Top Director of Sales Jobs in Chicago, IL

The Director of Field Sales will lead the Central Region's sales team, focusing on strategy, execution, and team development to drive significant revenue growth and foster a competitive sales culture.

The role involves leading and scaling the Central Field Sales organization, driving performance and operational rigor, and collaborating with teams to achieve regional growth.

Senior leader who builds and scales Sales Operations: owns HubSpot CRM architecture and governance, forecasting, compensation design, reporting, and cross-functional alignment. Leads a Sales Ops team to improve forecasting accuracy, data hygiene, automation, and quota-to-cash processes to enable predictable revenue and scalable marketplace growth.

Lead sales and partnership efforts with employee benefits consultants, brokers, advisors, and employers. Build and maintain partner relationships, demonstrate Milu's value proposition, drive business development, meet sales targets, and ensure excellent customer support in a remote environment.

Lead and execute enterprise new-business strategy, build and coach a high-performing sales organization, cultivate executive relationships and strategic partnerships, and personally support major enterprise pursuits. Drive revenue, bookings, forecasting discipline, pipeline governance, and sales productivity while partnering with hyperscalers and cross-functional teams to scale growth and improve sales effectiveness.

The Director of Field Sales Engineering leads a team focused on incubating new products, driving adoption, and ensuring cross-functional collaboration to deliver technical value to customers.

The Director of Sales will drive revenue growth, establish customer strategies for logistics services, manage executive relationships, and oversee pipeline management and CRM processes.

Lead revenue growth and new business for an ecommerce/digital commerce agency. Develop and execute outbound/inbound sales strategy, manage full sales cycle, build pipeline, negotiate contracts, and create scalable sales processes. Partner with leadership and client teams to drive onboarding, retention, upsells, and forecasting while using CRM tools to track performance.

The Director of Sales Operations & GTM Strategy will lead the go-to-market strategy, manage sales processes, forecasting, financial models, and collaborate with cross-functional teams to drive revenue growth and efficiency.

Lead the Sales Strategy & Analytics function to deliver reporting, KPI tracking, profitability and competitive analysis, and sales technology ownership. Partner cross-functionally to provide executive insights, optimize tools and processes, drive adoption, and develop a high-performing analytics team that improves sales productivity, profitability, and strategic decision-making.

Lead development and execution of Sales Readiness strategy and programs to prepare sellers, drive adoption, and improve field performance. Manage a team delivering coaching, enablement content, field engagement, and readiness initiatives. Partner cross-functionally to translate priorities into scalable resources, measure program impact, and continuously improve seller capability and productivity.

Own quota and drive revenue for Garner’s Insights and Referrals products by selling into healthcare delivery organizations and digital health companies. Execute full sales cycle—prospecting, discovery, positioning, contracting, and closing—while managing pipeline forecasting. Collaborate with SVP and cross-functional teams to inform go-to-market, enablement, and product roadmap through structured market feedback. Individual contributor role with occasional travel to HQ.

The Director of Sales oversees global sales activities, develops strategies, manages a team, and ensures customer relationships and profitability in the Power Generation market, requiring extensive travel.

Lead Costco-focused sales strategy and execution regionally, driving top-line revenue, retailer relationships, and program implementation. Train and manage cross-functional teams, maintain executive-level communication, perform market visits and monthly Costco club walks, manage client communications and meeting follow-ups, and ensure tools, processes, and best practices are used to grow incremental sales.

Lead and develop a team of quota-carrying sellers to meet team revenue targets. Own pipeline health, forecasting, territory design, playbook creation, coaching, and performance management. Partner cross-functionally to remove blockers, join client meetings, handle escalations, and represent Chicory externally. Deliver data-informed forecasts and build repeatable sales processes while fostering team culture and retention.

The Channel Leader drives Zerigo Health's channel strategy through partner relationships, facilitating sales, managing account health, and ensuring growth.

The Sales Enablement Director at Skillsoft leads scalable programs to enhance solution-selling behaviors across sales teams, focusing on performance improvement and manager enablement.

The Director of Sales, Casino is responsible for acquiring new clients within the casino market, managing the sales cycle, and establishing long-term partnerships with senior executives.

Lead global sales operations for Latitude within Megaport, building scalable forecasting, quote-to-cash, CRM processes, reporting, and governance. Partner with sales leadership and cross-functional teams to improve revenue predictability, optimize Salesforce workflows, drive CRM adoption, support GTM and marketplace initiatives, and mentor sales operations staff.

Lead and scale a national enterprise sales organization to drive adoption of Axon's Drone as First Responder and counter-drone solutions. Build go-to-market strategy, support agencies deploying aerial response programs, cultivate government and regulator relationships, partner with product and engineering, and deliver measurable revenue growth in a metrics-driven environment.

The Director of Sales Training develops and oversees training for sales hires, ensuring they become high-performing revenue producers. Responsibilities include designing training systems, leading training sessions, monitoring performance, and optimizing sales strategies based on data analysis.

The Director of Strategic Partnerships will lead enterprise employer growth strategy, negotiate high-impact partnerships, and enhance sales outcomes across teams in a fast-paced environment.

The Sales Director will lead the sales process to close partnerships with research sites, managing all sales activities including discovery and negotiation, while collaborating with Customer Success for onboarding.

Lead AMPP's commercial revenue strategy across advertising, media, exhibits, sponsorships, publications, digital products, and PPS. Build and coach a high-performing sales organization, set targets and forecasts, implement sales playbooks and CRM-driven processes, drive cross-selling and market expansion, oversee high-value negotiations, and report performance to senior leadership.

Lead sales efforts across multiple regions, mentor sales teams, build strategic relationships, and implement effective sales strategies to achieve company goals.