Frame
Turn Jira context, acceptance criteria, and repository conventions into an executable plan.
Resume / 2026
Bob
Heineman
Security Platform Engineer Cloud Security AutomationRepeatable Tooling
I build security and platform systems that make complex engineering organizations faster, safer, and easier to operate.
My work spans cloud security, automation, developer experience, and dependable distributed systems in regulated environments.
- Based
- Sugar Grove, Illinois
- Connect
$800Kvendor cost avoided over four years
$48K/yrobservability spend reduced
45 minsaved per developer, per day
300+enterprise servers supported at Abbott
01 / AI Workflow Engineering
Repeatable tooling for faster, more dependable delivery.
I design AI-enabled development workflows with human judgment, source evidence, tests, and security controls built into the process.
Build
Use Codex, Claude, ChatGPT, Gemini, and Antigravity through editor extensions and CLIs.
Verify
Keep human review, tests, security controls, and production evidence in the loop.
Report
Generate concise progress summaries, blockers, implementation notes, and Jira updates.
In practice
I build custom agents for repeatable repository and delivery tasks, connect work to Jira context, and use Codex or Gemini Pro to organize implementation, surface blockers, and prepare concise progress summaries. Claude, ChatGPT, Gemini, Codex, and Antigravity are part of my daily editor and CLI workflow.
02 / Experience
Engineering leverage across security, cloud, and operations.
A career built around turning recurring operational friction into reliable platforms and durable automation.
CurrentAug 2025 - Present
Wonder / Grubhub
Senior Software Security Engineer
Building the service identity, ownership, and security platform that unifies Wonder's multi-brand, multi-cloud engineering estate.
- Designed a cohesive service registry spanning multiple brands and cloud environments, connecting technical assets, services, organizational structures, and accountable owners.
- Built a dynamic entity-resolution layer using authoritative data, resource tags, naming rules, structural evidence, and weighted similarity strategies to identify service ownership.
- Created a tiered confidence model that automatically accepts high-trust mappings, surfaces ambiguous candidates for review, and exposes missing ownership data as actionable gaps.
- Evaluated 1,455 services in a representative automation run, classifying 1,222, identifying 233 gaps, and synchronizing 13 downstream projects.
- Turn cloud-security findings into service-aware, owner-aware remediation workflows with measurable SLAs and a consistent cross-team operating cadence.
- Use Jira-connected AI workflows to organize ticket context, structure implementation work, and produce accurate progress and blocker summaries.
- Create repeatable agents with Codex and Gemini Pro for repository analysis, evidence synthesis, documentation, and delivery support.
SkillsPython / AWS / GCP / Service Registry / Entity Resolution / Confidence Scoring / Cloud Security / AI Agents
Nov 2021 - May 2025
Fetch
Senior Software Engineer
Built and modernized the distributed systems behind e-receipt processing, deployment, observability, and production operations.
- Refactored tightly coupled e-receipt infrastructure into independently deployable components with safer release workflows and clearer production ownership.
- Built controlled rollout and rollback capabilities, reusable deployment annotations, and traceability that improved release safety and production investigation.
- Created self-service operational tooling that allowed internal users to manage routine configuration without depending on an engineer for every change.
- Migrated observability platforms, reducing ongoing operating cost by $48,000 per year.
- Automated lifecycle and cleanup workflows across Kafka, Lambda, EventBridge, DynamoDB, and Redis systems, reducing manual work and operating overhead.
SkillsDistributed Systems / Python / Go / AWS / CI/CD / Observability / Kafka / Redis / DynamoDB
2019 - 2021
Olcott Plastics / Rush Street Gaming
Independent Consultant
Delivered focused software-delivery, cloud-cost, and security-automation improvements for two former industry partners.
- Improved Java delivery at Olcott Plastics with Jenkins automation, containerized workflows, and generated technical documentation.
- Reviewed Rush Street Gaming's AWS estate and built Python automation to identify idle resources and reduce unnecessary cloud spend.
- Improved Rush Street Gaming's security alerting and operational visibility through practical cloud automation.
SkillsJava / Python / AWS / Jenkins / Docker / Cloud Security / Cost Optimization
2019 - 2020
divvyDOSE
Senior Software Engineer
Built reliable pharmacy software and delivery infrastructure in a regulated, high-consequence environment.
- Developed backend services and operational tooling for a growing digital pharmacy platform.
