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About the Role

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. This role is a foundational component of F5’s AI security strategy, helping global organizations deploy LLMs and AI-powered applications with confidence. 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.

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

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
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

Skills

Generative AI
LLM
Cybersecurity
Enterprise Security
Enterprise Software Sales
Product Specialist
Sales
Communication
Consultative Selling
Value-based Selling
MEDDIC
Command of the Message
LinkedIn Sales Navigator
HubSpot

Location

Remote

Work Type

Full-time

Experience Level

4+ years of experience in enterprise software sales

Benefits

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

About the Company

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.
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.

Equal 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.