IT Help Desk Manager

QUICK SUMMARY Lead and scale a high-performing help desk team, driving service quality, automation, and seamless employee IT experiences across a growing, remote-first organization. Please note this role is based in Chicago, IL. The Help Desk Manager is expected to work on-site at our Chicago office at least once per week and must be able to commute to the office on short notice when needed. WHO WE ARE Kin makes life simpler, more affordable, and better for homeowners — especially in the places where climate risks, rising costs, and outdated systems make it harder. We start with smarter homeowners insurance and expand to everything homeowners need to thrive. Using data, technology, and thoughtful human support, we’re building products that are clear, fair, and help homeowners feel confident — so homeowners aren’t left behind when they need help most. Founded in 2016, Kin is a remote-first employer with Kinfolk across more than 35 states. We serve customers in 13 states (and counting). Our disciplined growth, strong customer satisfaction, and focus on long-term sustainability fosters outstanding growth, attracts marquee investors, and earns recognition and accolades, including: - Built In Chicago's Best Places to Work, Midsize Companies (2021-2026) - Forbes' America's Best Startup Employers (2021-2024) - Inc. 5000 Fastest-Growing Private Companies - Forbes’ Fintech 50 (2025-2026) - Great Places to Work Certified (2024-2026) Most importantly, we’re building Kin to be a place where people do meaningful work with real impact — for our customers, our communities, and each other. We're excited to tell you more about how you can contribute to our rapid growth, strong unit economics, profitability, and excellent customer ratings. To learn more about how we work and what we’re building, visit kin.com http://kin.com and see how we work https://www.linkedin.com/company/kin-insurance/life/kin/. THE OPPORTUNITY 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. YOUR 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 SUCCESS IN THIS ROLE In your first 6–12 months at Kin, success is less about checking boxes and more about the impact you create. You’ll use your skills and judgment to take ownership of meaningful work, improve how we operate, and help move Kin’s mission forward. Along the way, you’ll deliver outcomes that make a real difference for both Kinfolk and the homeowners we serve. BY THE END OF YOUR FIRST YEAR, YOU SHOULD FEEL CONFIDENT IN YOUR ROLE, TRUSTED AS AN OWNER, AND PROUD OF THE PROGRESS YOU’VE HELPED MAKE. - Help desk SLAs are clearly defined, consistently met, and transparently reported - The team is engaged, growing, and operating with strong ownership and accountability - Onboarding and offboarding processes are seamless, documented, and audit-ready - Measurable improvements in efficiency are achieved through automation and process optimization - Stakeholders across the business view IT support as proactive, reliable, and high-impact WHAT YOU’LL BRING - 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 HOW WE HIRE We believe a great hiring experience should be clear, respectful, and human. We’ll accept applications for this position until May 29, 2026. While our recruiting team uses AI tools for efficiency, resumes are still screened by Kin’s in-house recruiters, and candidate evaluations and hiring decisions are made by recruiters and hiring teams. Rest assured, real people make real decisions. The hiring process and timeline for each role will vary, depending on the position. However, here are some things you can expect from us: - Prompt updates and feedback following interviews - Interviews with recruiters, hiring managers, and members of teams - Skills assessment relevant to the position, if applicable - Genuine, thoughtful human interaction at every step HOW WE SUPPORT YOU We offer a comprehensive, competitive benefits program, allowing you to choose the benefits that are best for you and your family, starting on the first day of the month following your start date. Core 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 Health & Wellbeing - 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 Growth & Development - Career mobility and internal growth opportunities across the organization - Professional development budgets for certifications, conferences, and learning available, subject to management approval HOW WE WORK We don’t just hire for skills. We hire for alignment. Kinfolk bring diverse perspectives, but we’re united by a shared set of values that shape how we work and how we show up for each other and our customers. Run through walls, together - Our industry is stuck in the status quo. But Kin is different. We are challengers. Innovators unwavering in our mission to fix insurance for those who need it most. We are changing insurance for good. We roll up our sleeves, take action, and get “impossible” things done every day with grit and teamwork. Raise the bar. Drop the ego - Attitudes are contagious. Every one of us is responsible for creating the culture we want to work in. High performance. Low drama. Always respectful. Like professional sports teams, we win by working in sync. We show up, work hard, and play to each other’s strengths. Act like an owner - We are owners, fully accountable for achieving Kin’s mission. That requires positive, proactive, big-picture thinking well beyond our job descriptions. Ask questions, Take ownership. Do the right thing, even when it‘s hard. Because when Kin thrives, so do you. And so do our customers. Operate lean. Deliver more - We build efficiency into everything we do. Each dollar we save gets reinvested to deliver more to our customers: better pricing, more products, and new innovations. We work smarter by relentlessly prioritizing and using technology, including AI, to multiply our impact. Lean is about focus, not deprivation. Lean isn't a limitation – it's our competitive advantage. Keep asking ‘What if?’ - We value curiosity. To make insurance better for our customers, we experiment. We embrace insights. And we base decisions on data rather than assumptions. We see setbacks as opportunities for growth and are always learning and improving. Both individually and as a company. WHERE WE WORK We are a remote-first company with offices in Chicago, IL and St. Petersburg, FL where teams can come together for collaboration. For Sales Agents and Customer Service Agents: These roles sit in any of the following 30 states: AL, AZ, CO, FL, ID, IL, IN, KS, KY, MA, MD, ME, MI, MO, MT, NC, NE, NM, NV, NY, OH, OK, PA, SC, TN, TX, UT, VT, VA, WA, and WI. For all other positions, these roles can sit in any of the following 40 states: AL, AR, AZ, CA (exempt only), CO, CT, FL, GA, ID, IL, IN, IA, KS, KY, MA, ME, MD, MI, MN, MO, MT, NC, NE, NJ, NM, NV, NY, OH, OK, OR, PA, SC, SD, TN, TX, UT, VT, VA, WA, and WI. Please only apply if you are able to live and work full-time in one of the states listed above. For remote technical positions located in Canada, we are only able to hire individuals who reside in Ontario. Applicants must be able to live and work full-time in Ontario to be considered. State locations and specifics are subject to change as our hiring requirements shift. EEOC STATEMENT Kin is proud to be an Equal Employment Opportunity and Affirmative Action Employer. We don't just accept difference – we honor it, nurture it, and celebrate it. We don’t discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Kin welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process. If you require accommodation, please contact us by sending an email to careers@kin.com