About Ease:
Ease is the #1 rated benefits administration and HR software for businesses with 2–250 employees, powered by insurance brokers. 70,000+ employers trust Ease’s innovative SaaS service model to set up and manage benefits, onboard hires, stay compliant and offer their employees one destination for all their human resources information. Headquartered in San Francisco with offices in New York, Las Vegas, and Omaha, Ease was ranked number 57 in Forbes 2020 list of the top 500 startup employers in America. Ease recently earned a spot on G2’s 2022 Best Software Awards, placing 18 on the Highest Satisfaction Product list and 50 on the HR Product list.

About the Position:
Ease is looking for an experienced product leader with a technical background to own and define the roadmap for the core benefits administration experience of the. Ease platform. Ease serves a diverse set of user personas: insurance brokers, HR administrators at small employers, employees , general agents, insurance carriers, third party administrators and others.

Ease is a multi-sided B2B2E (E = employee) platform that is transforming how the industry serves small businesses through automation and standardization of digital enrollments. Our mission is to make benefits easy and to enable small businesses to offer their employee’s benefits packages that are competitive with what the very largest companies can offer. We operate in a complex, heavily regulated, and technically lagging industry. The challenges are great – but the rewards are even larger.

Do you enjoy building a high performing product team? Can you help the team see the big picture while maintaining an attention to the level of detail needed to drive successful execution? Do you have the necessary determination and perseverance to keep chipping away at problems, while being receptive and staying alert to potentially game changing solutions? Do you enjoy driving consensus across a broad array of internal and external stakeholders? This could be the opportunity for you!


  • Define the vision for and the direction for core user experience.
  • Grow the product team and mentor junior product managers.
  • Work closely with our lead designer and other product managers to refine the customer discovery process following the latest practices in dual-track agile.
  • Meet regularly with key customers and build out a customer-advisory board.
  • Prioritize feature work and coordinate dependencies with other product development teams.
  • When needed step in as an individual contributor and define detailed requirements and work closely with developers.
  • Define the product roadmap for broker, employer and employee user experience and drive the quarterly planning activities.
  • Track execution status and communicate project status to internal leadership and partners.

Experience / Skills desired:

  • 10+ years of product management experience.
  • 4+ years experience managing and mentoring product managers.
  • Our delivery cadence is fast paced and iterative - but given the nature of the industry we operate in - the candidate will need to demonstrate experience with managing complex delivery cycles and managing risk over multiple quarters.
  • Familiarity in working with design teams. Managing design teams would be a bonus.
  • Experience with benefits industry or related (e.g, payroll, HR) would be an advantage but not required.
  • Experience working in a fast-paced SaaS environment and leveraging data to drive decisions.
  • Experience working in complex B2B digital supply chains. A bonus would be if you have experience with B2B2C platforms and/or marketplaces.
  • Sufficient business acumen to convey the vision and value to non-technical stakeholders.
  • A passion for detailed feature design and problem solving.
  • Ability to translate high level requirements into detailed product specifications.
  • Exceptional analytical and decision-making skills, and experience making data driven UX decisions based on a multitude of complex, interdependent factors.
  • Exceptional written and oral communication skills.
  • Must have proof of legal authority to work in the U.S.
Ease is an equal opportunity employer and makes employment decisions without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability status, or any other status protected by law. 

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