IT Operations Lead at Loadsmart

ARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY? 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 — while collaborating closely with Security, Platform Operations, HR, and Finance. Job Type: Exempt DEPARTMENT: Technology LOCATION: Chicago, USA WHAT YOU GET TO DO: • 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 REQUIRED QUALIFICATIONS: • 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 have • 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 (~300–500 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 WORKING AT LOADSMART: • Competitive base salaries - we believe in rewarding top talent  • Extremely competitive Equity package - become a shareholder in our company! • Loadie Time Off - PTO and sick days without a limit • Comprehensive Medical, Dental, and Vision insurance plans • 401k Match  *Applicants must be currently authorized to work in the United States on a full-time basis. Loadsmart will not sponsor applicants for work visas. At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability. It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.