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Datadog - Senior Technical Curriculum Developer - Security
===========================================================
:date: 2025-11-03
:slug: datadog-senior-technical-curriculum-developer-security-cover-letter
To Datadog:
For over 15 years of infrastructure & security experience—combined with extensive technical content creation—positions me perfectly for the Senior Technical Curriculum Developer role at Datadog. I introduced Datadog to both Remind & Coursemojo, deploying EC2 agents across 60+ Ubuntu microservices & Fargate sidecar agents for APM, logging, & custom metrics. This hands-on implementation experience means I understand customer pain points, common pitfalls, & best practices from real production environments. Cofense implemented a SOC2 & FedRAMP compliance (Terraform-based AWS controls, Okta integration, DefectDojo vulnerability management). At Coursemojo, I built educational tools for public school teachers—designing monitoring dashboards & real-time student activity tracking. Creating engaging curriculum that helps teams learn complex technical topics resonates deeply with my experience building tools that empower users. Most often I am a root holder for the orgs I work with which means the highest level of access. I held a secret security clearance when working for CSC (General Dynamics DoD contractor) working with classified information systems.
My technical content creation spans multiple formats & audiences. Blog posts since 2011 cover infrastructure, DevOps, & system administration topics. Pemaculture YouTube channel (https://www.youtube.com/c/RussellBallestrini). "uncloseai.com: Machine Learning Reference Guide to Inference Clients" documents AI inference implementations & streaming techniques across 42 programming languages—a massive educational undertaking requiring clear technical writing & code generation & automated testing to make sure examples compile & execute properly!
AWS expertise (CloudFormation, ECS, Fargate, EC2, SQS, RDS) pairs with deep Docker & Kubernetes knowledge. Infrastructure as Code proficiency includes CloudFormation, Terraform, Ansible, & SaltStack. Open source contributions & knowledge sharing to grow reusable educational materials.
I align with Datadog's mission to provide unified observability across infrastructure, applications, security & to break down silos between Dev, Ops, & Security teams. Creating hands-on labs, writing application & infrastructure code for learning projects, & designing course roadmaps would leverage both my technical depth & teaching experience. Security knowledge spans OWASP principles, AWS security best practices, container security, & compliance frameworks (SOC2/FedRAMP). I would value the opportunity to transform complex security & observability topics into engaging training courses & to help businesses & partners maximize their ROI on Datadog integrations. My hands-on Datadog implementation experience, security expertise, & content creation skills should help accelerate customer success & strengthens Datadog's training offerings.
Thank you for any consideration,
Russell Ballestrini

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@ -40,9 +40,9 @@ Full Stack Engineer
Led the development & scaling of an AI assistant teacher for public schools, focusing on infrastructure management & application scaling.
Key Achievements:
Designed and implemented CI/CD pipelines for two monolithic services using AWS CloudFormation and GitHub Actions. Scaled AI-powered educational tools using commodity language models (openai & anthropic). Implemented student monitoring tools to enhance the teacher's birds eye view of the classroom! Websocket enhancements like class pause, fastforward, & single-student restarts!
Designed and implemented CI/CD pipelines for two monolithic services using AWS CloudFormation and GitHub Actions. Introduced Datadog with Fargate sidecar agents for APM, logging, & custom metrics. Scaled AI-powered educational tools using commodity language models (openai & anthropic). Implemented student monitoring tools to enhance the teacher's birds eye view of the classroom! Websocket enhancements like class pause, fastforward, & single-student restarts!
Technologies: AWS (CloudFormation, ECR, ECS, ALB), GitHub Actions, Docker, Nginx, uWSGI, Python
Technologies: AWS (CloudFormation, ECR, ECS, ALB), GitHub Actions, Docker, Nginx, uWSGI, Python, Datadog
Senior Security Engineer
@ -61,9 +61,9 @@ Lead Software Engineer
Managed AWS infrastructure and led cloud cost optimization, security enhancements, and developer productivity improvements.
Key Achievements:
Ensured critical services scaled during COVID-19 lockdowns, supporting distance learning initiatives. Implemented infrastructure-as-code using Python and Stacker. Contributed to SlashDeploy, a Ruby-based tool enabling GitHub deployments via Slack commands, pioneering deployment automation before modern CI/CD platforms. Authored technical blog posts.
Ensured critical services scaled during COVID-19 lockdowns, supporting distance learning initiatives. Introduced Datadog with EC2 agents for container APM, logs, & custom metrics. Implemented infrastructure-as-code using Python and Stacker. Contributed to SlashDeploy, a Ruby-based tool enabling GitHub deployments via Slack commands, pioneering deployment automation before modern CI/CD platforms. Authored technical blog posts.
Technologies: AWS (ECS, EC2, SQS, RDS, DynamoDB), GNU/Linux, Python, Ruby, CloudFormation
Technologies: AWS (ECS, EC2, SQS, RDS, DynamoDB), GNU/Linux, Python, Ruby, CloudFormation, Datadog
Earlier Career Highlights
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@ -98,4 +98,5 @@ Additional Information
- Make Post Sell: https://www.makepostsell.com
- Remarkbox: https://www.remarkbox.com
- uncloseai.com 42 inference clients & book: https://uncloseai.com
- YouTube channel: https://www.youtube.com/c/RussellBallestrini/featured
- All Russell's self-hosted gitlab repos: https://git.unturf.com/engineering/