Current salary data based on 20 job postings with disclosed compensation.
Chicago offers solid compensation for sales leaders, particularly in B2B SaaS and manufacturing tech. Lower cost of living compared to coastal cities provides better purchasing power.
Based on 20 job postings with disclosed compensation, VP Sales roles in Chicago pay between $151K and $222K base salary. The 46% spread reflects differences in company stage, industry, and specific role scope. OTE typically adds 30-50% for revenue-carrying roles.
The 46% salary spread reflects real market variation. Key factors: (1) Company stage - Series A pays 20-30% less base but offers more equity; (2) Deal size responsibility - enterprise sales leaders ($500K+ ACV) command premiums; (3) Team size - managing 50+ reps vs 10 impacts compensation; (4) Industry - fintech and cybersecurity pay 15-20% above average. The 'right' salary depends on your specific situation.
Chicago VP Sales salaries average $222K, which is 14% below the national average of $261K.
Focus on base salary for stability and comp benchmarking, but understand the full picture. At startups, negotiate equity vesting and acceleration clauses. At public companies, ask about RSU refresh grants. For OTE, clarify quota attainment rates (ask: 'What % of the team hit quota last year?') and whether targets are realistic. A high OTE with 20% attainment is worse than moderate OTE with 80% attainment.
Our data comes from 20 actual job postings with disclosed compensation ranges, not self-reported surveys (which typically skew 10-15% high). We track VP Sales, SVP Sales, and CRO roles weekly, filtering for executive-level positions. Limitations: not all companies disclose salary, and posted ranges may differ from final offers after negotiation.
Weekly analysis of compensation trends, red flags, and negotiation insights for VP Sales and CRO roles.
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