Head of Customer Retention at OnTheGoSystems, Remote in Spain

Own retention metrics for a mature, profitable WordPress plugin company by setting targets, building plans, executing work, and reporting results. Lead the Retention team, collaborate directly with Support, Engineering, and Product, and report to the CEO on churn, renewals, NPS, and public ratings.

Key Responsibilities

• Own churn rate, renewal rate, and net revenue retention end-to-end.
• Set retention targets, create and execute the plan, ship initiatives, and report outcomes.
• Drive NPS and public review ratings on Trustpilot, Capterra, and G2.
• Lead and coach the existing Retention team, evolving its structure with AI scaling.
• Mine support trends and customer struggles directly using internal tools.
• Build business cases for Engineering and Product to prioritize retention fixes.
• Report directly to the CEO with a focus on measurable results over coordination.

Qualifications

• Proven ability to measurably improve retention metrics with specific numbers and actions from prior roles.
• Experience in self-serve B2B SaaS (SMB, prosumer, or developer tools), not enterprise CSM.
• Hands-on approach: comfortable writing strategy, running analysis, drafting communications, and shipping experiments yourself.
• Data-fluent; able to read funnels, write SQL, or precisely instruct analysts.
• Decisive: commit with 70 % information and adjust rather than escalate.
• Daily user of AI tools for analysis, drafting, and execution rather than delegation.
• Preference for doing the work over managing at a distance.

Benefits And Growth

• Direct ownership of a key business metric with authority to act.
• Regular, unfiltered access to the CEO.
• AI-amplified culture with investment in tooling and async norms.
• Competitive senior-leadership compensation.
• 100 % remote since 2008 with strong async culture and modest meeting load.
• Direct, on-demand access to customer-intelligence tools (no reports or meetings required).
• Generous time off, education/conference budget, and hardware allowance.
• Work inside a stable 17-year-old profitable company.