Top Remote Director of Sales Jobs in Chicago, IL

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.

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.

The Director of Sales manages and develops a team of Account Executives, focusing on coaching, live deal support, and leveraging AI tools to enhance sales performance.

Lead Sales Engineering & Effectiveness team to provide deal support, solution design, value calculations, and operational playbooks. Manage SMEs in analytics, payments, financial modeling, contracting, and deal desk operations; drive strategic opportunity identification, SLAs, tooling roadmap, executive deliverables, and cross-functional collaboration to accelerate growth.

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.

The Director of Sales Engineering will lead a team of Sales Engineers, manage enterprise sales, and collaborate with various teams to drive technical strategy and successful outcomes during the sales cycle.

Lead recruitment and growth strategy to source, attract, and onboard top sales talent for Relation Insurance. Build pipelines, manage agencies, design sourcing campaigns (cold outreach, social, job boards), partner with sales and marketing, conduct preliminary interviews, ensure compliance, track recruiting metrics, and represent the company at events.

Lead and scale a pre-sales Sales Engineering organization for enterprise SaaS. Own technical/value-selling across discovery, solution design, demos, executive presentations, RFPs, POCs, and cross-functional deal support to improve win rates, sales velocity, and deal quality.

The Sales Director will drive customer acquisition for Liftoff, managing the sales lifecycle, client engagement, and collaborating with teams to ensure success. Responsibilities include pipeline management and exceeding revenue targets.

The Senior Director, Regional Sales is responsible for managing the sales team, driving revenue growth, meeting quotas, and collaborating with marketing and partners.

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

Lead and scale a team focused on enterprise new-logo acquisition across the Eastern U.S. Own full sales lifecycle for complex six- to seven-figure deals, execute account-based strategies, coach Account Executives, engage prospects in-person, and collaborate with GTM, product, and solutions teams to refine positioning and close deals.

Own the sales technology strategy and roadmap, integrating tools (ZoomInfo, Outreach, Seismic, intent platforms, AI) into seller workflows. Drive adoption, measure ROI, align sales and marketing data, lead vendor negotiations, and manage a Sales Technology Manager. Partner cross-functionally with Sales, Marketing, IT, Legal, and L&D to operationalize AI-enabled selling and link technology adoption to pipeline and revenue outcomes.