Brandon Bolton Production Engineer
Open to senior infrastructure & systems engineering roles

Brandon Bolton.

Infrastructure, automation & endpoint security.

I build automation that runs unattended and write documentation people can actually follow.

Role Production Engineer · Comply
Based in Kenosha, Wisconsin
Reach me contact@BrandonBolton.com
Get in touch View experience Download resume
18+
Years of experience
2.6 hrs
Median ticket resolution time
200+
Scripts & playbooks shipped
900+
Endpoints secured & compliant
01

About

A short version, for hiring managers.

I'm a production engineer. Most days are spent automating infrastructure and keeping a mixed Windows, macOS, and Linux environment running smoothly. When things are working well, nobody notices, which is usually the goal. I also spend a lot of time documenting what I do so the team is not dependent on one person knowing how everything works.

I started on a high school help desk and spent about ten years working with customers before moving into infrastructure and production engineering. Along the way, I led an eight-person team for four and a half years. Those experiences taught me that good documentation, shared knowledge, and a little patience go a lot further than being the person who always has the answer.

5,300+
Support tickets & cases closed
57
Broker-feed automations across 38 institutions
50+
People led, mentored, or trained across my career
40+
Knowledge base articles authored
02

Expertise

Where I do my best work.

01

Infrastructure automation

I automate the second a task repeats. Across PowerShell, Python, and Bash I've shipped 200+ scripts: broker feed delivery for 38 financial institutions, endpoint remediations, and patch management. Ansible playbooks on AWX keep our Linux fleet patched and compliant, and a library of hardening scripts handles VPN, BIOS, and Secure Boot. If it runs more than once, it runs unattended.

02

Cloud & endpoint management

I configured Intune for Windows workstation administration on a 4-day deadline, having never touched it before. I went on to roll it out across the fleet, now 420+ workstations, migrate every on-premises GPO to cloud conditional access, and cut new-hire setup to minutes with Autopilot. We're partway through moving device management fully to the cloud. On the Apple side, I built Jamf for the macOS and iOS fleet starting from an empty tenant, writing every configuration and security policy and automating patching.

03

Production support leadership

I run support on metrics and runbooks. I've closed 5,300+ tickets and cases across Jira and Salesforce, holding a 2.6-hour median resolution time with over a third resolved inside the first hour. I own broker feed data delivery for 38 financial institutions and carry a 24/7 on-call rotation for critical incidents, often the escalation point even outside my scheduled weeks. The team also covers SFTP, SSO, email, APIs, and help-desk support.

04

Mentoring & documentation

At Comply I've written 40+ knowledge base articles and a set of Jupyter notebooks the team can run step by step. When new specialists come on, I'm usually the one bringing them up to speed, through Q&A sessions and platform deep-dives. I've been teaching since my first IT job, where I ran an after-school Tech Crew and got 20+ students into hardware repair and troubleshooting.

03

Experience

Help desk to production engineering, the long way around.

  1. Feb 2025 — Present Remote

    Production Engineer

    Comply

    Infrastructure and production engineering for a compliance technology platform serving the financial services industry. Own escalated infrastructure issues, deliver large-scale modernization projects, and build automation so the team can take on more work without adding headcount.

    • Closed 2,300+ tickets across 2025–2026 at a median resolution time under 3 hours
    • Led the Windows 10 → 11 migration of the 124 workstations still on Windows 10 with a two-stage rollout (stage the installer fleet-wide, then trigger the upgrade) that held average end-user downtime to 10–15 minutes; finished 2 months ahead of schedule
    • Configured Intune for Windows workstation administration inside a 4-day deadline, having never touched it before, then rolled it out across the fleet, now 420+ workstations under management
    • Built Jamf Pro for the macOS and iOS fleet starting from an empty tenant: every configuration and security policy, plus automated patch management
    • Built 57 PowerShell automation scripts that pull, transform, and stage broker feed files from 38 financial institutions including UBS, Chase, Schwab, Goldman Sachs, and Merrill Lynch, so nobody touches the files between pickup and ingestion
    • Remediated a critical patching gap across a 150+ server Linux fleet (Amazon Linux, Ubuntu, and Red Hat), automating the full patch cycle with Ansible on AWX
    • Remediate a monthly cross-platform vulnerability report across Windows, macOS, and Linux, and built the hardening automation behind it: VPN onboarding, BIOS and Secure Boot enforcement, and fleet-wide File Integrity Monitoring
    PowerShellPythonBashIntuneAWSLinuxWindowsSecurity
  2. Mar 2022 — Jan 2025 Remote

