Sr Territory Account Manager (Enterprise)

F5•Field Township, IL

1d•$119,200 - $178,800

About The Position

F5, through CalypsoAI, is hiring an experienced enterprise sales professional to support secure and responsible adoption of generative AI. The role serves as a subject-matter expert and product specialist for CalypsoAI’s AI security platform, partnering with F5 enterprise sales teams to drive adoption across strategic and global accounts, including named financial services accounts. The position engages senior stakeholders in security, risk, technology, and business functions, and explains how CalypsoAI can deliver trustworthy AI at enterprise scale. The successful candidate will own complex enterprise sales cycles, drive new customer acquisition, and help expand existing customer relationships. They will connect the platform’s technical capabilities to business, security, regulatory, and risk outcomes; lead demonstrations and proof-of-value engagements; and contribute customer and market insights to product and go-to-market strategy. The role combines CalypsoAI’s AI-focused innovation with F5’s global reach and resources. The stated annual base pay is $132,500–$198,700 with commission-based variable compensation and stated on-target earnings of $264,900–$397,300 or more at quota. The posting also gives another annual base-pay range of $119,200–$178,800. Base salary and level depend on qualifications, skills, experience, location, and market conditions. Full-time employees are offered health, wellness, paid time off, 401(k), and other benefits.

Requirements

At least 5 years of experience in enterprise software sales.
Proven success selling complex, high-value solutions into large enterprise environments.
Experience engaging senior decision-makers within large, matrixed organizations.
Experience operating as a product-focused seller or overlay specialist in partnership with core account teams.
Solid grounding in qualification and value-based selling methodologies.
Ability to operate effectively in fast-paced, evolving environments while navigating enterprise-scale processes.
Excellent communication skills and ability to influence technical and executive audiences.
Comfort working to targets and managing pressure with professionalism and integrity.
Strong interest in AI, cybersecurity, and emerging enterprise technologies.

Nice To Haves

Enterprise sales experience in cybersecurity, infrastructure, or AI-related solutions.
Cybersecurity background or experience selling security solutions, particularly engaging CISOs, security architects, and risk teams.
Familiarity with MEDDIC and Command of the Message selling methodologies.
Familiarity with LinkedIn Sales Navigator, HubSpot, and modern enterprise sales technology stacks.
Prior startup, scale-up, or post-acquisition integration experience.
Knowledge of generative AI and LLM ecosystems.

Responsibilities

Own the full sales cycle within named financial services accounts, from prospecting, discovery, and business-case development through evaluation, negotiation, and close.
Build and execute territory and account plans targeting senior financial, security, risk, compliance, technology, and AI stakeholders.
Drive new-logo acquisition and generate pipeline through outbound activity, 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 with F5 enterprise account teams to drive new revenue and expand existing customer relationships.
Engage C-level and senior stakeholders, including CISO, CIO, CTO, AI/ML, risk, and compliance leaders.
Translate CalypsoAI’s technical capabilities into 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 go-to-market strategy.