Top Senior Sales Jobs in Chicago, IL

Leads and scales Braze’s SMB SaaS sales organization by owning revenue strategy, pipeline generation, forecasting, sales productivity, hiring, coaching, and performance management. Builds repeatable inbound, outbound, partner-led, and sales-assisted motions while developing relationships with venture capital firms, agencies, consultants, system integrators, and technology partners. Partners cross-functionally with Marketing, Customer Success, Product, Finance, and Sales Operations to improve demand generation, customer adoption, and predictable growth.

Drives revenue across the Retail and CPG advertising vertical by prospecting top brands, generating meetings, building client relationships, partnering with agency sales teams, sharing industry insights, serving as a vertical subject matter expert, and achieving sales quotas. Requires strong research, data interpretation, motivation, collaboration, and knowledge of programmatic advertising, ad technology, measurement, advanced TV, streaming, and data-driven media buying.

Leads the Financial Services and Insurance advertising vertical, drives revenue, develops relationships with major brands and agencies, generates meetings, provides industry trend updates, serves as a subject matter expert, and achieves divisional sales quotas. The role requires 7+ years of relevant advertising experience and knowledge of programmatic media, ad technology, audience targeting, measurement, attribution, and advanced TV.

Leads national sales strategy and execution for AI-enabled provider analytics and value-based care platforms. Builds executive relationships with health systems, develops high-performing sales teams, drives complex enterprise growth, and advises providers on population health, quality, risk, utilization, reimbursement, and financial performance. Partners cross-functionally on go-to-market strategy, commercialization, forecasting, and responsible AI adoption. Requires up to 75% national travel.

Leads a team of advertising account executives serving automotive dealers and agencies in the Chicagoland market. Responsibilities include hiring, training, coaching, evaluating staff, developing client and industry relationships, supporting sales proposals and presentations, fostering automotive category expertise, forecasting sales, and reviewing business performance. The role requires independent judgment, punctual attendance, and flexibility to work nights, weekends, variable schedules, and overtime.

Lead development and expansion of payments business for Diversified Industries clients by selling integrated payments solutions, building pipeline, managing proposals and cross-functional delivery, and collaborating with product, coverage, and operations teams to retain and grow client relationships.

Leads end-to-end Data and Analytics solution sales cycles, partnering with account executives to develop opportunities, close business, and drive adoption. Sells ServiceNow’s D&A portfolio, creates strategic account plans, conducts discovery sessions, value-based presentations, and technical demos, and engages data, analytics, AI, CIO, and platform executives. The role focuses on AI-ready data modernization, analytics strategy, executive relationship building, and measurable customer outcomes.

Owns enterprise data sales across retail, restaurants, CPG, and digitally native brands. Builds target accounts, maps complex buying committees, leads executive conversations, develops opportunities, and closes multimillion-dollar deals. Translates advanced data, identity, analytics, and privacy solutions into business outcomes while partnering with category sales, agencies, solutions engineering, and product teams.

Supports AWS, Azure, and Google Cloud sales operations by leading GTM transformation readiness, assessing operational risks, and coordinating cross-functional solutions. Owns annual territory and coverage design, sales compensation planning, quota modeling, headcount planning, and planning deliverables. The role presents recommendations to leadership, manages operational workstreams, and ensures successful launches without disruption to sales cycles or representative compensation.

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.

Sells Comcast Business networking, security, internet, voice, and connectivity services to government entities. Manages strategic account modules, develops partnerships, generates leads, conducts sales presentations, meets quotas, and maintains customer relationships. Collaborates with sales engineering and operations teams, supports customer retention, tracks sales activity, and advises clients on network solutions and government procurement processes, including E-rate procedures.

Supports sales and upselling by leading product demonstrations, ROI narratives, RFPs, implementation and integration discussions, and client discovery through deal close. Partners with sales, product, marketing, delivery, and vendors to scale commercialization, tailor solutions to healthcare providers and EHR environments, and improve sales engineering productivity and messaging. Requires strong client-facing, analytical, presentation, and problem-solving skills, with 10–20% domestic travel.

