5+ years of successful quota-carrying experience selling cybersecurity consulting or technical professional services; offensive security services strongly preferred. Demonstrated track record of exceeding annual bookings targets. Strong understanding of penetration testing methodologies, red teaming frameworks, and enterprise security needs. Exceptional consultative selling, communication, and negotiation skills. Highly self-motivated, autonomous, and comfortable in a remote-first environment. Existing network of CISOs, security leaders, or procurement contacts across the mid-Atlantic (preferred). Experience with multi-year programs, managed offensive services, or high-value red team engagements (preferred). Experience selling to or within highly regulated sectors (preferred). Experience working with or selling managed services (preferred). Ability to incorporate offensive testing insights into broader security initiatives (preferred).