Top Mid-Market Account Executive Jobs in Chicago, IL

Drive new mid-market business for BILL’s AP and cash-flow automation solutions through the full sales cycle. Responsibilities include self-sourcing pipeline, cold calling, consultative selling, product demonstrations, relationship building with financial stakeholders, CRM management, and accurate forecasting. The role requires consistently exceeding sales targets while selling digital payment solutions to finance departments and fintech customers.

Acquire new mid-market customers by advising C-level audiences, identifying business and data-management needs, proposing Boomi solutions, developing account plans, coordinating cross-functional resources, and driving pipeline, bookings, forecasting, and account-metric performance. The role is fully remote for candidates in the Fort Lauderdale-Miami area and requires complex relationship-selling experience.

Acquire mid-market customers through complex solution selling, advise C-level stakeholders, identify business and data-management needs, develop account plans, coordinate cross-functional resources, create post-sale implementation plans, and drive pipeline, bookings, forecasting, and sales-metric performance.

Own full-cycle B2B sales for Sprout Social’s public sector segment, including prospecting, pipeline generation, relationship development, deal management, and quota attainment. The Account Executive will engage decision-makers across organizations, manage qualified opportunities, collaborate with internal teams, and deliver tailored product value. Success includes building a pipeline exceeding four times monthly quota, consistently meeting revenue targets, expanding account adoption, and eventually sharing sales best practices with peers.

Drives new business growth for PAR’s unified commerce solutions among mid-market and SMB restaurant operators. Responsibilities include prospecting, consultative selling, product demonstrations, executive relationship building, regional campaign development, competitive research, pipeline and forecast management, KYC maintenance, and CRM administration. The role partners with sales engineering, solution architecture, marketing, and service teams, and requires travel up to 50%.

Own the full mid-market sales cycle across North America, from prospecting and account research through negotiation and close. Generate new business, expand existing accounts, manage pipelines and RFI/RFQ processes, build value-based proposals, and sell complex SaaS or PaaS solutions to executive stakeholders. Partner with Sales Engineering, Solutions Architecture, Partnerships, Business Development, Account Management, and Customer Success teams to drive revenue and customer growth.

Drives net-new revenue from mid-market construction accounts through prospecting, inbound lead management, platform demonstrations, negotiation, and full-cycle deal closure. Builds and maintains pipeline, partners with Hilti sales teams, manages complex sales cycles, and achieves revenue quotas. Travels quarterly to meet customers and support field sales teams. The role is remote within the United States.

Sell Housecall Pro to mid-market home service businesses using consultative, account-based techniques. Run multiple 60–90 minute demos daily, manage pipeline, close deals, and coordinate onboarding with specialists to ensure customer success and long-term partnerships.

Sell Champify to mid-market accounts: qualify inbound, create outbound pipeline, run discovery, demos, POCs, build champions, and close $20–100K SaaS deals while partnering with GTM teams.

Drive full-cycle, value-led sales for mid-market mobile app customers: generate outbound pipeline, run discovery/demos, represent RevenueCat at events, advise on monetization and onboarding, and collaborate with Sales Engineering and Customer Success to grow customer revenue.

Own the full mid-market sales cycle across an assigned territory, including prospecting, cold outreach, pipeline development, product demonstrations, qualification, negotiation, and closing. The Account Executive will conduct at least 10 demos weekly, collaborate cross-functionally, track performance, achieve quota, attend required industry events and company meetings, and build customer relationships within the construction technology market.

Drives new business acquisition in the mid-market segment through prospecting, networking, trade shows, presentations, product demonstrations, and client relationship development. Collaborates with Sales Development Representatives, manages sales opportunities and RFP responses, travels regularly to client sites and events, and supports new customers during their first 90 days. Requires strong communication, public speaking, organization, SaaS understanding, CRM proficiency, and consistent achievement of sales goals.

Generate new mid-market business, prospect independently and through BDR leads, serve as a product specialist, manage qualified pipelines, conduct customer research, deliver demonstrations, meet sales metrics, and become a trusted advisor on Sprout Social’s platform and social media trends.

