Top Director of Sales Jobs in Chicago, IL

Leads sales, marketing, occupancy, pre-sales, and fill-up efforts for a senior living community expansion. Oversees entrance-fee Independent Living sales, rental occupancy, marketing strategy, lead conversion, CRM reporting, team performance, business development, community outreach, and regulatory compliance. Partners with development, operations, finance, and home-office teams to achieve pre-sale and occupancy targets while guiding the transition to a Life Plan community.

Leads the SMB sales organization, including up to five managers and approximately 42 account executives. Owns pipeline, forecasting, bookings, revenue attainment, hiring, coaching, and high-velocity inbound sales operations. Drives adoption of BILL’s unified financial platform, develops scalable processes, partners cross-functionally on go-to-market execution, and provides market insights to influence product strategy.

Leads company-wide sales operations, performance analytics, leadership accountability, process standardization, CRM compliance, and operational improvement. The role monitors KPIs, identifies underperforming offices, develops corrective strategies, supports market expansion, and partners with executive leadership to improve sales productivity, profitability, consistency, and scalability across multiple locations.

Own full-cycle, net-new enterprise sales for the MapQuest mapping platform. Build outbound pipeline across targeted verticals, sell location APIs and SDKs to technical executives, manage technical evaluations and proofs of concept, negotiate enterprise contracts, and close multi-year deals. Partner with Solutions Architecture, procurement, product, and company leadership while providing market feedback. This is a remote individual-contributor role with prospect and event travel.

Leads global small and medium business sales strategy for the upper-medium segment. Analyzes market, customer, competitive, and performance insights; develops go-to-market strategies, growth plans, investments, and execution metrics; aligns Finance, Marketing, Engineering, and Sales stakeholders; leads cross-organizational programs; and embeds AI to improve planning, customer engagement, sales execution, and performance.

Lead and scale U.S. revenue growth by managing outbound pipeline development and selling content syndication, intent-based lead generation, data nurturing, and qualified lead services to B2B technology clients. Own the full sales cycle, use intent-data and account-based outreach platforms, present ROI strategies to executive stakeholders, achieve revenue quotas, collaborate on delivery and renewals, and represent the company at industry events.

Leads Seppic’s North America Personal Care sales and marketing operations, including commercial P&L, performance goals, budgeting, pipeline management, pricing, customer negotiations, key account relationships, staffing, coaching, and strategic planning. Partners with technical sales and regional marketing teams to expand distribution and product sales, support bids, and represent the company at industry events. Requires beauty care formulation expertise, sales and marketing experience, management experience, and 30% domestic travel.

Leads enterprise sales across the Southeastern United States, managing Strategic Account Executives and owning regional bookings, revenue, forecasts, territory strategy, and pipeline health. Responsibilities include hiring, coaching, performance management, customer relationship development, go-to-market execution, sales enablement, and cross-functional collaboration with Renewals, Marketing, and Sales Operations. The role is fully remote and supports adoption of GitLab’s AI-powered DevSecOps platform.

Leads the Very Small Business and Mid-Market sales organization, overseeing Account Executives and Account Managers in a remote environment. Drives new-logo and account-management revenue through scalable sales processes, high-velocity sales motions, territory design, funnel optimization, and KPI accountability. Coaches sales leaders and representatives, partners with Product on roadmap feedback, and collaborates with Customer Success to expand accounts.

Lead the launch and growth of JoVE’s corporate learning sales division. Develop the US mid-market go-to-market strategy, build pipeline and revenue, lead early customer deals, hire and coach a high-performing sales team, establish onboarding and sales processes, and drive forecasting, accountability, and performance across US and international markets.

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

Leads Prisma’s enterprise sales strategy for the multifamily housing and HOA market. Builds and manages SDR and AE teams, develops sales processes, drives pipeline growth, forecasts revenue, and personally closes strategic accounts. Partners cross-functionally on marketing, onboarding, product feedback, pricing, and revenue planning. Requires enterprise sales expertise, multifamily industry experience, team-building ability, and strong executive communication and negotiation skills.

Leads hotel sales and catering strategy during a boutique hotel repositioning. Manages sales staff, revenue targets, client relationships, group and transient business, forecasts, proposals, events, marketing initiatives, and partnerships with revenue management and hotel operations. Conducts outside sales, site visits, networking, and client presentations while ensuring elevated guest experiences and strong financial performance.

