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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. 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.
Responsibilities
- Own the full sales cycle from prospecting, discovery and business case development through evaluation, negotiation and close within named financial services accounts.
- Build and execute territory and account plans targeting CIO, CISO, CRO, CDO, Heads of Fraud/Risk, Compliance and AI/Innovation leaders.
- Drive new logo acquisition with a clear hunter mindset, building a self-generated pipeline through outbound, events, partners and executive networking.
- Lead complex sales cycles involving security, AI, data and risk stakeholders, aligning technical capabilities with regulatory, risk and business-value outcomes.
- 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
- 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.
Skills
- Enterprise software sales
- Cybersecurity
- Infrastructure
- AI-related solutions
- Selling security solutions
- Engaging with CISOs
- Engaging with security architects
- Engaging with risk teams
- Complex sales cycles
- Value-based selling
- MEDDIC
- Command of the Message
- LinkedIn Sales Navigator
- HubSpot
- Generative AI
- LLM ecosystems
Location
- Remote
Work Type
- Full-time
Experience Level
- 5+ years of experience in enterprise software sales
Salary/Compensations
- Base pay: $132,500-$198,700
- OTE: $264,900-$397,300 or more
- 50/50 pay mix (base/commission)
Benefits
- Health
- Wellness
- PTO
- 401(k)
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.
- CalypsoAI is at the forefront of the AI security market, addressing the urgent need for purpose-built AI security as LLMs drive the next major platform shift in enterprise software and create new AI-driven threat vectors.
- 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.
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.