Enterprise Account Executive / Product Specialist

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 on the field 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 & sales 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

Co-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

Work with BDR teams to help convert inbound enterprise demand into closed new business

Collaborate with field sales teams to provide insights in order to 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

10+ yearsof demonstrated success in enterprise software/technology sales and account management, including4+ years in a specialized overlay / subject matter expert (SME) roleco-selling alongside core sales teams.

Strong domain expertise in AI:Proven understanding ofGenerative AI architectures and fundamentals, paired with practical knowledge ofAI Security concepts(e.g., AI Gateway/Guardrails, LLM vulnerability management, prompt injection defenses, model governance, and compliance).

Cross-functional leadership:Track record of driving complex sales cycles, educating field sales teams, and engaging technical leadership (CISOs, CIOs, Chief AI Officers) on AI risk and security posture.

This role requires approximately50% regional travel across Latin Americato support strategic customer meetings, field sales alignment, and regional events.

Proven success selling complex, high-value solutions into large enterprise environments in Latin America

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

You should be fluent in Spanish and English. Portuguese is a plus.

Reside in Mexico, Colombia, Chile or Brazil

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

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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 accommodations@f5.com.