Chief of Staff

Full Time
Los Angeles, CA
Apply Now

EnterMedicare is building technology to improve healthcare for America's 60 million Medicare recipients. We partner with the largest health insurers in the world to empower consumers to utilize their benefits, access quality care and take control of their healthcare experience.

Our company is at an inflection point. After raising several million earlier this year, we are finalizing major partnerships with some of the largest insurers in the world. We are now building our team of exceptional professionals to help us make our vision a reality.

The Role

We are looking for a resourceful hands-on Chief of Staff to power scale and maximum impact for our rapidly growing software business. Reporting to the co-founder and CEO, this position will directly contribute to a wide range of projects and workflows around internal and external matters. A day at EnterMedicare could include data analysis, industry research, internal initiatives related to product development, organizing operational complexities or creating expert presentations for new expansion explorations. The ideal candidate possesses an exceptional EQ, is highly data-driven and is an energetic and optimistic person who is able to multi-task, communicate and work cross-functionally in a dynamic startup environment.

What You’ll Do

  • Develop a deep understanding of EnterMedicare’s product, customers, clients and internal business fundamentals including data analysis
  • Design and create investor updates, sales presentations, written branding and marketing literature including Medicare-related content, and various other high-stakes communications for internal and external audiences
  • Collaborate with teams across the company on a range of ad-hoc projects involving Product, Customer Success, People Operations and Business Development
  • Identify, assume ownership and manage cross-functional operations and administrative processes that don’t have a clear home within the organization
  • Support day-to-day operations and execution tracking of the team and the company

What You’ll Need

  • Strong business, product and financial acumen with experience in a highly analytical role (examples include management consulting, business analysis, product management, investment banking or operations at a high-growth company)
  • Excellent written and verbal communication skills in a variety of settings: e-mails, Slack, in-person in team meetings, and in front of high-stakes clients or investors
  • Proven experience with designing and producing high-quality presentations for internal, marketing, fundraising and branding purposes
  • Highly organized strategic-thinking capabilities with a keen attention to detail
  • High-energy team player who thrives in a fast-paced start-up environment
  • Self-starter able to take initiative and power through ambiguity by taking action and problem solving

What We Offer

In addition to offering a competitive salary, we want to create an environment where you are given the tools and benefits that allow you to do your best work:

Ownership: We cultivate an environment where team member feels a deep ownership of the work you do and the product you help build. The right candidate will have meaningful equity compensation in an exciting venture-backed startup

Wellness: Comprehensive Medical, Dental, Vision. Competitive PTO and unlimited sick days. Monthly allowance for fitness and health expenditures

Learning: Unlimited reimbursement for relevant industry-specific education and licensing. Fast paced work environment geared towards professional growth

A supportive work environment: Access to weekly healthcare-focused education and networking opportunities. Commuter benefits. Cell phone stipend. Unlimited free snacks. Centrally located office with bright city and ocean views

Get to Know Us

We are building digital experiences to help people manage their Medicare benefits, and transform the way an entire generation will interact with the health system in retirement.

EnterMedicare is backed by top-tier venture capital firms including Greycroft, Innovation Endeavors (former Google Chairman Eric Schmidt), Peterson Partners, actor Will Smith and quarterback Joe Montana. Learn more at

Apply now

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.