Top Sales Executive Jobs in Chicago, IL

Enterprise Sales Executive responsible for selling complex SaaS solutions to large organizations, managing full enterprise sales cycles, presenting to executive stakeholders, building strategic account plans, developing territories, creating new business opportunities, and exceeding revenue targets. The role requires experience with six-figure deals, enterprise customers, executive presentations, cross-functional collaboration, and strategic relationship management.

Responsible for developing new business within an assigned territory by prospecting construction professionals, conducting presentations and software demonstrations, managing sales cycles, closing deals, and meeting revenue targets. The role requires consultative selling, CRM documentation, territory research, sales forecasting, and collaboration with sales development, marketing, customer success, research, and account management teams. This is a fully remote position with travel to industry events and client meetings.

Research target businesses, conduct outbound calls and emails, qualify prospects, run product demonstrations, and book qualified sales opportunities. Maintain accurate CRM records, test messaging, follow up consistently, and collaborate with account managers and the London team. The role serves US and Canadian businesses remotely, requires clear communication and disciplined prospecting, and focuses on building repeatable qualified pipeline for Jodie AI’s receptionist and phone-answering service.

Own the full enterprise B2B sales cycle, from prospecting and discovery through negotiation and close, while achieving quarterly revenue targets. Sell subscription-based information products to financial and technology buyers, manage post-sale relationships, identify expansion opportunities, relay customer feedback to product leadership, and help establish scalable enterprise sales practices.

Own mid-market and enterprise sales pipelines targeting DSOs, multi-site dental groups, and regional chains. Develop partnerships with dental labs, manufacturers, and technology companies, navigate complex multi-stakeholder deals from initial discussion through rollout, and improve CRM, pipeline, handoff, and partner-tracking systems. Collaborate with founders, customer success, and product teams while representing the company at industry events.

Manage customer accounts across the Chicago and Northwest Indiana territory, maintaining satisfaction and resolving issues. Develop sales strategies, grow revenue, commercialize new applications, identify savings projects, and achieve sales targets. Provide application testing, process troubleshooting, equipment maintenance, service reports, forecasts, and business reviews. Collaborate with customers and internal teams to optimize chemical or digital solutions, reduce costs, improve processes, and support implementation.

Drives revenue growth for legal technology products across an assigned territory. Develops strategic sales plans, pursues new business within law firms and corporate legal departments, manages existing accounts, and exceeds revenue quotas. Responsibilities include prospecting, account planning, upselling, cross-selling, CRM management, forecasting, and sales reporting. Requires field sales experience, territory management, quota achievement, and experience selling to the legal industry.

Sell heyLibby AI agent to fitness, wellness, and recreation businesses. Qualify inbound leads, prospect and cold call, manage pipeline in a CRM, demo value, close deals, and refine sales strategy with the executive team.

Own the full sales cycle for Bloomlife’s remote maternal care and fetal monitoring solutions, targeting OB/GYN practices, maternal-fetal medicine organizations, and health systems. Responsibilities include pipeline generation, consultative selling, product demonstrations, clinical workflow analysis, ROI and reimbursement discussions, contract negotiation, forecasting, and implementation handoffs. The role requires established healthcare relationships, medical device or digital health sales experience, strong knowledge of reimbursement and billing, and approximately 70% travel.

Sell Hilton Grand Vacations vacation ownership opportunities through professional presentations and consultative conversations. Build rapport with guests, understand their travel goals, recommend suitable ownership solutions, achieve sales targets, and represent the brand with professionalism. The role requires ongoing training and working five days per week, including weekends and holidays.

Manage clients’ sales pipelines through inbox management, LinkedIn and cold-email outreach, prospect research, CRM maintenance, qualification, proposals, scheduling, follow-ups, and pipeline reporting. Prepare sales collateral, support referrals and networking, coordinate handoffs, maintain outreach compliance, protect confidential data, and handle related administrative tasks. The role requires independent client ownership, strong communication, and at least 20 hours weekly in a remote contractor capacity.

Generates and qualifies high-volume outbound sales opportunities for the Scale segment, builds pipeline, conducts discovery and product demonstrations, closes transactional deals, maintains CRM records, and supports revenue targets. The role collaborates with Marketing and Account Management, develops prospect relationships within commercial real estate, follows sales processes, and participates in ongoing coaching and skill development.

Drive new enterprise business and expand strategic relationships for default servicing solutions. The role develops sales plans, prospects mortgage servicers and institutional stakeholders, manages complex sales cycles, maintains a Salesforce pipeline, negotiates multimillion-dollar agreements, and collaborates on implementation and delivery. Responsibilities include executive relationship building, consultative selling, conference participation, market development, and navigating mortgage default servicing, regulatory, foreclosure, REO, auction, and CWCOT processes.

