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 

• 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 

• 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 

Why Join Us 

• Play a key role in shaping F5’s AI security portfolio following the CalypsoAI acquisition 

• Work at the intersection of cutting-edge AI innovation and global enterprise adoption 

• Engage with some of the world’s largest and most sophisticated enterprise customers 

• Join a high-caliber team operating in a fast-growth, strategically critical market 

• Benefit from the reach, resources, and stability of F5 combined with the innovation and expertise of CalypsoAI 

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.

F5 maintains broad salary ranges for its roles in order to account for variations in knowledge, skills, experience, geographic locations, and market conditions, as well as to reflect F5’s differing products, industries, and lines of business. The pay range referenced is as of the time of the job posting and is subject to change.

You may also be offered incentive compensation, bonus, restricted stock units, and benefits. More details about F5’s benefits can be found at the following link: https://www.f5.com/company/careers/benefits. F5 reserves the right to change or terminate any benefit plan without notice. 

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).