Chief Of Staff

About Us

Cachet is building the insurance infrastructure to help Europe's platform economy thrive. Our technology and services are enabling platforms to control risk and prevent loss at scale.

The Role

We're hiring a Chief of Staff to be the CEO's strategic right hand: translating the company's ambitions into structured plans, maintaining the operating rhythm of the leadership team, and making sure the most important strategic questions are always well-researched, clearly framed, and moving forward.

This role sits at the intersection of strategy, operations, and communication. You will do the analytical and organisational work that lets the CEO operate at the highest possible level, and act as a connective layer across the leadership team to keep cross-functional work aligned and progressing. You are a trusted, discreet partner who works in the background to make the whole organisation run better.

You'll report to the CEO and work closely with the full leadership team.

What You'll Do

• Own Cachet's market research function, turning market, opportunity, and competitor analysis into input for the CEO's strategic decisions.
• Lead the internal analytics and business intelligence that support sustainable growth.
• Support the CEO ahead of board meetings, investor conversations, and partner discussions, facilitate the annual and mid-year strategy reviews.

• Own the company-wide OKR process, from cadence to alignment across teams.

• Own the delivery of strategic initiatives that span cross-function and have no natural single-function owner, acting as accountable lead and driving them to completion.
• Chair cross-functional working groups as needed, providing structure, maintaining momentum, and keeping outputs true to the strategic intent.
• Maintain a live view of the company's most important in-flight projects so the CEO always knows what is progressing, what is delayed, and what needs a decision.

• Design, own and run the leadership team's operating rhythm & process: meeting cadence, agenda formats, pre-read standards, and decision-making processes.

• Own Cachet's internal communications framework so strategy, leadership decisions, and organisational change reach the team clearly, consistently, and at the right level of detail.
• Plan and run the company all-hands with the CEO, structuring the agenda and content so the meeting delivers genuine clarity and connection.
  
  

What We're Looking For

• 3+ years in a strategy, management consulting, chief of staff, or operations role, ideally including time in a fast-scaling company.
• Strong analytical and research skills: you can take an ambiguous strategic question, structure it, gather the data, and turn it into a clear, decision-ready recommendation.
• Proven track record owning cross-functional initiatives end to end and driving them to completion across teams you do not directly manage.
• Comfortable designing and running operating frameworks such as OKRs.
• Excellent judgement and discretion: people trust you with sensitive information and rely on your read of a situation.
• Confident operating in a fast-moving, founder-led environment where you build as much as you run.
• Excellent English communication skills, written and verbal.
  
  

Nice to Have

• Experience in insurtech, fintech, or platform/marketplace businesses.
• Background in management consulting, corporate strategy, or venture-backed scaleups.
• Experience evaluating new markets or geographies for expansion.
• Familiarity with business intelligence and unit economics in a subscription or platform model.
  
  

Work Setup

This is a hybrid role. Our HQ is in Tallinn, where the team works together regularly each week. Because this role works so closely with the CEO and leadership team, we expect regular in-person collaboration in Tallinn. English is our working language, and EU work authorisation is required. Location can be remote in the EU.

Recruitment Process Overview

1. Intro with HR (30 min)
2. Interview with the CEO (1 h)
3. Case task (approx 2 h to prepare)
4. Case presentation (20 min) and interview with the CEO (40 min)
   
   

This role is hired on an ongoing basis and applications are reviewed continuously.