Top Director of Sales Jobs in Chicago, IL

Leads global sales compensation strategy, commission plan design, implementation, optimization, and roadmap prioritization. Partners with senior leaders to align incentives with go-to-market strategy, sales productivity, and revenue growth. Analyzes plan effectiveness, identifies automation opportunities, coordinates cross-functional execution, and manages a high-performing compensation operations team.

Directs sales, marketing, and revenue-generating strategies for a resort hotel. Leads and develops the sales and marketing team, grows group and transient business, manages client relationships, oversees campaigns and public relations, maintains digital and OTA presence, analyzes market and sales performance, manages budgets, forecasts demand, and collaborates with hotel operations and revenue management to achieve commercial goals.

Directs hotel sales activities, including lead generation, customer solicitation, proposal development, negotiation, and closing. The role supports guest satisfaction and communicates with hotel teams and customers. Requirements include a high school diploma or GED, at least two years of hospitality sales, conference planning, or convention experience, strong English communication skills, and availability for weekends, holidays, overtime, shift work, and emergency on-call coverage.

Leads hotel group sales strategy and commercial performance across rooms, catering, and events. Develops pricing and revenue strategies using performance data, demand forecasts, and competitive insights. Builds relationships with Hilton Worldwide Sales, convention bureaus, travel partners, and key clients. Facilitates business reviews, supports site visits and pre-convention meetings, and contributes to annual and long-range commercial planning.

Owns partner sales strategy and execution across an AMER territory. Builds account and partner mappings, activates delivery, technology, and marketplace partners on opportunities, supports customer retention, leads joint business planning, develops executive relationships, coaches account executives, identifies ecosystem gaps, and mentors regional partner sales managers. The role drives revenue through partner-engaged deals and influences sales leadership without direct authority.

Leads business development and relationship management for enterprise technology payments clients. Drives consultative sales, pipeline growth, revenue, profitability, account planning, and wallet share expansion across cash management, liquidity, merchant acquiring, commercial card, foreign exchange, and trade solutions. Partners with banking, product, service, onboarding, and global teams while coaching sales associates and client managers.

Leads national core and political advertising sales across assigned markets, overseeing managers and support staff. Owns regional budget attainment, develops sales strategies, manages major client and agency relationships, forecasts performance, negotiates business opportunities, and collaborates with cross-functional teams. The role also drives team culture, account stewardship, and revenue growth while traveling as needed to support clients and partners.

Leads strategic and national account growth by developing customer strategies, securing new business, expanding market share, and driving profitable revenue. Partners with regional sales teams and internal stakeholders to deliver packaging and automation solutions, conduct executive business reviews, negotiate proposals and contracts, forecast revenue, and monitor market trends. The role requires extensive travel during peak seasons and focuses on customer retention, revenue generation, and long-term partnerships.

Directs sales strategy and supervises Regional Sales Managers to achieve revenue targets, expand the customer base, forecast sales and profit, monitor performance, adjust strategies, and maintain customer relationships. The role includes attending trade shows and traveling with sales managers to customers and company locations. Candidates need sales management experience, a bachelor’s degree, strong communication skills, and proficiency with Microsoft Office; dealership and Salesforce experience are preferred.

Leads sales and marketing strategy for a senior living community, driving occupancy, revenue, census growth, and long-term performance. Builds referral networks, manages prospects through the CRM, conducts market and competitive analysis, oversees move-in coordination and compliance, manages sales budgets, and coaches teams. The role also develops healthcare facility partnerships, delivers presentations, reports sales performance, and meets revenue targets.

Leads and scales Square’s Central Region Field Sales organization, managing Sales Managers and Territory Account Executives. Responsibilities include territory and go-to-market strategy, pipeline and KPI management, field coaching, consultative selling, product expertise, team development, cross-functional collaboration, and regional revenue growth. The role builds a competitive, accountable, high-performing sales culture while representing Square with local business leaders and partners.

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 Microsoft Dynamics 365 alliance strategy, sales enablement, revenue growth, executive relationships, account planning, cross-functional pursuits, and go-to-market programs. Develops sales plans, identifies expansion opportunities, translates market insights into positioning and campaigns, coordinates solution development, tracks alliance performance, and mentors teams. Requires a bachelor’s degree and at least eight years of partner or alliance management experience with demand-generation success.

