Top Remote Sales Jobs in Chicago, IL

The role involves leading and scaling the Central Field Sales organization, driving performance and operational rigor, and collaborating with teams to achieve regional growth.

Lead end-to-end sales pursuits for IT infrastructure managed services, build and execute strategic sales plans, penetrate target markets, shape messaging, manage proposals and commercial models, and ensure smooth handoffs to delivery while mentoring teams and driving growth.

Lead and grow a specialist product sales team (6-8 AEs) to achieve quarterly product targets; coach onboarding and outbounding, collaborate with mainline AEs and cross-functional pods (product, marketing, strategy) to optimize GTM, monitor pipeline and build account plans, and embed company cultural principles.

The Senior Sales Executive drives growth in the ULTRUS digital platform by engaging clients, identifying opportunities, and maintaining relationships throughout the sales cycle while achieving sales targets.

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.

The Senior Sales Executive will drive sales strategies for field evaluation clients, engaging with customers, managing accounts, and meeting sales targets.

Lead Ethoca sales to top-tier issuers, digital banks and fintechs in North America. Drive SaaS/network product adoption via consultative selling, partner with Mastercard account and product teams, manage senior relationships, accelerate revenue, support implementations, and represent Ethoca at industry and executive events. Travel as needed.

Responsible for prospecting and closing new business within the Central region. Develop GTM strategy, engage with potential customers, and navigate complex sales cycles with technical teams.

The Enterprise Account Executive will prospect and close new business in the Central US, develop GTM strategy, and manage customer relationships.

Lead and grow a team of learning designers and content developers to build scalable, measurable sales learning programs. Partner with sales and enablement stakeholders to prioritize requests, set instructional standards, manage delivery, and iterate using data and feedback to improve seller effectiveness.

Manage and engage dealerships through regular in-person visits to drive sales of GM vehicles and parts. Support product launches, marketing, inventory management, training, customer satisfaction, and dealer performance through analysis, mentorship, and hands-on collaboration. Frequent travel within assigned territory required.

Lead and scale a national sales organization focused on payers, providers, and employers. Manage and mentor Regional VPs, own individual quota, drive enterprise new business and expansion, oversee forecasting and pipeline, support C-level engagements and contract negotiations, and align sales strategy with marketing, product, and client success to meet revenue goals.

Lead and grow a distributed Enterprise Sales Engineering team, partner with regional sales and cross-functional stakeholders, manage pre-sales escalations, participate in customer calls, hire and develop talent, and scale the sales engineering motion to drive enterprise SaaS/IoT product adoption. Role requires travel and close collaboration with product, support, and customer success.

The Senior Director of Inside Sales leads a team of over 70, focusing on sales strategy, performance management, and talent development to drive revenue growth in a high-volume, fast-paced fintech environment.

The Sales Engineer will support Account Executives by aligning Superhuman's solutions with educational institutions’ needs, delivering demos, conducting POCs, and engaging with technical stakeholders.

The Account Executive will lead the sales cycle for mid-enterprise clients, developing strategies, building relationships, and collaborating with teams to drive business growth and customer success.

Lead and develop a SLED sales team to drive revenue through retention, upsell, cross-sell and new customer acquisition. Build pipeline, align solutions to customer strategy, manage forecasting and pipeline health, partner with sales, marketing and customer success, and navigate public sector contracting to achieve quota and growth goals.

Partner with senior sellers to lead technical pre-sales activities: demos, POCs, RFI/RFP responses, integrations, and product evaluations. Drive technical storytelling, objection handling, advanced integrations, and SE team enablement while carrying quota and contributing to product and process improvements.

Lead and scale a high-performing commercial sales team focused on outbound pipeline generation and predictable forecasting. Drive quota attainment, improve ACVs and win rates, influence cross-functional GTM strategy, and run strategic initiatives. Coach, performance-manage, and mentor Account Executives to improve qualification, territory planning, and outbound rigor while contributing as a senior operator to product, marketing, and RevOps alignment.

Lead and scale a high-performing enterprise sales team to exceed targets through account-based execution, forecasting discipline, and coaching. Drive strategic cross-functional initiatives with Marketing, Product, RevOps, and Solutions Engineering to improve win rates, ACVs, and deal velocity. Act as a senior thought leader, manage performance, mentor AEs, and influence GTM strategy and product direction.

Lead and scale the Enterprise AI & Digital Natives sales segment in the NYC region. Own revenue targets, recruit and mentor a field sales team, advise CTOs and engineering leaders on Cloudflare solutions (Workers AI, R2, network security), drive new logo acquisition and account expansion, partner with Product/Customer Success/Solutions Engineering for go-to-market execution, and personally help close complex, high-value enterprise deals.

Lead Mid-Enterprise Healthcare sales for a U.S. region, managing Regional Sales Directors and Account Executives to drive bookings, ARR, pipeline, and forecasts. Execute MEDDPICC-driven territory plans, build executive-level healthcare relationships, partner cross-functionally, recruit and develop sales talent, oversee negotiations and Salesforce pipeline hygiene, and travel extensively to increase market penetration and customer acquisition.

Lead go-to-market efforts for selling software and SaaS solutions, engage with prospects and partners, and ensure customer success while managing a team and maintaining compliance.

Originate and manage payments partnerships with PSPs, fintechs, and banks to launch stablecoin payment products. Own full deal lifecycle from diligence through negotiation, closing, and post-launch success. Lead executive client conversations, coordinate cross-functional onboarding and integration, and surface market insights to influence product roadmap.

Lead and grow a team of 6-8 Product Specialist AEs to drive new product adoption and quarterly targets. Hire, onboard, coach, and enable reps; coordinate with Mainline AEs, Sales Engineers, and cross-functional pods (product, marketing, strategy) to optimize GTM, manage pipeline, create account plans, and execute high-value enterprise deals. Embed company culture and scale Specialist support globally.