Chicago is a hub for numerous industries, and salespeople are in high demand.

In the heart of the city, financial services firms seek sales experts to navigate the complex world of investments and banking. Meanwhile, Chicago’s tech scene is on the rise, with startups and established companies alike needing salespeople to market their innovative products and services.

Manufacturing remains a cornerstone of the regional economy, relying on sales teams to connect with clients and suppliers across the globe. Additionally, the healthcare sector in Chicago, anchored by some of the nation’s leading hospitals and medical research facilities, offers opportunities for sales professionals to play a critical role in advancing medical technologies and services.

If you’re wondering where you can make the most as a sales rep in Chicago, we’ve got you covered. Check out the highest paying sales jobs in Chicago below.

How do we define “Highest Paying” Sales Jobs?

The companies on this list are included based on median on-target earnings (OTE) for Account Executive salaries in Chicago and the surrounding areas. Data is reported by either current or former employees for each company, and is current as of time of publication.

You should always keep in mind that OTE is not the same as take-home pay, so be sure to factor in quota attainment whenever comparing this data.

Find real-time updates for reported highest paying sales orgs here.

Top 10 Highest Paying Sales Jobs in Chicago 

1. Tecsys, Inc. – $450,000 OTE

Tecsys, Inc. specializes in providing supply chain management solutions that help organizations streamline their operations and manage inventory more efficiently. Their products include software for warehouse management, distribution, and transportation management, as well as analytics tools to improve supply chain visibility and decision-making.

Account Executives at Tecsys, Inc. report earning a base salary of $140K and on-target earnings of $450K, with 42% of the sales team hitting quota. Top performers report earning $850K.

2. OneSpan – $300,000 OTE

OneSpan specializes in digital identity and anti-fraud solutions that secure online transactions and business operations. Their offerings include multi-factor authentication, mobile application security, and risk analysis to protect against cyber threats. The company provides tools and services that help ensure the integrity and security of digital interactions for businesses and consumers.

AEs at OneSpan report earning a base salary of $150K and on-target earnings of $300K, with 20% of the sales team hitting quota. Top performers report earning $580K.

3. Cleo – $300,000 OTE

Cleo provides integration software solutions that facilitate seamless data exchange and workflow automation across various business ecosystems. Their platform supports cloud integration, data transformation, and connectivity services, enabling organizations to streamline their supply chain, e-commerce, and business-to-business processes. Cleo’s solutions aim to enhance operational efficiency and data-driven decision-making for businesses of all sizes.

Account Executives at Cleo report earning a base salary of $150K and on-target earnings of $300K, with 43% of the sales team hitting quota. Top performers report earning $658K.

4. project44 – $300,000 OTE

project44 offers a supply chain visibility platform that enables real-time tracking and analytics for shipments across various transportation modes. Their technology integrates with carriers and logistics providers to offer predictive insights and automation, improving the efficiency of the supply chain and logistics operations. The company’s services help businesses optimize delivery performance and enhance customer satisfaction.

AEs at project44 report earning a base salary of $150K and on-target earnings of $300K, with 34% of the sales team hitting quota. Top performers report earning $880K.

5. Tegus – $280,000 OTE

Tegus is a platform that provides comprehensive market and company insights, facilitating informed investment decisions. It offers access to a vast library of expert interviews, financial data, and industry analysis, enabling investors to conduct deep-dive research on companies and sectors. Tegus serves as a resource for investors seeking to gain a detailed understanding of market trends and company performance.

Account Executives at Tegus report earning a base salary of $145K and on-target earnings of $280K, with 28% of the sales team hitting quota. Top performers report earning $573.6K.

6. Flexera – $280,000 OTE

Flexera specializes in IT management software, helping organizations optimize software licensing, compliance, security, and resource allocation. Their products include solutions for software asset management, IT asset management, and cloud cost optimization. Flexera’s services enable businesses to manage and reduce IT costs while ensuring regulatory compliance and minimizing security risks.

AEs at Flexera report earning a base salary of $140K and on-target earnings of $280K, with 29% of the sales team hitting quota. Top performers report earning $1.08 million.

7. Origami Risk – $275,000 OTE

Origami Risk provides risk management and insurance software solutions that help organizations manage and mitigate various types of risk. Their platform offers tools for claims management, policy administration, and data analytics, supporting clients in improving their risk management processes. Origami Risk aims to enhance operational efficiency and provide insights that help organizations make informed decisions about risk and insurance.

Account Executives at Origami Risk report earning a base salary of $130K and on-target earnings of $275K, with 37% of the sales team hitting quota. Top performers report earning $667.5K.

8. Threekit – $265,000 OTE

Threekit offers a platform that enables businesses to create interactive 3D, augmented reality (AR), and virtual photography visualizations for their products. This technology allows companies to showcase their products online in a more engaging and detailed way, enhancing the customer experience. Threekit’s solutions are designed to help businesses increase sales and customer engagement by providing immersive and customizable visual product experiences.

AEs at Threekit report earning a base salary of $120K and on-target earnings of $265K, with 13% of the sales team hitting quota. Top performers report earning $314K.

9. NowSecure – $260,000 OTE

NowSecure provides mobile application security testing and certification services to help organizations protect their mobile apps from security threats. Their platform offers automated security testing, vulnerability assessment, and compliance monitoring to ensure mobile apps are secure and meet industry standards. NowSecure’s solutions aim to safeguard sensitive data and enhance mobile app security for businesses and their users.

Account Executives at NowSecure report earning a base salary of $130K and on-target earnings of $260K, with 38% of the sales team hitting quota. Top performers report earning $470K.

10. Basis Technologies – $260,000 OTE

Basis Technologies offers automation and optimization software for SAP environments, enabling businesses to improve their operational efficiency and agility. Their products include tools for change management, test automation, and system analysis, which help streamline SAP system processes and deployments. Basis Technologies’ solutions are designed to support continuous improvement and innovation in SAP-centric organizations.

AEs at Basis Technologies report earning a base salary of $125K and on-target earnings of $260K, with 39% of the sales team hitting quota. Top performers report earning $380K.

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