Supports the sales organization by resolving operational issues, optimizing workflows, maintaining accurate sales data, and improving processes and automation. Partners with Revenue Operations, Finance, Legal, GTM Systems, and Engineering to resolve cross-functional issues. Responsibilities include financial reconciliation, data auditing, reporting, sales technology enhancements, workflow documentation, and practical use of AI tools such as Claude and Serval.

Manage Hilton’s business travel sales accounts, including strategic account planning, annual RFP leadership, customer and TMC partnerships, and revenue growth. Use market intelligence, analytics, technology, and AI tools to influence buying decisions, increase room-night production, and expand market share. Collaborate across Hilton’s matrixed organization and participate in client meetings, trade shows, travel fairs, and business reviews. The role requires hospitality and business travel sales experience, with travel up to 40%.

Leads national advertising sales across linear TV, streaming, digital, and addressable platforms. Develops agency and client relationships, drives revenue, creates multi-market advertising solutions, leads RFP responses and negotiations, and uses market trends, audience data, and competitive insights to identify opportunities and guide pricing and sales strategy.

Leads New Relic’s AMER partner sales organization, building a channel sales team and driving partner-sourced revenue through VARs, GSIs, MSPs, and regional partners. Coaches sales teams, orchestrates partner-led deals, strengthens alignment with direct sales, expands partner relationships, and improves pipeline conversion and quota attainment. Requires extensive North American and LATAM partner networks, proven channel deal-making experience, resilience in ambiguous environments, and deep observability, APM, or log management expertise.

Leads the West region’s Mid-Market and Small Group sales team, managing approximately 10–12 direct reports. Responsibilities include coaching sellers, improving pipeline discipline, forecasting revenue, progressing deals, setting CRM and activity standards, supporting broker relationships, recruiting, onboarding, and addressing performance issues. The manager owns the region’s combined new-business target, develops sellers across consultative and transactional sales motions, and travels periodically for field coaching, client meetings, and industry events.

Leads the East region’s Mid-Market and Small Group sales team, coaching sellers, managing pipeline and forecasts, driving quota attainment, and developing talent. The role oversees approximately 10–12 direct reports, supports broker and consultant relationships, attends client and industry events, contributes to sales-model improvements, and partners cross-functionally on hiring, onboarding, performance management, and seller development.

The Manager, Sales Architect leads the Sales Architect team, qualifying prospects, managing project handoffs, and designing solutions for technology sales.

Manages strategic partnerships with benefits technology firms to drive sales growth, market expansion, partner enablement, data integration, and go-to-market initiatives. Owns partner relationships, develops joint business plans, coordinates cross-functional teams, manages pipeline development, and tracks performance metrics. Requires experience in group benefits or insurance distribution, benefits administration platforms, relationship management, and strategic stakeholder influence.

Owns net-new revenue as a quota-carrying individual contributor. The Sales Director develops pipeline through prospecting, referrals, partnerships, events, and inbound leads; leads consultative sales cycles; manages complex proposals, RFPs, negotiations, and contracts; builds senior buyer relationships; sells integrated data, research, media, technology, and measurement solutions; maintains CRM forecasts; and coordinates internal teams through successful client handoffs.

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.

Lead and develop a team of Account Executives through hands-on coaching, performance management, data-driven sales strategy, and accountability. Set goals, analyze KPIs, address performance issues, remove operational roadblocks, and collaborate with sales leadership, marketing, product, and operations to improve productivity, lead quality, customer satisfaction, and quota attainment.

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 group sales growth for a luxury resort by generating new business, converting inquiries, qualifying leads, conducting outreach, and achieving sales targets. Coordinates with property leadership and internal departments to fulfill contracted services and maintain client satisfaction. Responsibilities include property visits, site inspections, FAMs, direct sales calls, and attending trade shows. The role is remote within the U.S. and requires travel of up to 35%.