Top Mid-Market Account Executive Jobs in Chicago, IL

Source and close complex, multi-location grocery, liquor, and convenience retail deals. Build pipeline, conduct executive discovery, deliver value-based demonstrations and business cases, negotiate contracts, and manage full-cycle sales. Navigate buying committees, RFPs, compliance, and lengthy sales cycles while partnering with internal teams on implementation, product feedback, and deal structure. Establish repeatable upmarket sales processes, maintain Salesforce discipline, and optimize long-term revenue.

Own full-cycle B2B sales for Uber for Business mid-market accounts with 1,000–5,000 employees. Responsibilities include prospecting, building territory and account plans, developing pipeline, qualifying opportunities, presenting solutions, negotiating contracts, closing new business, forecasting, maintaining Salesforce updates, and managing customer relationships. The role is hybrid in Chicago or New York and requires consistent quota achievement.

Owns the end-to-end new business sales cycle for mid-market corporate accounts, including prospecting, relationship building, product demonstrations, trials, forecasting, pipeline development, negotiation, and closing. Targets Fortune 1000 organizations and stakeholders in strategy, competitive intelligence, business development, investor relations, and M&A. Partners with SDRs, product specialists, account management, and leadership to drive quota attainment, customer success, upsells, and product feedback.

As a Mid-Market Account Executive, you will drive adoption of EliseAI by engaging potential clients, managing the sales cycle, and collaborating with internal teams to enhance customer experiences.

Own the full mid-market B2B sales cycle, including prospecting, discovery, demos, solution alignment, negotiation, and closing. Build and manage self-sourced and SDR-supported pipelines, acquire new customers, track sales performance, and collaborate with SDR, Customer Success, and Technical Support teams. Manage deals typically under $50,000 ACV while nurturing mid-sized client relationships and identifying business needs.

Own the full mid-market sales cycle for Zapier’s AI-powered automation platform, including prospecting, discovery, negotiation, closing, and expansion. Build relationships from practitioners to executives, develop business cases around automation, and navigate complex deals with Solutions Engineering, Customer Success, and Product. The role also involves attending events, generating pipeline independently, and helping establish Zapier’s mid-market go-to-market motion.

The Mid Market Account Executive sells AssetWatch solutions to new and existing manufacturing customers. Responsibilities include identifying customer pain points, developing tailored sales strategies, conducting demonstrations, researching leads, maintaining CRM records, attending industry events, managing sales activities, and transitioning closed deals to post-sale teams. The role requires strong consultative selling, relationship-building, independent time management, resilience, critical thinking, and at least five years of hunter-level B2B sales experience.

Own outbound net-new revenue in the mid-market (250–1000 employees). Proactively prospect 600+ accounts, engage Director+ and C-level buyers, run discovery/demos/negotiations, and close full-cycle deals with a data-driven, multi-threaded approach to meet quota and maintain accurate pipeline and forecasts.

Own outbound pipeline generation and full-cycle sales for mid-market B2B SaaS customers. Responsibilities include prospecting, account targeting, product demonstrations, business-case development, negotiations, closing deals, building the upmarket sales playbook, collaborating with Product, Marketing, and RevOps, and managing pipeline coverage, forecasting, and sales targets.

Owns strategic growth, retention, renewals, and expansion across mid-market B2B accounts. Develops account plans, conducts customer and executive meetings, manages consultative sales cycles, negotiates commercial terms, and drives cross-sell and upsell opportunities. Partners with service managers, solutions architects, and sales overlays to develop solutions and quantify customer outcomes. Requires MSP industry experience, CRM proficiency, and travel of up to 50%.

Drives new business and revenue growth across mid-market life sciences accounts by selling electronic benefit verification, prior authorization, and data analytics solutions. Owns territory strategy, prospecting, complex enterprise sales cycles, contracting, executive relationships, and quota attainment. Partners cross-functionally on solution development and implementation while translating healthcare data capabilities into customer value. The role requires approximately 50% U.S. travel and focuses on commercialization, patient access, reimbursement, and market access needs.

Source, pitch, close, onboard, and scale mid-market supply-side partners for Nift’s performance marketing network. Build pipeline among consumer apps, publishers, and monetization platforms; engage decision-makers, overcome objections, meet sales quotas, and manage concurrent opportunities through short sales cycles. Collaborate with marketing, partner success, creative, and engineering teams while maintaining expertise in market trends and competitive dynamics.

