Top Mid-Market Account Executive Jobs in Chicago, IL

The Account Executive will prospect, build pipeline, and close mid-market sales of Samsara’s IoT solutions. Responsibilities include researching prospects, conducting high-volume cold outreach, managing proofs of concept and trials, coordinating multiple stakeholders, negotiating complex pricing, selling to executives, and consistently achieving quota. Typical deals range from $20,000 to $100,000, with approximately 25% travel required across the Midwest territory.

Sell Google Cloud professional services, AI/ML solutions, and managed engagements to mid-market and enterprise clients across North America. Own full sales cycle, build pipeline, meet quotas, collaborate with Google field teams, and position consulting capabilities to drive large services engagements and revenue growth.

Manage a portfolio of mid-market mobile app prospects and customers through full-cycle, value-led sales. Generate outbound pipeline, build field relationships at conferences, conduct demos and technical evaluations, advise on mobile monetization and paywall optimization, and collaborate cross-functionally to onboard and grow customers.

In this role, you will engage with mid-market customers, driving sales through cold calling and building relationships to close deals ranging from $20k to $100k.

As an Account Executive, you will drive sales to mid-market customers, handling POCs, negotiations, and building relationships to enhance operations through IoT data.

Own the full sales cycle for net-new mid-market audit and advisory accounts, from prospecting through negotiation and close. Build executive, operational, and technical relationships; conduct consultative discovery; deliver solution walkthroughs; develop territory and account plans; maintain accurate CRM forecasting; collaborate cross-functionally; and achieve revenue targets. The role is remote in the United States and requires up to 30% regional and national travel.

Own and grow a book of ~40 mid-market accounts across LATAM, driving net-new sales and expansion. Lead cross-functional deal teams, qualify and close complex multi-threaded SaaS deals using MEDDPICC, negotiate contracts, forecast pipeline, and maintain executive relationships. Collaborate with channel, product, and customer success and travel occasionally for customer meetings and events.

Drives new-logo acquisition and revenue growth among mid-market healthcare organizations. The Account Executive owns healthcare decision-maker relationships, builds high-volume pipelines, conducts consultative discovery and product demonstrations, manages opportunities through close, and meets sales quotas. The role requires SaaS sales experience, acute healthcare selling experience, strong solution-selling abilities, and effective collaboration with Sales Development, Marketing, and cross-functional teams.

The Mid-Market Account Executive will manage the full sales cycle, meet sales quotas, build client relationships, conduct demos, and travel as needed.

Own the full outbound sales cycle for mid-market merchants, including prospecting, pipeline development, discovery, demonstrations, negotiations, and closing. Develop tailored multi-product solutions, acquire new logos, collaborate with business development and cross-functional teams, maintain accurate Salesforce forecasting, and consistently achieve revenue targets.

Own the full outbound sales cycle for mid-market merchants, from prospecting and pipeline development through discovery, demonstrations, negotiation, and close. Build multi-product solutions, acquire new logos, manage complex multi-stakeholder deals, maintain Salesforce forecasting accuracy, collaborate cross-functionally, and consistently achieve revenue targets.

Generates new mid-market telecommunications and technology revenue through quota-driven sales, while managing select existing accounts. Develops proposals, sells connectivity, voice, cloud, security, and managed network solutions, manages opportunities and forecasts in CRM systems, submits contracts, resolves customer issues, and coordinates with engineering and customer care through product delivery.

Drive new business and account growth across mid-market and SMB clients. Responsibilities include prospecting, originating and closing deals, managing complex sales cycles, building trusted client relationships, consulting with C-level legal executives, collaborating cross-functionally, and providing thought leadership. The role requires consultative B2B selling, executive communication, CRM usage, organization, and a strong service orientation.

Own the full mid-market sales cycle, including prospecting, discovery, solution positioning, pricing, forecasting, and closing net-new opportunities. Meet revenue targets, maintain accurate CRM records, research competitors, and partner with sales engineering, operations, product management, and account management. Build trusted customer relationships, use feedback to improve strategy, and apply AI tools to streamline sales workflows. Travel up to 10% to events and customers.

