Enterprise Account Executive

This is a fully remote position, open to applicants in New York, +1 more state.

📋 Description

• Take ownership of the entire sales process, from prospecting and discovery to business case development, evaluation, negotiation, and closing within designated financial services accounts.

• Develop and implement territory and account strategies aimed at targeting CIOs, CISOs, CROs, CDOs, Heads of Fraud/Risk, Compliance, and AI/Innovation leaders.

• Drive acquisition of new logos with a strong hunter mentality, establishing a self-generated pipeline through outbound efforts, events, partnerships, and executive networking.

• Lead intricate sales cycles that involve stakeholders in security, AI, data, and risk, ensuring alignment of technical capabilities with regulatory, risk, and business-value outcomes.

• Act as a CalypsoAI product expert within F5’s enterprise go-to-market team.

• Collaborate closely with F5 enterprise account teams to generate new revenue and enhance existing customer relationships.

• Manage and influence complex enterprise sales cycles, from initial discovery and technical validation through to negotiation and closure.

• Engage with C-level and senior stakeholders, including CISOs, CIOs, CTOs, AI/ML leaders, and Risk & Compliance professionals.

• Convert CalypsoAI’s technical capabilities into impactful business, security, and risk outcomes.

• Lead customized product demonstrations, high-level presentations, and proof-of-value sessions.

• Transform inbound enterprise demand into successfully closed new business.

• Oversee pipeline management, forecasting, and deal strategy while assisting in the maturation of the enterprise sales playbook.

• Gather customer feedback and market insights to shape the product roadmap and go-to-market strategy.

⛳️ Requirements

• A minimum of 5 years of experience in enterprise software sales, preferably within the cybersecurity, infrastructure, or AI solution domains.

• A background in cybersecurity or selling security solutions is highly advantageous.

• Demonstrated success in selling complex, high-value solutions to large enterprise clients.

• Experience functioning as a product-focused seller or overlay specialist in collaboration with core account teams.

• Strong experience in engaging senior decision-makers within extensive, matrixed organizations.

• Solid foundation in qualification and value-based selling methodologies (MEDDIC, Command of the Message preferred).

• Capacity to operate effectively in fast-paced, dynamic environments while navigating enterprise-scale processes.

• Familiarity with tools such as LinkedIn Sales Navigator, HubSpot, and modern enterprise sales technology stacks.

• Exceptional communication skills with the ability to influence both technical and executive audiences.

• Comfortable meeting targets and managing pressure with professionalism and integrity.

• Previous experience in startups, scale-ups, or post-acquisition integration is a plus.

• A strong interest in AI, cybersecurity, and emerging enterprise technologies; knowledge of Generative AI and LLM ecosystems is a significant advantage.

🏝️ Benefits

• Incentive compensation

• Bonus

• Restricted stock units

• Benefits