Head of Customer Retention at OnTheGoSystems, Remote in Spain - 9 Jun

Own and drive customer retention outcomes for a profitable WordPress plugin company serving hundreds of thousands of B2B customers. Set retention targets, build and execute plans, lead the existing retention team, and collaborate with Support, Engineering, and Product to reduce churn and improve renewal metrics while reporting directly to the CEO.

Key Responsibilities

• Own churn rate, renewal rate, and net revenue retention; set targets and deliver results
• Lead and coach the Retention team, evolving its structure alongside AI-driven workflows
• Mine Support interactions and internal intelligence tools to identify churn signals and customer friction
• Build business cases and partner with Engineering and Product to ship retention-critical fixes
• Move NPS, Trustpilot, Capterra, and G2 ratings through active execution rather than status reporting

Qualifications

• Proven track record of measurably improving retention metrics with specific numbers and actions
• Experience in self-serve B2B SaaS (SMB, prosumer, or developer tools)
• Data-fluent; comfortable writing SQL or directing precise analyst queries
• Hands-on operator who prefers executing strategy, analysis, comms, and experiments over pure management
• Uses AI tools daily as part of the workflow and embraces an AI-amplified culture
• Able to decide with 70% information and avoids escalating decisions upward

Benefits And Growth

• Direct reporting line to CEO with no intermediate layers
• Competitive senior-leadership compensation
• 100% remote since 2008 with strong async culture and modest meeting load
• Generous time off, education and conference budget, and hardware allowance
• Access to internal customer-intelligence tools for on-demand churn and behavior insights
• Stable, profitable 17-year-old company without bureaucracy