Top Remote Entry Level Sales Jobs in Chicago, IL

Guide prospective customers through loan applications via inbound and outbound calls, explain product benefits, encourage application completion, maintain accurate account records, and deliver professional customer service. The role includes a three-week training program and requires strong communication, empathy, multitasking, adaptability, and comfort working remotely in a high-volume environment.

Identify and research prospects, qualify inbound and outbound leads, understand customer needs, schedule qualified meetings for the enterprise sales team, maintain Salesforce activity records, conduct outreach to conference attendees, and meet pipeline and opportunity-generation goals.

Drives enterprise sales growth for GitLab across the Northeast by managing strategic accounts, developing account plans, generating pipeline, and leading complex B2B software sales cycles. Builds C-level relationships, coordinates solutions architects and partners, guides customers through evaluation to implementation, expands platform adoption, forecasts opportunities, analyzes wins and losses, and presents business value. The role is fully remote and focused on AI-powered DevSecOps solutions.

Build and manage customer relationships, drive sales opportunities, and represent Zscaler’s Zero Trust Exchange and cloud security platform. This posting is for consideration for future Sales Account Executive opportunities in the East region. The role operates within a collaborative, customer-focused, inclusive organization and may follow Zscaler’s hybrid work model.

Full-cycle enterprise sales role responsible for prospecting, developing, qualifying, and closing deals with large, multi-stakeholder organizations. The position sells FacilitiesLink, a facilities information platform for planning, building, and operating large-scale campus environments. Compensation includes 50% commission, a $20-per-hour guaranteed draw, and on-target earnings starting at $150,000 annually. Flexible work arrangements are available, with occasional travel required.

Own the full sales cycle for high-value small-business customers, including inbound and outbound prospecting, product demonstrations, lead qualification, objection handling, deal closing, and onboarding routing. Build and refine scalable outbound and sales processes, use AI tools to improve productivity, identify customer trends, and provide structured feedback to product teams.

The Strategic Account Executive sells SailPoint’s Identity Security solution to strategic enterprise accounts. Responsibilities include territory and account planning, prospect discovery, competitive positioning, partner coordination, product demonstrations, RFP responses, negotiations, forecasting, pipeline development, and closing. The role owns the full sales cycle, collaborates with presales, marketing, professional services, and customer success teams, maintains Salesforce and Clari accuracy, and builds executive-level customer and partner relationships. Approximately 50% business travel is expected.

Develop and close enterprise public-sector business across state, local, and education accounts. Build executive relationships, lead account strategies, manage complex proofs of concept and trials, support RFP wins, exceed revenue quotas, and collaborate with sales engineering, product, software engineering, and partners to address customer needs and demonstrate integrated solutions.

Own revenue and quarterly quota for the West territory covering Oregon, Idaho, Montana, and Hawaii. Build and expand relationships with benefits brokers, consultants, general agents, and employers in the 1,000–9,999 employee market. Develop strategic advisor partnerships, lead complex cross-functional deals, close new business, and shape regional sales strategy with enterprise and account teams.

Owns Shield AI’s USMC business development, sales pipeline, revenue forecast, and quota across autonomy software and unmanned systems. Identifies and shapes opportunities, builds relationships with Marine Corps stakeholders, translates operational needs into funded procurement, leads capture and proposal efforts, and manages deals through contract award. Coordinates engineering, product, program management, and capture teams while driving adoption of fielded capabilities. The role requires defense sales or military operations experience, USMC familiarity, DoD procurement knowledge, up to 50% travel, and eligibility for TS/SCI clearance.