Drive new-customer sales for SaaS order-to-cash and payment solutions. Responsibilities include prospecting, developing sales strategies, managing complex enterprise sales cycles, conducting product demonstrations, building executive relationships, creating tailored proposals, collaborating cross-functionally, monitoring market trends, and exceeding revenue targets.

Lead complex enterprise SaaS sales for engineering firms across North America. Manage the full sales cycle from qualified leads and discovery through pilots, procurement, negotiation, and multi-year contract close. Build relationships with executives, engineers, and internal champions; generate outbound pipeline; represent the company at industry events; and collaborate with Product, Marketing, and Customer Success to support onboarding and expansion.

Drives new business with hospitals and health systems by building executive relationships, generating pipeline, managing complex multi-stakeholder sales cycles, developing account strategies, negotiating contracts, and closing deals. The role sells to CFO, Finance, and Revenue Cycle leaders, maintains Salesforce pipeline discipline, partners with Customer Success on onboarding and expansion, and improves the sales process.

Owns national enterprise sales across strategic accounts, driving new revenue for SAP consulting, migration, and managed services engagements. Responsibilities include strategic account planning, executive-level negotiation, complex opportunity management, pipeline ownership, consultative storytelling, and closing multi-year deals exceeding $5M in contract value. The role collaborates with SAP and hyperscaler partners, positions AI-enabled managed services, and manages complex decentralized buying groups in regulated industries.

Develops and closes broadband access and marketing agreements with multifamily property owners, builders, and developers across the Chicago area. Responsibilities include prospecting, needs analysis, relationship building, property tours, presentations, pipeline management, contract negotiation, and coordinating with Verizon engineering. The role requires consultative selling, customer and stakeholder influence, competitive knowledge, and frequent field travel to generate revenue growth for Verizon Home Internet and mobility services.

Own the full sales cycle for JoVE’s educational video products, from prospecting through close. Build and maintain pipelines, present to academic stakeholders, acquire new customers, grow existing accounts, and meet revenue targets. Collaborate with Marketing and Customer Success on renewals, campaigns, and team initiatives. Analyze sales trends, attend trade shows, and travel at least two days per week while working remotely.

Owns commercial relationships with current and prospective enterprise healthcare accounts in the Northeast. Drives renewals, expansions, new use cases, revenue growth, and long-term account strategies. Leads consultative sales motions, executive stakeholder relationships, account planning, and ROI-based positioning. Coordinates Customer Success, Solutions, Product, and Delivery teams while prospecting for new opportunities and providing market insights. Requires healthcare expertise, enterprise account management, value-based selling, executive communication, PowerPoint proficiency, data analysis, and up to 50% travel.

Drives revenue growth by selling deposit, liquidity, and cash management solutions to enterprise and merchant clients. Responsibilities include generating leads, developing account plans, managing complex sales cycles, closing opportunities, building executive relationships, presenting financial solutions, maintaining CRM pipelines, forecasting, and sharing market insights. The role requires regular travel and focuses on business-to-business sales within financial services, payments, treasury, and related solutions.

Owns national enterprise sales across SAP consulting, ECC-to-S/4HANA migration, and managed services. This quota-carrying executive develops strategic account plans, navigates complex buying groups, builds executive relationships, negotiates multi-million-dollar contracts, and drives new revenue. The role partners with SAP and hyperscaler alliances, positions agentic AI-enabled transformation, manages the full sales lifecycle, and maintains pipeline discipline. It requires 30–50% travel and deep experience selling complex, annuity-based enterprise engagements.

Own and exceed quota for Salesforce Sales Performance Management products across Federal, State and Local Government, and Higher Education customers. Build sales strategy, manage complex enterprise sales cycles, lead executive discovery, coordinate with account teams and partners, navigate public-sector procurement and compliance, maintain pipeline forecasts, and expand pilot deployments into enterprise rollouts.

Grows existing indirect-channel accounts and acquires new customers through prospecting, relationship building, lead qualification, estimating, negotiation, and closing. Manages brokers, distributors, manufacturers’ representatives, creative agencies, printers, and converters within an assigned territory. Maintains the sales pipeline, forecasts monthly revenue, resolves pricing and sales issues, and supports account receivables while meeting sales targets.

Account Executive responsible for acquiring new PR agency accounts, building strategic relationships, managing a self-generated sales pipeline, executing sales cycles, and achieving bookings quotas. The role involves prospecting, cold calling, networking, presenting solutions, coordinating internal sales resources, developing agency activation strategies, and expanding agency partnerships. Candidates should have new-account sales experience, strong relationship and communication skills, quota achievement history, and willingness to travel within the assigned territory.