Drive new customer acquisition for Peek's activity-operator network using consultative SaaS sales. Manage territory strategy, deliver product demos, meet monthly/quarterly targets, maintain forecasts in Salesforce, and provide market insights to senior management. Role requires travel as needed and deep travel-industry knowledge.

Drive new business sales for TCP’s workforce management SaaS solutions across State, Local Government, and Education accounts. Responsibilities include territory planning, prospecting, consultative selling, managing RFPs and procurement processes, conducting demonstrations, forecasting opportunities, maintaining CRM records, achieving revenue quotas, and developing customer relationships throughout the full sales cycle. The role requires at least 3 years of SaaS sales experience and involves 20–30% travel.

Own the full-cycle sales process for mid-market FMCG and food-company customers across North America. Responsibilities include running 12+ weekly demos, targeting strategic accounts with SDRs, creating subscription packages, negotiating contracts, closing deals, refining regional messaging, and attending trade shows and customer meetings. The role requires building the North American market, collaborating with marketing and product marketing, and working with international colleagues. Chicago presence or relocation is required, along with travel and U.S. work authorization without visa sponsorship.

Build and close new-account and expansion revenue pipelines for a private capital CRM serving mid-market customers. Responsibilities include qualifying inbound leads, conducting discovery and presentations, developing outbound prospecting plans, managing forecasts and quotas, partnering with Customer Success and Marketing, and advising financial services prospects on CRM, API integrations, data enrichment, and reporting solutions.

Generate and manage a mid-market sales pipeline, prospect and cold-call churches, conduct product demonstrations, develop value propositions, negotiate contracts, close deals, and meet revenue quotas. Maintain Salesforce records, collaborate with SDRs, marketing, partner success, and implementation teams, and build relationships with church leaders. The role requires visiting 30–40 churches monthly and supporting the full sales lifecycle.

Own mid-market sales cycles from first meeting through signature for substantial, six-figure deals with independent psychiatry practices. Diagnose customer needs, build financial and ROI cases, displace incumbent solutions, qualify opportunities, maintain accurate forecasts, and coach founding BDRs. The role requires fluency in practice financial metrics, experience selling services alongside software, autonomous startup experience, and quarterly travel to industry conferences.

As a Mid-Market Account Executive, you'll manage the full sales cycle for mid-market accounts, engaging technical buyers to drive complex deals and define go-to-market strategies.

Develop and close new business with mid-size public companies by targeting finance executives. Manage the full sales cycle, including prospecting, presentations, RFPs, negotiations, forecasting, CRM updates, and customer transition. Build sales pipelines, exceed revenue quotas, use consultative selling, communicate market insights, and maintain strong customer and internal relationships. Travel up to 50% of the time.

Own the full mid-market sales cycle for Supio’s AI platform, including prospecting, cold calling, relationship building, product demonstrations, negotiation, and closing. Meet or exceed revenue targets, attend industry events, maintain accurate CRM pipeline data, and collaborate with marketing, product, and customer success teams. The role focuses on selling to law firms and legal decision-makers in the Mid-Atlantic region.

Own the full mid-market sales cycle, including prospecting, cold calling, relationship building, product demonstrations, negotiations, and closing. Meet or exceed revenue quotas, maintain accurate CRM pipeline data, attend industry events, and collaborate with marketing, product, and customer success teams. The role focuses on expanding Supio’s AI platform sales within the legal community and helping law firms improve knowledge work.

Drive revenue for Material Security’s commercial segment by generating pipeline, conducting outbound prospecting, communicating product value, managing efficient sales cycles, and exceeding revenue targets. The role also includes managing customer relationships for renewals and upsells, developing repeatable sales strategies, and collaborating with go-to-market and partner teams. Candidates should have security sales experience, strong communication skills, ownership, versatility, and success in early-stage, high-growth environments.

Hunt and close net-new mid-market accounts in industrial and manufacturing organizations. Own the full sales cycle from cold outreach to contract negotiation, run technical discoveries and ROI business cases, build multi-stakeholder champions, maintain pipeline and forecasts in HubSpot CRM, and navigate procurement and legal to close high-value deals. Travel up to 25%.

The Mid-Market Account Executive develops new business among organizations with 500–5,000 employees. Responsibilities include prospecting, managing the full sales cycle, engaging decision-makers, presenting tailored solutions, closing deals, meeting revenue targets, monitoring market intelligence, collaborating with internal teams, and maintaining CRM records, forecasts, and pipeline reports.