Founding Head of GTM - Cipherscale

Who We Want

• You have personally helped take a deeply technical B2B security, infrastructure, identity, developer, cloud, or AI

product from near-zero to repeatable initial revenue.

• You can sit with a CISO, CTO, security architect, platform engineer, and AI-platform leader and earn credibility.

• You understand enough security architecture to reason about identity, delegated authority, credentials, policy,

enforcement, trust boundaries, auditability, and blast radius.

• You are comfortable selling before there is a polished playbook and learning directly from rejection.

• You treat AI as operating leverage. Your instinct is to build agentic workflows before asking for headcount.

• You are analytical enough to distinguish activity from evidence and evidence from causality.

• You are comfortable challenging the CEO and product assumptions when customer evidence disagrees.

Strong Background Signals

• Early-stage Zero Trust, identity, cloud security, developer security, infrastructure security, AI security, developer infrastructure, or adjacent enterprise-security categories.

• Founder, first-GTM, product-led commercial operator, technical seller, or hands-on GTM executive backgrounds can all fit.

• Large-company titles alone are not compelling.

Anti-Profile

• Your first answer to a growth problem is "hire a team."

• You depend on agencies for core positioning or customer discovery.

• You optimize lead volume before proving deployment and retention.

• You cannot personally run technical discovery or executive selling.

• You treat AI as a copywriting assistant rather than an operating system.

• You blur probabilistic AI recommendations with authorization or security enforcement.

First 90 Days: Window Expected outcome

• 0-30 days: 10-15 qualified ICP conversations; ~5 credible design-partner candidates; evidence-backed recommendation on ICP, problem, buyer, positioning, and wedge.

• 31-60 days: Convert the strongest partners into real or production-like deployments; measure time-to-value, blockers, security objections, and willingness to pay.

• 61-90 days: Target 5+ production or production-intent deployments where product readiness permits; first paying customers; prove or disprove repeatability with a second cohort; document the acquisition/onboarding motion.

How Success Is Measured

• Business: paid customers, initial ARR/MRR, expansion and eventually defensible unit economics.

• Customer: time-to-first-value, production activation, repeated authorized usage, protected resources/principals,

retention and expansion.

• Funnel: qualified conversations -> design partners -> deployments -> production -> paid -> expansion.

• Learning velocity: experiment cycle time, evidence quality, speed at which weak assumptions are killed or corrected.

Operating Model and Reporting

This role works directly with the CEO during zero-to-one discovery and partners closely with Rod, Head of Growth.

Decision rights will be explicit: CipherScale market discovery cannot become an overlapping second growth

organization, and OpenVPN growth priorities cannot dilute CipherScale category discovery. As the motion becomes

repeatable, responsibilities can be consolidated based on evidence rather than titles.

Security Expectations

You will operate with customer and prospect data, AI agents, email/CRM systems, call transcripts, and potentially

technical environments. Treat agents as potentially compromised actors. Use scoped identities, least privilege,

deterministic authorization for external actions, credential isolation, customer-data boundaries, prompt-injection

defenses, audit trails, and human approval for high-impact commitments until explicitly delegated.