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

Now is the perfect time to join the journey. Here's why

  • It's working. We're in multiple 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. We are supported by some of the top investors globally, 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.

Job Details

Openly is seeking an innovative problem solver, highly experienced with HRIS system selection and implementation, to join our PeopleOps Leadership Team reporting to the Chief People Officer. The Director of HRIS and People Operations will build and lead a team managing all HR technology and process improvement/automation and benefits, leaves, immigration, metrics, SOX compliance, and total rewards.

The Director will work closely with internal stakeholders to identify business requirements and solutions that meet current and future needs through process, data, and technology. The Company is building for scalability as it continues its strong growth trajectory. If this multifaceted role sounds like your type of challenge, then let's talk Openly.

Key Responsibilities

  • Drive HR technology thought leadership, transformation, and innovation
  • Deliver HR technology solutions from requirements gathering/definition, solution design, planning and budgeting, development, and production support
  • Build, lead, and develop your team, including HRIS, benefits, rewards, reporting, and people analytics, to provide the infrastructure needed to support a rapidly growing, fully distributed company
  • Identify opportunities to improve HR programs and services by leveraging technology and implementing process improvements
  • Create documentation for requirements, design, technical specifications, change management, and implementation
  • Build and implement the roadmap and sustainable model for the continuing evolution of the use of technology to support HR service delivery and strategic initiatives
  • Engage with other functional areas to understand and provide HR support for technology projects that impact HR processes and systems.
  • Ensures appropriate HR SOX controls design and adherence and appropriate permissions design for HR systems and access to HR records.
  • Guide the design of robust data management processes to ensure HR data integrity and security.
  • Oversee reporting design and execution of required EEO and other data


  • Strong technical skills and an ability to learn technology tools quickly.
  • Self-starter with the ability to work independently as well as with the team in a dynamically changing environment.
  • Must be flexible and willing to undertake a wide variety of challenging tasks
  • A Bachelor's degree or equivalent training in fields such as Computer Science, Information Technology, Business, or related field with an IT focus
  • Advanced degree or education such as a Master's degree or advanced certification in Business or Management a plus
  • Executive-level presence with an ability to build and maintain trust-based relationships with senior leaders
  • 10+ years experience in HRIS and HR Operations roles of progressive responsibility, including managing a cohesive, multidisciplinary team
  • Innovation mindset continually looking for opportunities to improve established products and increase impact for the business
  • Ability to establish solid relationships with vendors in support of initiatives; ability to negotiate and manage outside vendors and strategic partners against deliverables
  • Solid project management skills, including the ability to effectively deploy resources and manage multiple projects of various diverse scopes in a cross-functional environment
  • Experience driving one or more significant projects implementing HRIS from planning through implementation. Substantial project and program management skills and experience are a must.
  • Significant and broad HR subject matter experience including topics such as compensation, People Analytics, Benefits, Immigration, and SOX compliance
  • Passion for problem-solving and continuous improvement.

Benefits & Perks

  • Competitive salary, corporate bonus program, equity position in a startup company
  • Company-sponsored medical, dental, vision insurance plans, short-term and long-term disability, life insurance, 401k with corporate contribution, and FSA plan
  • Company-paid 12 weeks parental leave policy
  • The Company fully embraces the "work-from-anywhere" mentality, even before COVID restrictions.
  • Paid Time Off
  • Fun, fast-paced, startup environment

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 under applicable law.