Charles Stephen Thompson



But did you die?

Fun Facts and Random Things About Me

  • Website:
  • Sign: Libra
  • Birth City: Kansas City, MO, USA
  • Favorite Food: Bacon
  • Email:
  • Freelance: Available


I know some things.

Mobile Device Management 98%
Server Administration: Linux, Windows, & macOS90%
Shell Scripting93%
Cloud Computing & Network Mangement85%
Service & Application Virtualization (Docker, Kubernetes, & Podman)82%
Identity and Access Management (IAM)99%


For a PDF version of the resume, please click here.


Charles Stephen Thompson

Innovative and deadline-driven technologist with over a decade of experience in IT and DevOps Engineering designing and implementing user-centered solutions for complex problems at small, medium, and large startups alike.


Bachelors of Arts, Modern American Legal History

2005 - 2010

The University of Chicago, Chicago, IL

BA Thesis was on the misuse and abuse of copyright law as compared to that seen in the patent field.

Professional Experience

Founder, CEO, & Principal Consultant

Jan 2018 - Present

Brooklyn Helpdesk, Inc., Brooklyn, NY

  • Consumer and SMB IT/DevOps, automation and integration engineering.
  • Manage network equipment and server stacks in the tristate area totaling just under 500 client devices with revenue nearing $7,500/month.
  • Identity & Access Management/SSO Setup and Integration
  • CI/CD Pipeline Setup and Automation
  • LAN/WiFi Installation and Maintenance
  • Automation and Integration Engineering
  • Smart Home/Office Automation, Setup, and Configuration including lighting, window coverings, A/V, scene creation, and server management.
  • General technical and IT support

DevOps Software Engineer

Nov 2019 - Dec 2021, New York, NY

  • Worked with cross-company stakeholders to reduce onboarding time by 25% with cost reduction of 12% via a streamlined process integrating SAAS, automations, configurations of IAM/MDM tools (Active Directory, GSuite, Okta, JAMF) to achieve SSO from hardware to cloud.
  • Designed, built, tested, deployed, and monitored various automation/process streamlining software integrations to accomplish critical tasks with respect to corporate IAM, user management, and hardware de/provisioning.
  • Analyzed currently available technologies to ensure best practice methodologies, on-time delivery, and practical solutions that actually work for complex corporate hardware/software integration requirements.
  • Deployed, monitored, and maintained Kubernetes and Docker stacks for a team of three dozen software engineers while also running IT functionalities for a burgeoning fintech startup.

Software Infrastructure Engineer and Interim Director of IT

Aug 2018 - Feb 2019

Blink Health, New York, New York

  • Provisioned and maintained all Windows server instances, focusing on the authentication/SSO subsystem (Active Directory) to provide fault tolerance and high availability using Chef, Ansible, and Terraform.
  • Served as subject matter expert on SSO design and implementation while working closely with Engineering Security team to achieve increased adoption of core SSO technologies across platforms and business units.
  • Automated Active Directory credential writing to GSuite, simplifying user provisioning and de-provisioning while creating a true SSO experience for end users on mobile, Macs, PCs, and the Internet.
  • Leveraged Google SAML to reduce endpoint maintenance and external attack surface when connecting SSO to SAAS applications, achieving higher security, lower cost of delivery, and increased efficiency.
  • Integrated Windows/Mac/Linux/GSuite authentication using LDAP to provide cross platform SSO for VPNs, databases, critical websites, etc., reducing end user credential management and increasing security.
  • Automated HR process across Greenhouse, Jira, AD, and GSuite, reducing steps involved for onboarding by 90% (from 40 steps to 4).

Lead IT Infrastructure Engineer

Oct 2016 - Aug 2018

Blink Health, New York, New York

  • Designed, built, and managed UniFi 802.1X LAN and WiFi infrastructure at three sites with connectivity to AWS data centers via site-to-site VPN, providing seamless SSO-backed network auth to 200+ staff.
  • Achieved scaleable, reusable, and reviewable infrastructure as code with Github pull request support, CircleCI integration, and revision history across multiple AWS accounts via Terraform.
  • Reconfigured engineering Jira workflows to take advantage of Github pull request and CircleCI automations, decreasing launch time and manual integration testing for the DevOps team.
  • Grew IT team to become integral part of organization with 10 members operating across three geographic locations.
  • Supervised growing IT staff while working closely with management to develop SOPs for new units.
  • Managed annual technology budget of $5mm+ with inventory comprising hundreds of endpoints.
  • Implemented MDM fleet management software to achieve compliance and security policy goals.
  • Successfully oversaw opening of four offices in three states; conducted five successful office moves.

AVP, Technology - Level III System and Network Engineer

Feb 2013 - May 2016

Build America Mutual Assurance Company, New York, NY

  • Designed and implemented Active Directory server backbone to provide SSO for Windows, Mac, and Linux client and server endpoints using AD, Kerberos, and LDAP technologies in conjunction with MFA.
  • Implemented Jabber/XMPP with SSO and VOIP integration for pre-existing phone system.
  • Moved servers and applications to cloud providers, resulting in over $250K in savings over five years.
  • Conducted non-developer technology audit process and compliance reviews (Sarbanes-Oxley, etc).
  • Provided application/hardware service, support, and training to nearly 100 users across three locations.
  • Supervised allocation, planning, and monitoring of hardware and software resources.

Support Technician II

Jan 2012 - Jan 2013

SecondMarket, Inc, New York, NY

  • Configured and maintained a single sign-on solution utilizing SAML/XML and Active Directory Federation Services to provide seamless integration and usage of AD passwords for third-party web apps such as Yammer, Salesforce, and Zendesk—saving the company $36 per user per year.
  • Managed all technology purchasing for a rapidly growing technology/finance services startup with an annual technology budget of over $1.5 million for three locations—two domestic, one international (New York City, San Francisco, and Hong Kong).


If you feel the need to reach out, my contact information is below and I do freelance work often. Hit me up.


Brooklyn, NY 11238