Top Sales Leader Jobs in Chicago, IL

Lead and coach federal enterprise sales teams, drive net-new agency acquisition and contract expansion, and grow ARR across civilian, DoD, and intelligence agencies. Develop go-to-market strategies, manage complex multi-year software procurements, engage senior government executives, oversee pipeline and forecasting, and coordinate with solution engineering, marketing, and system integrator partners. The role requires extensive federal SaaS sales leadership, procurement expertise, and knowledge of FedRAMP and government contract vehicles.

Lead and coach a team of 6–8 enterprise account executives selling SaaS and Generative AI solutions to Financial Services organizations. Drive net-new logo acquisition, ARR growth, complex seven-figure deal closures, pipeline management, forecasting, executive engagement, and vertical go-to-market strategy. Partner with Solution Engineering, Product Management, and Marketing to develop tailored sales plays and expand market penetration.

Leads U.S. Life Sciences and Payers sales strategy, revenue growth, enterprise selling, partner development, forecasting, and customer expansion. Manages frontline sales leaders and enterprise account executives while engaging C-suite stakeholders across healthcare organizations. Builds high-performing teams, drives complex SaaS sales cycles, strengthens partner ecosystems, and collaborates cross-functionally with Product, Marketing, Customer Success, and Solution Engineering.

Leads and coaches enterprise sales leaders and account executives serving the Services sector. Drives net-new logo acquisition, ARR growth, pipeline generation, forecasting, executive engagement, and complex multi-year enterprise SaaS deals. Develops vertical go-to-market strategies, sponsors strategic opportunities, and collaborates with solution engineering, product management, and marketing teams to expand market penetration and revenue.

Lead North American enterprise sales for Qualtrics’ Technology and Telecommunications vertical. Manage and coach 4–6 sales leaders and 20+ account executives, drive net-new logo acquisition, oversee complex seven-figure SaaS deals, develop vertical go-to-market strategies, engage C-level stakeholders, manage pipelines and forecasts, and collaborate with Product, Marketing, and Solutions Engineering to accelerate revenue growth.

Leads North American Market Solutions teams, owning customer experience, ARR growth, retention, expansion, renewals, and platform adoption. Manages and coaches regional leaders, drives solutioning excellence, oversees customer lifecycle execution, and leads organizational transformation. Partners with Sales, Customer Success, Professional Services, Product, Marketing, and Enablement to standardize operating models, improve forecasting and pipeline discipline, develop channel capabilities, and deliver executive-level customer outcomes.

Leads profitable growth of Hiscox’s SME insurance products through digital partnerships. Owns channel P&L, distribution strategy, partner relationships, sales practices, and revenue goals while managing and developing business development and enablement teams. The role requires deep knowledge of insurance distribution technology, strong executive stakeholder management, and the ability to identify emerging market opportunities and deliver innovative solutions.

Leads an institutional retirement market, overseeing client-facing teams and approximately $50 billion in assets under administration. Develops multi-year growth plans, retains and expands institutional relationships, strengthens partnerships with consultants and brokers, and drives commercial performance. Builds high-performing teams through coaching, accountability, collaboration, and operational excellence while growing assets, clients, and product adoption.

Own worldwide AI Business Process sales strategy, revenue, consumption, pipeline, and forecasting across Dynamics 365, Copilot Studio, agents, and related solutions. Lead and coach a global specialist sales community, engage executive customers, drive partner co-sell motions, enforce sales methodology and execution standards, develop talent, and translate field insights into global go-to-market strategy. The role also drives adoption, consumption planning, technical skilling, deal inspection, and business performance across regions.

Lead and scale Zebra’s machine vision sales team across the Midwest. Responsibilities include coaching sales professionals and leaders, establishing regional sales plans, managing budgets and forecasts, overseeing performance and staffing, developing policies, and leveraging machine vision portfolio expertise to achieve significant sales targets and expand customer and channel partner relationships.

Lead nationwide business development for energy and infrastructure services, selling surveying, engineering, environmental, zoning, assessment, and construction offerings. Build strategic client relationships, secure vendor approvals and service agreements, originate and close profitable opportunities, expand accounts, coordinate proposals and negotiations, maintain forecasts, and support client retention and repeat work. The role targets energy developers, utilities, operators, investors, and contractors while coordinating delivery capacity across departments.

Leads sales growth and profitability for an employee benefits business across a designated geography. Establishes sales strategies, goals, and performance plans; coaches and develops producers; supports talent acquisition and retention; identifies new business and partnership opportunities; evaluates results; and maintains carrier relationships. Requires extensive progressive sales and leadership experience, insurance expertise, and a valid producer insurance license.

Leads a mid-market sales development team through hands-on coaching, call mentoring, outbound strategy, performance management, recruiting, and culture building. The role models phone-first prospecting, uses data to guide coaching, collaborates with account executive leaders, and partners with strategy teams to improve messaging and pipeline generation. Success is measured by target attainment, rep development, talent retention, and quality pipeline.

Executive leader responsible for building and scaling Career Connect, a workforce solutions business. Owns growth strategy, employer partnerships, revenue generation, pilot launches, learner solution design, placement outcomes, operating model development, and cross-functional delivery. Builds and leads sales, solutions design, and delivery teams while establishing repeatable workforce programs across high-demand industries. Success is measured through employer acquisition, revenue, placements, learner outcomes, satisfaction, and sustainable business integration.

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

Sell GE HealthCare products directly to customers, partners, and distributors while supporting channel sales and development. Build knowledge of assigned territories, product lines, markets, sales processes, and customer segments. Develop strong customer relationships, communicate technical information, exercise judgment within defined guidelines, solve business problems, and coordinate effectively with colleagues and business teams.

Lead the creation and scaling of the U.S. enterprise sales organization for a Salesforce DevOps and data management platform. Build the sales process, personally drive prospecting and high-value deal closure, establish forecasting and KPIs, coach an initial team of 8–10 representatives, and scale it to 40+ remote representatives. Hire and develop sales managers while building a high-performance, accountable remote culture.

Leads private-sector growth across environmental and water engineering markets by developing strategic growth, sales, pursuit, and client plans. Drives revenue and profit growth, market analysis, partnerships, key pursuits, client relationships, team performance, resource allocation, and succession planning. Coaches growth and client service teams, oversees performance and operations, and aligns business-unit strategies with company objectives.

Drive commercial growth and market leadership for Sikich’s insurance vertical. Develop insurance-specific growth strategies, expand pipelines, lead consultative solution selling, shape executive-level pursuits, and cross-sell Salesforce, Microsoft, data and AI, cybersecurity, risk management, and managed services. Build relationships with insurance executives, provide industry thought leadership, guide go-to-market campaigns, monitor market trends, and develop an integrated insurance playbook across Sikich practices.

Leads enterprise sales across the Western United States, driving revenue growth, customer expansion, new business development, forecasting, and quota achievement. Manages, hires, trains, and motivates Account Executives; develops regional sales strategies, campaigns, channel partnerships, and upsell programs. Supports complex customer engagements, communicates technical and business value, provides market feedback, and influences product positioning. Requires cybersecurity vendor experience, executive-level relationship skills, and at least 50% travel.

Leads outside sales and business development across Southern California, growing accounts and market share for hygienic fluid handling equipment and services. Prospects food, dairy, beverage, pharmaceutical, OEM, and fabrication customers; promotes pumps, valves, heat exchangers, instrumentation, tank cleaning, parts, and repair services. Builds customer and internal relationships, follows up on leads, supports sales strategy, identifies market opportunities, and provides regional business intelligence. Frequent customer travel, including overnight, weekend, and holiday travel, is required.

As Market Leader, you will oversee Brokerage services in Chicago, drive growth, recruit talent, and foster client relationships while ensuring a strong team culture and operational success.

Leads business development for EHS and industrial hygiene consulting services, including strategic growth planning, client acquisition, key account management, contract negotiation, proposal development, and revenue targets. Builds trusted-advisor relationships, ensures client satisfaction and delivery quality, represents the company at industry events, mentors team members, reviews technical deliverables, and supports project execution and organizational leadership.

The Sales Leader drives revenue growth by managing strategic client relationships, leading presales activities, and winning multi-million-dollar Quality Engineering deals.

Lead and grow a high-performing software sales team for Splunk/Cisco in the SLED public sector. Deliver and forecast revenue, direct sales activities, build pipeline, coach reps on value-based selling, and negotiate deals to achieve quarterly and annual targets.