    Technical Support Specialist

    Comply

    Tier 1/2/3 customer support for a compliance platform serving financial-services clients. Grew from front-line support to Level 3 infrastructure escalations within 18 months, eventually owning major-client relationships and back-end production systems.

    • Closed 1,954 tickets in 2024 at an 82.4% within-24-hour SLA and a 2-hr median, the best full-year median on record, nearly double my 2023 volume of ~1,000 cases across Salesforce and Jira
    • Became one of two primary front-line support contacts for the flagship platform within the first 9 months on the team
    • Promoted to Level 3 support in 2023, taking on infrastructure escalations and complex multi-platform troubleshooting
    • Authored 40+ knowledge base articles and trained a newly formed specialist team through Q&A sessions and platform deep-dives
    • Owned the primary support relationship with a major institutional client, including SSO/SAML integration troubleshooting
    C#.NETSQLSAMLSSOSalesforceJiraCustomer Support
  3. Sep 2022 — Aug 2023 Chicago, IL · Remote

    Independent Contractor, Website Maintenance

    Between Friends

    Originally engaged through Code for Chicago to help rebuild Between Friends' website, a Chicago-based domestic-violence-prevention nonprofit. After the rebuild shipped, they retained me directly on a one-year on-call maintenance contract to keep the site running while their small staff focused on the mission.

    • Shipped monthly WordPress security updates across core, plugins, and themes
    • Resolved usability, hosting, and code issues on a 48-hour response SLA
    • Kept the platform at zero downtime across the full contract for a nonprofit serving survivors of domestic violence
    • Owned contract, scope, and invoicing as a sole independent contractor
    WordPressElementorMaintenanceSecurityNonprofit
  4. Aug 2017 — Mar 2022 Pleasant Prairie, WI

    Merchandiser

    PepsiCo

    Field representative for PepsiCo across a multi-store retail territory. Built displays, managed product rotation, handled escalations from store managers, and served as the brand's day-to-day face for retail partners.

    • Served as PepsiCo's primary in-store representative across a multi-store retail territory, owning partner relationships and resolving escalations on the spot
    • Trained retail staff on product handling, rotation, and merchandising standards
    Customer ServiceOperationsRetailBrand Representation
  5. Feb 2013 — Aug 2017 Waukegan, IL

    Receiving Associate → Department Head

    Jewel-Osco

    Promoted to Department Head and led an 8-person team through daily receiving operations for a busy grocery store. Hired, coached, and managed performance in my first formal leadership role, which still shapes how I think about people management today.

    • Led an 8-person team for 4.5 years with consistent positive evaluations and low turnover
    • Managed receiving department operations: scheduling, performance coaching, training, and inventory documentation
    • Developed junior associates who advanced into supervisory roles
    • Implemented quality control procedures and documentation improvements that reduced errors and streamlined workflows
    Team LeadershipOperationsInventory ManagementPerformance Coaching
  6. Aug 2008 — Jun 2012 Zion, IL

    Help Desk Technician

    Zion-Benton Township High School

    First IT role, supporting 500+ faculty and students across a comprehensive school environment: desktops, servers, printers, VoIP, classroom AV, and smart whiteboards. Also taught an after-school Tech Crew program that put hardware in students' hands.

    • Supported 200+ devices and 500+ users across a full school IT environment
    • Resolved end-user tickets using a formal ticketing system and built detailed documentation for recurring issues
    • Managed purchase orders and vendor relations for IT equipment and supplies
    • Taught an after-school Tech Crew program, mentoring 20+ students in hardware repair and troubleshooting
    • Several of those students went on to study or work in IT
    IT SupportHardwareNetworkingProcurement & Vendor RelationsMentoringTeaching
04

Projects

Migrations, automation, and a little civic tech.

