Director of Sales
Pursuit
Chicago, IL · $180k a year · Posted November 4, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about sales jobs
- Best cities for sales jobs #1 New York (2,774 openings)
- Best cities for sales pay after cost of living #1 Santa Clara ($175k)
- Most requested AI skills in sales jobs #1 AI tools in daily work (4.1%)
- AI tools named most often in sales jobs #1 Gong (0.93%)
- Employers with the most sales jobs #1 Charter Communications (389 roles)
Pay compared with the market
This listing pays about $180,000 a year. Across 46 open director of sales listings that state pay, the middle half runs $140,500 to $200,000 and the median is $158,500. That is inside the middle half of those listings, 14% above the median.
Listed pay is what employers advertise, not what people are paid.
How AI is used in this kind of work
AI use among sales managers is little observed so far. Measured exposure for sales managers: 4% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
About the job
...partnered with a rapidly growing, private equity-backed leader in commercial fleet solutions that is looking to add a Regional Director of Sales to its team! With over 20 years of success, consistent year-over-year growth, and an aggressive expansion strategy, this is...