Head of Retention Management

Overview

Application

The role

Own service delivery excellence as we scale to our next stage, while keeping the boutique, personal touch that makes OKTOBER different. You'll lead up to 5 Senior Retention Managers and a Creative Lead, to ensure every brand gets why they came to us.

This is a behind-the-scenes leadership role. You're not the main-face to clients, you're the person making sure we deliver work we're all proud of.

What you’ll own

Team leadership & development (50%)

Lead 4 Senior Retention Managers (pod leads) + 1 Creative Lead

Weekly 1-on-1s focused on growth, performance, and impact

Coach Senior RMs on complex retention strategies

Hire and develop 15+ people this year

Build career paths that keep top talent

Fast, direct feedback when standards aren't met

Service quality & results (30%)

Spot-check quality regularly across all accounts

Step into any account when needed, you can take over if a Senior RM is stuck

Oversight on new client onboarding (not hands-on, but ensuring it's done right)

Flag underperformance early, work with Senior RMs to course-correct

Join strategic work on key accounts

Handle escalations with calm and clarity

Strategic oversight (20%)

Own the "OKTOBER Way of Working" (how we do our work)

Partner with Operations Lead on systems and training

Own metrics: client retention rate, NPS, referrals

Weekly sync with founder on team health and results

Escalate big issues, handle the rest autonomously

Some client touchpoints: key account QBRs, onboarding clients, escalations

About You

• Deep retention/email/lifecycle marketing expertise (you're elite at this)
• Managed teams before (20+ people)
• Managed managers (Senior RMs need a leader, not a peer)
• Scaled through rapid growth (been part of a team that doubled)
• Agency experience required (you understand utilization, profitability, client dynamics)
• You're obsessed with results
• You can audit any retention account and immediately see what's working, what's broken, and what's missing
• You know great retention strategy when you see it, and you can teach it
• You hold the bar high without being a perfectionist
• You spot trends before they become problems
• You're a natural coach
• You develop Senior RMs through questions, not orders
• You give direct, clear feedback without ego
• You make people better, not smaller
• Fast to intervene when someone's not meeting standards, but always human about it
• You're open and adaptable
• You can take feedback as easily as you give it
• Low ego, high ownership
• You observe before changing things
• You trust your team until they give you a reason not to
• CET timezone, able to meet quarterly in Europe
• The set-up
• Salary that matches experience and impact
• 20 days PTO + local holidays
• Remote-first with Amsterdam office
• Autonomy once trust is earned
• Work directly with founder

Start May/June 2026

• Not a fit
• Can't evaluate retention strategy at an elite level
• Haven't led teams through growth
• High ego or non-empathetic style
• Need to be client-facing (this is behind-the-scenes leadership)
• Can't work CET timezone or meet quarterly in Europe
• Succes metrics
• Client retention rate (high bar, tracked quarterly)
• New business through referrals (proof clients love the work)
• NPS scores (are we delivering the boutique experience?)
• Team performance (Senior RMs growing, RMs executing well)