Two Chicks With A Side Hustle

Employer: Circle Medical


  • Circle Medical is a Y-Combinator healthcare technology startup on a mission to bring quality, delightful primary care to everyone on the planet.
  • Built by top-tier entrepreneurs, engineers, designers, and physicians, our telemedicine software has pioneered how people find and receive care.
  • Our founding team has decades of experience with successful technology startup exits.
  • We’ve used our most recent round of funding from WELL Health, backed by Sir Li Ka-shing, to scale from California to over fifteen states across the US.
  • We’re now entering the hypergrowth phase, expanding nationwide from over fifteen states to all fifty states in the next six months. And this is only the beginning.


  • We are currently looking for a People Operations Specialist to join the People & Operations team at Circle Medical Technologies.
  • As we continue to grow, we are constantly searching for exceptional talent to be a part of our team.
  • This position may be based out of our Montreal, Quebec, San Francisco, CA offices or be remote in the U.S. for the right candidate.
  • As a People Operations Specialist, you will work closely with the team to help support our growth, policy, culture, and strategy.
  • You will play an integral role in building up the foundation of success for our network by coordinating employee onboarding, talent management, performance management, and career development across our company.
  • Our People Operations Specialists thrive in a fast-paced, ever changing environment while wearing multiple hats.
  • You will have the opportunity to work to improve upon processes, procedures and programs relating to the team member lifecycle to ensure transparency and efficient allocation of resources.


  • Coordinate and facilitate the on-boarding and new hire orientation program to ensure we are providing new hires with the right tools to be effective in their new role
  • Monitor and generate insight on the employee wellbeing in the company.
  • Support talent acquisition initiatives including full-cycle recruiting, offer letter creation and brand awareness
  • Support and manage the payroll function in partnership with our Finance team
  • Answer employee inquiries and drive new initiatives that support employee engagement
  • Gather data and compile HR metrics to measure the effectiveness of our HR programs
  • Serve as a primary point of escalation and internal team member support for more complex cases, providing policy guidance and interpretation as needed
  • Support administration of various surveys, conduct exit interviews and provide useful data to guide decision making
  • Support and assist with the development of onboarding and offboarding processes
  • Advise on and support employee interpretation of our many employee programs, processes, and benefits, such as performance management, open enrollment, leaves of absence, etc.
  • Support data entry, confidential records management, audits, analysis, etc.


  • Prior HR experience
  • Understanding of the entire team member lifecycle, with the ability to recommend process-oriented and/or operational solutions to improve the team member experience
  • Knowledge of HR standards, legislation and best practices
  • Strong organizational and prioritization skills
  • Appropriate and authentic interpersonal and communication skills
  • Professional judgement when dealing with employee issues
  • Adaptability and flexibility with a demonstrated ability to take initiative
  • Ability to work within a distributed team and as an individual contributor in a fast-paced, changing environment
  • Strong verbal and written communications with the ability to effectively communicate at multiple levels within the company
  • Strong problem solving and organizational skills – able to manage multiple priorities in a dynamic and occasionally ambiguous environment
  • Ability to use discretion and handle highly sensitive information
  • Ability to establish strong relationships at all levels and across functions
  • Ability to operate at both the strategic level and the tactical execution level


  • Proven track record with other startups or VC backed companies


In alignment with our values, Circle Medical has transparent salaries based on location (San Francisco, Montreal, or remote in US), output levels, and options to trade cash for stock.

This is a full-time, salaried position with an annual salary (cash and stock combined) of $78,000 – $100,000 plus, generous vacation, full medical/dental benefits.


Circle Medical is proud to be an equal opportunity workplace. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status.