Business Operations Assistant

ApostropheHC Apostrophe

The health plan that can fix America

Apostrophe is building the health plan that can fix America.

The largest most creative self-insured employers have figured out how to cut 40% from their healthcare costs. Our SaaS platform makes their best practices plug-and-play for the other 80% of US employers who self-insure their health benefits.

We replace the existing health plan administrator (think: Cigna, Aetna or United Healthcare) to deliver healthcare savings as a service and — in our customer’s words — a benefit that feels like a benefit again.

Think of us as the Southwest Airlines of health plans. In an industry defined by complexity, opacity and indifference Apostrophe is delivering simplicity, transparency and love.

What We Need.

We need a dynamic do’er who can figure things out. You’ll be part office operations, part sales support, and part “right hand assistant” to the founders. We need someone who can anticipate needs, see a problem and develop a solution, and will do what it takes to help us succeed. In exchange you’ll see every aspect of our business and as we grow you’ll have a chance to decide what area interests you the most to go deep.

This is the classic ground floor, “seat on the rocketship” opportunity to help solve a wicked problem with experienced founders at a values-based company. You’ll initially report to the CEO but will assist all three co-founders and our functional team leaders.

What You’ll Do.

Sales Enablement

  • Assist with research for sales proposals and lead generation.
  • Run logistics for marketing events and and coordinate sales and member onboarding collateral.
  • Work with the provider team to identify facilities, quality, and pricing for a core group of commonly used services in prospective markets. Present this information in a compelling way that will be used in both the sales and initial client onboarding process.

Health Plan Operations

  • Deliver bottoms-up savings analysis for strategic accounts using a combination of internal reports and spreadsheet magic.
  • Help out with member tech support or provider support in a pinch.

Team Experience

  • Assist hiring managers in posting job descriptions and generating a pipeline of diverse candidates.
  • Make the interview and on boarding experience at Apostrophe awesome for the candidate/new hire and seamless for the founders.
  • You’ll help with prep for our monthly all hands and summer offsite plus keep the office operating smoothly. This will include everything from weekly metrics reviews to taking over our account and our office beverage fund and running office errands.

Founder Support

  • Assist with board prep and Monday morning ops meeting, including updating KPI progress with team leaders and from internal reports..
  • Build ad hoc spreadsheet models to answer business questions for founders.
  • Help founders with scheduling and travel booking when needed.

What You’ll Bring.

  • You’ll bring grit and hustle. You’ll seek out learning and can solve problems cleanly.
  • You are comfortable in a fast changing and collaborative startup environment.
  • You write clearly and concisely.
  • You are comfortable comfortable working with or learning WordPress, Photoshop/light graphics tools, and HTML email tools.
  • You can do ad hoc spreadsheet modeling in Excel/Google Sheets to answer questions the founders have about the business.
  • A passion for fixing the problems in healthcare is a plus.

Who We Are

We are a Techstars Boulder ‘17 company and certified B Corporation. Royal Street Capital, Techstars Ventures, and are helping us build a fast-growing sustainable business based around our core values.

Full-time folks at Apostrophe get an early-stage options package and an open time off policy. Medical, dental, vision and 401K are available. Company contribution to these benefits and other opportunities will expand as we grow.

Our home base is in the Rino area of Denver. There is ample free parking and we are just a couple blocks from the new 38th and Blake Light Rail stop. We split our time between the office and work from home.

Apostrophe does not discriminate based on race, color, religion (creed), gender, gender expression, age, national origin (ancestry), disability, marital status, sexual orientation, or military status, in any of its activities or operations. We are committed to providing an inclusive and welcoming environment for all members of our staff, clients, volunteers, subcontractors, vendors, and clients.


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