Top Remote Director of Sales Jobs in Chicago, IL

Leads revenue growth for data center services across colocation, cloud infrastructure, connectivity, and managed offerings. Develops go-to-market strategy, manages enterprise and hyperscale sales teams, secures strategic accounts, oversees CRM and sales operations, supports pricing and capacity planning, and provides executive forecasts. Requires deep data center economics knowledge, complex deal negotiation skills, and an established industry network.

Owns strategic enterprise sales for consumer-directed healthcare benefits, managing named accounts and complex 9+ month sales cycles. Responsibilities include stakeholder mapping, discovery, business-case development, technical demos, procurement and legal coordination, forecasting, and closing high-value B2B partnerships. The role requires executive communication, multi-threaded relationship building, technical integration fluency, and experience with HSA, HRA, FSA, benefits platforms, or related markets.

Leads the East enterprise sales team, driving quota attainment, account-based execution, forecasting discipline, win-rate improvement, and complex deal strategy. Manages, coaches, and performance-manages Account Executives while developing scalable sales processes and enterprise go-to-market motions. Partners cross-functionally with Marketing, Product, RevOps, Enablement, Solutions Engineering, Legal, and Customer Success to improve deal velocity, customer engagement, and segment performance.

Lead four Account Executives selling platform partnerships to ISVs and SaaS providers. Define the ISV go-to-market strategy, manage complex negotiations, oversee opportunities from creation through launch and activation, improve prospecting and forecasting, and represent partner insights in commercial and product decisions. Responsibilities include coaching, hiring, talent planning, performance management, executive relationship building, and driving revenue growth across the platform ecosystem.

Leads and scales the global Sales Engineering team while serving as Field CTO and the company’s external technical voice. Owns technical sales methodology, demos, evaluations, proof-of-value cycles, solution design, deployment handoffs, executive engagements, competitive positioning, market content, and field-driven product feedback. The role is a player-coach position requiring deep cybersecurity expertise, executive presence, public speaking, and significant travel.

Leads the Central U.S. immunology sales region, overseeing District Managers and field sales teams. Responsibilities include recruiting and developing talent, managing customer relationships and experience, executing strategic and omnichannel plans, coordinating payer and reimbursement strategies, achieving regional P&L and business goals, supporting product launches, and ensuring regulatory compliance. This remote, field-based role requires up to 50% travel and extensive pharmaceutical sales leadership experience.

Leads and transforms a sales performance analytics organization into a strategic, insight-driven business partner. Oversees analytics products, dashboards, forecasts, KPIs, governance, adoption, data quality, and responsible AI initiatives. Partners with senior sales, business, and technical leaders to rationalize reporting portfolios, prioritize high-value analytics, guide technical delivery, and translate complex data into actionable decisions. Coaches a multidisciplinary team and leads organizational change across a complex commercial environment.

Lead US sales growth for an educational video platform: own revenue targets, build and coach a high-performing sales team, drive pipeline and deals, align GTM with Marketing and Customer Success, manage forecasting and Salesforce discipline, and lead regional bids and stakeholder relationships.

Leads a mid-market SaaS sales team, owns revenue quotas and pipeline growth, and manages Account Executive performance. Responsibilities include recruiting and coaching sales talent, forecasting through Salesforce, developing regional sales strategies, improving conversion rates with cross-functional teams, engaging customers and decision-makers, negotiating and closing deals, and ensuring employee onboarding and ramp-up. The role requires extensive B2B SaaS sales leadership, HR technology expertise, and experience with mid-market or enterprise clients.

The Enterprise Sales Director - Health will manage the sales cycle for AI-powered solutions in health insurance, cultivate relationships, and achieve sales targets.

Leads the creation and operation of HPE's Telco Service Provider security sales organization. Responsibilities include hiring and managing 6–8 sales specialists, owning P&L and revenue targets, developing go-to-market strategies, expanding channel partnerships, enabling partners, and coordinating with sellers, product, and marketing teams. The role sells security solutions including SASE, SRX, SD-Branch, NAC, ClearPass, and SSR, with approximately 50% nationwide travel.

Lead enterprise sales for Fulfillment IQ’s implementation practice across warehouse technology platforms. Build pipeline, develop strategic enterprise relationships, conduct discovery, coordinate technical and delivery specialists, lead proposals and negotiations, and close complex services engagements. Manage long sales cycles, forecasting, partner relationships, and account expansion across supply chain, logistics, and warehouse operations clients.

Lead and scale U.S. revenue growth by managing outbound pipeline development and selling content syndication, intent-based lead generation, data nurturing, and qualified lead services to B2B technology clients. Own the full sales cycle, use intent-data and account-based outreach platforms, present ROI strategies to executive stakeholders, achieve revenue quotas, collaborate on delivery and renewals, and represent the company at industry events.