Own the full sales cycle for net-new mid-market SaaS customers, including prospecting, discovery, demonstrations, negotiation, and closing. Build self-sourced pipeline, manage forecasts in Salesforce, engage multiple stakeholders, and consistently achieve revenue quotas. The role requires consultative selling of sophisticated software solutions, strong business-value communication, and collaboration with sales, marketing, solutions, and other internal teams. Travel is up to 10% for team collaboration, customer engagements, and company events.

Own a mid-market territory and book of business, prospecting and managing new and expansion opportunities through complex sales cycles. Present GitLab’s AI-powered DevSecOps platform to technical and business stakeholders, maintain pipeline and forecasts, negotiate and close deals, and support customer adoption and expansion. Collaborate with sales development, customer success, renewals, marketing, partners, and technical teams while contributing customer insights and sales process improvements.

Sell Hightouch’s solutions to mid-market companies through full-cycle sales, including discovery, relationship building, strategic deal management, and value selling. The role requires a self-starting, coachable professional with strong communication, interpersonal, problem-solving, and adaptability skills. The Account Executive will manage varied deals across industries and personas while contributing to a rapidly growing remote-first startup.

Drive revenue growth for procurement and compliance SaaS products by managing the full sales cycle across mid-market hospital pharmacy accounts. Generate pipeline, prospect new and existing customers, achieve recurring-revenue quotas, engage senior stakeholders, deliver presentations, negotiate contracts, maintain CRM reporting, and collaborate with marketing, business development, clinical strategy, customer success, and implementation teams. The role is remote across the continental United States and requires occasional travel.

Own inbound mid-market sales from qualification through close. Research product-qualified opportunities, conduct customer discovery, lead technical product demos, navigate security and procurement reviews, negotiate terms, and close B2B software deals. The role requires technical understanding of data models, APIs, permissions, integrations, ERP and CRM workflows, plus familiarity with enterprise buying requirements including SOC 2, DPAs, and GDPR.

Generates new mid-market sales for corporate travel management solutions through prospecting, consultative discovery, presentations, technology demonstrations, proposal development, contracting, and pipeline management. Builds relationships with C-level executives, CFOs, procurement leaders, travel managers, partners, and internal stakeholders. Tracks new accounts through implementation and activation while achieving sales, transaction, and KPI targets. Up to 50% travel is required within the assigned territory.

Manage the full sales cycle focusing on mid-market corporations and law firms, build strong relationships, deliver product demos, and collaborate with cross-functional teams.

Acquire new business within an assigned territory by prospecting, building executive relationships, developing account strategies, managing complex sales cycles, and closing cybersecurity and InfoSec solution deals. The role requires pipeline development, competitive positioning, pricing and contract negotiations, forecasting, CRM management, and consistently achieving sales quotas while engaging senior security and IT stakeholders.

Acquire new business within an assigned territory by prospecting, building executive relationships, developing account penetration strategies, managing complex sales cycles, positioning cybersecurity solutions, negotiating contracts, and maintaining accurate pipeline forecasts. The role targets senior security and IT leaders, requires quota attainment, and involves selling cybersecurity, SaaS, or enterprise technology solutions in a fast-paced environment.

Manage and grow a portfolio of Mid-Market advisor, asset management, and institutional clients. Serve as primary contact, drive retention and expansion, own full sales cycle, deliver revenue and retention targets, conduct client meetings and demos, partner with cross-functional teams to drive adoption and forecasting.

Source and close complex, multi-location retail technology deals across grocery, liquor, and convenience operators. Build pipeline, conduct executive discovery, demonstrate platform value, structure and negotiate deals, manage lengthy buying cycles, and ensure implementation handoffs. The role also develops repeatable sales processes, partners cross-functionally on product and commercial gaps, maintains Salesforce pipeline discipline, and represents retailer needs in product decisions.

Source and close complex, multi-location retail technology deals across grocery, liquor, and convenience operators. Build pipeline, conduct executive discovery, deliver value-based demonstrations, structure and negotiate deals, manage multi-stakeholder sales cycles, and own contracts through close. Partner cross-functionally on implementations, product feedback, and repeatable sales processes while maintaining Salesforce discipline, forecasting accuracy, and long-term revenue quality. This remote role requires 30% or more travel.