Leads enterprise new-business growth for health and benefits solutions, including go-to-market strategy, sales team development, pipeline discipline, consultant and broker relationships, strategic employer pursuits, forecasting, and cross-functional coordination. Owns enterprise revenue targets, competitive intelligence, sales operating standards, and performance KPIs while personally supporting complex, executive-level opportunities and consultant-led RFPs.

Leads Microsoft Dynamics 365 alliance sales strategy and enablement programs to drive revenue, pipeline growth, market expansion, and client pursuits. Builds executive relationships, coordinates go-to-market campaigns, develops solution positioning, tracks alliance performance, identifies opportunities, and promotes AI-enabled sales processes. The role also provides strategic direction, oversees projects, supports business development, and mentors future leaders.

Lead and grow a team of account partners to sell enterprise eQMS SaaS to large manufacturers. Drive pipeline generation, accurate forecasting, complex deal strategy, contract negotiation, and long-term relationships across Quality, IT, Operations, and Procurement. Hire, coach, and manage performance while ensuring use of CRM and expansion of multi-year, multi-region agreements.

Lead and scale Square’s Central Region field sales organization by managing Sales Managers and Territory Account Executives. Set regional strategy, optimize territories and go-to-market plans, drive pipeline and revenue performance, coach teams in the field, develop talent, and collaborate with Marketing, Sales Operations, Partnerships, and Product. Serve as a product expert and regional representative while building a high-performance, accountable sales culture.

Leads business development and capital formation for a global special situations investment strategy. Builds institutional investor relationships, originates prospects, manages the sales pipeline, communicates complex investment strategies, coordinates diligence with investment professionals, gathers market feedback, and expands distribution across credit, alternatives, and fixed-income investors. Extensive travel and FINRA Series 7 and 63 licenses are required.

Owns the full-cycle provider sales process, from prospecting and segmentation through closing, while carrying an individual quota. Builds executive relationships with hospitals, health systems, ACOs, physician groups, digital health companies, and consultants. Uses data-driven selling to position Garner’s healthcare solutions, partners cross-functionally on product and account handoffs, and helps develop the provider-segment sales playbook, messaging, targeting, and objection handling.

Leads and develops a team of senior enterprise Account Executives selling complex solutions to major retail merchants. Owns pipeline, forecasting, deal progression, merchant acquisition, expansion, and revenue outcomes. Coaches strategic deal execution, builds executive merchant relationships, shapes enterprise retail go-to-market strategy, and partners cross-functionally across Product, Client Success, Marketing, Finance, Legal, and RevOps. Uses data, AI, automation, and modern sales tools to improve effectiveness. Travel supports merchant meetings, events, and team gatherings.

Lead and coach a regional team selling IG infusion services, develop regional strategy for target specialties, recruit and train talent, collaborate with operations/nursing/marketing, manage budgets and travel, build relationships with healthcare professionals and manufacturers, and drive regional sales goals while ensuring compliance and customer service excellence.

Directs sales strategy and growth for robotic welding systems across the Americas, particularly the U.S. Leads customer and channel relationships, develops opportunities, oversees quoting and forecasting, negotiates contracts, supports regional sales managers, and collaborates with marketing, engineering, applications, and customer support teams. Provides product demonstrations and training while maintaining accurate sales and expense records.

Leads regional sales efforts across assigned senior living communities, overseeing occupancy goals, budgets, sales reporting, lead management, staff hiring, training, coaching, and performance monitoring. Partners with executive directors on strategy and business development, analyzes market and sales trends, conducts competitor research, and supports onsite sales when needed. The role requires regional leadership, senior living or healthcare sales experience, strong software skills, interdisciplinary collaboration, and approximately 60% travel.

Leads leisure sales strategy for Hilton Los Cabos and Conrad Punta de Mita. Manages sales managers, develops wholesale, FIT, tour operator, and luxury consortia accounts, conducts client presentations, oversees travel and trade show activity, and drives revenue growth through account development, marketing initiatives, negotiations, and customer relationships. The role includes ownership and asset management collaboration and up to 30% international travel.

Own sales strategy and operations for the Groups business, including segmentation, territory design, capacity planning, forecasting, sales process, operating cadence, and executive reporting. Lead AI and automation adoption across the sales motion, partner with finance, systems, enablement, and data teams, and translate analysis into business decisions. Hire and manage a team of analysts and strategy partners while serving as the primary strategic partner to the VP of Sales.