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F5, through its acquired CalypsoAI division, is seeking an experienced Enterprise Account Executive to drive adoption of its AI security platform among enterprise customers. CalypsoAI provides foundational AI security capabilities that help global organizations deploy large language models and AI-powered applications with confidence and compliance.
In this role, you will serve as a subject-matter expert and product specialist for CalypsoAI's AI security platform, working alongside F5's enterprise sales teams to drive adoption across strategic and global accounts. You will engage senior stakeholders across security, risk, and technology functions, articulating how CalypsoAI delivers trustworthy AI at enterprise scale.
Key responsibilities include:
- Own the full sales cycle from prospecting and discovery through evaluation, negotiation, and close within named financial services accounts
- Build and execute territory and account plans targeting CIO, CISO, CRO, CDO, and heads of fraud, risk, compliance, and AI/innovation
- Drive new logo acquisition with a hunter mindset, building self-generated pipeline through outbound, events, partners, 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 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
- Engage C-level and senior stakeholders (CISO, CIO, CTO, AI/ML leaders, risk & compliance)
- Translate technical capabilities into compelling business, security, and risk outcomes
- Lead tailored product demonstrations, executive presentations, and proof-of-value engagements
- 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
This is a unique opportunity to combine the innovation and speed of an AI-native security company with the scale, reach, and market leadership of F5. As LLMs drive the next major platform shift in enterprise software, entirely new AI-driven threat vectors are emerging—creating an urgent need for purpose-built AI security.
REQUIREMENTS:
- 10+ years of experience in enterprise software sales, ideally in cybersecurity, infrastructure, or AI-related solutions
- Background in cybersecurity or selling security solutions (strong advantage), 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 (MEDDIC, Command of the Message preferred)
- Ability to operate effectively in fast-paced, evolving environments while navigating enterprise-scale processes
- Familiarity with LinkedIn Sales Navigator, HubSpot, and modern enterprise sales technology stacks
- Excellent communication skills with ability to influence both technical and executive audiences
- Comfortable working to targets and managing pressure with professionalism and integrity
- Prior startup, scale-up, or post-acquisition integration experience is a plus
- Strong interest in AI, cybersecurity, and emerging enterprise technologies; knowledge of Generative AI and LLM ecosystems is a strong advantage
