Top Senior Account Executive (AE) Jobs in Chicago, IL

Drive enterprise sales for Atlassian across the East and Central regions of the Americas, working remotely with large organizational customers and supporting their business goals.

Lead enterprise sales for named accounts or territory: develop strategic account plans, build C-level relationships, negotiate complex contracts, collaborate cross-functionally, forecast and close deals, and drive expansion and customer success across Atlassian products.

The Regional Account Executive identifies and secures regional business opportunities for uniform rental and direct-sale programs. Responsibilities include achieving sales quotas, managing customer relationships, maintaining contact records, pursuing corporate accounts, monitoring contracts, improving customer margins and processes, and preparing activity and results reports. The role requires frequent communication with prospects, customers, and executives through phone, email, and in-person visits.

Drives new customer acquisition for Okta’s identity and access management solutions among SMBs. Responsibilities include prospecting, pipeline development, product demonstrations, territory and quota management, forecasting, closing new business, customer onboarding, and handoff to account executives. Requires B2B SaaS or cloud sales experience, structured sales methodology knowledge, strong presentation skills, and collaboration across marketing, SDR, sales engineering, customer success, and channel partners.

Drive new revenue within enterprise financial institution accounts, nurture BDR-generated leads, develop digital transformation and customer experience expertise, build ROI analyses, and negotiate complex contracts involving multiple stakeholders. The role requires strategic, data-driven selling, strong communication, complex sales navigation, and proficiency with advanced methodologies such as MEDDIC or Command of the Message.

Drive revenue growth across large enterprise accounts by building pipeline, achieving license, support, and services targets, and managing complex sales opportunities. Develop territory and account plans, expand executive relationships, leverage channel partners, and orchestrate cross-functional deals. The role requires enterprise software sales experience and familiarity with SaaS, cloud, security, DevOps, analytics, consultative selling, and sales methodologies.

Develops and manages digital sales opportunities for RRD’s products and solutions. Builds consultative relationships with new and existing clients, identifies revenue opportunities, creates sales strategies, supports solution implementation, and grows customer accounts. The role requires programmatic digital media sales experience, quota-carrying success, client education, forecasting, CRM proficiency, and frequent communication with internal and external stakeholders. Travel is required.

Drives net-new enterprise sales for digital media, AdTech, and MarTech solutions. Prospects and closes brand and agency accounts, manages consultative sales cycles, develops customized media strategies, and builds executive relationships. Advises clients on programmatic media, CTV, retail media, data targeting, and omnichannel campaigns. Maintains sales forecasts and CRM records while collaborating with strategy, product, operations, and internal sales teams. Requires 20–30% business travel.

Own and grow strategic enterprise accounts through consultative, value-based selling. Develop account plans, build executive relationships, identify expansion opportunities, manage complex sales cycles, negotiate high-value software and services agreements, maintain pipeline and forecasts, and lead cross-functional deal teams. The role requires consistently exceeding quotas, using CRM and sales engagement tools, applying structured sales methodologies, leveraging AI and data, and traveling up to 25%.

Owns the full enterprise sales cycle within an assigned territory, from prospecting through contract close. Develops strategic territory plans, builds relationships with executive stakeholders, manages complex sales cycles, forecasts accurately, and uses value-based selling to guide prospects through discovery, proof of concept, and purchase. Partners with business development, marketing, regional partners, and system integrators while consistently achieving sales targets.

Own full-cycle enterprise and mid-market sales for the Posh AI platform, from pipeline generation through close and implementation handoff. Sell to credit unions and banks, manage complex multi-stakeholder buying processes, build ROI-driven business cases, conduct SPICED discovery, coordinate internal teams, and maintain accurate forecasts. The role requires consultative selling, executive-level communication, and experience closing multi-month SaaS or enterprise technology deals.

Lead prospecting, consultative solution selling, and closing of new business for Twilio’s Messaging, Voice, and Email products. Own enterprise and mid-market sales cycles, develop territory strategies, manage forecasts and pipelines in Salesforce, and collaborate with product, finance, legal, pricing, operations, and engineering teams. Translate customer business and technical needs into communications API solutions while driving customer acquisition and revenue growth.

Sells digital intelligence hardware, software, and training solutions to state and local government and law enforcement agencies across the Midwest. Responsibilities include developing strategic account plans, prospecting, managing pipelines and forecasts, presenting proposals, navigating public-sector procurement, expanding existing accounts, coordinating resellers and internal teams, and representing products at industry events. The role requires enterprise technology sales expertise, law enforcement or public-sector contacts, strong product knowledge, and 40–50% travel.

Drive net-new and expansion sales for Workday Adaptive Planning. Develop account strategies, build relationships with enterprise prospects, customers, and partners, manage opportunities, connect customer needs to planning solutions, and maintain accurate pipeline and forecast data. The role requires selling cloud-based planning applications to C-level stakeholders, particularly within educational systems, managing complex sales cycles, generating leads, and demonstrating business outcomes.

Drive revenue growth through RSA’s North American channel ecosystem by building partner relationships, developing pipeline, advancing partner-led opportunities, and closing enterprise and public-sector cybersecurity deals. Collaborate with field sales and channel partners on account planning, go-to-market execution, enablement, solution positioning, and performance monitoring. Serve as a key partner sales contact while tracking market trends and competitive activity.

Manage the full sales cycle for KEV’s School Cash Suite across an assigned Texas territory, including prospecting, discovery, platform demonstrations, negotiations, and closing. Build pipeline through outbound outreach, events, and meetings; meet sales quotas; maintain customer and stakeholder relationships; collaborate with Customer Success on onboarding; represent KEV at conferences; and maintain accurate CRM reporting and forecasts. The role requires K-12 and fintech/SaaS sales experience, executive-level relationship building, and frequent regional travel.

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.

Drive sales growth for WEX Expense Management by identifying expansion opportunities within existing customers. Prospect, build pipelines, manage territories, conduct consultative discovery and presentations, maintain Salesforce records, meet sales KPIs, forecast accurately, and close business with finance and operational leaders. The role sells payment processing, virtual card issuing, and expense management solutions while competing against incumbent providers.

Sell Dataminr’s cybersecurity solutions to enterprise accounts in the TOLA territory. Responsibilities include meeting sales quotas, building pipeline through prospecting and partners, developing senior client relationships, navigating complex enterprise deals, understanding customer needs and buying processes, conducting competitive analysis, and providing product feedback to Product and Engineering teams.

Develop and close federal technology sales opportunities across civilian, defense, intelligence, and systems integrator accounts. The role manages pipelines, account plans, capture strategies, proposals, contract vehicles, negotiations, partner relationships, forecasts, and post-award transitions. It sells cybersecurity, cloud, infrastructure, managed services, and OEM solutions while coordinating cross-functional teams and meeting revenue and margin objectives.

Own end-to-end enterprise sales engagements, from strategic prospecting and qualification through complex negotiations and close. Build executive-level relationships, manage POCs and trials, sell $100,000–$500,000 solutions, and consistently exceed quota in named enterprise accounts. The role requires solution-based selling, C-level engagement, strategic outbound prospecting, and monthly customer travel while partnering with stakeholders across Operations, Finance, and IT.

Own enterprise sales cycles from prospecting through close, developing executive relationships within strategic accounts and selling Samsara’s connected operations solutions. Manage complex deals involving POCs, trials, multiple stakeholders, pricing negotiations, and C-level engagement. Consistently exceed quota on $100K+ ARR transactions, conduct strategic outbound prospecting, and travel monthly to meet customers.

Own enterprise sales cycles from prospecting through close, developing executive relationships within strategic accounts and managing complex $100,000–$500,000 deals. The role involves solution-based selling, trials, proof-of-concepts, multi-stakeholder negotiations, executive engagement, and strategic outbound prospecting. Candidates will sell Samsara’s connected operations solutions, consistently exceed quota, and travel monthly to meet customers. The position is remote for U.S.-based candidates working in the MST or PST time zones.

Own complex enterprise sales cycles for Samsara’s Connected Operations Cloud, from strategic prospecting and qualification through close. Build executive relationships, manage POCs and trials, navigate multi-stakeholder negotiations, and sell $100,000+ ARR solutions to enterprise customers. Consistently exceed quota, engage operations, finance, and IT stakeholders, and travel monthly to meet customers across the Southeast.