Head of Sales

About the Role

Today our inbound is handled by Operations. You would turn it into Insify's first dedicated sales function, starting with a team of two in the Netherlands and growing into other markets later. We're ~60 people, so you work directly with the founders, Product, Insurance and Operations, and your results are visible to everyone.

It's a player-coach role, roughly 40% selling and 60% leading. One morning you're running the daily huddle, the next you're on a call with a 25-person company that needs the right cover, and in the afternoon you're listening back to your team's calls and giving feedback. You know what great selling sounds like, and you can show it, not just describe it.

Our customers are self-employed people and SMEs. They buy like businesses but often behave like consumers, so you need both instincts: the structure of B2B sales and the warmth and pace of a good consumer conversation.

What You'll Be Doing

Building and leading our sales team end to end: how it sells, how it's measured, and who you hire and grow as it scales
Selling yourself, especially early on: demos and proposals for larger SMEs, and closing the deals that matter
Coaching the team every day: listening in on calls, running the huddle, and raising the bar on sales technique
Owning conversion, cross-sell and customer satisfaction, for yourself and for the team
Building the foundations: playbook, CRM setup, pipeline reporting and ways of working that hold up as we grow
Bringing what customers tell you back to Product and Insurance, so we build the cover they actually need
Shaping our discounting strategy together with the people who own pricing
Challenging our ideas and bringing your own. We encourage each other to act this way, so you can expect the same from others

What You'll Need

You've managed salespeople before, including hiring, coaching and feedback. It doesn't have to be a big team, but it has to be real, and you have to want more of it
Years of hands-on B2B sales experience, ideally selling to SMEs or self-employed customers. You still love being on the phone, and you're very good at it
A track record of building, not only running: a playbook, a process or a team that didn't exist before you
Energy and conviction. You can sell almost anything, and you win on trust: customers should feel helped, not pushed
You use AI tools in your own work and you're curious how they can make your team sharper
Fluent Dutch, and comfortable working in English
You want to be in our Amsterdam office five days a week, next to your team

Nice to Have

Experience at a startup or scale-up, especially in insurance, fintech or SaaS
Some insurance knowledge. Eagerness to learn matters more than what you know today
A Wft certificate. Not required to start, but we'll expect you to get it once you join
Experience selling across different country markets

We Offer

Competitive compensation. A salary plus a bonus tied to your and your team's results. In addition, performance-based equity grants.
Holidays. 25 holiday days
Pension. 6% employer contribution
Wellbeing budget. €50 net a month via Epassi, from the gym to takeaway, rolls over
Learning and coaching. Internal leadership programs and coaching
Central Amsterdam office. Shared lunches, dogs, Friday drinks, high-spec 
MacBook Pro

About Insify

Insify is a high-growth scale-up backed by €43M in total funding from world-class investors like Accel, Munich Re Ventures, and Formula 1 champion Nico Rosberg. In five years, we've expanded from the Netherlands into France and Germany, and we're just getting started. Our mission: become the European leader in AI-powered SME insurance.

We aren't just building a company; we're leading a revolution. Our culture is intense, high-stakes, and mission-driven. We hire smart, ambitious "owners" who possess a relentless drive to win. This is an environment for those who thrive on challenges, value intellectual honesty, and share our mindset of becoming a global category leader.

Our founding team consists of seasoned entrepreneurs who have previously built iconic businesses like HelloFresh, Bloomon, and SumUp. We bring that same bias for speed, scale, and high standards to one of the most structurally broken experiences in financial services. Together, we combine that deep fintech and e-commerce expertise with cutting-edge AI to stay ahead of the curve.