Owns mid-market merchant sales opportunities from prospecting through contracting, launch, and handoff for Cash App Pay and Afterpay. Responsibilities include account planning, outbound pipeline generation, discovery, business-case development, commercial negotiation, cross-functional deal coordination, Salesforce forecasting, and meeting revenue targets. The role requires consultative selling to senior commerce, marketing, finance, and technology stakeholders, plus market insight sharing and occasional travel.

Own the full sales cycle for mid-market commerce merchants across Cash App Pay and Afterpay. Responsibilities include prospecting, pipeline development, discovery, business-case creation, proposal development, negotiation, contracting, cross-functional deal coordination, forecasting, and merchant relationship management. The role requires meeting revenue targets, providing market feedback, improving sales processes, and representing the company at merchant meetings and industry events.

Generates new revenue and manages select existing mid-market accounts through quota-driven telecommunications and technology sales. Sells connectivity, voice, cloud, security, managed network, and related solutions; develops proposals, manages opportunities and forecasts in CRM, submits contracts, resolves customer issues, and coordinates with sales engineering and customer care to ensure timely product delivery.

Own the full sales cycle for mid-market clinics and practices, including prospecting, relationship-building, demonstrations, negotiation, and closing. Build and manage a qualified pipeline while consistently exceeding quotas. Partner with leadership, product, marketing, operations, and account teams to shape go-to-market strategy, refine messaging, develop sales processes, and ensure smooth onboarding handoffs. Serve as a trusted advisor on agentic AI and healthcare solutions while helping establish a newly launched product line.

Manage the full SaaS sales cycle for mid-market accounting firms, including prospecting, lead qualification, outbound engagement, discovery, demonstrations, pipeline development, forecasting, and closing new business. Use consultative selling to communicate Karbon’s value, maintain accurate Salesforce and Gong records, and leverage AI tools such as ChatGPT and Gemini for research and follow-up. The role is remote within the United States and requires consistently exceeding quota.

Own the full sales cycle for acquiring mid-market customers, from outbound prospecting and pipeline creation through closing complex, multi-stakeholder SaaS deals. Conduct consultative discovery, deliver ROI-focused demonstrations, engage executive stakeholders, manage forecasts, and meet revenue targets. The role requires strong hunter instincts, organized deal management, CRM proficiency, and experience selling complex B2B solutions.

Own the full sales cycle for mid-market fleets (50–174 trucks): prospect, qualify, demo, negotiate, and close new business. Drive outbound lead generation, meet revenue quotas, collaborate cross-functionally, manage trials, and maintain accurate forecasting.

Own the full sales cycle for mid-market accounts, from outbound prospecting and pipeline creation through closing and expansion. Build account and territory strategies, conduct discovery with HR and executive stakeholders, deliver product demonstrations, manage complex multi-stakeholder sales cycles, maintain accurate CRM forecasts, and exceed revenue targets. The role requires proactive cold calling, consultative selling, strong negotiation, and collaboration with SDRs, marketing, legal, security, finance, solutions consulting, and customer success.

Own full-cycle mid-market sales, working with diverse companies and stakeholders on strategic, complex deals. The Account Executive will conduct discovery, build relationships, communicate value, solve customer problems, and drive successful outcomes. The role requires a proven sales track record, strong work ethic, coachability, adaptability, entrepreneurial spirit, and understanding of the technology industry.

Hightouch seeks a Mid-Market Account Executive to manage full-cycle sales, conduct discovery, build customer relationships, and close strategic, complex deals across varied industries and use cases. The role requires a proven sales track record, strong communication and interpersonal skills, adaptability, curiosity, ambition, humility, and knowledge of the technology industry. Candidates should have at least two years of corporate or mid-market sales experience and thrive in a fast-growing startup environment.

Own the full-cycle sales process for mid-market cybersecurity customers, from prospecting and pipeline generation through contract closure, renewals, and expansion. Manage a defined territory, exceed new ARR quotas, qualify customer needs, present ROI-driven value, and collaborate with Sales Engineering, Product, Marketing, and Customer Success. The role requires disciplined selling, effective stakeholder engagement, and comfort working in resource-constrained environments.