Top Director of Sales Jobs in Chicago, IL

Lead Blueland’s retail sales strategy and execution across grocery, e-commerce, specialty, and discount channels. Own customer P&Ls, annual business plans, forecasting collaboration, shopper marketing, trade, retailer relationships, broker performance, and innovation presentations. Partner cross-functionally to achieve revenue and profitability goals, build data-backed selling stories, and expand sustainable products across retail accounts. Travel is required 1–2 times per month.

Lead sales and business development for HABA and OTC Costco accounts. Responsibilities include building Costco merchandising relationships, developing growth strategies, managing client business, creating sales presentations, delivering distribution and budget plans, coordinating with analytics and supply chain teams, and monitoring sales performance. The role requires extensive consumer business sales experience, Costco HABA and OTC expertise, strong relationship-building and presentation skills, and willingness to travel.

Leads group sales for Hilton Aruba and The Westerly, soliciting and negotiating complex group accommodations, contracts, pricing, and agency agreements. Directs sales staff, oversees performance, training, forecasts, budgets, reporting, trade shows, client presentations, and market research. Builds customer relationships, develops sales strategies, monitors departmental performance, and travels domestically and internationally up to 30% of the time.

Leads sales performance across a portfolio of senior living communities, driving occupancy growth, lease-up results, revenue performance, and sales-process consistency. Coaches Directors of Sales and Marketing, enforces CRM standards, monitors pipelines and outreach, delivers portfolio scorecards, oversees competitive intelligence, and partners with community leadership. The field-based role requires extensive travel, regular onsite visits, executive reporting, and development of high-performing sales teams.

Lead Hilton’s technology-focused corporate group sales accounts by developing account strategies, expanding relationships, identifying revenue opportunities, forecasting growth, and achieving sales targets. The role manages national and global accounts, analyzes account data, collaborates cross-functionally, advises executive decision-makers, and delivers tailored hospitality solutions. It is remote and requires travel of up to 40%.

Lead sales and marketing strategies to grow occupancy for a senior living community. Manage the prospect journey from inquiry through move-in, conduct tours, build referral relationships, oversee community outreach and events, track pipeline performance in Salesforce, and supervise marketing staff. Partner with leadership and corporate marketing teams, present reports, maintain compliance, and support exceptional resident and family experiences.

Leads sales and marketing strategy to grow occupancy and revenue for a senior living community. Manages the full prospect-to-move-in sales process, community tours, referral relationships, outreach, events, digital and print marketing, CRM tracking, reporting, and performance metrics. Supervises marketing staff, collaborates with community and corporate leadership, maintains regulatory compliance, and supports exceptional resident and customer experiences.

Lead the transition from founder-led sales to a scalable revenue function. Own outbound strategy, prospecting, pipeline development, and deal closing for healthtech and life sciences buyers. Sell both platform access and expert marketplace services, focus on cardio and brain health segments, identify new revenue opportunities, and establish repeatable sales processes while preparing for future team growth.

Lead and build Element 74’s new-business sales function, owning bookings, pipeline generation, forecasting, complex public-sector and nonprofit deals, market expansion, contract management, and sales and marketing efficiency. Recruit and develop the sales team, establish repeatable playbooks and CRM discipline, personally manage strategic pursuits, and partner with leadership on pricing, packaging, and growth initiatives.

Leads national education sales strategy and strategic account growth across K-12, higher education, and educational organizations. Builds pipelines, navigates complex procurement processes, manages forecasting, develops partnerships, negotiates high-value deals, and expands multi-location accounts. Builds relationships with senior decision-makers and collaborates cross-functionally through implementation and expansion. Requires national travel to customer meetings, conferences, and education events.

Leads enterprise sales excellence and development programs, including onboarding, training, coaching, leadership development, sales effectiveness, KPIs, playbooks, and commercial enablement. Partners with Sales, Marketing, Revenue Operations, Category Management, and HR to improve productivity, accelerate ramp time, strengthen leadership capabilities, and support customer and market engagement. The role requires up to 75% travel and reports to the VP of People & Rewards.

Leads contract sales operations for a commercial kitchen equipment supplier. Responsibilities include full P&L ownership, sales planning, forecasting, budgeting, business development, team leadership, project management oversight, distribution center management, process improvement, coaching, troubleshooting, and ensuring profitable growth. Travel is required.

Leads GitLab’s National Security Group regional sales team, driving new and expansion revenue across U.S. federal agencies. Responsibilities include hiring and coaching Account Executives, forecasting, pipeline management, complex deal strategy, executive negotiations, federal procurement, FedRAMP-related selling, partner engagement, and account expansion. The role collaborates with Customer Success, Product, Marketing, Renewals, distributors, and systems integrators while traveling as needed for customer and team engagements.

