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RevPilots

Enterprise Account Executive

RevPilots, Chicago, Illinois, United States

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Overview Connecting companies with full time vetted sales, marketing, and CS talent. This role is for RevPilots' client.

Location Chicago, IL (Central Region Coverage)

About Our Client Our client is a publicly traded leader in artificial intelligence solutions, specializing in Generative AI, multi-agent orchestration, AI readiness, governance, and advisory services for enterprise and regulated industries. They are positioned to help organizations securely, scalably, and profitably integrate AI into mission-critical operations, delivering measurable business impact and competitive advantage.

Position Overview Our client is seeking a high-performing Enterprise Account Executive to drive new business acquisition across multiple industries in the Central United States. Based in Chicago, IL, this is a hunter role designed for top performers who excel at winning new logos and building executive relationships. The Account Executive will focus on industries such as healthcare & life sciences, financial services, manufacturing, logistics, retail/CPG, energy & utilities, telco, public sector, and technology/media. You will leverage GTM automation and agentic AI sales workflows to accelerate prospecting, qualification, and customer onboarding—while applying advanced enterprise selling methodologies to close high-value, complex deals.

Key Responsibilities

Drive new customer acquisition across multiple industries in the Central U.S., securing new logos and strategic relationships.

Generate pipeline and immediate revenue using your existing network and targeted outbound prospecting.

Leverage AI-driven sales tools for contact harvesting, ICP definition, buyer personas, USPs, automated outreach, and sales process acceleration.

Manage the full enterprise sales cycle—from discovery and qualification to solution design, ROI business case, negotiation, and close.

Apply advanced sales methodologies: MEDDIC, Miller Heiman, Challenger Sale, SPIN.

Collaborate with Sales Engineering, Product, Marketing, and Delivery to design and present tailored Agentic AI solutions and workflows (e.g., operations optimization, customer experience, analytics, compliance, automation).

Build and expand relationships with executives including CEO, President, CIO, CTO, CDO, CAIO, CFO, COO, CISO, and Heads of AI/Data/Security.

Partner with channel and alliance partners, identifying opportunities and executing joint selling activities.

Achieve and exceed metrics for SQLs, SQOs, pipeline coverage, and closed revenue.

Represent our client at industry events, AI summits, and executive forums across the Central region.

Qualifications Required

Bachelor's degree in Business (Finance, Economics, Marketing) or Computer Science, Electrical Engineering, Data Science with deep technical understanding of AI, ML, Data, Cloud, Systems, and Programming.

Multiple AI-focused certifications (business, legal/ethical, security, compliance).

10+ years of enterprise B2B software sales with consistent quota attainment in complex, multi-stakeholder sales cycles.

Proven success selling AI, data, or cloud solutions into multiple industries (healthcare, financial services, manufacturing, logistics, retail, energy, telco, public sector, media/tech).

Expertise in software licensing, commercial structuring, negotiation, and closing.

Practitioner-level proficiency in MEDDIC, Miller Heiman, Challenger Sale, and SPIN.

Strong executive presence, communication, and consultative selling skills.

Preferred

Master's degree in a technical or business discipline.

Track record of closing $1M+ enterprise deals (ARR/TCV) in AI, data, or cloud software.

Established relationships with senior leaders across Central U.S. enterprises and partner ecosystems.

Compensation Benefits: Health + Other Benefits; Equity

What We Offer

Competitive Compensation – Strong base salary plus commission plan.

Cutting-Edge Sales Enablement – Access to GTM automation, AI sales acceleration platforms, and agentic AI tools.

Immediate Market Impact – Join at a pivotal growth stage, win new logos, and shape AI adoption across multiple industries.

Career Growth & Visibility – Work directly with the Chief Revenue Officer, gaining exposure and advancement opportunities in a global, market-shaping company.

Seniority level

Mid-Senior level

Employment type

Full-time

Job function

Sales and Business Development

Industries

Technology, Information and Internet, IT Services and IT Consulting, and Software Development

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