Top Remote Director of Sales Jobs in Chicago, IL

The Director of Sales and Business Development will drive revenue growth through strategic sales processes, build client relationships, and oversee sales operations. Responsibilities include creating sales playbooks, negotiating deals, and forecasting revenue, while managing a team as the company scales.

Lead and scale a team focused on enterprise new-logo acquisition across the Eastern U.S. Own full sales lifecycle for complex six- to seven-figure deals, execute account-based strategies, coach Account Executives, engage prospects in-person, and collaborate with GTM, product, and solutions teams to refine positioning and close deals.

Drive revenue for Garner's fully- and self-insured products in the 500–5,000 life segment. Expand and manage broker, consultant, general agent, and employer partnerships; build sales and partnership pipeline infrastructure; collaborate with market teammates to support in-market activities and broker relationships. Remote role with occasional travel to HQ.

Lead and develop a national B2B sales organization: manage quota-carrying AEs, coach through complex deals, drive pipeline/forecasting discipline, enablement, cross-functional alignment, participate in customer meetings and negotiations, and scale sales processes and playbooks.

The Director of Sales owns outbound prospecting, lead generation, qualification, pipeline development, and new client acquisition for a radiology revenue cycle management organization. Responsibilities include managing HubSpot CRM records and reporting, attending healthcare and radiology conferences, coordinating follow-up, supporting proposals, and collaborating with marketing, operations, and executive leadership. Regular overnight travel is required. The role requires healthcare and radiology sales experience, strong communication skills, and a proven record of business development success.

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 and scale enterprise sales across the Central U.S., managing five Enterprise AEs. Own regional revenue targets, pipeline hygiene, forecasting, and deal execution. Coach and develop the team, engage personally in strategic accounts, and partner cross-functionally (Marketing, Product, CS, Legal, Finance) to drive growth. Represent Ontic at industry events and drive regional market development. Travel extensively across the region.

Lead and scale the SMB and Franchise sales organization, managing Sales Managers and field/inside teams to drive revenue, quota attainment, forecasting accuracy, and scalable sales processes. Coach leaders, optimize territory coverage, partner cross-functionally, hire and ramp talent, and use performance metrics to improve conversion and efficiency.

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.

Lead and scale enterprise sales across the Central U.S., owning regional revenue, pipeline hygiene, forecasting, and team coaching. Drive new logo acquisition and expansion, engage in strategic deals, collaborate cross-functionally, and represent the company with executives and partners.

Lead and own the full learning lifecycle for sales hires: design onboarding and role-specific curricula, run training cohorts and enablement, review calls at scale, build performance-based coaching frameworks tied to revenue, partner with Sales Directors, maintain playbooks and SOPs, and continuously optimize training to shorten ramp time and improve conversion and productivity.

Sell RTB Houses adtech solutions to enterprise retail/e-commerce clients by owning full sales cycles, building strategic account plans, closing deals, updating CRM, collaborating with technical teams, and traveling domestically up to 20%. Drive new business, nurture relationships, and meet revenue targets.

Sell AKASA's AI-native revenue cycle management solutions to health systems. Build C-level relationships, drive business development, lead full sales cycle from prospecting to close, deliver consultative presentations, work with BDRs, attend industry events, and collaborate cross-functionally. Travel domestically up to 60%.

Lead full-cycle enterprise sales into large health systems: prospecting, qualifying, demos, negotiation, and closing. Run high-volume outbound, build pipeline, translate value into financial terms for C-suite, refine messaging, keep accurate forecasts, and create a repeatable playbook for selling to healthcare providers.

Lead and develop a team of enterprise account executives selling data integrity solutions to banks and capital markets. Coach AEs to engage CXOs and technical buyers, drive multi-solution platform deals, enforce MEDDPICC, use pipeline analytics for coaching and forecasting, align cross-functionally, and own executive relationships and operating cadence to grow deal size, pipeline, and strategic account penetration.

Lead Sales Operations and Inside Sales to build commercial systems, governance, and repeatable processes. Own Salesforce administration, territory and quota design, forecasting, reporting, compensation administration, KPI governance, and inside-sales standard work to convert commercial strategy into predictable execution and measurable revenue outcomes.

Lead global sales compensation, quota strategy, and incentive planning for Dropbox. Design governance, quota methodologies, and scalable incentive programs; partner with Sales, Finance, HR, and Systems; own incentive operations and Forma platform; drive quota planning, payout accuracy, and automation; build and mentor a high-performing compensation team while influencing executive decision-making through data-driven recommendations.

Lead new business sales for North America by building a pipeline, prospecting and closing clients, meeting quarterly targets, delivering product demos, maintaining forecasts, and collaborating with cross-functional teams to grow a profitable market research SaaS business.

Lead and coach a team of Account Executives while carrying an individual quota. Drive complex enterprise SaaS sales cycles, maintain pipeline health and forecasting accuracy, coach sellers on MEDDPICC and deal strategy, and partner cross-functionally to allocate resources and improve sales processes.

Lead new business development and exceed individual revenue targets while coaching and scaling a team of Account Executives. Build agency and regional advertiser relationships, manage pipeline and forecasting, recruit and develop sales talent, and shape territory and regional sales strategy to drive growth.

Lead new business and exceed individual revenue targets while recruiting, coaching, and developing Account Executives. Build relationships with agencies and regional advertisers, manage pipeline and forecasting, influence sales strategy, and collaborate cross-functionally to scale regional growth and sales processes.

Lead and develop Keystone's ESCO sales channel and Territory Managers. Set strategy, drive sales execution, manage budgets, coach the team, oversee CRM and pipeline, strengthen partner relationships, guide pricing and competitive positioning, and collaborate cross-functionally to grow profitable ESCO, contractor, and distributor business. Frequent travel to support field coaching and customer engagement.

Lead and grow the West sales organization by driving revenue, coaching account executives, optimizing sales processes and CRM usage, aligning with marketing, recruiting and onboarding reps, and ensuring accurate forecasts and KPIs. Focus on public-sector selling, consultative approaches, and scaling teams while traveling up to 30%+.

Lead execution of industrial cloud and AI sales strategy, drive pipeline progression and forecasting, enable sellers with pitches/demos, align cross-functional teams, manage key accounts, and partner with marketing and product to deliver customer value.

You're responsible for owning new logo revenue and building an AI-first sales organization. You will architect an AI-powered sales engine, lead team operations, and drive strategic deals while ensuring AI enhances productivity throughout the sales process.