Founding Head of GTM
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Job Description
Founding Head of GTM creating a repeatable market and initial revenue for OpenVPN’s AI-native Cipherscale security platform. Leading customer discovery, deployments, and enterprise sales.
Responsibilities:
- Own ICP discovery, exclusion criteria, buyer/champion mapping, problem validation, positioning, initial wedge, and design-partner recruitment
- Lead early customer discovery, technical/commercial conversations, executive outreach, design-partner conversion, and initial closing
- Build an evidence-driven GTM system with supporting and contradicting evidence and falsification tests
- Use AI agents 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
- Define the first repeatable acquisition, deployment, conversion, and expansion motion before scaling a team
- Generate qualified ICP conversations and design-partner candidates during the first 30 days
- Convert partners into deployments, measure time-to-value, blockers, security objections, and willingness to pay during days 31-60
- Target production or production-intent deployments, first paying customers, and a documented acquisition/onboarding motion during days 61-90
- Operate with customer and prospect data, AI agents, email/CRM systems, call transcripts, and potentially technical environments under strict security controls
Requirements:
- Personally helped take a deeply technical B2B security, infrastructure, identity, developer, cloud, or AI product from near-zero to repeatable initial revenue
- Can sit with a CISO, CTO, security architect, platform engineer, and AI-platform leader and earn credibility
- Understands security architecture, including identity, delegated authority, credentials, policy, enforcement, trust boundaries, auditability, and blast radius
- Comfortable selling before there is a polished playbook and learning directly from rejection
- Treats AI as operating leverage and builds agentic workflows before asking for headcount
- Analytical ability to distinguish activity from evidence and evidence from causality
- Comfortable challenging the CEO and product assumptions when customer evidence disagrees
- Background signals in 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 background
- Able to personally run technical discovery and executive selling
- Able to use AI agents for GTM operations rather than only copywriting
- Able to distinguish probabilistic AI recommendations from authorization or security enforcement
Benefits:
- Highly competitive salary + Bonus
- Fully remote work environments
- Self-managed time off
- Long-term B2B contract
- Permanent employment opportunity for candidates based in Spain, Poland, and Germany
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