IT Help Desk Manager

Kin Insurance•Chicago, IL

2d•Hybrid

About The Position

We’re looking for a Help Desk Manager to lead and evolve our IT support function as Kin continues to scale. This role exists to ensure employees receive fast, reliable, and high-quality technical support while building systems, processes, and a team that can grow with the business. You’ll operate at the intersection of people leadership, service delivery, and operational excellence — owning the performance of the help desk while partnering closely with Security, Engineering, and People teams. This is a high-impact role where your work directly shapes employee experience, productivity, and trust in IT. This role requires Chicago-based candidates. The Help Desk Manager works on-site at our Chicago office at least once per week, and must be able to reach the office quickly in the event of an urgent need. During your first month, you'll be expected in the office five days a week to build relationships with the team and get hands-on with the operation. Additionally, during catastrophe (CAT) events — when Kin onboards large groups of independent adjusters to respond to weather events — this role provides extended support coverage seven days a week. This is a real and recurring part of the job, and we want candidates to come in with a clear picture of what that looks like.

Requirements

3–5 years of experience in IT support, including at least 1–2 years leading or supervising a team
Proven experience managing a help desk or IT support function in a fast-paced environment
Hands-on experience with ITSM platforms (e.g., Jira Service Management, Zendesk, ServiceNow)
Strong knowledge of macOS and Windows environments, SaaS administration, and endpoint management
Experience with identity and access management tools (e.g., Okta, JumpCloud)
Experience using JumpCloud for directory and device policy management
Experience with BetterCloud for SaaS operations and workflow automation
Working knowledge of networking fundamentals, including VPNs, firewalls, and troubleshooting
Ability to analyze operational data and translate insights into action
Clear, effective communication skills with both technical and non-technical stakeholders

Nice To Haves

Experience with Google Workspace and Slack administration
Exposure to SOC 2 or SOX compliance environments
Experience supporting a remote-first workforce
Familiarity with ITIL or similar frameworks

Responsibilities

Lead, coach, and develop a team of Help Desk Analysts and interns, driving accountability, engagement, and continuous improvement
Own help desk operations end-to-end, including ticket queue management, SLA definition, and service quality outcomes
Establish and optimize workflows, runbooks, and escalation paths to improve efficiency and reduce resolution times
Track, analyze, and report on key performance metrics (CSAT, SLAs, time-to-resolution), using insights to drive improvements
Administer and enhance ITSM tools and platforms to support scalable service delivery
Identify and implement automation opportunities to reduce manual effort and improve team productivity
Own the IT onboarding and offboarding experience, ensuring seamless device provisioning, access setup, and returns
Manage hardware inventory and vendor relationships, ensuring accountability, cost-effectiveness, and SLA adherence
Partner cross-functionally with Security, Engineering, and People Ops on access management, compliance, and workflows
Support audit readiness and compliance requirements (e.g., SOC 2, SOX) through strong documentation and controls
Coordinate support coverage and prioritization during high-demand periods, including catastrophe (CAT) events

Benefits

Competitive salary and company equity through Restricted Stock Units (RSUs), granted as part of our standard compensation package and based on role and level
401(k) with company match up to 4% of eligible earnings
Multiple medical plan options, plus dental and vision coverage
Company-funded HSA contributions (based on medical plan selection)
Company-paid life insurance and short-term disability
A variety of supplemental benefit options, including long-term disability, critical illness, accident, legal, and pet insurance
Access to mental health support and confidential counseling resources
Flexible PTO for exempt employees (most employees take 15–20 days per year), plus 8 company-observed holidays
Paid parental leave, including up to 14 weeks at 100% pay for birthing parents and 8 weeks at 100% pay for non-birthing parents
Career mobility and internal growth opportunities across the organization
Professional development budgets for certifications, conferences, and learning available, subject to management approval