CI/CD pipelines that build, scan, push to ECR, and deploy to EKS with rollback and basic policy guardrails.
Implement observability basics (metrics, logs, health checks) and simulated failures to validate recovery paths.
Produce clear runbooks, diagrams, and READMEs that explain design choices and operational procedures.

Infrastructure as code (IaC)Continuous Integration and Continuous Delivery (CI/CD)Site Reliability EngineeringDevOpsMentoringAmazon Web Services (AWS)+4

Womentech network

Engineering Mentor

Oct 2025 – Present · 6 mos · Remote

Mentor engineers pivoting into SRE/DevOps with practical roadmaps, weekly goals, and feedback loops.
Review portfolios/resumes/GitHub; suggest impact-focused rewrites and project upgrades.
Publish playbooks and templates to support mentees and the broader community.
Promote inclusive, accessible practices; connect mentees to opportunities and peer support.

Site Reliability EngineeringDevOpsMentoringSoftware Engineering

Datasnipper

Senior Site Reliability Engineer

Jan 2025 – Oct 2025 · 9 mos · Remote

Executed multi-region AWS to Azure migration with phased cutover; deployed infra through existing Terraform modules.
Built observability stack and dashboards reducing MTTR via automated anomaly detection and better signal-to-noise.
Extended CI/CD with Playwright testing for safer, faster releases.
Partnered with platform teams to improve performance while controlling cost.

Infrastructure as code (IaC)Continuous Integration and Continuous Delivery (CI/CD)Site Reliability EngineeringDevOpsMentoringMicrosoft Azure+3

American express

Enterprise Site Reliability Engineer & Senior Software Engineer

Oct 2019 – Jan 2025 · 5 yrs 3 mos · Sunrise, Florida, United States

Scaled Automation Platform to 1.2M+ annual runs; standardized CI/CD to cut deploys < 5 minutes.
Introduced SLA-breach alerting for 3rd-party APIs; eliminated hidden reliability gaps.
Led incident reviews and root cause improvements that tightened MTTD/MTTR by > 40%.
Mentored engineers across reliability practices and observability culture.

Infrastructure as code (IaC)Continuous Integration and Continuous Delivery (CI/CD)Site Reliability EngineeringDevOpsMentoringMicrosoft Azure+3

Dycom industries, inc

Senior Software Engineer

May 2018 – Oct 2019 · 1 yr 5 mos · Palm Beach Gardens, Florida

Built and reviewed multi-tier cloud-native services; strengthened release management with pre-flight checks and rollback paths.
Delivered in Python, NodeJS, Angular; authored IaC for repeatable infra changes.
Mentored junior engineers in SWE best practices and test automation.

Infrastructure as code (IaC)Continuous Integration and Continuous Delivery (CI/CD)MentoringAmazon Web Services (AWS)Cloud ComputingTerraform+2

Float left interactive

Software Engineer

May 2016 – Dec 2017 · 1 yr 7 mos · Jupiter, Florida

Contributed across a polyglot OTT/TVE platform (Roku, Fire TV, Apple TV, Android, iOS, LG, Samsung) used by major media brands.
Shipped high-throughput media features while standardizing service integration patterns across devices.

Continuous Integration and Continuous Delivery (CI/CD)Mentoring

New media studios, llc

Technical Co-Founder

Jan 2014 – Sep 2022 · 8 yrs 8 mos · Palm Beach County, Florida, United States

Delivered web/mobile solutions for local businesses and startups; introduced CI, basic IaC, and observability appropriate for small teams.
Pivoted from video production into a multimedia technology consultancy, advising on product/ops trade-offs and incremental delivery.

Infrastructure as code (IaC)Continuous Integration and Continuous Delivery (CI/CD)Site Reliability EngineeringDevOpsMentoringAmazon Web Services (AWS)+4

Palm beach state college

4 roles

New Media Club Advisor and Computer Club Co-Advisor

Jan 2012 – Dec 2013 · 1 yr 11 mos

• Organized hands-on projects and talks to grow student skills and community.

Enterprise Systems Programmer

Promoted

Aug 2010 – Aug 2015 · 5 yrs

Built and enhanced core transaction systems (Natural/COBOL, JCL, Adabas, SUSE Linux) and Java EE web apps (SQL Server, Tomcat, IIS).
Partnered with stakeholders to modernize services safely, emphasizing testing and operability.

Programming Tutor

Jan 2005 – Aug 2010 · 5 yrs 7 mos

• Led tutoring for programming fundamentals; translated complex topics to diverse learning styles.

Mentoring

IT Help Desk

Jan 2004 – Jan 2005 · 1 yr

• Supported faculty/staff; triaged and resolved incidents with clear communication.

Mentoring

Self employed consultancy

Software Developer / IT Support

Jan 2000 – Jan 2013 · 13 yrs

Built custom software and WordPress themes/plugins; delivered end-to-end websites and e-commerce.
Drove quality standards for code review, UI, and performance; prepared and presented technical proposals.
Implemented analytics and email marketing; monitored site performance for continuous improvement.