Enterprise Sales Specialist Jobs in Chicago, IL
Enterprise Sales Specialist jobs in Chicago are in strong demand, concentrated in the Loop, River North, and the Fulton Market district across enterprise software, financial technology, healthcare technology, and professional services. Employers actively hiring include Meta, Amazon Web Services, and Datadog. See the openings below and apply to the ones that match your experience.
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Note: By applying to this position you will have an opportunity to share your preferred working location from the following: Chicago, IL, USA; Atlanta, GA, USA; Austin, TX, USA; New York, NY, USA; San Francisco, CA, USA.
Minimum qualifications:
- Bachelor's degree or equivalent practical experience.
- 7 years of experience in a sales role in the enterprise software or cloud space.
- Experience selling software as a service (SaaS), productivity, or collaboration technology solutions to clients.
Preferred qualifications:
- Experience carrying and exceeding business goals in a sales role.
- Experience prioritizing, planning, and organizing solution-based sales activity within complex sales cycles, including qualifying high value accounts and leveraging our partner ecosystem.
- Experience working with internal/external teams, including account teams, technical leads, procurement, and legal, to inventory existing software estate, build business cases for transformation with implementation plans, and close agreements.
- Knowledge of market trends, products, and solutions in Cloud and Productivity and Collaboration.
About the job
The Google Cloud Platform team helps customers transform and build what's next for their business — all with technology built in the cloud. Our products are developed for security, reliability and scalability, running the full stack from infrastructure to applications to devices and hardware. Our teams are dedicated to helping our customers — developers, small and large businesses, educational institutions and government agencies — see the benefits of our technology come to life. As part of an entrepreneurial team in this rapidly growing business, you will play a key role in understanding the needs of our customers and help shape the future of businesses of all sizes use technology to connect with customers, employees and partners.As a Workspace Sales Specialist, you will help us grow our Productivity and Collaboration business by building and expanding relationships with new and existing customers. In this role, you will work with customers to deliver true business value, demonstrate product functionality, and provide a comprehensive overview of key business use cases. You will lead day-to-day relationships with cross-functional team members and external customers, leading with empathy, while identifying ways to multiply your impact and the impact of the team as a whole to drive overall value for Google Cloud.
Google Cloud accelerates every organization’s ability to digitally transform its business and industry. We deliver enterprise-grade solutions that leverage Google’s cutting-edge technology, and tools that help developers build more sustainably. Customers in more than 200 countries and territories turn to Google Cloud as their trusted partner to enable growth and solve their most critical business problems.Individual pay is determined by factors including job-related skills, experience, and relevant education or training.
US: $116000 - $170000 (USD) + 100% bonus target + equity + benefits
Learn more about benefits at Google.
Responsibilities
- Build relationships with customers as a subject matter expert and trusted advisor, managing complex business cycles, identifying solution use cases, and influencing long-term direction of accounts.
- Deliver against quota and achieve or exceed business and growth goals while forecasting and reporting your territory’s business.
- Work with Google accounts and cross-functional teams (e.g., Customer Engineering, Marketing, Customer Success, Product, Engineering, Channels) to develop go-to-market strategies, drive pipeline and business growth, close agreements, understand the customer, and provide excellent prospect and customer experience.
- Construct and execute an effective territory development plan.
- Lead prospecting, acquisition, and development of new Workspace opportunities in your assigned territory, creating and building customer relationships from scratch, while also maintaining and building current accounts.
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Find JobsEnterprise Sales Specialist Job Market in Chicago
Who's Hiring
- Meta6

- Amazon Web Services3

- Datadog2

- Google1

- Nutanix1

Top Industries Hiring
- Technology & Software10
- Distribution & Wholesale3
- Consulting & Professional Services2
- Education1
- Cybersecurity1
Enterprise Sales Specialist Jobs in Chicago: Frequently Asked Questions
How do I get an enterprise sales specialist job in Chicago?
Focus your search on Chicago's Loop and River North corridors, where enterprise software, fintech, and B2B SaaS companies concentrate their sales teams. Familiarity with complex, multi-stakeholder deal cycles and experience selling into financial services or healthcare gives candidates a clear edge in this market. Networking through Chicago-area tech and sales communities and targeting employers with Midwest regional headquarters also accelerates the process.
Which companies hire enterprise sales specialists in Chicago?
Chicago enterprise sales specialist roles are posted by Meta, Amazon Web Services, and Datadog and others right now, based on current listings on Migrate Mate as of June 2026. Chicago's mix of legacy enterprise technology firms, fast-growing B2B SaaS companies, and large financial institutions creates consistent demand for enterprise sales talent across a wide range of employer sizes.
Are there remote enterprise sales specialist jobs in Chicago?
Yes, though enterprise sales roles are less fully remote than most desk-based positions because client relationship-building and on-site presentations remain central to closing large deals. About 33% of enterprise sales specialist openings tied to Chicago are remote or hybrid as of June 2026, reflecting hybrid structures that blend in-office collaboration with flexible client travel. Prospecting and pipeline management work are the functions most commonly handled remotely.
How can I get an enterprise sales specialist job in Chicago with little or no experience?
The most realistic entry path is landing a sales development representative or inside sales role at one of Chicago's many B2B software or fintech companies, where structured training and clear promotion tracks into enterprise roles are common. Companies in Fulton Market and River North frequently hire junior sales talent and develop them internally. Demonstrating comfort with long sales cycles, CRM tools, and Chicago's financial services client base will set you apart early.
Which industries hire the most enterprise sales specialists in Chicago?
The sectors hiring the most enterprise sales specialists in Chicago are Technology & Software, Distribution & Wholesale, and Consulting & Professional Services, based on current listings on Migrate Mate as of June 2026. Chicago's status as a major financial hub and a growing technology center drives concentrated demand from large institutional buyers who require dedicated enterprise sales coverage.
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