Technology Sales Careers in Chicago


Careers in Technical Sales

Chicago is a legendary city.

And thanks to the combined growth of tech businesses and a rich sales environment, Chicago is an excellent city to launch and nurture an ambitious career in SaaS, fintech, and innovative tech sales.

As tech companies abandon the high costs of living in coastal states, they find Chicago wonderfully supportive. Compared to New York and California, Illinois’ flat-rate income tax is advantageous to most technology workers, and the cost of office space in this state is around half that of San Francisco. With a lower cost of living compared to other tech sales hubs, it’s not surprising Chicago has experienced nearly 20% growth in its tech sector over the past few years.

Life In Chicago

Chicago is the third-most populous city in the United States and the most populous city in Illinois. The Chicago metropolitan area, one of the largest urban areas in the world, is a great place to live and is regarded as one of the best places to live in Illinois.

Chicago enjoys a rich history and a distinctive, friendly culture. It’s a city with some of the best food in the country, the home to legendary sports teams, and an essential hub of American art, music, and comedy.

Located in the Great Lakes and Midwest regions of the United States, Chicago provides its residents with first-rate amenities and dependable public transportation to help them adjust to city life. Tech sales specialists who find themselves in Chicago quickly realize what a welcoming, supportive city it is.


Tech and Financial Growth In Chicago

According to the Chicago Tech Effect report from the Chicagoland Chamber of Congress, Chicago’s technology environment has grown by 18% over the past ten years. Chicago’s tech sector supports over 8% of the city’s workforce and accounts for 87% of all new jobs created in the region over the past ten years.

With the median wage in the tech ecosystem 1.5 times higher than the median wage for the entire economy, Chicago is fueling upward mobility and better economic equality than many other regions in the US. Many people find Chicago particularly welcoming because nearly half of Chicago’s tech sector hires are in non-technical roles such as sales and support.

Sales Opportunities In Chicago

In Chicago, there are openings at every level of the technology sales industry. Rainmakers matches exceptional applicants with companies that are the most compatible with their skills. This way, everyone comes out ahead.

Sales Development Representative

Good SaaS sales teams rely on the contributions of their Sales Development Representatives (SDRs). An SDR mainly performs the duties of an inside salesperson, focusing on cold calling to create sales pipelines for the rest of the team. Their position is typically entry-level, doesn’t require much initial expertise, and serves as a great starting point for a long, successful sales career.

Account Executive

Account Executives (AE) close deals with new clients, attend to the needs of existing clients, and draw in new ones. AEs strive to fulfill predetermined quotas and revenue targets, with commissions accounting for a sizeable amount of their remuneration.

Mid-Market Account Executive

This is the ideal next step for sales professionals who are passionate about their jobs and seeking to advance them. Mid-Market Account Executives use SaaS/cloud technology to manage training, assist sales growth, and provide services while facilitating sales, closing agreements, and upholding solid client relationships. Middle-market businesses are their primary source of new sales.


Enterprise Account Executive

Enterprise Account Executives serve manufacturers, software developers, telecommunications businesses, and retail chains. The level of responsibilities that come with this position makes it one with high earning potential. Enterprise Account Executives must be committed, capable, and well-prepared for businesses to maintain positive sales partnerships and promote innovation on both ends.

Customer Success Manager

Customer Success Managers (CSMs) strive to build solid, enduring client connections. Businesses must demonstrate the worth of their products after concluding a sale, and it’s up to the Customer Success Manager to encourage success and repeat business by promoting goods and services. CSMs are used to great effect by nearly half of high-tech enterprises, despite being a relatively new type of sales function.

Sales Director

Sales Directors ensure that the sales force completes all necessary responsibilities, creates and offers new products and services strategically, and upholds the company’s commitment to providing excellent customer service. Sales Directors oversee the sales staff, conduct training, and ensure that staff achieves their goals. Strong organizational, leadership, and sales skills are required.


Sales Career Opportunities at Rainmakers

Successful sales careers often pay well and offer substantial opportunities for personal growth. For individuals willing to put in the time and effort required to exceed expectations and prove their value, many career prospects provide good avenues for promotion.

The sales funnel of any successful organization depends on every role, from Sales Development Rep to VP in Sales. Anyone can succeed if they put in the necessary effort, have the required talents, and are dedicated to the task at hand.

If you're curious about tech sales jobs in high demand in Chicago, make sure to check out these existing opportunities.

Create a profile on Rainmakers right away to find out more about these fantastic opportunities and Start connecting with Chicago tech employers.

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