Top Remote Sales Executive Jobs in Chicago, IL

Leads sales strategy and solution wins for ServiceNow’s application security offerings. Partners with account teams, customers, solution consultants, and partners to identify use cases, develop digital transformation strategies, demonstrate business value, and manage sales cycles. Coaches account executives and development representatives on specialty solution opportunities while supporting territory and account planning. Requires cybersecurity sales experience, knowledge of specialty solution ROI, business sales process expertise, and 30–50% travel.

Drives net-new enterprise SaaS business by prospecting, managing complex sales cycles, building ROI-based business cases, presenting to finance and C-suite leaders, negotiating contracts, and closing opportunities. The role requires territory planning, pipeline forecasting, CRM hygiene, cross-functional collaboration, and approximately 30% travel for in-person customer engagement.

Own a territory and manage the complete outbound sales cycle for Adapt, an AI-powered dynamic pricing product. Prospect property management company leaders, deliver revenue business cases, run pilots, negotiate contracts, close deals, attend regional events, and relay customer feedback to product teams. The role is remote within a territory and requires regular travel. The successful candidate will help establish the sales process as the founding seller in the region.

Own sales growth across a Midwest territory by prospecting, developing business, managing pipelines, closing new opportunities, and partnering with Customer Success on onboarding. The role requires consultative selling experience, knowledge of NGS or genomics products sold to hospitals and laboratories or enterprise software sales, strong new-business development skills, and willingness to travel at least 50%.

Develops and closes new enterprise business for payment and messaging solutions, targeting consumer finance, auto finance, and fintech clients. Responsibilities include prospecting, consultative solution selling, account strategy, executive engagement, pipeline management, contract negotiation, forecasting, and cross-functional proposal development. The role requires deep payments ecosystem knowledge, strong presentation skills, and travel to build client relationships and business cases.

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.

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 and onboard Part 135 charter operators in the Northeast, owning full sales cycle from prospecting to implementation, managing pipeline and forecasts, driving new client acquisition and expansion, and supporting adoption and product feedback.

Lead recruitment, enablement, and commercial activation of reseller channel partners (TSPs and DSPs). Build channel playbook, design pricing/incentives, co-sell with partners, track pipeline and partner health, and align cross-functional teams to drive measurable channel revenue.

Drives net-new and expansion sales of Zebra’s Demand Intelligence SaaS solutions to enterprise retail and CPG accounts. Responsibilities include pipeline development, full sales-cycle ownership, solution positioning, stakeholder engagement, contract negotiation, and closing multi-year recurring-revenue agreements. The role requires deep knowledge of retail merchandising, inventory, and supply chain, collaboration with cross-functional teams, and frequent customer-facing field activity. It is a remote individual-contributor hunter role with approximately 75% travel.

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.

Lead commercial strategy, deal-making, and complex negotiations for Microsoft’s strategic U.S. customers. Develop commercial and account plans, optimize pricing and concessions, manage renewals, and align customer, partner, and internal stakeholders. Build trusted relationships while ensuring compliant, profitable deal execution and supporting revenue, quota, and consumption targets. The role requires strong sales and negotiation expertise, strategic thinking, and knowledge of Microsoft licensing and contracting programs.

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.

Drive U.S. sales growth for POS hardware and Business IoT solutions by developing territories, generating leads, managing the full sales cycle, closing and onboarding clients, and supporting existing accounts. Represent the company at trade shows, analyze markets and competitors, collaborate with internal teams, and potentially train sales representatives or independent agents. The role requires autonomy, relationship management, technical product knowledge, and travel as needed.

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.

Find, qualify, pitch, and close clients seeking web design, website development, e-commerce, or digital product services. Responsibilities include outreach through LinkedIn, cold email, calls, and professional networks; lead follow-up; discovery call coordination; and deal closing with support from the technical team. Compensation is commission-based, with flexibility to work remotely and potential progression to a base retainer plus commission.

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 the full enterprise sales cycle for healthcare accounts, building relationships with hospitals, health systems, surgical centers, home health organizations, and post-acute facilities. Lead consultative sales involving C-suite and cross-functional stakeholders, navigate AI governance and integration requirements, develop value propositions, and build a robust pipeline. Close new business and expansion opportunities while collaborating with Marketing and Customer Success to drive territory and company growth.