Comply
Shipped
2025

Windows 10 → 11 Enterprise Migration

Migration of the 124 workstations still on Windows 10 to Windows 11 using a two-stage, PowerShell-driven rollout: stage the installer across the fleet first, then trigger the upgrade. Splitting the prep from the upgrade kept each interruption short, with no hands-on work per machine.

  • 124 workstations migrated
  • 2 months ahead of schedule
  • Two-stage rollout: stage installer → trigger upgrade
  • ~10–15 min average end-user downtime
  • PowerShell-driven bulk orchestration
PowerShellWindowsAutomationProject Mgmt
Live
Nov 2024 — Present

Intune Deployment & Cloud Device Management

Took an Intune project from nothing to production: configured it for Windows workstation administration inside a 4-day deadline, then enrolled the fleet, migrated every on-prem GPO to conditional access, and set up Autopilot onboarding. I took this on while still on the support team, and it is part of what moved me into production engineering.

  • 420+ workstations under management
  • Reduced device setup time from hours to minutes
  • On-prem GPO → cloud conditional access
  • On-prem → hybrid → cloud-only roadmap
  • Autopilot-based employee onboarding
IntuneEntra IDConditional AccessAutopilot
Live
2024 — Present

Linux Server Patching & Compliance Automation

Ansible-driven patch and compliance automation for a 150+ server Linux fleet (Amazon Linux, Ubuntu, and Red Hat) across dev, UAT, and production, orchestrated through AWX. I built it after finding servers drifting out of patch compliance, and designed every step to run unattended and stay safe to re-run.

  • Brought a 150+ server Linux fleet (Amazon Linux, Ubuntu, and Red Hat) into patch compliance across dev, UAT, and production environments
  • Wrote an Ansible patching playbook that covers the full cycle in under 25 minutes per server: disk-space preflight, OS version upgrades, orphaned-package cleanup, and conditional auto-reboot
  • Scheduled the playbooks through AWX with per-run logging for repeatable, auditable patch runs
  • Standardized time synchronization with chrony and enforced mandatory system software across the fleet
  • Designed the playbooks to be idempotent, so any run is safe to repeat without unintended side effects
AnsibleAWXLinuxSecurityCompliance
Live
2024 — Present

CVE Vulnerability Remediation & Security Hardening

Ongoing vulnerability management across a 900+ endpoint fleet of Windows, macOS, and Linux machines, working a monthly report of findings to close outstanding CVEs and harden endpoint protection.

  • Triage and remediate a monthly vulnerability report spanning Windows 11, Windows Server, macOS, and Linux
  • Resolve CVEs across the fleet, prioritized by severity
  • Built a FortiClient IPSec VPN script (PowerShell + Bash) that detects, installs, upgrades, and fully configures the client on Windows and macOS, turning a slow manual setup into part of device onboarding
  • Wrote a library of endpoint-hardening scripts: BIOS passwords and Secure Boot enforced fleet-wide via the Dell PowerShell module, automated Windows Defender management, and File Integrity Monitoring across Windows, macOS, and Linux
  • Automated bulk removal of the deprecated Teams Classic client and Linux patch automation across the fleet
SecurityCVEAutomationInfrastructure
Code for Chicago · Volunteer
Shipped
Apr 2021 — Aug 2022

Between Friends: Website Rebuild

Full website rebuild for a Chicago nonprofit supporting survivors of domestic violence. Drove user research with staff and survivors, ran an accessibility audit, and migrated the site to Elementor so the team could manage it themselves.

  • User research with case managers and therapists
  • Accessibility audit and UX improvements (scannability, safety exit visibility)
  • Migrated from custom WordPress to Elementor visual builder
  • Implemented Spanish-language support with language toggle
WordPressUXAccessibilityNonprofit
Shipped
2021 — 2023

Chicago Defender Charities: Salesforce

Connected five disparate SaaS platforms into Salesforce through a no-code integration platform (Automate.io), replacing manual data entry with automated flows across the organization.

