Private sector

Vice President of Operations

San Francisco or Sacramento, CA, USA
Job Type
6+ years
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About the role

About Us We are a profitable and fast-growing healthcare startup – a small and mighty team of around 50, helping people to find, enroll in, and use ACA health coverage. We’ve doubled in each of the past two years and are now the largest ACA enrollment platform after, having helped over 5 million people enroll in health coverage. We're a mission-driven team that advocates for and cares deeply about the people we serve.

We are a double bottom-line company: revenues and enrollments in ACA coverage. The ACA brings high quality, comprehensive, and affordable health coverage within reach for low-income Americans. And we exist to make that promise a reality. Your contribution will positively impact hundreds of thousands of people, helping them to navigate the complex and confusing health insurance industry and to access health care when they need it.

About The Role HealthSherpa is a growing company in an operationally intensive industry. We have doubled enrollments and revenue in each of the last two years and are now at an eight-figure run rate. Every month, a hundred different organizations pay us and in turn we pay thousands of others. Our operational infrastructure has lagged that growth, and historically, we’ve relied on heroics and duct tape to guarantee Ops did not limit growth.

Your job as our VP of Operations is to fix that dynamic and build the teams and infrastructure to allow us to grow from millions enrolled to tens of millions and from eight figures to nine figures of revenue.

The VP of Ops will be someone responsible for the following companies teams/functions: Agency Operations covers carrier relations, carrier audits, 1099 payments, and revenue analytics. This is the small team that runs the machine that ingests millions of dollars every month, audits those payments, and generates thousands of checks and ACH payments. This team also maintains contractual and interpersonal relationships with the insurers that pay us, and performs analysis on those payments to inform the work of the company.

Company Operations covers facilities, HR, accounting/payroll, legal and IT. This team performs traditional company operations responsibilities, with the extra complexity of handling a seasonal workforce that is 150% larger than our full-time team.

Fraud Prevention, Compliance and Licensure. Millions of health insurance enrollments flow through our systems, and inevitably some bad actors will try to use our systems. We catch them, report them, and ban them as quickly as possible. We are also subject to a giant web of overlapping federal and state rules and regulations. We need to carefully navigate that web and ensure we stay in compliance.

Fortunately, you’ll have capable lieutenants - many whom are already in place - to lead the teams that perform many of these essential functions.

Your Opportunity Reporting to the CEO, the ideal candidate will have experience scaling a growing organization. You will manage 3 direct reports and approximately 6-10 full-time employees, across our Sacramento and San Francisco offices. You will require proficiency in operations, process optimization, analytics, management, and a working knowledge of IT, HR, and facilities. You are passionate about management and care about your people and their professional development. You enjoy understanding and overseeing complex processes, like diving into problems to help out, and take pride in doing things right. You dream in flowcharts. You love architecting elegant processes that use technology to do large amounts of repetitive, essential work faster and better than anyone thought possible.

Your Responsibilities -Oversee payment infrastructure and processes -Oversee relationships with insurance companies -Oversee company operations including, IT, Facilities and HR Oversee accounting and finance -Contribute to financial modeling and budgeting processes -Oversee compliance including managing fraud prevention unit (FPU), state reporting requirements and maintaining insurance licenses

Your Background -Manage and grow the operations team -6+ yrs experience in operational roles in companies with high growth -3+ yrs of management with experience in successful mentorship and development of direct reports -Data literacy & technical comfort -Excel (complex functions) -Experience developing complex operational processes -Expert at making thoughtful tradeoffs and can handle a volume of responsibility that may at times exceed your team’s capacity/bandwidth -Experience with compliance and complex regulatory frameworks -Passionate about social impact and improving access to health care

Nice to have -Worked at an insure-tech related startup Affordable Care Act and Health policy knowledge -You've worked for one or more growth-stage startups, having helped scale from eight to nine figures of revenue. -SQL experience -Familiarity with R, Ruby, Python or other programming languages

What HealthSherpa Offers -Great compensation package including meaningful equity in a high growth, profitable company -Health, vision and dental coverage for you, your spouse and dependents -401K after grace period -Paid vacation and holidays -Catered or restaurant lunch, daily -Parking / Commuter benefit

We're building a diverse and inclusive work environment where we learn from each other, respect one another and welcome different lived experiences. We encourage people of diverse backgrounds, experiences, identities, abilities and perspectives to apply. We are an equal opportunity employer and a fun place to work. Come join the team at HealthSherpa.

Must be authorized to work in the US.

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