Head of Customer Success

Do you have experience in leading a Customer Success or post‑sales team that delivers real results? Do you thrive at the intersection of strategy, leadership and technology? At Trustoo we’re looking for a Head of Customer Success to take Customer Success to the next level!

Why this role exist

Trustoo has scaled fast. Four countries, thousands of local service providers on the platform, and a Customer Success function that has done a serious job building real relationships and a working foundation. The opportunity now is to do more with what we’ve built.

We believe the next chapter of Customer Success is built on three things: AI‑driven workflows that predict churn before it happens, automations that turn every customer signal into the right next action, and Customer Success Managers who focus their time on the conversations and decisions where human judgment and contact make the real difference.

We are seeking a visionary leader with deep Customer Success expertise who actively drives the AI transition. Someone who sees exactly what should be automated, what can be made smarter, and where people create value that technology cannot.

The role

You own the Customer Success, ‘Existing Customers’, value stream end to end. That means full ownership of retention, expansion and customer health for our local service providers in NL, BEL, GER and ES. You lead a cross‑functional team of around 25 people: Customer Success (15 to 20 CSMs across NL and GER, led through other leads rather than managed directly by you), CRM and email marketing, a Product Manager, developers and UX. You report directly to the founders and sit on the leadership team as a full member. In that role, you don’t only represent Customer Success. You co‑own the company’s strategic direction and help set priorities across the business.

This is a role where strategy, technology and leadership come together. You are accountable for margin, churn, reclaims and Csat. You define what the function looks like 18 months from now and you lead the implementation. In addition, you develop your team: you grow the leads that report to you and create the conditions for people to do their best work, supported by the right technology.

What you will do

Redesign the function around AI and automation. You design and deliver the AI‑first operating model for Customer Success: automated health scoring and risk prediction, AI‑assisted next best actions for CSMs, smart triage, and automated onboarding and reactivation flows. You and your team focus on human attention where it matters most. You set the AI roadmap together with the PM and engineering, and you measure progress in outcomes: retained customers, margin improvement, not activity.

Lead and develop your team

You manage the CS lead, and (dotted line) the Product Manager, Engineers and Designers in the Existing Customers value stream. You invest in developing your people and the leaders around you. You raise the bar on how leadership is practiced across both teams and markets.

Own margin, churn, reclaims, CSAT & health score

These are your north stars. You define the KPI framework, set targets per market, report progress to the leadership team monthly, and make clear decisions when trade‑offs arise.

Drive a customer‑centric approach across the value stream

CS insights structurally feed product and acquisition decisions, not as a quarterly report but as a continuous loop. You actively connect with Sales, Marketplace, Marketing and Product so the customer perspective shapes how we build and grow.

Shape Trustoo beyond your value stream

As a member of the leadership team, you actively shape Trustoo’s direction beyond your own value stream. You contribute to company‑wide priorities, support other leads, and help build the kind of company people are proud to work at.

What success looks like in your first 6 months

• A clear assessment of the current set‑up, processes and customer health, with a sharp view on what to build on and where to change direction.
• An 18‑month roadmap for the Existing Customers value stream: AI first, with measurable targets on margin, churn, reclaims and CSAT, aligned with the leadership team.
• At least three AI‑driven improvements in production that demonstrably move one of the four north stars.
• Strong working relationships with your team, the CS leads, the other value stream leads and the founders. The team feels the difference.

We are looking for someone who

• You have led a modern Customer Success, Account Management or post‑sale function at scale, with team leads or managers reporting to you. You are comfortable with a larger span of control and you invest in developing other leaders.
• You are AI‑first in how you think and operate. You have personally built or delivered AI‑driven workflows or automations that replaced manual work or created new leverage. You can talk specifics: which tools, which trade‑offs, what worked and what did not. And you have a clear view on where human connection and judgment matter more than any tool.
• You build and transform. You’ve proven you can take something from where it is to where it needs to be. You hold a vision and you ship the implementation. You move easily between strategy and execution.
• You are sharp on data. You define the KPI framework yourself, read dashboards critically, and you ask the right questions when the numbers feel off. You do not outsource analytical thinking.
• You are fluent in Dutch and strong in English. Marketplace or SaaS experience is a strong plus. International experience (DACH or Southern Europe) is a plus.

What we offer

• A real seat at the table. You report to the founders, sit on the leadership team, and your value stream is one of the three pillars of Trustoo/Trustlocal.
• A company at an inflection point. Profitable and growing fast.
• A mandate to take Customer Success to the next level in 2026, with the team, tools and ambition to make it happen.
• Competitive total compensation package.
• Hybrid working flexibility + a laptop to make it easy.
• Two weeks per year to work remotely from abroad.
• €1.000,- training budget to use as you wish.
• Travel reimbursement to and from our Amsterdam office.
• 25 vacation days & Pension plan.
• Fun monthly team activities, such as drinks, sports, cooking workshops, or boat trips.
• An annual company incentive trip abroad if we reach our targets.

#J-18808-Ljbffr