  • Mapped and researched five SaaS platforms for integration feasibility
  • Evaluated multiple integration approaches and selected Automate.io
  • Implemented automated workflows to sync data across all platforms
  • Eliminated manual data entry and reduced operational friction
SalesforceIntegrationMulti-Platform ArchitectureNonprofit
Shipped
Apr 2021 — Mar 2022

Chicago Defender Charities: Website Platform & Development

Evaluated CMS platforms and built the nonprofit's consolidated web presence on Squarespace, chosen for simplicity and long-term self-sufficiency without ongoing technical support.

  • Researched and evaluated multiple CMS platforms for feasibility
  • Identified Squarespace as solution balancing usability and long-term sustainability
  • Developed website within platform constraints and limitations
  • Built solution the client could independently manage and maintain
SquarespaceCMS SelectionWeb DevelopmentNonprofit
Code for America · Volunteer
Shipped
2021 — 2022

Reimagine 911: Emergency Response Data Standardization

A crowdsourced push to standardize fragmented 911 call data, which has no national standard across the country's ~5,748 dispatch centers.

  • Collaborated with nearly 1,000 volunteers across 280 organizations to collect PSAP data
  • Sanitized and normalized disparate 911 data across incompatible systems
  • Analyzed data from 327+ Public Safety Answering Points to identify critical gaps
  • The cleaned dataset helped seed Classifyr, an open-source tool for comparing how cities route emergency calls
Civic TechData AnalysisData EngineeringPolicy Impact
05

Skills

A working list of the things I reach for often.

Languages
  • Python
  • PowerShell
  • Bash
  • YAML
  • SQL / T-SQL
Cloud & Infrastructure
  • AWS (EC2, S3, SES)
  • Microsoft Entra ID
  • Microsoft Intune
  • Jamf
  • Ansible / AWX
Systems & Platforms
  • Linux administration
  • Windows Server & Client
  • SSO / SAML / OAuth
  • SFTP & file transfer
  • Vulnerability management & FIM
  • Monitoring & alerting (LogicMonitor, Grafana, Prometheus)
Tooling
  • SQL Server
  • Jupyter Notebooks
  • Git / Bitbucket
  • Salesforce
  • Jira
Documentation & Knowledge
  • Runbooks
  • Architecture documentation
  • Technical writing
  • Knowledge bases
  • Process documentation
Practice
  • ITIL service management
  • Root cause analysis
  • On-call & incident response
  • Change management
  • Metrics-driven leadership
06

Credentials

Certifications, education, and community work.

Certifications

ITIL 4 Foundation
Current
PeopleCert
Oct 2025 — Oct 2028
CompTIA Project+
Current
CompTIA
Aug 2024 — Aug 2027
AWS Certified Cloud Practitioner
Current
Amazon Web Services
Aug 2023 — Aug 2026

Education

B.S. Software Engineering
Western Governors University
Expected August 2026
99%
Board of Governors Associate Degree
Pierpont Community & Technical College
Completed
100%

Community

Code for Chicago
Volunteer Software Engineer
Apr 2021 — Oct 2023 · 2.5 years

Two and a half years on cross-functional civic-tech teams of 5 to 15 contributors. Built a Salesforce CRM for Chicago Defender Charities and rebuilt the Between Friends website, then stayed on through a one-year maintenance contract, so each nonprofit could run independently without ongoing technical support.

SalesforceWordPressAccessibilityUX ResearchCivic Tech
Code for America
Reimagine 911 · Volunteer Data Analyst
2021 — 2022

Joined the Reimagine 911 National Action Team during the 2021 National Day of Civic Hacking, contributing to a national effort to standardize fragmented 911 call data across thousands of dispatch centers. The work became the foundation for Classifyr, an open-source tool for comparing how cities route emergency calls.

Civic TechData StandardizationOpen SourcePolicy Impact
07

Let’s talk.

I’m open to senior infrastructure and systems engineering roles. If you’re building systems that have to stay up, or your nonprofit needs a hand keeping the lights on, email me.

Email me LinkedIn Resume
Email contact@BrandonBolton.com
Time zone Central Time (CT)
LinkedIn BrandonLeeBolton
GitHub BrandonBolton
Location Kenosha, Wisconsin