Strategic Enterprise Cybersecurity Sales Executive

Cengage Group; Chicago (IL); Remote; USD 83,000 - 100,000; Full time

Job summary

Cengage Group is seeking an experienced Enterprise Sales professional to lead new business in large, strategic accounts across the United States. You will build a robust pipeline, engage CISO/CIO/CTO discussions, and manage multi-stakeholder cycles from prospecting to close.

The role emphasizes solution selling in InfoSec, navigating complex deals, and aligning pricing and contracts with company guidelines in a fast-paced environment.

Qualifications

• Over 3 years of experience in B2B sales.
• Experience selling cybersecurity, SaaS, or enterprise technology solutions preferred.
• Experience engaging and influencing senior collaborators, including C-level executives (CISO, CIO, CTO).
• Strong understanding of complex sales cycles and ability to manage multiple opportunities simultaneously.
• Demonstrated ability to meet or exceed sales quotas in a high-growth environment.
• Excellent communication, negotiation, and presentation skills.
• Experience with CRM tools (e.g., Salesforce) and sales engagement platforms.
• Bachelor’s degree or equivalent experience preferred.

Responsibilities

• Take charge of new business acquisition within the enterprise territory (2,000+ employees).
• Develop and complete account penetration strategies to break into net-new organizations and expand market presence.
• Build and manage a robust pipeline of high-value opportunities through proactive prospecting.
• Identify and engage key collaborators, including CISO, CIO, CTO, and other senior IT leaders.
• Lead complex, multi-stakeholder sales cycles from initial engagement through negotiation and close.
• Position and articulate the value of InfoSec solutions in the context of business risk, compliance, and organizational resilience.
• Drive deal strategy, including competitive positioning, pricing, and contract negotiations in alignment with company guidelines.
• Maintain accurate pipeline management and forecasting, with clear access to deal progression and risk.
• Self-motivated, dedicated, independent thinker, resilient, and comfortable operating in a fast-paced, determined environment.

Skills

New business acquisition

Enterprise software sales

Executive engagement

Complex sales cycles

Quota attainment

Communication & negotiation

Salesforce

Education

Bachelor’s degree or equivalent experience

Tools

Salesforce

Job description

Cengage Group is seeking an experienced Enterprise Sales professional to lead new business in large, strategic accounts across the United States. You will build a robust pipeline, engage CISO/CIO/CTO discussions, and manage multi-stakeholder cycles from prospecting to close.

The role emphasizes solution selling in InfoSec, navigating complex deals, and aligning pricing and contracts with company guidelines in a fast-paced environment.