Head of Retention Management

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 OwnTeam 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)

Compensation Range: €65K - €120K