CalypsoAI, acquired by F5, is seeking an experienced Enterprise Account Executive / Product Specialist to support its mission of enabling enterprises to securely and responsibly adopt Generative AI. As part of F5, CalypsoAI is a foundational component of F5's AI security strategy, helping global organizations deploy LLMs and AI-powered applications with confidence.

In this role, you will act as a subject-matter expert and product specialist for CalypsoAI's AI security platform, working alongside F5 enterprise sales teams to drive adoption across strategic and global accounts. You will engage senior stakeholders across security, risk, and technology functions, clearly articulating how CalypsoAI delivers trustworthy AI at enterprise scale.

The ideal candidate brings a strong background in enterprise software sales, excels in complex, consultative deal cycles, and has a meaningful understanding of cybersecurity and enterprise security buying motions.

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. CalypsoAI is at the forefront of this market.

What You'll Do

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 (CISO, CIO, CTO, AI/ML leaders, Risk & Compliance)
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 GTM strategy

What You Bring

5+ years of experience in enterprise software sales, ideally in cybersecurity, infrastructure, or AI-related solutions
Background in cybersecurity or selling security solutions is a 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 the 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

The Job Description is intended to be a general representation of the responsibilities and requirements of the job. However, the description may not be all-inclusive, and responsibilities and requirements are subject to change.

Please note that F5 only contacts candidates through F5 email address (ending with @f5.com) or auto email notification from Workday (ending with f5.com or @myworkday.com).

Equal Employment Opportunity

It is the policy of F5 to provide equal employment opportunities to all employees and employment applicants without regard to unlawful considerations of race, religion, color, national origin, sex, sexual orientation, gender identity or expression, age, sensory, physical, or mental disability, marital status, veteran or military status, genetic information, or any other classification protected by applicable local, state, or federal laws. This policy applies to all aspects of employment, including, but not limited to, hiring, job assignment, compensation, promotion, benefits, training, discipline, and termination. F5 offers a variety of reasonable accommodations for candidates. Requesting an accommodation is completely voluntary. F5 will assess the need for accommodations in the application process separately from those that may be needed to perform the job. Request by contacting [HIDDEN TEXT].

Enterprise Sales Executive - AI Security