Top Remote Sales Jobs in Chicago, IL

Lead and scale Square’s Central Region field sales organization by managing Sales Managers and Territory Account Executives. Set regional strategy, optimize territories and go-to-market plans, drive pipeline and revenue performance, coach teams in the field, develop talent, and collaborate with Marketing, Sales Operations, Partnerships, and Product. Serve as a product expert and regional representative while building a high-performance, accountable sales culture.

Leads and scales Square’s Central Region Field Sales organization, managing Sales Managers and Territory Account Executives. Responsibilities include territory and go-to-market strategy, pipeline and KPI management, field coaching, consultative selling, product expertise, team development, cross-functional collaboration, and regional revenue growth. The role builds a competitive, accountable, high-performing sales culture while representing Square with local business leaders and partners.

Own the full B2B sales cycle for SaaS solutions serving independent insurance agencies, from outbound prospecting and pipeline generation through discovery, negotiation, and closing. Build trusted-advisor relationships, understand agency goals, map needs to technology solutions, manage territories, and achieve sales quotas. The role requires consultative selling, strong communication, CRM proficiency, and experience meeting new-business or territory-growth targets.

Own the full B2B sales cycle for SaaS solutions, including outbound prospecting, account research, discovery, solution selling, negotiation, and closing. Build pipeline, advise independent insurance agencies on business challenges, manage territories, and consistently achieve or exceed sales quotas in a collaborative inside-sales environment.

Own the full B2B sales cycle for SaaS solutions, including outbound prospecting, pipeline generation, account research, discovery, solution selling, negotiation, and closing. Advise independent insurance agencies on technology solutions, manage territory plans, and consistently meet or exceed sales quotas. The role requires strong consultative selling, communication, and CRM skills in a hybrid team environment.

Leads sales strategy and execution for Property & Casualty insurance solutions. Manages enterprise opportunities, pipeline development, forecasting, strategic accounts, and revenue growth while coaching and developing a high-performing sales team. Partners cross-functionally with Product, Marketing, Legal, and Strategy teams, builds executive client relationships, and provides market insights to support product and go-to-market planning.

Own the full B2B sales cycle for UL Solutions’ wind software and data portfolio across North America. Generate and qualify leads, conduct technical demonstrations, scope customer requirements, manage proposals and negotiations, forecast pipeline, and close software, subscription, API, and data sales. Expand existing accounts, represent the company at industry events, collaborate with marketing and product teams, and provide market feedback. Requires wind energy expertise, consultative selling experience, and 10–15% travel.

Manage the full B2B sales cycle for SaaS solutions, including outbound prospecting, account research, discovery, solution consulting, negotiation, and closing. Build pipeline, advise independent insurance agencies, manage territories, and consistently achieve sales quotas. The role requires strong consultative selling, communication, and CRM proficiency, with experience in quota-carrying sales and new business development.

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.

Supports sales teams and broker partners through prospecting, quoting, proposals, enrollments, renewals, RFPs, licensing, and producer appointments. Maintains pipeline and process tracking, coordinates with internal teams and third-party administrators, responds to product inquiries, supports broker training, and manages Salesforce records. The remote role may require occasional travel of less than 10% for open enrollment meetings.

Drive enterprise sales growth among healthcare providers by managing strategic relationships, acquiring and expanding accounts, presenting tailored proposals and product demonstrations, negotiating complex agreements, and coordinating cross-functional teams. The role requires maintaining accurate Salesforce records, applying MEDDIC/MEDDPICC methodologies, building pipeline, forecasting accurately, and achieving revenue targets across new and expansion business.

Drive enterprise sales growth among healthcare providers by acquiring new strategic accounts and expanding existing relationships. Manage complex sales cycles, build C-suite relationships, develop client plans, deliver presentations and demonstrations, negotiate agreements, maintain pipeline discipline using MEDDIC/MEDDPICC, and partner cross-functionally with client success, implementation, and advisory teams. Maintain accurate Salesforce records while meeting revenue and quota targets.

Drive enterprise sales growth within healthcare provider accounts by acquiring strategic customers, expanding existing relationships, managing C-suite relationships, and closing complex SaaS deals. Build territory and client plans, maintain pipeline and forecasts using MEDDIC/MEDDPICC, deliver presentations and demonstrations, negotiate agreements, and collaborate with client success, implementation, advisory, engineering, and operations teams.

Drive enterprise SaaS sales across healthcare provider accounts in the Western territory. Manage strategic client relationships, acquire and expand accounts, build pipeline, present solutions, negotiate complex agreements, and achieve revenue targets. Partner cross-functionally with client success, implementation, advisory, engineering, and industry teams. Maintain CRM accuracy in Salesforce and apply MEDDIC/MEDDPICC methodologies to forecast and close new and expansion business.

Drive enterprise SaaS sales to healthcare providers, including health systems, hospitals, and clinics. Manage strategic client relationships, retain and expand revenue, acquire new accounts, present tailored proposals and demonstrations, negotiate complex agreements, and coordinate cross-functional teams. Maintain accurate Salesforce records, use MEDDIC/MEDDPICC methodologies, build pipeline, forecast accurately, and achieve quota. The role requires healthcare-provider industry knowledge, enterprise closing experience, strong communication skills, and a bachelor's degree or higher.

Drive enterprise SaaS sales growth within healthcare provider accounts across the Western region. Manage strategic C-suite relationships, acquire new clients, expand existing accounts, lead complex negotiations, deliver presentations and demonstrations, and coordinate cross-functional teams. Maintain accurate Salesforce records, build pipeline, forecast performance using MEDDIC/MEDDPICC, and achieve revenue targets.

Drive enterprise SaaS sales to healthcare providers by managing strategic C-suite relationships, acquiring and expanding accounts, developing client plans, presenting tailored solutions, negotiating complex agreements, and coordinating cross-functional teams. Maintain accurate Salesforce records, use MEDDIC/MEDDPICC methodologies, build pipeline, forecast accurately, and achieve new-business and expansion quotas within the healthcare provider market.

Leads a team of Strategic Account Executives selling SaaS solutions to large enterprise customers. Responsibilities include hiring, coaching, enablement, account and territory planning, pipeline reviews, forecasting, CRM adoption, revenue target achievement, and direct support on high-priority deals. The role collaborates cross-functionally with Sales Development, Sales Engineering, Product, Marketing, Customer Success, Legal, and Sales Operations to drive strategic sales growth.

Own Flex’s go-to-market strategy and commercial execution for the auto loan vertical. Build executive-level relationships, develop pipeline, negotiate and close complex partnerships, and guide agreements through technical deployment and launch. Collaborate with Product, Engineering, Marketing, Finance, Legal, and Compliance to shape the offering, translate market feedback into improvements, and establish a repeatable sales motion. This zero-to-one role also requires developing scalable processes and using AI-assisted sales tools to improve pipeline and deal performance.

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.

Owns enablement for Enterprise and Strategic Account Executives by designing coaching programs, playbooks, certifications, battlecards, and sales training. The role focuses on MEDDPICC, complex deal execution, account expansion, executive alignment, negotiation, and objection handling. Responsibilities include analyzing call recordings, tracking ramp and certification metrics, partnering with sales leadership and top performers, and collaborating cross-functionally to translate product launches into field-ready materials.

Lead enterprise sales managers and teams serving the US state and local public sector. Drive quota attainment, customer acquisition, market expansion, sales-process improvements, forecasting, and high-growth strategy. Coach and develop sales leaders and representatives while building relationships with Fortune 1000 customers and managing complex technology sales cycles.

Supports Account Executives by leading consultative discovery, delivering tailored technical demonstrations, explaining API integrations and security concepts, and recommending customer-focused SaaS solutions. Collaborates with Product, Customer Success, and Professional Services teams, identifies technical blockers, incorporates customer feedback, and uses data and emerging technologies to improve sales effectiveness. The role requires strong communication, teamwork, curiosity, and comfort engaging both HR and IT stakeholders.

Leads group sales for Hilton Aruba and The Westerly, soliciting and negotiating complex group accommodations, contracts, pricing, and agency agreements. Directs sales staff, oversees performance, training, forecasts, budgets, reporting, trade shows, client presentations, and market research. Builds customer relationships, develops sales strategies, monitors departmental performance, and travels domestically and internationally up to 30% of the time.

Leads Garner’s provider sales growth by developing distribution models, closing strategic partnerships with healthcare providers, expanding brand presence, refining provider strategy, and achieving annual revenue goals. The role requires managed care or provider organization experience, expertise in value-based care and healthcare economics, strategic account planning, executive partnership, and regional travel across East Coast and Central clients.