Leads hotel sales strategy and team performance, drives prospecting and client development, negotiates contracts, manages revenue goals, analyzes markets, and oversees budgeting, forecasting, promotions, and sales reporting. The role develops new business across multiple market segments, supports repeat bookings, participates in tourism associations, and ensures the property meets or exceeds revenue and occupancy objectives.

Leads regional sales strategy across independent living communities, coaching Community Sales Directors and sales teams to improve occupancy, revenue, net move-ins, and waitlist growth. Responsibilities include sales execution, pipeline and CRM analytics, forecasting, pricing and inventory planning, performance reviews, prospect-centered selling, leadership development, and collaboration with Operations, Finance, and Marketing. The role also supports communities undergoing transitions, occupancy recovery, redevelopment, or expansion.

Leads global sales planning and strategy, including growth targets, capacity allocation, resource optimization, performance analysis, and executive reporting. Partners with Finance, Product, HR, Renewals, and other functions to support go-to-market decisions and improve planning methodologies. Oversees strategic initiatives involving seller productivity, capacity reporting, AI adoption, and business performance. Manages a distributed US and European team, develops talent, and presents insights to senior executives and the Board.

Leads a specialized platform sales team selling cloud, data, analytics, AI, and extensibility solutions to CIO and CTO organizations. Responsibilities include coaching account executives, managing complex $500K+ ARR sales cycles, coordinating presales and partner teams, overseeing AI and platform statements of work, developing technology roadmaps, forecasting revenue, and driving co-selling with AWS, GCP, and global systems integrators.

Leads a specialized enterprise sales team selling platform, data, analytics, AI, and extensibility solutions to CIOs and CTOs. Responsibilities include coaching account executives, managing complex $500K+ ARR sales cycles, orchestrating internal teams, overseeing AI and platform statements of work, developing technology roadmaps, forecasting revenue, and coordinating co-selling with AWS, GCP, and global systems integrators.

Leads a regional enterprise sales team selling Workday platform, data, analytics, AI, and extensibility solutions to CIOs and CTOs. Responsibilities include coaching account executives, managing complex $500K+ ARR sales cycles, coordinating presales and internal teams, overseeing AI and platform SOWs, developing technology roadmaps, forecasting revenue, and leading co-selling efforts with AWS, GCP, and global systems integrators.

Leads GitLab’s global SMB new-business organization across EMEA and AMER, overseeing regional sales, BDR, and SDR managers. Owns new-logo strategy, pipeline generation, quota and territory planning, forecasting, revenue reporting, hiring, manager development, and cross-functional alignment. The role drives outbound sales motions, develops team performance, analyzes market opportunities, and represents new-business strategy to senior leadership.

Lead Propelus’s Employer Growth Team across EverCheck and Immuware, owning revenue growth, pipeline creation, forecasting, territory coverage, sales processes, enablement, and team performance. The role manages eight direct reports and requires hands-on enterprise selling into hospitals and health systems, coaching, performance management, and development of outbound sales systems. The leader will also support new data solutions and a premium nursing module while partnering with Marketing and senior leadership in a PE-backed environment.

Leads Verizon’s AI Connect sales organization, focusing on Dark Fiber infrastructure and AI-enabled connectivity for hyperscalers, data centers, and AI-focused firms. Responsibilities include executing go-to-market strategy, expanding strategic partnerships, driving profitable revenue growth, managing complex enterprise relationships, and developing high-performing sales teams. The role requires expertise in networking infrastructure, AI transformation, solution selling, executive engagement, alliance management, and cross-functional leadership in matrixed environments.

Leads commercial strategy, sales growth, profitability, and market share for North American dewatering solutions. Builds customer, contractor, and stakeholder relationships; manages bids, contracts, pricing, P&L, and margin improvement. Partners with operations to ensure accurate quoting, billing, equipment utilization, project execution, and customer satisfaction. Leads and develops high-performing commercial teams while applying market and financial insights to guide business decisions.

Leads global sales compensation strategy, designing annual and in-year incentive plans, quota frameworks, pay curves, accelerators, and performance levers. Manages incentive designers and partners with Sales, Finance, Revenue Operations, data, and activation teams. Oversees analytics, dashboards, governance, payout accuracy, AI-enabled communications, change management, and continuous optimization while advising senior executives.

Lead a North American team of enterprise account managers responsible for SaaS upsells, cross-sells, AI sales, adoption, and customer expansion. Recruit, retain, and develop quota-carrying sellers; establish growth processes; identify install-base opportunities; coordinate with sales, marketing, customer success, legal, and operations; and participate in customer engagements and negotiations.