Head of Sales

Insify
Amsterdam, Netherlands
On-site

Who this role is best for

B2B sales professionals with team-building experience and fluency in Dutch will find this player-coach role in Amsterdam.

Best fit for

  • Candidates with prior experience building sales teams from scratch and a background in SME or self-employed B2B sales
    — “Years of hands-on B2B sales experience, ideally selling to SMEs or self-employed customers”
  • Individuals who thrive in mission-driven, high-intensity environments and are comfortable with leadership responsibilities
    — “Our culture is intense, high-stakes, and mission-driven. We hire smart, ambitious 'owners'”

Things to consider

  • Requires full-time presence in the Amsterdam office, five days a week
    — “You want to be in our Amsterdam office five days a week, next to your team”
  • Expect a heavy focus on coaching and feedback, which may demand significant time investment
    — “Coaching the team every day: listening in on calls, running the huddle, and raising the bar on sales technique”

How to stand out

  • Highlight your experience in building sales processes and teams from the ground up
    — “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”
  • Showcase your ability to sell to SMEs and self-employed customers with a focus on trust and helpfulness
    — “You can sell almost anything, and you win on trust: customers should feel helped, not pushed”
  • Demonstrate familiarity with AI tools and how they can enhance sales performance
    — “You use AI tools in your own work and you're curious how they can make your team sharper”
  • Emphasize your ability to provide actionable feedback and coach others effectively
    — “You know what great selling sounds like, and you can show it, not just describe it”
  • Mention experience in translating customer insights into product or service improvements
    — “Bringing what customers tell you back to Product and Insurance, so we build the cover they actually need”
Pace · Fast PacedCollaboration · HighAutonomy · HighDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • building and leading a sales team
  • selling to SMEs and self-employed customers
  • coaching sales team
  • owning conversion and customer satisfaction
  • shaping discounting strategy
Typical background
sales management experienceB2B sales experienceteam building

Skills & requirements

Required

Sales ManagementB2B Sales ExperienceTeam BuildingCoachingSales TechniqueCRM SetupPipeline ReportingCustomer Feedback AnalysisDiscounting StrategyAI Tool Usage

Preferred

Startup ExperienceInsurance KnowledgeWft CertificateCross-country Market Sales Experience

Stack & domain

SalesTeam ManagementB2B SalesAI ToolsLeadershipCommunicationCoachingProblem-solvingCustomer ServiceProduct Management

About the role

Original posting from Insify via Lever

Entrepreneurs already find us and want what we offer. Now we want to get much better at turning that interest into customers, with a dedicated sales team that sells the way we build: simple, honest and fast. You would build that team, and lead it from the front.

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.

Source: Insify careers (Lever)

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