Enterprise Account Executive

F5

8d • $124,000 - $186,000 • Hybrid

About The Position

At F5, we strive to bring a better digital world to life. Our teams empower organizations across the globe to create, secure, and run applications that enhance how we experience our evolving digital world. We are passionate about cybersecurity, from protecting consumers from fraud to enabling companies to focus on innovation. Everything we do centers around people. That means we obsess over how to make the lives of our customers, and their customers, better. And it means we prioritize a diverse F5 community where each individual can thrive. 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.

Requirements

• 4+ 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

Nice To Haves

• 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

Responsibilities

• 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 This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees