Top Remote Director of Sales Jobs in Chicago, IL

As Director of Sales, you will lead and develop the Enterprise Account Executives team, drive ARR growth, and enhance sales execution. You'll create territory plans, coach sellers on enterprise sales, and collaborate cross-functionally to optimize customer success and pipeline creation.

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 Director of Sales will drive revenue growth by pursuing new high-value drone OEM accounts, managing customer relationships, and overseeing complex commercial negotiations.

Lead and grow a team of account partners to sell enterprise eQMS SaaS to large manufacturers. Drive pipeline generation, accurate forecasting, complex deal strategy, contract negotiation, and long-term relationships across Quality, IT, Operations, and Procurement. Hire, coach, and manage performance while ensuring use of CRM and expansion of multi-year, multi-region agreements.

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.

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.

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.

Sell Narmi One to community financial institutions by running complex, consultative enterprise deals. Own quota, develop business cases, lead demos, negotiate contracts, and drive upsells across product lines. Build pipeline using regional relationships and work cross-functionally to close large ARR deals. Role requires travel and contributes to Growth team strategy.

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.

Lead Deal Desk for Enterprise, partner with Sales on large complex transactions, shape deal structures balancing growth, margin, and risk, drive process improvements, use data to inform decisions, and hire and develop a high-performing team while working cross-functionally across Sales, Finance, Operations, Accounting, Legal, and Product.

Drive new pipeline through strategic account planning, engagement with executives, and maintaining relationships to achieve revenue targets across enterprise sales.

The Sr. Pharma Direct Sales Director will develop and grow relationships with pharmaceutical clients, assess revenue potential, collaborate on proposals, and provide sales updates while staying informed on industry trends.

The AI Sales Director will drive sales for Wasabi's hot cloud storage solutions to AI/ML-focused clients, leveraging marketing resources and existing relationships.

The AI Sales Director will drive sales for Wasabi's hot cloud storage solutions focused on AI/ML customers, prospecting, engaging with clients, and providing consultative advice.

The Director of Revenue Operations will lead B2C operations, driving revenue growth while managing a team and optimizing Salesforce workflows.

Senior leader who builds and scales Sales Operations: owns HubSpot CRM architecture and governance, forecasting, compensation design, reporting, and cross-functional alignment. Leads a Sales Ops team to improve forecasting accuracy, data hygiene, automation, and quota-to-cash processes to enable predictable revenue and scalable marketplace growth.

Lead sales and partnership efforts with employee benefits consultants, brokers, advisors, and employers. Build and maintain partner relationships, demonstrate Milu's value proposition, drive business development, meet sales targets, and ensure excellent customer support in a remote environment.

Lead and execute enterprise new-business strategy, build and coach a high-performing sales organization, cultivate executive relationships and strategic partnerships, and personally support major enterprise pursuits. Drive revenue, bookings, forecasting discipline, pipeline governance, and sales productivity while partnering with hyperscalers and cross-functional teams to scale growth and improve sales effectiveness.

The Director of Sales will drive revenue growth, establish customer strategies for logistics services, manage executive relationships, and oversee pipeline management and CRM processes.

The Director of Field Sales Engineering leads a team focused on incubating new products, driving adoption, and ensuring cross-functional collaboration to deliver technical value to customers.

Lead revenue growth and new business for an ecommerce/digital commerce agency. Develop and execute outbound/inbound sales strategy, manage full sales cycle, build pipeline, negotiate contracts, and create scalable sales processes. Partner with leadership and client teams to drive onboarding, retention, upsells, and forecasting while using CRM tools to track performance.

Lead the Sales Strategy & Analytics function to deliver reporting, KPI tracking, profitability and competitive analysis, and sales technology ownership. Partner cross-functionally to provide executive insights, optimize tools and processes, drive adoption, and develop a high-performing analytics team that improves sales productivity, profitability, and strategic decision-making.

Lead development and execution of Sales Readiness strategy and programs to prepare sellers, drive adoption, and improve field performance. Manage a team delivering coaching, enablement content, field engagement, and readiness initiatives. Partner cross-functionally to translate priorities into scalable resources, measure program impact, and continuously improve seller capability and productivity.