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Lead Software Engineer



Software Engineering
Posted on Thursday, April 18, 2024

Lead Software Engineer

Counterpart believes in small businesses and is dedicated to helping them do more with less risk. By pairing leading insurance experts with cutting-edge technology, Counterpart empowers small business owners to grow with confidence. Exceptional underwriters, trusted insurance brokers, and prominent insurance carriers come together on the Counterpart platform to support small businesses by providing AI-driven management and professional liability underwriting and claims services. That’s where you come in…

As a Lead Software Engineer, you will balance being a prolific individual contributor with coordinating a distributed team of developers. You will help bridge the gap with Product & Business while driving the development of our systems. In addition, you will help to set the culture, rituals, and processes that underpin a high-functioning engineering team and the organization more broadly.


  • Lead a team of full-stack developers to execute roadmap projects.
    • Break-down product requirements and technical designs into actionable tasks.
    • Manage cross-team dependencies
    • Alternate between hands-on coding and providing strategic technical guidance (code reviews, technical design evaluations, troubleshooting complex technical challenges, and providing contextual information to ensure team members understand the broader impact of their work).
    • Adapt and refine technical plans as projects evolve to ensure continual alignment with business objectives.
    • Maintain a continuous and transparent dialogue to keep technical efforts aligned with evolving product and business needs.
  • Collaborate with Product Managers by providing detailed insights on the level of effort (LOE) and resource requirements to ensure the product roadmap balances business imperatives and technical feasibility.
  • Actively contribute to the project design phase by taking ownership of technical design to ensure it aligns with product requirements, is scalable, and minimizes technical debt.
  • Continuously mentor team members, provide constructive feedback, and conduct performance evaluations to foster professional growth and high performance.
  • Continuously improve existing systems with an eye toward long-term extensibility and maintainability.
  • Communicate effectively and transparently with all levels of the organization, ensuring the appropriate level of detail to facilitate understanding and engagement.


  • 10+ years building engaging and high-performance web applications with various frontend, backend, and cloud technologies. (We use Python, Django, AWS, React)
  • 5+ years leading team, demonstrating strong leadership skills and ability to manage and mentor.
  • Proven ability to manage complex projects from start to finish.
  • Passion for taking on new problems as we continue to innovate.
  • Experience working with a worldwide distributed team.
  • Excellent communication skills, including conveying complex technical concepts and decision points in an accessible manner to non-technical stakeholders and providing clear, actionable guidance to the team.
  • Demonstrated ability and willingness to contribute hands-on to code and other technical tasks as needed.

We are committed to being a welcoming and inclusive workplace for everyone. We are intentional about making sure people feel respected, supported, and connected at work—regardless of who they are or where they come from. We value and celebrate our differences and believe being open about who we are allows us to do the best work.

We are an Equal Opportunity Employer. We do not discriminate against qualified applicants or employees on the basis of race, color, religion, gender identity, sex, sexual preference, sexual identity, pregnancy, national origin, ancestry, citizenship, age, marital status, physical disability, mental disability, medical condition, military status, or any other characteristic protected by federal, state, or local law, rule, or regulation.