Leads new business development, account growth, commercial discussions, client relationships, and sales operations for AI and GenAI data solutions. Partners with engineering, delivery, and customer success teams to understand frontier lab needs, structure projects, close opportunities, and expand client accounts. Requires quota-based technology sales experience, startup experience, STEM education, and strong AI/ML market knowledge.

Lead regional enterprise sales for KARE, building relationships with senior living, nursing home, and rehabilitation organizations. Responsibilities include closing complex deals, securing pricing agreements, driving NASTi implementation, supporting customer success, collaborating cross-functionally, and traveling frequently to client communities and headquarters. Candidates need 5–7+ years of healthcare technology or strategic account sales experience, a strong closing record, executive presence, technology adoption skills, and operational adaptability.

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.

Leads the Midwest sales organization by developing and executing growth strategies, coaching sales teams, strengthening customer and supplier relationships, and managing regional revenue, margins, profitability, expenses, and strategic initiatives. Partners with Marketing, Finance, Operations, Procurement, and Category Management to improve customer experience, inventory planning, market expansion, and operational performance. Oversees talent planning, succession, performance management, and change leadership across the region.

Supports the sales and marketing team by maintaining CRM records, following up with prospects, tracking sales goals, preparing move-in paperwork, coordinating assessments, facilitating agreements, and welcoming new residents. The role guides families through the community selection process, supports sales events, ensures suite readiness, and maintains communication with prospects and families.

Leads sales performance, operational excellence, guest experience, and leadership development across a regional portfolio of European Wax Center locations. Oversees Center Sales Directors, drives KPI and financial results, develops talent and succession plans, reinforces brand standards, optimizes staffing and center operations, and partners cross-functionally to execute business initiatives. This field-based leader regularly visits locations and coaches teams to improve sales, retention, service, compliance, and overall center performance.

Lead sales and business development for Palette’s marketing services, building the sales playbook, pipeline, pricing strategy, forecasting, and revenue processes. Secure new client opportunities, develop proposals, negotiate deals, manage executive relationships, and coordinate campaign handoffs. The role also involves hiring and coaching sales representatives, tracking performance KPIs, and establishing scalable systems for growth across brands, agencies, and media partners.

Lead the development of Ethos’s sales training and enablement system across direct-to-consumer insurance sales. Own sales scripts, AI-powered call insights, experimentation, agent onboarding, remedial training, coaching programs, and manager development. Partner with Sales and Product leadership to improve customer engagement, conversion, agent performance, and sales strategy. Build measurable systems for script adherence, call analysis, ramp performance, and organization-wide manager coaching.

Supports the Sales and Marketing team by managing prospect records, following up with leads, tracking sales goals, preparing move-in paperwork, coordinating resident assessments, facilitating agreements, and ensuring suites are ready. Welcomes and orients new residents and families, supports sales and marketing events, and maintains communication throughout the decision and move-in process.

Direct new-business and account-expansion sales for SAP solutions across the Northeast region. Builds partnerships with SAP account executives, drives joint go-to-market activities, develops pipeline and revenue plans, manages end-to-end enterprise sales processes, and leads QBRs and business planning. Requires substantial SAP enterprise software experience, a strong SAP network, B2B consulting or software sales expertise, and deep knowledge of SAP S/4HANA and digital supply chain solutions.

Leads the day-to-day operations of Account Executive and Business Development Representative teams. Responsibilities include coaching, pipeline management, forecasting, quota execution, hiring, onboarding, deal strategy, sales process improvement, and cross-functional escalation. The Director of Sales partners with the VP of Sales on territories, compensation, enablement, and revenue strategy while deputizing for the VP when needed.

Own Flex’s go-to-market strategy and commercial execution for the auto loan vertical. Build executive-level relationships, develop pipeline, negotiate and close complex partnerships, and guide agreements through technical deployment and launch. Collaborate with Product, Engineering, Marketing, Finance, Legal, and Compliance to shape the offering, translate market feedback into improvements, and establish a repeatable sales motion. This zero-to-one role also requires developing scalable processes and using AI-assisted sales tools to improve pipeline and deal performance.