Top Director of Sales Jobs in Chicago, IL

Leads commercial planning, forecasting, sales operating rhythms, KPI reporting, customer planning, and performance management across Sales, Supply Chain, and Finance. Builds scalable systems, dashboards, workflows, and retailer and broker tools; supports budgeting, scenario modeling, inventory readiness, go-to-market planning, and commercialization. Manages the Sales Operations team, drives broker accountability, leads strategic operational initiatives, and provides executive reporting and recommendations for scalable CPG growth.

Leads national retail accounts and sales teams to drive revenue, distribution, velocity, market share, and profitability. Responsibilities include customer growth strategies, joint business planning, negotiations, broker management, retail execution, forecasting, trade investment, P&L ownership, and cross-functional commercialization. The role develops strategic retailer partnerships, coaches sales talent, uses customer and market insights to identify opportunities, and delivers performance recommendations to leadership across grocery, convenience, mass, and emerging retail channels.

Lead and scale Vega’s North Central enterprise sales organization. Responsibilities include hiring and coaching Regional Sales Managers, driving revenue and pipeline generation, managing strategic account plans, guiding complex enterprise deals, maintaining forecast discipline, leveraging channel partners, engaging senior security executives, and collaborating cross-functionally to expand enterprise accounts and win new logos.

Leads and scales Vega’s enterprise sales team across the Western U.S. Responsibilities include hiring and coaching Regional Sales Managers, driving pipeline and revenue performance, managing strategic enterprise deals, forecasting, developing account plans, leveraging channel partners, engaging security executives, and partnering cross-functionally to grow new and existing accounts.

The Director of Sales will scale sales enablement and go-to-market programs through onboarding, training, coaching resources, playbooks, product-launch readiness, and performance analysis. The role partners across Sales, Product, Marketing, Revenue Operations, Customer Experience, and leadership to improve sales processes, tool adoption, customer outcomes, ramp time, and conversion. Responsibilities include managing enablement content and tools, analyzing customer and sales data, sharing frontline feedback, and developing scalable communication and training programs.

The Director of Sales Enablement will build scalable onboarding, training, certification, coaching, playbooks, and product-launch readiness programs. They will analyze sales and customer data, review calls, measure enablement impact, manage enablement tools and content, and partner with Sales, Product, Marketing, Revenue Operations, Customer Experience, and leadership. The role focuses on improving sales readiness, customer experience, process adoption, ramp time, conversion, retention, and overall go-to-market effectiveness.

Lead and develop an enterprise sales team to acquire, grow, and retain health system customers. Build commercial strategy, coach sellers on account planning and negotiations, drive data-informed revenue growth, recruit and retain sales talent, and align cross-functional teams to scale repeatable processes and improve customer outcomes.

Leads sales planning, territory and account design, quota allocation, capacity modeling, and sales compensation strategy. Owns governance for quota exceptions and disputes, builds scenario models for executive decision-making, and continuously optimizes coverage, productivity, attainment, and cost of sale. Partners with Finance, HR, sales leadership, and GTM Engineering to improve planning systems, automate processes, and apply AI to quota and incentive management.

Lead enterprise sales for automotive dealer groups, owning the full sales cycle from pipeline development through close. Build relationships with dealer principals and operational leaders, conduct high-value discovery, lead pricing and contract negotiations, support demos and pilots, and convert pilots to paid customers. The role focuses on multi-rooftop deals, pipeline quality, revenue per deal, conversion rates, and representing Cerence at industry events. Approximately 30% travel to customer sites is required.

The Enterprise Sales Director - Health will manage the sales cycle for AI-powered solutions in health insurance, cultivate relationships, and achieve sales targets.

Leads GitLab’s Department of War regional sales organization, managing, recruiting, and coaching Account Executives while driving new and expansion revenue. Responsibilities include forecasting, MEDDPICC-based deal inspection, complex federal procurement, executive negotiations, partner and distributor engagement, FedRAMP go-to-market strategy, and land-and-expand growth. The role collaborates cross-functionally with Renewals, Customer Success, Product, and Marketing in an all-remote environment and travels as needed for customer and team engagements.

Leads sales strategy enablement for Microsoft Security SME&C, Corporate, SMB, and partner teams. Develops sales learning paths, technical skilling programs, content, communities, and feedback systems. Measures enablement impact through KPIs, customer feedback, pipeline, adoption, usage, and renewal outcomes. Advises senior leaders, identifies readiness gaps, influences cross-functional stakeholders, and accelerates sales motions across enterprise and partner channels.

Lead end-to-end segmentation strategy for Microsoft Advertising, translating business priorities into coverage, capacity, and resource-allocation models. Build measurement frameworks, analytical models, and cross-functional alignment to operationalize segmentation into territory design, quota and capacity planning. Advise senior leaders and continuously refine models using data-driven insights to drive growth.

Leads enterprise sales for Duck Creek’s insurance software solutions, targeting major P&C carriers. Responsibilities include winning and expanding strategic accounts, managing complex sales cycles, building executive relationships, developing pipelines, forecasting bookings, presenting proposals, and aligning solutions with customer strategies. The role also leads, coaches, mentors, and onboards Sales Directors while managing large deal pursuit teams and partner ecosystems.

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

Lead and scale a multi-region sales organization for Titan Electronics, driving net-new business, cross-selling integrated security solutions, and meeting revenue targets. Manage and coach a distributed team, develop go-to-market strategy, enforce CRM and pipeline discipline, and partner cross-functionally to ensure seamless solution delivery and client engagement.

Own Trellis’s sales go-to-market strategy from the ground up as its first senior sales leader. Personally acquire early customers, define ideal customer profiles and buyer personas, develop sales processes and messaging, establish CRM hygiene and forecasting, identify partnerships, and translate customer feedback into product and positioning decisions. The role is a hands-on player-coach position responsible for building a repeatable sales motion and preparing the business for future scale.

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 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.

Territory-focused sales leader responsible for building and growing dealer relationships in the Pacific NW. Perform consultative selling, prospecting, and account management; analyze dealer performance; resolve customer issues; provide product feedback; collaborate with internal teams to drive retention and growth. Frequent travel within the territory and remote work from a home office required.

Leads regional enterprise Sales Engineering strategy, execution, operations, and team development. Oversees frontline SE leaders, strategic customer engagements, technical sales cycles, resource allocation, forecasting, hiring, onboarding, coaching, and performance management. Partners with Sales, Product, Marketing, Enablement, Support, and channel organizations to scale go-to-market execution. Promotes observability and security solutions, drives operational excellence, tracks market developments, and positions the company effectively in cloud security and AI-driven technology markets.

The Director of Sales and Partnerships will drive revenue growth, establish a go-to-market strategy, and build relationships with enterprise and federal customers, focusing on secure infrastructure.

Drive new pipeline through strategic account planning, engagement with executives, and maintaining relationships to achieve revenue targets across enterprise sales.

Individual contributor responsible for territory sales growth focused on freight forwarding. Identify new business, manage key accounts, prepare RFQs/bids, price solutions, maintain CRM, meet revenue and volume targets, provide performance metrics, and travel frequently to support sales activities and implementations.

Lead and coach a team of Enterprise Account Executives on prospecting, account planning, forecasting, and closing Fortune-level accounts. Develop territory and strategic account plans, track KPIs, hire and enable talent, collaborate cross-functionally, and directly engage high-priority prospects to drive ACV and revenue goals while ensuring CRM and sales processes are followed.