Top Remote Director of Sales Jobs in Chicago, IL

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.

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.

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.

Leads and grows a SaaS sales team and Global Capital Markets business. Responsibilities include recruiting and coaching sales talent, developing sales strategy, managing performance and forecasts, supporting client engagements, delivering sales enablement, optimizing CRM and sales processes, and collaborating with Product and Marketing to drive revenue 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.

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 global channel sales excellence, including business rhythms, executive reviews, reporting, planning, partner performance insights, sales process adoption, and operational workstreams. The role designs scalable review practices, translates data into recommendations, supports go-to-market and revenue execution, manages quota and territory planning, and influences cross-functional stakeholders across a global organization.

Lead Hilton’s technology-focused corporate group sales accounts by developing account strategies, expanding relationships, identifying revenue opportunities, forecasting growth, and achieving sales targets. The role manages national and global accounts, analyzes account data, collaborates cross-functionally, advises executive decision-makers, and delivers tailored hospitality solutions. It is remote and requires travel of up to 40%.

Lead the transition from founder-led sales to a scalable revenue function. Own outbound strategy, prospecting, pipeline development, and deal closing for healthtech and life sciences buyers. Sell both platform access and expert marketplace services, focus on cardio and brain health segments, identify new revenue opportunities, and establish repeatable sales processes while preparing for future team growth.

Lead and build Element 74’s new-business sales function, owning bookings, pipeline generation, forecasting, complex public-sector and nonprofit deals, market expansion, contract management, and sales and marketing efficiency. Recruit and develop the sales team, establish repeatable playbooks and CRM discipline, personally manage strategic pursuits, and partner with leadership on pricing, packaging, and growth initiatives.

Leads national education sales strategy and strategic account growth across K-12, higher education, and educational organizations. Builds pipelines, navigates complex procurement processes, manages forecasting, develops partnerships, negotiates high-value deals, and expands multi-location accounts. Builds relationships with senior decision-makers and collaborates cross-functionally through implementation and expansion. Requires national travel to customer meetings, conferences, and education events.

Leads GitLab’s National Security Group regional sales team, driving new and expansion revenue across U.S. federal agencies. Responsibilities include hiring and coaching Account Executives, forecasting, pipeline management, complex deal strategy, executive negotiations, federal procurement, FedRAMP-related selling, partner engagement, and account expansion. The role collaborates with Customer Success, Product, Marketing, Renewals, distributors, and systems integrators while traveling as needed for customer and team engagements.

Leads GitLab’s global SMB new-business organization across EMEA and AMER, overseeing regional sales, BDR, and SDR managers. Owns new-logo strategy, pipeline generation, quota and territory planning, forecasting, revenue reporting, hiring, manager development, and cross-functional alignment. The role drives outbound sales motions, develops team performance, analyzes market opportunities, and represents new-business strategy to senior leadership.

Lead Propelus’s Employer Growth Team across EverCheck and Immuware, owning revenue growth, pipeline creation, forecasting, territory coverage, sales processes, enablement, and team performance. The role manages eight direct reports and requires hands-on enterprise selling into hospitals and health systems, coaching, performance management, and development of outbound sales systems. The leader will also support new data solutions and a premium nursing module while partnering with Marketing and senior leadership in a PE-backed environment.

Leads enterprise sales strategy initiatives focused on extended-stay lodging growth. Develops strategic roadmaps, business cases, ROI analyses, go-to-market plans, program charters, performance initiatives, and executive presentations. Partners with sales, product, marketing, finance, operations, technology, and regional teams to influence decisions, align stakeholders, and operationalize global commercial strategies.

Leads GitLab’s US Financial Services sales organization, managing Strategic Account Leaders and driving software sales, bookings, revenue, pipeline, and renewals. Responsibilities include territory planning, forecasting, performance management, recruiting, coaching, team development, executive customer relationships, and go-to-market strategy for regulated financial institutions. The role requires enterprise software sales leadership, familiarity with financial services regulations, cross-functional collaboration, and occasional travel as needed.

Own the weekly forecast and pipeline cadence, territory and quota administration, sales compensation operations, performance reporting, CRM data discipline, and operating calendars. Lead compensation administration and payout accuracy, translate coverage plans into territories and quotas, support evolving products and pricing, and build the Sales Operations team. Partner across Sales, Finance, Enablement, People, Legal, and executive leadership while improving internal revenue applications and AI-enabled reporting.

Lead and grow an inside sales team promoting a SaaS financial reporting platform. Responsibilities include recruiting and coaching representatives, developing sales and pipeline strategies, driving new business and account expansion, forecasting performance, supporting complex customer conversations, and presenting market insights to leadership. The role requires strong B2B enterprise software sales experience, sales methodology expertise, analytical forecasting skills, and the ability to build scalable revenue processes.

Owns net-new revenue as a quota-carrying individual contributor. The Sales Director develops pipeline through prospecting, referrals, partnerships, events, and inbound leads; leads consultative sales cycles; manages complex proposals, RFPs, negotiations, and contracts; builds senior buyer relationships; sells integrated data, research, media, technology, and measurement solutions; maintains CRM forecasts; and coordinates internal teams through successful client handoffs.

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.

Leads the Northeast Distributor Sales team by coaching Territory Managers and agency partners, developing sales strategies, expanding distributor relationships, and driving revenue growth. Responsibilities include sales training, performance management, forecasting, pricing and margin oversight, KPI analysis, account development, commercial negotiations, and cross-functional collaboration. The role owns team and agency performance while improving customer satisfaction and identifying opportunities for market-share growth.

Build and manage enterprise sales for AI solutions serving higher education institutions. Own pipeline development, qualify opportunities, navigate 6–9 month multi-stakeholder sales cycles, close contracts, and create ROI-driven business cases tied to enrollment and conversion outcomes. This senior individual contributor role requires proactive execution in a scaling startup, higher education market understanding, customer travel, and U.S. residency.

Leads and scales a high-ticket sales organization for a digital marketing agency. Responsibilities include recruiting and managing closers, developing sales scripts and processes, conducting daily coaching and call reviews, owning sales metrics and cash collection, closing calls personally, maintaining CRM quality, reporting performance, and partnering with marketing to improve lead quality and positioning.

Lead enterprise sales for AiDASH’s utility-sector climate resilience platform. Originate and close complex, multi-million-dollar deals, engage C-suite utility leaders, develop account and deal strategies, expand existing customer relationships, and collaborate with Customer Success and strategic partners. The role requires approximately 30% travel and involves elevating sales excellence across the go-to-market organization.