Tech Sales Jobs in Chicago, IL (2026)
A steady, deal-dense market anchoring Midwest enterprise sales.
The Chicago market right now
Chicago anchors Midwest enterprise sales for both legacy software vendors and modern SaaS companies expanding beyond the coasts. The market rewards reps who can sell into traditional industries like manufacturing, logistics, and insurance alongside standard SaaS ICPs, and comp tends to be steadier and less bonus-heavy than in hypergrowth coastal markets.
Pay
SDR OTE: $60k–$78k. AE OTE:
60k–$210k. One of the most affordable major metros for the OTE on offer, especially outside downtown.
Who is hiring in Chicago
- Salesforce
- HubSpot
- ZoomInfo
- Highspot
- Outreach
- Notion
The Loop and Fulton Market host most sales offices, with a growing cluster in the West Loop.
Hiring seasonality
Hiring is steady but slows noticeably around the winter holidays and picks back up in March.
Remote versus onsite
Hybrid is the norm, with many companies treating Chicago as a lower-cost hub for fully in-office SDR floors.
Frequently asked questions
What does a tech sales job pay in Chicago?
SDR roles in Chicago typically run $60k–$78k OTE and AE roles run
60k–$210k OTE in 2026. One of the most affordable major metros for the OTE on offer, especially outside downtown.
Which companies hire SDRs and AEs in Chicago?
Active employers include Salesforce, HubSpot, ZoomInfo, Highspot, Outreach, Notion. The Loop and Fulton Market host most sales offices, with a growing cluster in the West Loop.
When is the best time to apply for sales jobs in Chicago?
Hiring is steady but slows noticeably around the winter holidays and picks back up in March.
Can I work remotely for Chicago tech sales roles?
Hybrid is the norm, with many companies treating Chicago as a lower-cost hub for fully in-office SDR floors.
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