Head of Customer Retention Job at OnTheGoSystems

Job Responsibility

Churn rate, renewal rate, and net revenue retention are yours. You set the targets. You build the plan. You ship the work. You report the results
Our NPS program and our public-rating surfaces (Trustpilot, Capterra, G2) are metrics you move. They are not projects you status-report on
You lead the existing Retention team and shape its evolution. You coach the team. You get more from the people on it than they are getting from themselves today. The team’s shape will evolve as your AI-amplified work scales
You work with Support, Engineering, and Product as your three core counterparts. Support is where today’s churn signal lives. You constantly mine what is trending and what customers are struggling with right now. You will not request reports from Support. You will use our internal intelligence tools and look yourself. Engineering and Product are where you ship retention-critical fixes. You arrive with business cases that make prioritization obvious
You report to the CEO directly. No layers. No fancy slides. Only results.

You want to be doing the work, not just managing it. Your best weeks are the ones where you wrote the strategy, ran the analysis, drafted the comms, and shipped the experiment yourself. AI tools are part of your daily working stack. You use them to do more, not to escape doing. If you have been promoted away from doing the work and you miss it, this is the job
You have measurably moved a retention metric at a previous company. You can describe exactly how. Specific numbers. Specific actions. Specific results
You come from a self-serve B2B SaaS. SMB, prosumer, or developer tools. You know the difference between running a self-serve renewal motion and running an enterprise CSM team. You have done the former
You are data-fluent. You read funnels for fun. You can write SQL or instruct an analyst precisely
You decide. When you have 70% of the information, you commit and adjust. You do not escalate decisions back to your CEO that you were hired to make
You treat coordination as the cost of the work, not the substance of it.

A real metric to move. The authority to move it
Direct, regular access to the CEO. No politics. No committees
An AI-amplified working culture. The CEO uses AI tools daily for analysis, drafting, and strategic work. You are expected to do the same. We invest in the tooling and the team norms that let a small operation punch above its weight
Competitive senior-leadership compensation. Specifics with HR
100% remote since 2008. Strong async culture. Modest meeting load. Real flexibility on hours
Competent counterparts. Our engineering team ships. Our product team ships. Our support team is in daily contact with customers and produces real intelligence about what is breaking. You will not be the only person trying to make things happen
Direct access to customer intelligence. We have internal tools that let you probe support trends, ticket patterns, account behavior, and churn signals on demand. No reports to request. No meetings to schedule. The data is in front of you whenever you want to look
Generous time off. Education and conference budget. Hardware
A 17-year-old profitable company. Stability without bureaucracy