Top Sales Jobs in Chicago, IL

Own the full B2B SaaS sales cycle for Dropbox’s Product Suite and emerging AI products, from outbound prospecting and pipeline generation through closing and renewal. Develop mid-market and enterprise opportunities, lead discovery, apply MEDDICC or SPICED qualification and value-selling frameworks, forecast accurately, meet revenue targets, and collaborate with Product and go-to-market teams to refine messaging and sales strategy.

Own the full B2B SaaS sales cycle, from outbound pipeline generation through closing and renewal. Build strategic relationships with mid-market and enterprise customers, lead discovery, apply MEDDICC or SPICED qualification, communicate business value, forecast accurately, and consistently achieve revenue targets. Collaborate with internal teams to refine go-to-market strategy, identify new use cases, and influence product and sales initiatives.

Own the full B2B SaaS sales cycle across LATAM, from outbound pipeline creation through closing. Generate demand through prospecting, account mapping, events, and partners; qualify and advance complex mid-market and enterprise opportunities using MEDDICC, SPICED, and value-selling methods. Forecast accurately, meet revenue targets, engage executive stakeholders, and help shape Dropbox’s go-to-market strategy, messaging, use cases, and sales motion.

Own and grow strategic distribution and ecosystem partnerships across AI, hardware, developer, and SaaS ecosystems. Identify opportunities, build business cases and financial models, lead commercial negotiations, manage partnership lifecycle, and collaborate cross-functionally to drive customer acquisition, product adoption, and revenue growth while using data and AI-enabled tools to optimize outcomes.

Lead global sales compensation, quota strategy, and incentive planning for Dropbox. Design governance, quota methodologies, and scalable incentive programs; partner with Sales, Finance, HR, and Systems; own incentive operations and Forma platform; drive quota planning, payout accuracy, and automation; build and mentor a high-performing compensation team while influencing executive decision-making through data-driven recommendations.