IT Operations Lead

Loadsmart•Chicago, IL

11d•$80,000 - $110,000

About The Position

Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)! We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less. With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork. We are looking for a talented and driven IT Operations Lead to join our team! We are seeking someone who is hands-on, strategic, and thrives in a dynamic and fast-paced global company. In this role, you will run our Corporate IT function, ensuring that Loadsmart's technology environment is secure, reliable, and scalable. You will own IT strategy, day-to-day operations, SaaS governance, and the systems that keep our workforce productive â while collaborating closely with Security, Platform Operations, HR, and Finance.

Requirements

5+ years of experience in IT operations, systems administration, or corporate IT management, with at least 2 years in a leadership or lead role
Deep knowledge of identity and access management (Okta, Google Workspace Admin, SSO/SAML, SCIM)
Strong experience with endpoint management (MDM solutions for Mac and Windows), device lifecycle, and patching strategies
Comfort working with embedded or industrial hardware (edge devices, single-board computers, or similar), this is distinct from standard PC/laptop support and is a hard requirement
Solid networking fundamentals: routers, switches, firewalls, VPN, Wi-Fi, and DNS
Experience with SaaS vendor management: procurement, license optimization, contract negotiation, and Shadow IT discovery
Good understanding of information security concepts and compliance frameworks (SOC 2)
Experience with IT service management practices: ticketing systems, SLA management, and incident response
Excellent written and spoken English communication skills, ability to collaborate across a distributed, international team

Nice To Haves

Hands-on scripting ability (Python, Bash, or similar) for automation of IT workflows
Experience with AWS cloud fundamentals (IAM, basic networking, cost awareness)
Familiarity with IT asset management tools and practices
Experience with LTE/cellular networking and IoT or edge device management
Familiarity with drive imaging, OS flashing, and hardware-level diagnostics
Industry certifications (ITIL, CompTIA, Google Workspace Admin, Okta Certified)
Experience supporting a startup or mid-sized company (~300â500 employees) in a fast-paced environment
Familiarity with BI tools (PowerBI, Superset) and data-driven IT reporting
Experience with LTE/cellular networking and IoT or edge device management
Familiarity with drive imaging, OS flashing, and hardware-level diagnostics

Responsibilities

Own end-to-end IT service delivery, including help desk, incident management, request fulfillment, and escalation workflows
Administer identity and access management platforms (Okta, Google Workspace, Auth0), including SSO integrations, MFA policies, and employee lifecycle management
Manage core collaboration and productivity platforms (Google Workspace, Slack, JIRA/Confluence, Okta, Zoom), including configuration, integrations, and license management
Manage endpoint devices across Mac, Windows, and mobile via MDM, including patching, encryption, and compliance policies
Own IT vendor relationships, contract negotiations, license utilization, and budget tracking across the SaaS portfolio, including procurement of IT equipment and laptops
Partner with Security on endpoint protection, SOC 2 compliance requirements, and corporate security policy enforcement
Maintain a comprehensive SaaS inventory and lead Shadow IT discovery and rationalization to reduce risk and redundancy
Manage corporate network infrastructure, including LAN, WAN, Wi-Fi, firewalls, VPN, and DNS across office locations
Receive, configure, image, and test hardware units before field shipment; coordinate remote validation with engineering and perform component-level replacements
Automate repetitive IT processes such as onboarding, access provisioning, and inventory tracking through scripting and workflow tools
Define and communicate company-wide IT policies and track/report IT KPIs and operational health to stakeholders
Drive operational maturity through documentation, runbooks, knowledge base development, and continuous process improvement