- Improved delivery consistency and production visibility through infrastructure automation and observability practices.
- Worked across product, engineering, and operations to resolve reliability issues affecting medication workflows.
SkillsPython / AWS / Infrastructure as Code / Observability / Healthcare
Jul 2018 - Jul 2019
physIQ
Lead Backend Engineer
Delivered scalable APIs and a more productive engineering platform for FDA-regulated digital health systems.
- Designed and delivered scalable Python APIs under FDA-regulated constraints, improving system reliability and compliance.
- Standardized testing practices and introduced GCP Stackdriver monitoring, increasing observability and reducing production issues.
- Led the company-wide move from Vagrant to Kubernetes-based local environments, saving each of 35 developers 45 minutes per day and recovering 26.25 engineering hours daily - roughly 3.3 FTEs or an estimated $560,000 in annual engineering capacity.
- Enabled local services to connect securely to external GCP infrastructure, streamlining hybrid development workflows.
SkillsPython / GCP / Kubernetes / API Design / Testing / FDA-Regulated Systems
Sep 2014 - Jul 2018
Rush Street Gaming
Lead Software Engineer / Software Engineer
Built and operated casino-management systems, property data pipelines, and internal platforms in a tightly regulated gaming environment.
- Led engineering practices, code reviews, design sessions, stakeholder communication, and vendor relationships while establishing reusable foundations for future engineers.
- Developed, deployed, and monitored data pipelines that moved casino-property data into an Amazon Redshift warehouse.
- Architected AWS solutions for land-based casino operations within gaming-board regulatory constraints.
- Maintained jurisdiction-required gaming licenses for onsite access to regulated casino data and systems, traveling to properties for technical consultation, server management, and production support.
- Deployed Docker infrastructure across property environments and the company VPC and established CI/CD using Bitbucket, Jenkins, AWS, and custom automation.
- Avoided $800,000 in vendor fees across four years ($200,000 per year) with a multi-tenant employee-survey platform serving four casino properties.
- Designed a one-time-code model that protected employee anonymity while preserving organizational reporting through repeated annual survey cycles.
SkillsJava / Python / AWS / Redshift / Docker / CI/CD / Technical Leadership / Regulated Gaming
Jan 2013 - Aug 2014
Amazon
Software Development Engineer, Prime
Built and operated high-traffic Prime endpoints across multiple customer surfaces, combining Amazon-scale operations with rigorous cross-functional delivery.
- Owned customer-facing Prime endpoints handling exceptionally high request volume across retail and Amazon devices.
- Prepared Prime front-page entry points for holiday peaks by analyzing prior-year AWS traffic trends and building service-specific dashboards around critical hot paths.
- Operated within Amazon's ecosystem of thousands of interconnected services, using metrics and dependency analysis to protect customer-facing flows.
- Managed Prime promotional content through release-flagging and scheduling systems, enabling coordinated, reversible launches across customer entry points.
- Developed and tested Prime signup for an unreleased Kindle device inside a protected downtown Seattle building, working from a windowless secure room.
- Passed work through rigorous design reviews and disciplined sprints with technical program managers, product representatives, engineering managers, and engineers.
- Automated recurring operational work, recovering roughly three engineering hours per team member per day.
SkillsJava / AWS / Service-Oriented Architecture / Production Operations / Application Security
03 / Foundation
Earlier career.
The systems and consulting foundation behind my platform engineering perspective.
Passport
Senior Systems Administrator
Infrastructure automation, production operations, and developer enablement.
Sogeti
Senior Consultant
Enterprise systems consulting and delivery across complex client environments.
Abbott
Systems Engineering Roles
Automated configuration, deployment, and operational tooling across more than 300 enterprise servers.04 / Capabilities
Tools change. The operating principles stay useful.
- Security
- Cloud security, security automation, vulnerability management, threat modeling, detection engineering
- Cloud & Platform
- AWS, GCP, Kubernetes, Docker, infrastructure as code, observability, distributed systems
- Engineering
- Python, TypeScript, Java, API design, testing, CI/CD, systems integration
- AI Workflow Tooling
- Codex, Claude, ChatGPT, Gemini, Antigravity, custom agents, editor extensions, CLI workflows
- Leadership
- Technical strategy, cross-functional delivery, mentoring, incident response, regulated environments
05 / Education
Northern Illinois University
Bachelor of Science, Computer Science · 2010
Let’s build something dependable.