Top Mid-Market Account Executive Jobs in Chicago, IL

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.

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.

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.

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.

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.

Drive Superhuman Mail’s mid-market expansion through value-based B2B SaaS sales. Responsibilities include managing complex, multi-stakeholder deal cycles, negotiating contracts, building executive relationships, developing outbound strategies and account plans, forecasting, maintaining pipeline rigor, and collaborating with Sales Development, Customer Success, Sales Engineering, and Product teams.

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 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.

Manage the full sales cycle for mid-market HR technology prospects, from prospecting and relationship development through product demonstrations, negotiation, and closing. Build outbound pipeline, engage decision-makers, assess buying timelines, forecast accurately, and achieve revenue targets. Maintain sales data and metrics in Salesforce CRM while collaborating with Sales Engineers and Business Development representatives. Attend industry events and network with influencers, consultants, and partners.

Manage the full sales cycle for mid-market HR technology customers, from prospecting and relationship development through product demonstrations, pipeline generation, negotiation, and closing. Build relationships with decision-makers, forecast accurately, achieve revenue targets, maintain sales metrics in Salesforce, and collaborate with Sales Engineers and Business Development representatives. The role also involves networking with consultants and partners and attending trade shows, events, and conferences.

Own a portfolio of mid-market app customers and prospects in a value-led, product-led sales motion. Generate outbound pipeline, run discovery and demos, advise on mobile monetization and paywall optimization, represent RevenueCat at events, and collaborate with Sales Engineering and Customer Success to drive product adoption and revenue growth.

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.

The Account Executive will drive sales of IoT solutions to mid-sized customers through research, cold calls, and relationship building, focusing on 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.

The Account Executive will drive sales by building relationships with mid-market customers, managing trials, and executing complex negotiations while achieving sales quotas.

Manage full sales cycle for mid-market public sector accounts: prospect, qualify, run POCs, negotiate multi-stakeholder deals ($20k–$250k), build executive relationships, forecast in SFDC, and close business while traveling for onsite meetings.

The Account Executive for Mid Market is responsible for driving sales by engaging mid-sized customers, managing trials, and closing deals ranging from $20k to $100k, while traveling approximately 25% of the time.

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.

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.

Own the full sales cycle selling Google Cloud professional services, AI/ML solutions, and managed engagements to mid-market and enterprise clients across North America. Build pipeline, exceed quota, act as a trusted advisor to technical and executive buyers, collaborate with Google field teams, and align solutions to client business challenges.

The Growth Account Executive will sell SentiLink solutions to Fintech companies, managing relationships and navigating complex organizations to close deals and ensure partner success.

Drive adoption of LangChain products by sourcing, qualifying, and closing outbound mid-market deals. Build relationships with technical teams, help customers discover and evaluate AI solutions, and support their adoption. Work collaboratively with sales, engineering, and customer success teams in a fast-paced environment while developing expertise in generative AI technology and customer businesses.

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.