Enterprise AI Security Account Executive

F5; Illinois; On-site; USD 133,000 - 199,000; Full time

Benefits offered by this job

Health insurance

Wellness program

PTO

401(k)

Job summary

F5, in partnership with CalypsoAI, seeks an experienced Enterprise Account Executive / Product Specialist to drive AI security solutions across strategic accounts. You will engage senior security, risk, and technology leaders, translating CalypsoAI capabilities into enterprise-grade business value.

You will own complex, multi‑stakeholder deals, build executive relationships, and collaborate with F5 sales teams to expand revenue. Strong cybersecurity and AI domain knowledge is essential.

Qualifications

• 5+ years of experience in enterprise software sales, ideally in cybersecurity, infrastructure, or AI-related solutions.
• Background in cybersecurity or selling security solutions is strongly preferred, particularly experience engaging with CISOs, security architects, and risk teams.
• Proven success selling complex, high-value solutions into large enterprise environments.
• Experience operating as a product-focused seller or overlay specialist in partnership with core account teams.
• Strong experience engaging senior decision-makers within large, matrixed organizations.
• Solid grounding in qualification and value-based selling methodologies such as MEDDIC and Command of the Message.

Responsibilities

• Own the full sales cycle from prospecting to close within named financial services accounts.
• Build territory and account plans targeting CIOs, CISOs, CROs, CDOs, Heads of Fraud/Risk, Compliance leaders, and AI/Innovation stakeholders.
• Drive new logo acquisition with a hunter mindset, building a self-generated pipeline through outbound prospecting, events, partner relationships, and executive networking.
• Lead complex sales cycles involving security, AI, data, and risk stakeholders, aligning technical capabilities with regulatory, risk, and business-value outcomes.
• Serve as a CalypsoAI product specialist within F5's enterprise go-to-market organization.
• Partner closely with F5 enterprise account teams to drive new revenue and expand existing customer relationships.
• Own and influence complex enterprise sales cycles from discovery and technical validation through negotiation and close.
• Engage C-level and senior stakeholders, including CISOs, CIOs, CTOs, AI/ML leaders, and Risk & Compliance executives.
• Translate CalypsoAI's technical capabilities into compelling business, security, and risk outcomes.
• Lead tailored product demonstrations, executive presentations, and proof-of-value engagements.
• Convert inbound enterprise demand into closed new business.
• Manage pipeline, forecasting, and deal strategy while helping mature the enterprise sales playbook.
• Capture customer feedback and market insights to influence product roadmap and go-to-market strategy.

Skills

Enterprise software sales

CISO engagement

Complex sales cycles

Executive communication

Quota attainment

Strategic thinking

Tools

LinkedIn Sales Navigator

HubSpot

Job description

F5, in partnership with CalypsoAI, seeks an experienced Enterprise Account Executive / Product Specialist to drive AI security solutions across strategic accounts. You will engage senior security, risk, and technology leaders, translating CalypsoAI capabilities into enterprise-grade business value.

You will own complex, multi‑stakeholder deals, build executive relationships, and collaborate with F5 sales teams to expand revenue. Strong cybersecurity and AI domain knowledge is essential.