About Coverdash

Coverdash is the fastest-growing startup and SMB-focused insurtech agency, powered by the industry’s most advanced embedded technology and partnership strategies. Our mission is to help growing businesses purchase and manage business insurance from the places they trust most. Our simple and powerful embedded technology helps partners offer insurance to existing customers with a single line of code.

Coverdash was founded by a team with deep fintech and financial services experience and is the first insurance-as-a-service platform. We have raised over $16 million to date from top investors including NYCA (Affirm, Fundbox, Acorns, Gemini), Bling Capital (Lyft, Square, Instacart, Palantir), World Insurance Labs (HubSpot, DocuSign, Twitter), and Expansion VC (Postmates, AngelList, Lemonade).

Our rapidly growing team is a smart, dynamic, and fun-loving group privileged to be collaborating with some of the world’s most innovative embedded partners.

The Opportunity

We are seeking a Head of People Operations to play a critical role in shaping the future of Coverdash’s talent strategy and organizational culture. This is a senior leadership position, reporting directly to the executive team, with a mandate to design and execute the people strategy that supports our next stage of growth. We have already 3Xed our headcount this year; this role will be pivotal in sustaining that momentum. As we look ahead, we plan to scale from 70 to 150 team members over the next 12 months, making this a defining moment to shape how Coverdash grows.

You’ll own all aspects of People Operations from talent acquisition to employee experience while serving as a thought partner to leadership on org design, scaling teams, and building a best-in-class culture. This role begins as a hands-on leader that will build and manage a team as the company scales. 

Key Responsibilities

• Strategic Leadership
  • Partner with executive leadership to design and implement a holistic people strategy that aligns with business goals and scaling needs.
  • Own workforce planning, organizational design, and talent development initiatives to ensure we’re building the right teams for growth.
  • Advise on compensation, leveling frameworks, and benefits to ensure competitiveness and fairness.
• Talent Acquisition & Development
  • Lead recruiting strategy to attract and retain top talent across insurance, sales, product, and engineering.
  • Build scalable development and training programs that enable employees to succeed quickly and thrive long-term.
• Operational Excellence
  • Oversee HR operations including payroll, compliance, policies, and systems, ensuring we are scalable and legally compliant.
  • Continuously optimize processes, systems, and tools to support a rapidly scaling workforce.
• Culture & Engagement
  • Champion Coverdash’s culture, fostering a collaborative, inclusive, and high-performance environment.
  • Design and implement initiatives that strengthen employee engagement, satisfaction, and retention.
  • Serve as a trusted advisor and coach to managers and employees at all levels.

Who You Are

• 5+ years of experience in People Operations, HR, or Talent, with at least 2+ years in a leadership role at a high-growth startup or scale-up.
• Proven experience designing and executing people strategies across talent acquisition (including recruiting/sourcing), performance management, compensation, and culture.
• High EQ with exceptional ability to build trust, influence, and manage relationships across the org.
• Strong business acumen; you understand how people's strategy ties directly to company performance.
• Comfortable operating with autonomy in a fast-paced environment while balancing strategic vision with tactical execution.
• Must be NYC-based and able to work in the office 4 days per week.

Why Us?

• We’re the fastest-growing insurtech in the U.S., building the largest embedded insurance distribution network in the market.
• Operating at break-even, we’re growing rapidly from a position of stability. We’re playing the long game. 
• Competitive compensation with uncapped growth potential as we continue to expand and capture market share.
• A benefits package designed to support you inside and outside of work.
• Join a high-performing, innovative team that’s as focused on delivering impact as it is on building a fun, collaborative environment.

Title/level/compensation will be based on experience. We look forward to reviewing your application and seeing if you’re a fit for our team.