IT Manager

Spot Hero is looking for a hands-on IT Manager to lead and evolve our internal technology operations, ensuring our team has the tools, infrastructure, and support they need to do their best work. This is a player/coach role: you’ll be directly responsible for systems administration and hands-on technical work while also driving strategy, leading initiatives, and managing a small team. We’re seeking someone with deep IT operations expertise who thrives in fast-moving environments and can bridge engineering, security, and business teams.

At Spot Hero, we empower people to get everywhere, easier! Our marketplace connects drivers with parking spots through mobile, app and web, helping them save time and money. At the same time, we provide parking operators with powerful tools to manage inventory, reach new customers, and grow their businesses. We’re bringing the parking industry into the future through technology and innovation.

• Build and lead Spot Hero’s IT operations program across endpoint management, SaaS administration, networking, and corporate infrastructure.
• Manage and mentor IT team members, fostering a culture of accountability, continuous improvement, and service orientation.
• Own and optimize our corporate technology stack, including Google Workspace, Atlassian (Jira, Confluence), Slack, Zoom, and Okta.
• Define and oversee endpoint fleet strategy using Jamf and Intune, including security baselines, MDM configuration, and device lifecycle management across macOS and Windows.
• Champion IT service delivery and operational excellence, tracking SLAs, ticketing workflows, and self-service resources that reduce friction for employees.
• Partner with Security to ensure endpoint compliance, identity and access management best practices, and alignment on corporate security policies.
• Oversee onboarding and offboarding processes, ensuring seamless provisioning and deprovisioning of accounts, devices, and access across all systems.
• Manage and evolve the Chicago office network and infrastructure, including Wi-Fi, video conferencing and AV systems, and physical access controls.
• Drive vendor evaluation, procurement, and relationship management for IT hardware, software, and services.
• Develop and maintain IT documentation, policies, and runbooks to support operational consistency and knowledge sharing.
• Plan and manage the IT budget, tracking spend against forecasts and identifying cost optimization opportunities.
• Support compliance and audit efforts (SOC 2, etc.) by maintaining IT controls, access reviews, and asset inventory documentation.

• 5+ years in IT operations or systems administration, 2+ years of people or initiative leadership experience.
• Strong technical background with hands-on ability: scripting (Python, Bash, Power Shell), MDM platforms (Jamf, Intune), identity providers (Okta), and SaaS administration.
• Primary expertise in macOS with solid proficiency in Windows environments.
• Deep knowledge of corporate IT as it applies to modern cloud-first, SaaS-heavy organizations.
• Experience managing network infrastructure, including wireless access points, routers, switches, and VPN in a corporate office setting.
• Great communication skills and the ability to influence without authority across teams.
• Passion for mentoring, documentation, and building scalable, repeatable IT processes.

• Experience supporting compliance frameworks like SOC 2 or ISO 27001 from an IT controls perspective.

• Chicago, IL – 2 days per week in office

• Career game changer — A truly unique experience to work for a fast-growing company in a role with unlimited growth potential.

• Excellent benefits

• We cover a generous portion of Medical Premiums, 50% of Dental and Vision Premiums, company-sponsored Life Insurance, STD, and AD&D coverage, a 401(k) with match and immediate vesting, and comprehensive leave policies to meet your needs in creating space for life.

• Flexible PTO policy and outstanding work/life balance — We value and support each individual team member.

• Grubhub weekly lunch stipend for in-office days

• Udemy License and Personal Learning Budget — We support the…