Account Executive, Enterprise Sales (Chicago)

iCOUNTER • Chicago, IL

13h • Remote

About The Position

iCOUNTER is hiring an Account Executive to drive new business and expand relationships within enterprise and commercial accounts, focused on cybersecurity and threat intelligence solutions. This is a full-cycle sales role involving consultative selling, relationship-building across organizational levels, and managing complex, high-stakes deals. The position is remote for candidates residing in Chicago or the Great Lakes region.

The Account Executive will represent iCOUNTER’s AI-native Counter Threat Operating System (CTOS™), which combines threat intelligence, risk determination, and operational response to help organizations identify and act on threats across extended business ecosystems. The role works cross-functionally with sales engineers, product specialists, threat intelligence subject-matter experts, and integration partners, and represents the company in the security community.

Requirements

• At least 5 years of enterprise sales experience, with a demonstrated record of consistent quota attainment and successful new business development in competitive, complex enterprise environments.
• Proven success managing complex, multi-threaded enterprise deals with extended sales cycles, multiple stakeholders, and competitive RFP or evaluation processes.
• Executive-level relationships and the ability to identify, map, and engage C-level security decision-makers and buyers.
• Ability to understand customers’ security posture, threat landscape, and business drivers, and tailor solutions to customer outcomes.
• Fluency in security operations, threat detection, compliance frameworks, and the role of threat intelligence in the broader security stack.
• Experience working with security integrators, MSSPs, resellers, and technology partners, and the ability to collaborate and position for mutual success.
• Excellent interpersonal, presentation, and written communication skills.
• Ability to operate independently while collaborating effectively across functions.
• Completion of a background check is required.

Nice To Haves

• Active participation or demonstrated involvement in the security community, such as ISSA, ISACA, or local chapters.

Responsibilities

• Own the full enterprise sales cycle, from initial qualification through contract closure, and manage complex, multi-stakeholder deals with forecast accuracy and consistency.
• Build and maintain trusted relationships with C-level security and risk executives, technical sponsors, and procurement and legal stakeholders through extended evaluation and procurement cycles.
• Drive new business development through strategic prospecting, account planning, and executive-level business case development aligned with the go-to-market strategy and customer security priorities.
• Navigate enterprise procurement processes, including security and compliance reviews, vendor evaluations, legal negotiations, and consensus-building across Security, IT, Procurement, and Risk teams.
• Collaborate with sales engineers, product specialists, threat intelligence subject-matter experts, and integration partners to position iCOUNTER’s value and deliver tailored solutions in competitive evaluations.
• Maintain disciplined pipeline management, including quarterly forecasting, activity tracking, and deal staging in Salesforce, with consistent accuracy and predictability.
• Represent the company in security community chapters and build a thought leadership presence in the threat intelligence and security operations ecosystem.

Benefits

• Full health, dental, and vision coverage, with 100% of employee premiums and 90% of dependent premiums covered on base plans.
• 401(k), HSA, and FSA plans.
• Flexible PTO.
• Meaningful equity ownership.
• Company holidays and paid sick days.
• Monthly home-office stipend for internet, equipment, or other technology needs.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed