Chief Insurance Officer

A once-in-a-lifetime opportunity to work in an early-stage, well-funded InsurTech startup run by seasoned founders, backed by A-list investors, chasing a $250B global market. Reports directly to the CEO.


Verifly delivers on-demand insurance by the job to cover the 57 million people who work independently — such as photographers, handymen, DJs, and others — via our app. As more people freelance, many clients require them to be insured. These workers need easy, mobile access to quick, inexpensive, short-term insurance so they never lose a potential job or have to call an insurance broker. Verifly delivers this in seconds for as little as $5 for one hour and one million dollars of business insurance.


  1. Own the relationship with our carrier partners, including Markel and Global Aerospace. Work with our partners to support new features, geographies, and products.
  2. Own the roadmap, vision, and execution of our insurance product development (new features, lines of business, etc.).
  3. Own the strategy for insurance at the operational level (e.g. claims handling, capacity, structure).
  4. Own our insurance licensing and compliance functions.



  • Intellectually curious and ferociously detail-oriented.
  • You love creating amazing products and delighting customers, even if the industry has so far been holding you back.
  • High clock speed – able to function in a high-intensity, dynamic environment. Highly adaptable.
  • At home speaking to carriers, regulators, customers or our employees with authority, but never arrogant or dismissive.
  • Focused and organized, with strong follow-through.
  • Unrelentingly positive attitude – no job is too big, small, or odd. You are totally focused on the mission and winning, and so will roll up your sleeves and do what needs to be done, whatever it is, whenever it’s needed.
  • Exceptional oral, written, and presentation skills including the ability to communicate and simplify complex topics.
  • Intimate understanding of the insurance product development process from conception to scale in the admitted market. Able to present a portfolio of projects / products you’ve created / conceived / built.
  • Keen understanding of P&C insurance especially small commercial.
  • Willingness to defy convention and think outside the box.
  • You will have had direct underwriting responsibility for a large P&C commercial insurance book, ideally $100M+.

Product Development

  • Help us prioritize new features and product lines and perfect our current products and pricing.
  • Manage the evolution of our full-stack insurance product from CGL and Aviation to a full suite including but not limited to Events, Professional Liability, Inland Marine, Cyber, Workers’ Comp, Commercial Property, and Commercial Auto.
  • Manage our regulatory / product design firms.
  • Manage our internal and external actuaries.
  • Manage the filing and regulatory approvals process for our custom forms and rates.
  • Work with our product team to create a go-to-market plan for each new product / feature.
  • Help optimize new product lines for cross-selling.
  • Advise our product team on the state of the market and ideas for radical, non-traditional products.
  • Be intimately familiar with competitor filings and actively monitor the market for new developments.

Operations / Regulatory

  • Become one of our Designated Producers nationwide (we will cover the cost of any license upgrades required).
  • Be our ultimate authority on insurance questions from customers, partners, and regulators.
  • Ensure that our content and messaging is compliant, and our internal teams are working with digestible guidelines.
  • Help us manage compliance and build a formal compliance function.
  • Work with our outside counsel to address regulatory and compliance questions and issues.
  • Work with our carrier partners to streamline the claims process and provide input to the product team on how to reduce friction in the claims process and our loss ratio.
  • Develop our long-term strategy for buy vs build (e.g. handling claims, sharing upside / risk in our book, etc.).


  • Significant experience in a senior (e.g. CUO) underwriting position at a top P&C insurer.
  • Experience working in a venture-backed startup or small company environment prized.
  • Command and love of technology.
  • Demonstrable track record of building admitted products and a strong command of the insurance product development and regulatory approval process.
  • Proven ability to prioritize multiple projects and tasks, adapt to changing needs, and, and tackle new challenges daily.
  • Calm and comfortable in a fluid environment.
  • Strategic, tactical, and willing to be hands-on in building a world-class insurance function.
  • Action-oriented with an own-the-outcome mindset, applied at scale and through working with others.
  • Relentless in prioritization of goals, strategies and individual tasks.
  • Demonstrated experience hiring, mentoring, coaching and retaining a high-performing team.
  • Scrappy (and proud of it).

How to apply

Significant compensation package including stock options for the right candidate. Email to apply. No recruiters.