Inside Sales Representative
Dropbox
Chicago, IL · $75k–$114k a year · Posted November 2, 2026
Just laid off? Start here: a plan for the first weeks
See every open role at Dropbox
More in Illinois job market · All Inside Sales Representative jobs (998) · Technology & Software · Sales jobs
More roles at Dropbox
Similar jobs
- Inside Sales Representative (REMOTE) · Danaher · Chicago, IL
- Territory Sales Representative - Chicago NW Suburbs · Masco · Elgin, IL
- Inside Sales Representative · Flow Control Group · Melrose Park, IL
- Lead Technical Product Manager | Healthcare | APIs, Integrations, & Embedded AI Solutions · Wolters Kluwer · IL
- Technical Product Manager · Cisco Systems · Research Triangle Park, NC
- Technical Product Manager - Ecosystem Integrations · Cisco Systems · San Jose, CA
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 $94,500 a year. Across 247 open inside sales representative listings that state pay, the middle half runs $48,000 to $77,500 and the median is $62,500. That is 51% above the median, above the middle half of those listings.
Listed pay is what employers advertise, not what people are paid.
Inside Sales Representative salaries by state · Check your own pay
How AI is used in this kind of work
Among sales representatives, wholesale and manufacturing, technical and scientific products, AI is already used for some of the tasks. Measured exposure for sales representatives, wholesale and manufacturing, technical and scientific products: 27% (some).
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.
Dropbox has filed one layoff notice in the last twelve months, covering 57 workers, most recently October 2026. These are public filings with state labor departments, and an open role can sit alongside them. See the filings
About the job
We built the Inside Sales Representative seat at Dropbox for someone who can sell at $75,000 - $114,000 stakes and coach the team that follows. Boiled down: contract, $75,000 - $114,000, 5 years of Flexibility, and a seat at the table where Dropbox decisions get made....