Top Mid-Market Account Executive Jobs in Chicago, IL

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.

Lead a team of Mid-Market Account Executives through coaching, mentoring, hiring, performance management, pipeline reviews, forecasting, and customer call support. Establish performance expectations, improve sales processes, expand outbound programs, remove operational obstacles, and provide reporting on team performance and strategic initiatives. The role requires sales leadership experience in SaaS or B2B organizations, strong analytical skills, and a track record of developing high-performing representatives.

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.

Acquire and grow mid-market customers for AI-powered customer experience, contact center, unified communications, and business communication solutions. Generate pipeline through prospecting, referrals, networking, partners, and inbound opportunities; manage complex multi-stakeholder sales cycles; conduct consultative discovery; develop account plans; present solutions; maintain CRM data and forecasts; use AI-enabled sales tools and analytics; and collaborate with marketing, partners, solution consultants, customer success, and product teams.

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

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.

Own enterprise healthcare sales from prospecting through contract execution. Generate new-logo pipeline, lead consultative presentations, manage complex stakeholder-driven sales cycles, build executive relationships, coordinate cross-functional deal teams, maintain accurate CRM forecasts, and achieve sales targets for healthcare payment technology solutions.

As an Account Executive for Mid-Market Non-Profit Clients, you'll align Salesforce capabilities with client needs, generate revenue, and enhance social impact through strategic partnerships.

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.

Manage and renew an assigned mid-market client portfolio while increasing revenue through upselling services and fees. The role requires forecasting sales, completing Salesforce tasks, scoping cybersecurity compliance services, and maintaining strong relationships with clients, partners, and the service delivery team. Account Executives communicate client needs internally, conduct outreach through phone and internet channels, and participate in client site visits and industry trade shows.

Own a strategic Mid-Market territory and drive new-business and expansion revenue through account strategy, consultative selling, executive engagement, and complex deal execution. Responsibilities include territory planning, pipeline generation, forecasting, multi-threaded stakeholder management, value-based discovery, business-case development, procurement navigation, CRM discipline, and identifying expansion opportunities. The role also mentors peers, raises sales standards, and partners cross-functionally to improve win rates and deal velocity.

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%.

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.

Lead and scale the U.S. Mid-Market AE organization: define GTM strategy, set quotas and territories, recruit and coach AEs, own pipeline health and forecasting, develop sales playbooks for voice AI/API solutions, and partner cross-functionally to align positioning and drive expansion.

The role involves managing a portfolio of accounts, identifying new business opportunities, and maintaining knowledge of conversational AI to help meet revenue goals.

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.

As a Senior Account Executive, you will manage the entire sales cycle targeting mid-market customers, prospecting, closing deals, and collaborating with marketing to accelerate revenue growth.

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.

Own mid-market provider segment (100+ employee healthcare orgs). Self-source and manage pipeline, lead consultative discovery, close deals $5K–$75K, hand off to Customer Success, maintain HubSpot, track territory performance, and stay current on product, competitors, and regulations.

Quota-carrying Mid-Market Account Executive selling DIDOS invoice-matching SaaS to UK & Ireland retailers. Own full sales cycle from prospecting and demos to negotiation and close, build C-suite and functional relationships, expand accounts with ERP integrations and analytics, manage pipeline, and collaborate with product and engineering.