Generative AI Security: Enterprise Account Executive

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

Job summary

F5, integrating CalypsoAI, seeks an experienced Enterprise Account Executive / Product Specialist to drive adoption of CalypsoAI’s AI security platform across named enterprise accounts. You will engage security, risk, and technology leaders, articulating how CalypsoAI enables trustworthy AI at enterprise scale.

You will lead complex, high-value deals, partner with F5 enterprise teams, and develop a self-generated pipeline through outbound efforts and executive networking.

Qualifications

• 5+ years of experience in enterprise software sales in cybersecurity, infrastructure, or AI-related solutions.
• Experience engaging with CISOs, security architects, and risk teams.
• Proven success selling complex, high-value solutions into large enterprise environments.
• Product-focused seller or overlay specialist working with core account teams.
• Strong ability to engage senior decision-makers within large, matrixed organizations.
• Familiar with MEDDIC and value-based selling methodologies.
• Ability to operate in fast-paced, evolving environments with enterprise-scale processes.
• Experience with LinkedIn Navigator, HubSpot, and modern enterprise sales tech stacks.

Responsibilities

• Own the full sales cycle from prospecting to close within named financial services accounts.
• Build territory plans targeting CIO, CISO, CRO, CDO, heads of Fraud/Risk, Compliance and AI/Innovation leaders.
• Develop a self-generated pipeline through outbound, events, partners and executive networking.
• Lead complex sales cycles with security, AI, data and risk stakeholders to align tech with business value.
• Serve as CalypsoAI product specialist within F5’s enterprise go-to-market organization.
• Partner with F5 enterprise account teams to drive revenue and expand customer relationships.
• Manage discovery, technical validation, negotiation and close in enterprise cycles.
• Engage C-level and senior stakeholders (CISO, CIO, CTO, AI/ML leaders, Risk & Compliance).
• Translate CalypsoAI’s capabilities into business, security and risk outcomes.
• Lead product demos, executive presentations and value engagements.
• Convert inbound enterprise demand into new business.
• Manage pipeline, forecasting and deal strategy; contribute to the enterprise sales playbook.
• Capture customer feedback to influence product roadmap and GTM strategy.

Skills

Enterprise sales

Security sales

CISO engagement

MEDDIC

Stakeholder management

Tools

LinkedIn Navigator

HubSpot

CRM tools

Job description

F5, integrating CalypsoAI, seeks an experienced Enterprise Account Executive / Product Specialist to drive adoption of CalypsoAI’s AI security platform across named enterprise accounts. You will engage security, risk, and technology leaders, articulating how CalypsoAI enables trustworthy AI at enterprise scale.

You will lead complex, high-value deals, partner with F5 enterprise teams, and develop a self-generated pipeline through outbound efforts and executive networking.