Entry Level Tech Startup Jobs in Illinois (NOW HIRING)

Quick Summary
Support kinfolk, solve problems, reduce friction, automate processes. Make work-life easier and more pleasant for everyone at Kin. Hybrid in Chicago
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simpler, more affordable, and better for homeowners - especially in the places where climate risks, rising costs, and outdated systems make it harder.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 14 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 (2026)
• Inc. 5000 Fastest-Growing Private Companies
• Forbes' Fintech 50 (2023-2026)
• Great Places to Work Certified (May 2024-May 2027)

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 and see how we work.
The opportunity
We're looking for an IT Analyst to grow into ownership of our tier 2 helpdesk and the onboarding and offboarding process that touches every team at Kin. This is a step up from entry-level - you'll pick up escalations that Jr. Analysts can't resolve, run IT orientation for new kinfolk, and be the person who notices when a process is creating friction.
The first stretch of this role is about building real fluency with our systems and procedures; from there, you'll start shaping how the helpdesk actually operates, whether that's through automation, tighter documentation, or mentoring the analysts below you. If you're looking for a role with a clear growth trajectory rather than a ceiling, this is built for that.
Your responsibilities

• Owning Tier 2 helpdesk requests and taking Tier 1 escalations, routing to Tier 3 or IT Engineering when needed
• Owning the IT side of onboarding and offboarding, from access and equipment through to running IT orientation for every new hire
• Provisioning and deprovisioning access across Okta, Google Workspace, Slack, and BetterCloud, and auditing that access against RBAC procedures
• Managing accurate device records across the organization using Jira Assets and JumpCloud
• Maintaining our Chicago office day-to-day, including A/V for meetings and events, security posture (access badges), and covering extended hours during catastrophic events
• Triaging issues and enforcing security policy as the frontline for Security and IT Engineering
• Writing and maintaining the Confluence documentation and runbooks for the processes you run
• Spotting where our processes create friction, raising it, and owning improvement projects of your own
• Training and mentoring interns and Jr. Analysts as they ramp
• Using AI tools like Claude to work faster and more effectively - and building that fluency from day one if it's new to you

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.

• Your ticket handling and Tier 2 ownership move the team's SLA attainment toward our 90-95% target
• By month 6, you've built real fluency with our systems and procedures (Okta, Google Workspace, Slack, JumpCloud, BetterCloud) and need less direct guidance on Tier 2 work
• By month 12, you're contributing to actual helpdesk improvements - building or refining automations, or helping tighten up documented procedures
• Interns and Jr. Analysts are getting mentorship from you, not just escalation dumps

What you'll bring
Hard skills:

• 2+ years of IT experience, including hands-on tier 2 support and remote-first support
• Proficiency troubleshooting both macOS and Windows
• Administration experience with Google Workspace, Slack, Okta, JumpCloud, and/or BetterCloud
• Day-to-day fluency with a ticketing system (we use Jira Service Management) and a habit of documenting what you solve (we use Confluence)
• Some experience using AI tools (Claude, ChatGPT, or similar) for workflow efficiency - or strong aptitude and eagerness to build that skill quickly

Soft skills:

• White-glove service instinct - equal respect and responsiveness whether you're helping an intern or an exec
• Ability to identify issues, communicate solutions clearly, and collaborate for win-win outcomes across technical and non-technical audiences
• Able to provide in-office support at our Chicago location at least one week per month

How we hire
We believe a great hiring experience should be clear, respectful, and human. We'll accept applications for this position until October 2, 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 - Every one of us is responsible for creating the culture we want to work in. High performance. Low drama. Always respectful. We assume the best in each other and challenge ideas, not intentions. We show up, work hard, and play to each other's strengths - because that's how great teams win.
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 32 states: AL, AZ, CO, FL, ID, IL, IN, KS, KY, LA, 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 41 states: AL, AR, AZ, CA (exempt only), CO, CT, FL, GA, ID, IL, IN, IA, KS, KY, LA, 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