Head of People

Head of People

At Openly

Date Posted: 01 May, 2021


Openly is rebuilding insurance from the ground up, re-imagining, and improving every aspect of the customer experience.  Doing this requires a rapidly growing team of amazing, curious, empathetic people with a wide range of skill sets--spanning technology, data science, product, marketing, sales, service, claims handling, finance, etc.

And now is the perfect time to join the journey.  Here's why:

  • It's working.  We're now in eight states and on our way to operating countrywide.  We have thousands of agents selling our product and millions of dollars of annual customer premiums.
  • We're well backed & stable.  We closed our $40M Series B fundraise in December and have years of cash runway in the bank.  We're backed by some of the top investors in the world--including Google's “Gradient” AI-focused fund, Obvious Ventures (Beyond Meat, etc.), and Advance Venture Partners.
  • It's not too late!  Despite this traction and stability, we're still early enough in the journey that there's time to make a real difference during Openly's formative period.

If you'd like to understand more about Openly's mission, consider checking out this video from a company pitch we gave several years ago at Techstars.  It's outdated (before the initial product launch!) but still telegraphs the journey we're on.


Job Details

The Head People will report to the CEO and own all aspects of human resources. This is a career-defining opportunity to be a core member of the leadership team that turns Openly into a multibillion dollar household name.  Openly has grown from 20 to 80 employees over the last 12 months and expects to reach 150 employees by the end of 2021, with continued rapid growth expected for years beyond. Openly's employees span a wide variety of functions, including software engineering, actuarial/data science, sales, service, claims, and other support. We are a fully remote company and currently have employees spread across more than 20 states.  


Key Responsibilities

  • Build and manage a team (2-3 employees in the short term). Continue to leverage outside resources as needed, while transitioning more functions internally over time.
  • People strategy. Develop and own Openly's overarching approach to building and maintaining a talented, engaged workforce.
  • Recruiting and onboarding. Lead our efforts to grow to 3x our size over the next 12-18 months. Coordinate onboarding so that new employees feel welcome and equipped to be productive.
  • Training. Working with managers, identify, develop, and maintain appropriate general and role-specific training resources.
  • Compensation philosophy and execution. Develop compensation philosophy, cross-functional leveling framework, etc. Working with our TPA, oversee execution of payroll, benefits, and related processes (time tracking, etc.).
  • Compliance. Working with our TPA and external company counsel, ensure that Openly meets all employee-related compliance obligations.
  • Performance and talent management. Develop and implement regular processes to ensure that (a) employees receive performance feedback and (b) the management team has visibility into the talent strengths, gaps, opportunities, and risks within the organization.
  • Culture. Work cross-functionally to promote Openly's desired norms of behavior and engagement.
  • Workforce planning. Work with managers to understand and anticipate talent needs. Collaborate on evolving organizational structure ensuring clear lines of accountability.
  • Tech solutions. Evaluate and potentially adopt technology solutions for people-related tasks such as onboarding, time management, performance management, etc.

What will success in this role look like? Here are some of the key expected measures of success:

  • The leadership team sees you as a general thought partner who contributes to and understands the company's broad strategy.
  • Openly achieves its aggressive hiring goals, with appropriate emphasis on interviewing a diverse pool of candidates.
  • Employee engagement remains high, as measured for example by employee NPS.
  • Openly successfully adopts a majority-remote working model in a company with many disparate role profiles.
  • Openly is compliant with all relevant laws and regulations.
  • Employees trust that they can turn to you with sensitive topics and get a thoughtful response.



  • The candidate must have familiarity with standard best practices across all aspects of Human Resources and significant experience leading HR teams. This experience will have been obtained from working at a mid-sized or large established company.
  • The ideal candidate has helped rapidly scale an early or mid-stage company or function. We plan to triple in size, and we need someone who is excited about helping us build all the people operations and functions required to scale quickly.
  • A first principles thinker. We're an analytical group and will ask “why?” a lot. The opportunity here is that we're open to doing things a non-traditional way. The challenge is that someone needs to really think things through critically and creatively.
  • Organized. We have a portfolio of needs that no human could accomplish in a short period of time. Therefore, this candidate will need to be comfortable prioritizing, pushing back, and executing on competing priorities.


Benefits & Perks

  • Competitive salary based on experience and equity in a fast-growing startup
  • Generous benefits package including medical, dental, vision, disability, 401(k) company contributions, flexible spending accounts and monthly remote stipend
  • Fun, high-energy startup environment, remote workforce even before COVID restrictions
  • Flexible PTO
  • Training, coaching and development with an eye towards upward growth and mobility within roles at a new, growing insurtech firm

U.S. Citizens, Green Card Holders, and those authorized to work in the U.S. for any employer will be considered.

Openly is committed to equal employment opportunity and non-discrimination for all employees and qualified applicants without regard to a person's race, color, sex, gender identity or expression, age, religion, national origin, ancestry, ethnicity, disability, veteran status, genetic information, sexual orientation, marital status, or any characteristic protected under applicable law. Openly is an E-Verify Employer in the United States. Openly will make reasonable accommodations for qualified individuals with known disabilities, in accordance with applicable law.

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