Enterprise Account Executive

Enterprise Account Executive driving adoption of AI security solutions at F5's CalypsoAI. Engaging with top-level executives in financial services to deliver value-driven sales solutions.

Posted 6/5/2026full-timeRemote • Massachusetts, New York • 🇺🇸 United StatesMid-LevelSenior💰 $135,200 - $202,800 per yearWebsite

Tech Stack

Tools & technologies

Cyber Security

About the role

Key responsibilities & impact

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

What you’ll need

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
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.

Benefits

Comp & perks

incentive compensation
bonus
restricted stock units
benefits

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

enterprise software salescybersecurity solutionsAI-related solutionsvalue-based sellingqualification methodologiesMEDDICCommand of the Messagepipeline managementforecastingdeal strategy

Soft Skills

communication skillsinfluencehunter mindsetprofessionalismintegrityability to work under pressureengaging senior decision-makerscollaborationadaptabilitycustomer feedback capture