Enterprise Account Executive

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 combines the innovation and speed of an AI-native security company with the scale, reach, and market leadership of F5.

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.
• 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.

Qualifications

• Experience operating as a product-focused seller or overlay specialist in partnership with core account teams.
• 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 experience, preferably in cybersecurity, infrastructure, or AI-related solutions.
• Experience engaging with CISOs, security architects, and risk teams.
• Strong selling skills, particularly in complex, high-value solutions.
• Ability to operate effectively in fast-paced, evolving environments.
• Familiarity with LinkedIn Sales Navigator, HubSpot, and modern enterprise sales technology stacks.
• Effective communication skills, both technical and executive.
• Ability to manage targets and handle pressure professionally.
• Interest in AI, cybersecurity, and emerging enterprise technologies.

Benefits

The annual base pay for this position is: $143,200.00 - $214,800.00. 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. For more details about F5's benefits, please visit: here.

Pay

The annual base pay for this position is: $143,200.00 - $214,800.00.

Schedule

N/A