Principal Territory Account Manager (Enterprise)

F5•Ashfield, MA

1d•$138,900 - $208,300

About The Position

F5 is seeking an experienced enterprise software seller to act as a product specialist for CalypsoAI’s AI security platform. The role supports F5’s AI security strategy and helps enterprises securely and responsibly adopt generative AI. Working alongside F5 enterprise sales teams, the successful candidate will drive adoption across strategic and global accounts, engaging senior stakeholders in security, risk, technology, and AI. The position focuses on named financial services accounts and combines new-business acquisition with expansion of existing customer relationships. The role owns the full sales cycle, from prospecting and discovery through technical evaluation, negotiation, and close. It requires navigating complex enterprise buying processes and translating technical capabilities into business, security, regulatory, and risk outcomes. The role also contributes customer and market insights to product and go-to-market strategy and helps mature the enterprise sales playbook. The stated base salary ranges differ across the posting: one section lists $132,500–$198,700 and another lists $138,900–$208,300. The posting also describes a 50/50 base and commission pay mix, with stated OTE of $264,900–$397,300 or more upon meeting or exceeding quota. Full-time employees are offered a benefits package including health, wellness, PTO, and 401(k), among other benefits.

Requirements

At least 5 years of experience in enterprise software sales, ideally in cybersecurity, infrastructure, or AI-related solutions.
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.
Grounding in qualification and value-based selling methodologies; MEDDIC and Command of the Message are preferred.
Ability to work 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 and the 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

Cybersecurity background or experience selling security solutions, particularly engaging CISOs, security architects, and risk teams.
Experience with MEDDIC or Command of the Message.
Prior startup, scale-up, or post-acquisition integration experience.
Knowledge of generative AI and LLM ecosystems.

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, fraud and risk leaders, compliance leaders, and AI and innovation leaders.
Drive new-logo acquisition and build a self-generated pipeline through outbound activity, events, partners, and executive networking.
Lead complex sales cycles involving security, AI, data, and risk stakeholders, connecting technical capabilities to 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 generate new revenue and expand existing customer relationships.
Engage C-level and senior stakeholders, including CISOs, CIOs, CTOs, AI/ML leaders, and risk and compliance stakeholders.
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, and help mature the enterprise sales playbook.
Capture customer feedback and market insights to influence the product roadmap and go-to-market strategy.