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Chief of Staff

Tel Aviv, IL | General & Administration | Full-time

We’re looking for a Chief of Staff to work closely with Lemonade’s co-founder and co-CEO, Shai Wininger.

As a force multiplier to the co-founder and CEO, you will run point on strategic projects - big and small, follow-through on various initiatives, own key hires, and manage relationships with people across the organization.

The perfect candidate is a tech-savvy self-starter, an execution powerhouse and a great communicator. To succeed in this senior role, you’ll need to have great people skills, high EQ, and extensive business acumen.


  • Lead cross-functional strategic initiatives, facilitate special projects, and ensure action items are executed on behalf of the CEO
  • Operate at a tactical, strategic, and operational level, handling the oversight of projects that do not neatly fit within the organizational chart or that fall between departments or leadership areas of responsibility
  • Act as an extension of the CEO and as an information funnel, filter, and facilitator with internal and external stakeholders
  • Serve as the point of contact to the CEO, triaging incoming requests and working collaboratively with the CEO’s assistant to ensure his calendar is aligned with the priorities of the organization
  • Proactively follow up with the CEO’s team if and when goals are not being achieved, and provide actionable recommendations for improvement
  • Promote team integration as well as cross-functional communication and collaboration
  • Manage key relationships and build a process to track and nurture key stakeholders, investors, and clients
  • Track high priority initiatives for the CEO to identify any/potential obstacles
  • Serve as a thought partner and strategic advisor to CEO, standing in on meetings, challenging ideas, offering a fresh perspective, and following up on action items with the team accordingly


  • 5+ years experience working for a global tech company in senior roles. 
  • Great at matrix management, influence and communication skills.
  • Great communicator with strong rhetorical skills. Trusted, reliable, and highly available. 
  • Perfect English, solid Hebrew
  • Organized and methodical.
  • Strong data / analyst background. Great at solving problems through data, research and thinking out of the box.
  • Smart, energetic and hungry to do whatever it takes to succeed in this challenging role.
  • Super smart, fast thinker.
  • Entrepreneurial - ambitious, self-starter, able to dive into any area of the business or product, look at the big picture and identify opportunities and issues.
  • Get shit done attitude - always finds a way to make things happen, scrappy and efficient with limited resources.
  • Executive presence - confident in managing up and relaying feedback to top executives.
  • Proven experience leading large scale, multi faceted tech projects.
  • Extremely organized and detail oriented, a multi-tasker.
  • Inquisitive mind. Reader. Constantly learning.
  • Exceptional EQ - natural ability to ‘read’ people, a great listener, and a good sounding board for others in the company. 
  • Flexibility - this role may require travel from time to time.
  • Direct - able to provide open honest feedback to others, including their manager.
  • Humble, approachable and loved by peers.
  • Understanding of customer-centric products, operations, business development, and marketing. 
About Lemonade

Lemonade is a licensed insurance carrier offering renters, homeowners, car, pet, and life insurance in the United States, contents and liability insurance in Germany and the Netherlands, and renters insurance in France. We’re powered by artificial intelligence and behavioral economics, and driven by social good.

A Certified B-Corp, Lemonade donates unused premiums to nonprofits selected by its community as part of our annual Giveback program. We incorporate our values into everything we do—from our business model to our office culture.

Things to know…

Lemonade is an equal opportunity employer committed to diversity and inclusivity. We never discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. If you require reasonable accommodations due to religious beliefs, pregnancy, or disabilities, let us know at any time.

As a certified B-corp, Lemonade is committed to pursuing social and environmental efforts. We do this in a variety of ways, from providing sponsored opportunities for our employees to give back to their community, to partnerships with organizations that enable our team to autonomously contribute their time to causes they care about.