Top Remote Entry Level Sales Jobs in Chicago, IL

Manages and hires Solutions Consultants in a player-coach role, mentoring the team and partnering with sales, marketing, security, and product teams. Solutions Consultants advise prospective customers during the sales process through product expertise, strategic guidance, and best practices. The role requires experience selling into accounts with sophisticated pre-sales consulting or sales engineering teams, strong communication skills, and knowledge of at least two relevant technology or marketing domains. Travel may reach 50% during peak periods.

The Associate Sales Engineer partners with sales, product, customer success, and professional services teams to support SaaS sales. Responsibilities include conducting consultative discovery, delivering tailored technical demonstrations, explaining API integrations and security protocols, identifying technical blockers, recommending solutions, incorporating customer feedback, and communicating technical value to HR and IT stakeholders. The role also requires collaboration, continuous learning, competitive awareness, and use of data and AI tools to improve buyer engagement.

Own outbound prospecting and lead generation for school district partnerships. Identify, qualify, nurture, and deliver opportunities to Partner Development Managers through high-volume phone, email, and creative outreach. Learn product offerings, manage territory strategy, meet demo-booking goals, collaborate with Sales and Marketing, and eventually mentor newer associates and support brand and product marketing initiatives.

As an Account Executive, grow existing accounts and acquire new business. Focus on value selling, strategic account development, and customer relationships to ensure sales effectiveness and execution of plans.

Own the full sales cycle for new plaintiff law firm clients across a regional territory. Responsibilities include self-sourced outbound prospecting, pipeline development, referrals, events, partnerships, discovery, ROI-focused demos, deal management, and consistently exceeding revenue targets. The role requires managing a high-velocity sales book, attending industry conferences, and traveling up to 50%.

Research and identify prospective clients, engage them through email, phone, and social media, understand their needs, present Airwallex solutions, qualify opportunities, and schedule appointments for Account Executives. The role involves developing compelling value propositions, building partnership-oriented conversations, collaborating with sales teammates, and learning in a fast-paced, high-growth technology environment.

Founding Retail BDR for Toast90: build prospect lists and perform high-volume outreach (80+ activities/day) to convenience stores, grocery and bottle shops; qualify leads, schedule meetings for Account Executives, use Salesforce to track activity, partner on sales strategy, and position the Toast Retail solution against competitors.

Handle inbound calls to deescalate and retain clients enrolled in financial hardship programs. Educate clients on program benefits, assess financial situations, record interactions in CRM, negotiate solutions, meet retention targets, and provide empathetic customer service.

Drive new customer acquisition and revenue growth as part of the Outbound Sales Development team. Collaborate with cross-functional teams to build a strong sales pipeline and understand customer needs in the ASR space.

Work as an independent contractor showing homes, hosting open houses, and attending inspections on a flexible schedule. No sales closings required; earn flat-rate payments per field event. Must affiliate license with the brokerage and join local MLS and Realtor Association.