Leads global sales operations and excellence strategy, governance, forecasting, pipeline management, CRM adoption, analytics, territory planning, quota setting, and incentive design. Partners with regional leaders to standardize processes while supporting local execution. Assesses sales capabilities, identifies skill gaps, and oversees targeted training and development programs. Coordinates cross-functional initiatives with Finance, Marketing, and HR to improve sales performance, operational efficiency, customer experience, and measurable business results.

Leads sales and revenue growth in the logistics sector by developing new business, managing customer relationships, creating tailored transportation and warehousing solutions, negotiating contracts, and implementing sales strategies. Analyzes markets and competitors, maintains CRM records, forecasts sales, collaborates with operations and pricing teams, resolves customer issues, ensures compliance, and represents the company at industry events.

Lead Runpod’s Americas sales organization and revenue number across new business, expansion, and renewals. Manage and coach Account Executives and Account Managers, oversee forecasting and pipeline, lead complex enterprise deals and contract negotiations, build regional go-to-market strategy and sales playbooks, and convert product-led demand into revenue. Partner with Marketing, Product, Legal, and Finance while improving sales efficiency through AI and developing a remote-first team.

Lead a regional sales organization of Account Executives and Customer Success Managers, owning ARR, new business, renewals, expansions, forecasting, and customer retention. Develop go-to-market and territory strategies, coach teams, improve pipeline and forecast performance, and collaborate with Marketing, Product, and Enablement. Drive customer adoption, advocacy, operational discipline, and market growth across the education technology sector.

Leads and scales a field sales organization serving the architecture, engineering, and construction market. Responsibilities include managing sales teams and quotas, developing strategic accounts, closing major opportunities, building executive client relationships, overseeing pipeline and forecasting, maintaining Salesforce data, and partnering with marketing, technical, and delivery teams. The role requires strong AEC networks, consultative technical-services sales experience, team-building expertise, and accountability for revenue growth and retention.

Lead enterprise sales for zerohash’s crypto and fintech payments infrastructure. Responsibilities include identifying revenue opportunities, conducting pre-sales consultations, delivering customized presentations, negotiating and closing complex contracts, exceeding revenue targets, maintaining Salesforce pipeline records, pursuing cross-selling opportunities, and providing customer feedback to product teams. The role requires strong fintech and crypto knowledge, persuasive communication, relationship-building, deal sourcing, and travel up to 40%.

Lead the Americas sales organization for MedTech Solutions, driving profitable growth across medical device materials, components, and CDMO solutions. Responsibilities include strategic account management, new business development, cross-selling, pricing, forecasting, pipeline management, customer engagement, and commercial execution. The role manages global account, technical account, and business development teams while partnering cross-functionally with marketing, product management, operations, engineering, quality, and finance.

Own global sales strategy and operations for a rapidly scaling B2B travel technology company. Responsibilities include segmentation, account scoring, territory design, capacity modeling, goal setting, forecasting, pipeline reviews, QBRs, sales process design, and executive reporting. Lead AI strategy across prospecting, forecasting, deal execution, and coaching, while partnering with systems, finance, enablement, growth, and data teams. Build analyses directly and hire and manage a team of analysts and strategy partners.

Directs sales operations and revenue operations activities, including sales reporting, dashboard development, CRM governance, forecasting, compensation administration, and performance analysis. Manages and develops BDRs, creates outreach and handoff processes, partners with Marketing and Finance, supports quota and territory planning, and provides leadership with actionable insights on pipeline health, forecasting, and sales performance.

Leads Knock’s Account Executive organization, owning sales targets, lead and loan application volume, forecasting, coverage strategy, compensation, hiring, onboarding, coaching, and performance standards. Develops distinct sales playbooks for lending partners and broader lender and agent channels, while translating market feedback into product, marketing, and operations improvements. Requires deep mortgage or proptech sales expertise, recent lending experience, remote-team leadership, and strong analytical and communication skills.

Leads national sales growth for wireless infrastructure assets by developing executive carrier relationships, originating leasing and collocation opportunities, negotiating portfolio-level agreements, managing pipeline forecasting, and collaborating across real estate, operations, legal, finance, and asset management teams.

Develop and execute digital advertising sales strategies to exceed a $1.5M–$2.5M annual revenue quota. Build executive relationships with agencies, brands, and partners; identify and close managed-service and programmatic deals; present Viamedia.ai solutions; collaborate on tailored client offerings; provide forecasts and market insights; represent the company at industry events; and mentor junior sales staff.