Enterprise Account Executive - Cybersecurity Services

What You’ll Do

• Own a defined territory and develop a strategy for generating net-new enterprise business.
• Build qualified pipeline through outbound prospecting, executive networking, referrals, partnerships, events, and territory development.
• Identify and open new relationships with CISOs, CIOs, CTOs, security leaders, compliance leaders, and other executive stakeholders.
• Sell cybersecurity consulting, penetration testing, offensive security, managed security services, MDR, incident response, compliance, risk management, vCISO, assessments, and related services.
• Lead the complete sales cycle from prospecting and qualification through discovery, proposal development, negotiation, and close.
• Conduct consultative discovery conversations focused on security risk, compliance requirements, business impact, and desired outcomes.
• Work with RedLegg’s consultants and technical teams to develop solutions aligned with client needs.
• Build and maintain a consistent pipeline of qualified opportunities.
• Maintain accurate opportunity, pipeline, and forecasting information in the CRM.
• Meet or exceed assigned revenue and sales targets.
• Stay current on cybersecurity threats, industry developments, competitive offerings, and enterprise security priorities.

Required Qualifications

• At least five years of quota-carrying B2B sales experience, including recent cybersecurity sales experience.
• Recent experience selling cybersecurity services, MSSP, MDR, penetration testing, offensive security, incident response, compliance, assessments, advisory services, or security consulting.
• Demonstrated success generating self-sourced pipeline through outbound activity and territory development.
• Proven record of acquiring net-new customers and closing new-logo business.
• Experience owning and developing a sales territory.
• History of meeting or exceeding individual sales quotas.
• Experience managing complex, consultative enterprise sales cycles.
• Ability to communicate cybersecurity services in terms of business risk, operational impact, and measurable outcomes.
• Experience engaging CISOs, CIOs, security leaders, compliance leaders, and executive buyers.
• Strong discovery, presentation, negotiation, forecasting, and closing skills.
• Self-directed and comfortable operating in a remote sales environment.
• Authorization to work in the United States without current or future employer-sponsored visa support.

Preferred Experience

• Experience selling penetration testing or offensive security services.
• Experience selling managed security services, MSSP, MDR, incident response, vCISO, or security consulting engagements.
• Experience selling compliance, risk, or assessment services.
• Experience working with highly regulated industries.
• Existing relationships within enterprise cybersecurity organizations.
• Experience developing opportunities through channel partners, technology alliances, referrals, and executive networks.
• Familiarity with enterprise cybersecurity buying cycles, statements of work, and services-based proposals.

What Success Looks Like

Success in this role requires the ability to:

• Create opportunities rather than depend primarily on inbound leads.
• Establish relationships within new enterprise accounts.
• Build a repeatable and measurable outbound pipeline.
• Maintain disciplined follow-up and accurate forecasting.
• Navigate technical and executive stakeholders.
• Convert cybersecurity needs into professionally scoped opportunities.
• Close net-new cybersecurity services business.

Why Join RedLegg

• Sell a broad portfolio of cybersecurity services addressing real business, risk, and compliance needs.
• Work directly with experienced cybersecurity consultants and technical specialists.
• Represent a veteran-owned cybersecurity services organization established in 2008.
• Operate with meaningful ownership of your territory and sales process.
• Receive ongoing sales and cybersecurity enablement through RedLegg University.
• Join a remote team focused on expertise, transparency, and trusted client partnerships.

Compensation and Benefits

• Performance-based commission plan
• Full benefits package
• Gym reimbursement
• Ongoing sales and cybersecurity training
• Remote work within the United States