Account Executive, Enterprise Sales (Chicago)

About iCOUNTER

iCOUNTER is redefining how enterprises defend against cyber threats originating across their extended business ecosystems.

Our AI-native Counter Threat Operating System (CTOS™) combines threat intelligence, risk determination, and operational response to help organizations identify and act on threats involving third parties, subsidiaries, portfolio companies, and interconnected business relationships.

We believe enterprises need to move beyond traditional risk assessments and static security scores toward intelligence-led, proactive defense.

We’re building a new category of cybersecurity, and we’re looking for exceptional talent to help us bring it to market.

Position Overview

We are looking for a driven and experienced Account Executive to join our growing team. In this role, you will be responsible for driving new business and expanding relationships within enterprise and commercial accounts, with a focus on cybersecurity and threat intelligence solutions.

This is a full-cycle sales role for someone who thrives in a consultative environment, builds lasting relationships at every level of an organization, and brings both the discipline and the emotional intelligence to navigate complex, high-stakes deals. If you are passionate about the security community and want to represent a company that genuinely puts customers first, we want to hear from you.

This is a remote role with candidates residing within Chicago or the Great Lakes region.

Key Responsibilities

• Own the full enterprise sales cycle from initial qualification through contract closure, managing complex, multi-stakeholder deals with enterprise-level forecast accuracy and consistency.

• Build and maintain trusted relationships with C-level security/risk executives (CISO, VP Security, Chief Risk Officer), technical sponsors (security engineers, architects), and procurement/legal stakeholders throughout extended evaluation and procurement cycles.

• Drive new business development through strategic prospecting, account planning, and executive-level business case development aligned with our go-to-market strategy and customer security priorities.

• Navigate complex enterprise procurement processes, including security/compliance reviews, vendor evaluations, legal negotiations, and multi-department consensus-building across Security, IT, Procurement, and Risk teams.

• Collaborate effectively with sales engineers, product specialists, threat intel SMEs, and integration partners to position our differentiated value in competitive evaluations and deliver tailored solutions.

• Maintain disciplined pipeline management with quarterly forecasting, activity tracking, and deal staging within Salesforce, demonstrating consistent accuracy and predictability for leadership.

• Actively represent the company within security community chapters and build thought leadership presence in the threat intelligence/security operations ecosystem.

Required Skills

• 5+ years of enterprise sales experience with demonstrated track record of consistent quota attainment and successful new business development within competitive, complex enterprise environments

• Proven success managing complex, multi-threaded enterprise deals with extended sales cycles, multiple stakeholders, and competitive RFP/evaluation processes

• Executive level relationships with ability to identify, map, and engage security decision makers and buyers at the C-level

• Ability to understand customer security posture, threat landscape, and business drivers; tailoring solutions to customer outcomes

• Fluency in security operations, threat detection, compliance frameworks, and how threat intelligence fits into broader security stack

• Experience working alongside security integrators, MSSPs, resellers, and technology partners; ability to collaborate and position for mutual success

Additional Qualifications

• Excellent interpersonal, presentation, and written communication skills

• Ability to operate independently while collaborating effectively cross-functionally

• Active participation or demonstrated involvement in the security community (e.g., ISSA, ISACA, local chapters) is strongly preferred

Benefits & Perks:

• Full Health, Dental, & Vision Coverage, with 100% employee premiums covered and 90% dependent premiums covered on base plans

• 401(k), HSA, & FSA Plans

• Flexible PTO

• Meaningful equity ownership

• Company Holidays & Paid Sick Days

• Monthly home-office stipend for internet, equipment, or other technology needs

iCOUNTER is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability or veteran status, or any other applicable state or federal protected class. iCOUNTER provides affirmative action in employment for qualified Individuals with a Disability and Protected Veterans in compliance with Section 503 of the Rehabilitation Act and the Vietnam Era Veterans’ Readjustment Assistance Act.

Accommodation: If you need accommodations, reach out to accommodations@icounter.com.

Completion of a Background Check is required for employment at iCOUNTER