Top Senior Sales Jobs in Chicago, IL

Leads and develops a team of Sales Executives to achieve revenue, quota, pipeline, forecasting, and growth objectives. Responsibilities include coaching, performance management, territory and account strategy, prospecting, cross-selling, CRM data integrity, customer retention, recruiting, onboarding, and collaboration with internal teams. The role also manages escalations, ensures sales-process compliance, and drives regional and business-unit objectives.

Leads sales operations consulting engagements by analyzing client needs, developing customer sales and service strategies, managing client accounts, supervising teams, and driving revenue growth. Oversees project planning, budgeting, execution, and delivery while coaching team members, improving sales effectiveness, supporting prospecting, and enabling cross-selling and upselling initiatives. Uses business transformation, strategic planning, and technology innovation to improve customer satisfaction and operational efficiency.

Drive revenue for T-Mobile Advertising Solutions by expanding agency and brand relationships, developing prospects, building pipeline, closing new business, and managing high-impact accounts. The role requires strong digital advertising expertise, existing agency and client networks, and experience with programmatic, location-based data, and analytics. The Senior Account Executive will work with business leaders in a hybrid Chicago role and maintain client relationships through service and campaign performance.

Advises large corporate clients on treasury management, commercial card, payments, receivables, payables, and liquidity solutions. Leads complex consulting initiatives, payment modernization, and working capital optimization efforts while partnering with relationship teams, product groups, and senior executives. Develops strategic solutions, drives revenue growth, mentors colleagues, and influences CFOs, treasurers, controllers, and procurement leaders. The role requires up to 20% travel and follows a hybrid schedule.

Leads and builds Inspira’s sales enablement function for its Health & Benefits go-to-market organization. Owns onboarding, training, field readiness, sales content, proposals, partner enablement, competitive intelligence, AI productivity, CRM adoption, analytics, reporting, and change management. The role develops enablement strategy, improves ramp and sales performance, manages a team of 8–12, and partners with Sales, Marketing, Product, Technology, Partnerships, and Account Management to drive growth and channel effectiveness.

Lead enterprise sales for Braze AI Decision Studio by developing new and existing senior customer relationships, guiding AI solution evaluations, quantifying business impact, and supporting proofs of value. Partner with sales, pre- and post-sales, implementation, product, and marketing teams. Train colleagues on reinforcement learning in marketing, communicate customer needs, and represent Braze AI at executive meetings, events, conferences, and trade shows.

Partners with AMER sales leadership on territory, quota, capacity, and headcount planning. Improves sales processes, scopes Salesforce automations, documents workflows, and builds dashboards using sales technology and BI tools. Analyzes performance, forecasting, KPIs, and trends to provide recommendations. Identifies AI opportunities to automate Sales Operations workflows and presents insights to senior stakeholders.

Designs and validates enterprise solutions for strategic customers using HERE APIs, SDKs, platform services, and mapping technologies. Leads technical discovery, architecture design, demonstrations, workshops, evaluations, and proof-of-concept engagements. Partners with Sales, Product, Engineering, Services, and Customer Success teams to address customer requirements, risks, integrations, and implementation readiness. Communicates technical recommendations and tradeoffs to business and technical stakeholders while supporting account planning, competitive evaluations, expansion opportunities, and successful presales-to-implementation handoffs.

Oversee market success for Moveworks solutions by supporting territory strategy, account planning, customer digital-transformation initiatives, solution roadmaps, and sales-cycle execution. Coach account executives and sales development teams on specialty-solution knowledge, identify opportunities, align recommendations with value principles, and partner with customers, solution consultants, and external partners to drive solution wins.

Drive new subscription sales and expand existing Preqin accounts across a Midwest territory. Manage full sales cycle, build pipelines, deliver demos and proposals, negotiate deals, and support renewals to achieve quota and revenue growth.

Own enterprise sales activities for SLED or Healthcare accounts, including executive relationship development, account strategy, stakeholder collaboration, trusted-advisor engagement, and alignment of cloud security solutions with customer goals. The role requires full-cycle software or security sales experience, enterprise and C-level selling, strategic planning, net-new logo acquisition, quota achievement, and knowledge of AI/ML solutions.

