IT & CRM Operations Lead

Job Summary

We are seeking an IT & CRM Operations Lead to manage our end-user support, business application administration, and IT operations team. The role involves coaching and working alongside a team of 4-5 specialists supporting 100+ employees and their stakeholders across multiple entities.

Description & Responsibilities

• Serve as the primary handler for Tier 2 escalated helpdesk tickets, resolving complex end-user issues across hardware, software, and connectivity.
• Manage ticket queue health, escalation paths, and coverage windows to ensure SLA compliance.
• Define, track, and improve support KPIs including ticket SLA compliance, resolution times, and user satisfaction.
• Drive operational improvements including knowledge base articles, workflow automation, and ticket volume reduction.
• Oversee vendor relationships for support tooling including Datto RMM and the ticketing platform.
• Manage device support across Windows and macOS; handle networking troubleshooting including DNS and VPN.
• Liaise with HR on employee onboarding and offboarding workflows.
• Partner with Infrastructure & Cloud, Security & Compliance, and Engineering on cross-functional support issues.
• Champion the data integrity agenda by implementing CRM best practices and overseeing HubSpot requests.
• Administer and support HubSpot, including workflow and process automation, pipeline management, and data design and maintenance of relational database structures to support business operations and reporting needs.
• Identify opportunities to streamline business processes through automation and system improvements.
• Support cross-functional stakeholders with CRM-related requests, reporting, and system enhancements.

Qualifications

• 5+ years in IT operations with at least 2 years in a management or team lead role.
• Proven experience handling Tier 2 helpdesk or service desk functions with measurable SLA accountability.
• Deep understanding of CRM systems and experience administrating CRMs, HubSpot preferred.
• Hands-on proficiency in at least 3 of: device management/MDM, Microsoft 365 administration, HubSpot or comparable CRM, AWS WorkSpaces/VDI, or ticketing platforms (Datto RMM, ServiceNow, Zendesk).
• Microsoft 365 administration — Exchange, Teams, SharePoint, OneDrive.
• Device management across Windows and macOS; basic networking knowledge (DNS, VPN, troubleshooting).
• Demonstrated experience coaching junior staff, building team discipline, and managing performance.
• Familiarity with ITIL or a comparable service management framework.
• Strong written communication skills for documentation, KB articles, and escalation notes.

What Makes Someone Successful Here

• You have a player coach mentality and operate both in the weeds and at a high level.
• You thrive in operational roles where you can build systems and processes.
• You can shift quickly between strategic thinking and tactical problem-solving.
• You communicate clearly and preemptively, not reactively.
• You hold yourself and others accountable to high standards.

Benefits

• Base Compensation: $80,000-120,000 Per Year + Performance Bonus
• Comprehensive Health, Dental, and Vision Insurance
• Retirement Plan with Company Contribution
• Paid Time Off and Holidays

Requirements

• This role is fully onsite, five days a week, at 1123 W Washington Blvd Unit 3, Chicago, IL 60607.
• In-person presence is essential given the hands-on nature of the role.