Insurtech Chicago Jobs (NOW HIRING)

Amazing Career Moments Happen Here 

Transforming the insurance industry is ambitious, we know. That's why at Applied, we're building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers - all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we're not just redefining what's achievable; we're creating a place where amazing career moments are made possible. 

Position Overview

We're searching for a Senior Compensation Analyst to join the People team in a remote or hybrid capacity out of our Chicago office. We're in the middle of a multi-year compensation roadmap built around high-impact, employee-centric initiatives, and you will be a driving force behind it. As a Senior Compensation Analyst, you'll own meaningful work across our full compensation spectrum: job architecture, market pricing, variable pay programs, and the annual planning cycle.

To keep us headed in the right direction, we're looking for people who see compensation as a lever for fairness and retention, not just a formula to administer, someone who welcomes complexity and brings a point of view. If you thrive in a lean, high-visibility environment where your work makes a real impact, we want to hear from you.

What You'll Do

• Drive the development and administration of compensation and job architecture frameworks that keep Applied both internally equitable and externally competitive.
• Own the annual compensation planning cycle from start to finish, including system configuration, UAT, budgeting, cycle execution, and hands-on training and consultation with People Team Partners and leaders.
• Partner with People Team to evaluate roles, navigate job placement, and ensure consistent, accurate job documentation across the organization.
• Build compensation models that bring salary grades, pay equity analyses, and variable pay targets to life. Translate what you find into near- and long-term cost and benefit decisions.
• Serve as the team's compensation systems expert. You will own system administration, identify opportunities to automate, and drive the efficiency gains that free the team up for higher-impact work.
• Support the administration of equity programs, including analysis and recommendations to inform grant decisions, refresh cycles, and candidate equity packages.
• Conduct compensation benchmarking for international markets, including India, with the ability to independently research statutory requirements, interpret market dynamics, and make data-driven pay recommendations.
• Stay ahead of emerging AI and data analytics trends and actively apply them to modernize compensation processes, reduce manual lift, and sharpen accuracy.
• Stay current on compensation-related laws and regulations, translating legislative changes into clear guidance and ensuring our programs and practices remain compliant.
• Bring others along. Share what you know with junior team members and help build compensation literacy across the People function.

We're Excited to Learn More About You

Your experience may include:

• 5+ years of progressive compensation experience covering base pay, variable pay, and job architecture.
• Advanced Excel skills: combined functions, pivot tables, queries, and the ability to turn that analysis into a clear, compelling story.
• A track record of administering full compensation planning cycles, including system configuration, UAT, reporting, and stakeholder support.
• Hands-on experience with third-party compensation surveys (Radford/Aon, Culpepper, WTW) and conducting market pricing analyses.
• A natural consultative style. You build trust with People Team partners and leaders and know how to make complex comp topics accessible.
• Familiarity with pay equity analysis and evolving multi-jurisdictional pay transparency and reporting requirements (e.g., state pay data reporting, EU legislation).

You may have other skills or credentials, including:

• Bachelor's degree or equivalent work experience required.
• Certified Compensation Professional (CCP) certification preferred.
• Proficiency with HRIS and compensation platforms (such as UKG, Bettercomp, Pequity, or similar).
• Background in a company that was scaling through a high-growth phase. 
• Experience supporting or administering compensation programs across multiple countries or regions, including familiarity with international statutory requirements and market dynamics.
• Experience building enablement resources and training for HR partners and People Leaders.

We know that talent comes from all backgrounds and experience levels. We encourage military members and their spouses as well as candidates without a degree or a background in tech to apply! 

When You Join Team Applied, You Can Expect: 

A culture that values who you are and recognizes that you aren't just an employee; you are a teammate, and you matter. We thrive on the benefits of our different experiences and celebrate the uniqueness our teammates bring to work with them every day. 

We flex our time together, collaborating remotely and in-person to empower our teams to work in the ways that work best for them. 

A comprehensive benefits and compensation package that centers our teammates and helps them to bring their best to work every day: 

• Medical, Dental, and Vision Coverage 
• Holiday and Vacation Time 
• Health & Wellness Days 
• A Bonus Day for Your Birthday 

  Learn more about the people behind our products at https://www1.appliedsystems.com/en-us/about-us/jobs/ 

Our targeted starting base salary in the United States for this position ranges from $100,000-135,000 USD. To determine a new team member's starting pay, we consider a variety of factors, including someone's depth, breadth, and variety of experience, skills, and responsibilities. Depending on the role, team members may also be eligible to participate in additional compensation plans such as bonus and commission.

Your Security Matters:   Our candidates' personal information and online safety are top of mind for us. At Applied, we proactively protect your personal information and only communicate with candidates via a secure @appliedsystems.com email or through our official careers portal. Recruiters will never request payments, ask for financial account information or sensitive information like social security numbers.  

AI Utilization

We leverage AI tools to streamline parts of our recruitment workflow (such as resume parsing and interview scheduling). However, candidate screening, interviews, and final decisions are conducted by real humans.

EEO Statement   

Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don't discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law.  

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