Manage and transform global sales operations by optimizing processes, leading cross-functional programs, improving Salesforce workflows, overseeing governance, and driving adoption of scalable sales capabilities. The role partners with senior leadership, analyzes business opportunities, manages requirements and UAT, develops transformation roadmaps, and presents data-driven recommendations.

Leads regional insurance sales growth through territory expansion, broker and employer-group development, direct sales, and revenue accountability. Recruits and coaches distributed sales leaders and brokers, manages regional accounts, ensures licensing and regulatory compliance, and uses CRM and market analytics to track pipelines, forecast performance, allocate territories, and identify opportunities. The role requires significant regional travel while operating remotely.

Serves as the technical bridge between customers, Sales, and technology teams. Leads technical discovery, solution architecture, demonstrations, workshops, proofs of concept, and evaluations using HERE data, APIs, mapping, routing, spatial analytics, cloud, AI, and enterprise integration. Partners with Sales to qualify opportunities, reduce technical risk, develop proposals and reusable presales assets, and guide customers toward location-intelligence solutions.

Designs scalable merchant solutions for Affirm’s enterprise customers by leading technical discovery, architecting integrations, supporting pre-sales activities, developing demos, and advising sales, engineering, and product teams. The role serves as a trusted technical advisor, influences product priorities through customer feedback, creates reusable enablement materials, and supports complex e-commerce, checkout, payment, and point-of-sale implementations.

The Senior Sales Executive will lead sales efforts for UL Prospector, focusing on account relationships, product demonstrations, and meeting sales targets in the compliance data platform and DaaS sectors.

Lead and develop a high-performing SDR team to generate pipeline for Risk & Compliance software. Own outbound/inbound prospecting strategy, hiring, onboarding, coaching, performance management, metrics analysis, CRM hygiene, forecasting, and alignment with Sales and Marketing to convert leads into opportunities.

Customer-facing pre-sales engineer supporting ULTRUS software, leading technical/business discovery, delivering tailored demos, shaping solution approaches, preparing RFIs/RFPs, documenting requirements in Salesforce, quantifying value, and supporting handoff to services and implementation teams.

Manages sales support activities, budgets, staffing, policies, and procedures. Resolves sales process and customer issues, improves productivity, and leads direct reports through performance objectives, coaching, feedback, and career development. Presents project or schedule information to senior management and ensures compliance with company policies, including physical and digital security practices.

Drive programmatic direct revenue for Zynga’s mobile and in-app media business. Build strategic relationships with agency holding companies, trading desks, DSPs, SSPs, and retail media partners; package curated demand; optimize deal performance and revenue; and co-sell with account executives. The role also supports pipeline development, buyer education, deal structuring, RFP responses, and overcoming technical objections. Success requires strong programmatic sales expertise, an established industry network, quantitative skills, and a proven record of closing significant commitments.

Sell Comcast Business Internet, Video and Voice solutions to small and mid-size businesses. Develop territory and local partnerships, generate leads via prospecting, deliver face-to-face presentations, promote bundled and advanced communications solutions (PRI, Hosted PBX), manage pipeline to exceed sales targets, and coordinate with technical and support teams to ensure customer satisfaction and revenue growth.

Sell Comcast Internet, Data, Video, and Voice services to SMBs, focusing on advanced communications solutions while managing territory and maintaining customer satisfaction.

Leads Pacific Northwest employer sales by managing Regional Directors and Account Executives serving organizations with 50–9,999 employees. Responsibilities include developing sales strategies, driving revenue growth, pursuing new business, analyzing regional performance, ensuring compliance, and building relationships with benefits brokers and partners. The role requires sales leadership, team quota delivery, strategic thinking, and strong people-management skills.

Own sales, onboarding, and customer success operations, including territory management, commissions, pipeline and lifecycle processes, CRM data hygiene, reporting, health scoring, segmentation, and workflow improvements. Translate operational needs into buildable requirements for Business Systems, reduce manual work, improve process consistency, and support revenue teams through data-informed decisions and cross-functional partnership.

Own the SMB sales revenue target, pipeline coverage, forecasting, CRM discipline, and close rates. Build an AI-first sales motion, establish deal stages and reporting, hire and ramp at least two account executives, and coach the team on urgency, pipeline hygiene, qualification, and deal execution. Partner with Finance on forecasting and use data to improve win rates and conversion across the sales funnel.