Founding Head of GTM - Cipherscale

OpenVPN

Remote job 9/22/2026 ExperiencedRemote

The Opportunity: Zero-to-one category creation for AI-Native Zero Trust Access<a rel="noopener" target="_blank" href="https://cipherscale.com/">Cipherscale</a> is building an AI-native Zero Trust access and enforcement plane for humans, software/workloads, and AI agents. The product doctrine is simple: AI may reason and propose; deterministic policy authorizes; trusted enforcement executes. We are looking for a commercial founder/operator who can turn that architecture into a category, a repeatable customer problem, real deployments, and initial revenue.Mission: discover and prove the repeatable commercial truth for Cipherscale - who urgently needs it, what gets them to deploy, what makes them pay, and what causes them to expand.What You Own• Own ICP discovery, exclusion criteria, buyer/champion mapping, problem validation, positioning, initial wedge, and design-partner recruitment.• Personally lead early customer discovery, technical/commercial conversations, executive outreach, design-partner conversion, and initial closing.• Build an evidence-driven GTM system: every important assumption has supporting/contradicting evidence and a next falsification test.• Use AI agents aggressively for research, account intelligence, personalization, competitive monitoring, meeting preparation, call synthesis, content, and experiment analysis.• Work directly with the CEO on category creation and major strategic accounts.• Work with Product and Engineering to convert recurring customer evidence into governed product inputs - without turning prospect anecdotes into roadmap commitments.• Define the first repeatable acquisition, deployment, conversion, and expansion motion before scaling a team.What This Role Is Not• It is not a traditional marketing leadership job.• It is not an MQL, impressions, content-calendar, or brand-campaign role.• It is not a decision to hire SDR, demand-gen, content, and marketing-ops teams before product-market evidence exists.• It is not ownership of OpenVPN growth. Rod, Head of Growth, owns the established-business growth mandate;This role is focused on Cipherscale zero-to-one GTM and must collaborate cleanly without duplicating authority.Important:<ul><li>This is a full-time remote job, and it will be a long-term B2B contract.</li><li>This can be a permanent employment opportunity for candidates based in Spain, Poland, and Germany.</li></ul>Our philosophy is that we are a small, close-knit team, and we care deeply about you:<ul><li>Highly competitive salary + Bonus</li><li>Fully remote work environments.</li><li>Self-managed time off.</li></ul> Who We Want• You have personally helped take a deeply technical B2B security, infrastructure, identity, developer, cloud, or AIproduct 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 ReportingThis 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 growthorganization, and OpenVPN growth priorities cannot dilute CipherScale category discovery. As the motion becomesrepeatable, responsibilities can be consolidated based on evidence rather than titles.Security ExpectationsYou will operate with customer and prospect data, AI agents, email/CRM systems, call transcripts, and potentiallytechnical environments. Treat agents as potentially compromised actors. Use scoped identities, least privilege,deterministic authorization for external actions, credential isolation, customer-data boundaries, prompt-injectiondefenses, audit trails, and human approval for high-impact commitments until explicitly delegated.Compensation PhilosophyWe would rather pay exceptional compensation and meaningful upside for one outstanding founder-level operatorthan assemble a large conventional GTM organization. Final structure should reflect experience, location, scope, anddemonstrated ability to create zero-to-one enterprise value.The TestA strong candidate should be able to take the Cipherscale thesis, identify the first market to attack, design the first tencustomer experiments, explain what evidence would invalidate the strategy, and show how they would use AI toexecute the work with minimal human headcount.Find <a href="https://www.arbeitnow.co.uk">Jobs in United Kingdom</a> on Arbeitnow</a>

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Founding Head of GTM - Cipherscale

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