Vice President of Operations

Sacramento, CA /
Operations /
Full Time
About Us
We are a profitable and fast-growing healthcare startup – a small and mighty team of around 65, helping people to find, enroll in, and use ACA health coverage. We’ve doubled in each of the past three years and are now the largest ACA enrollment platform after healthcare.gov, having helped over 9 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: revenue, 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.  

We are committed to building a team balanced in representation to best serve the people who use our products. We believe in creating inclusive and equitable spaces, which build trust and respect and foster a sense of belonging. These values are at the core of our culture, and we genuinely believe they will continue to lead our organization to successful outcomes.

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 to build the teams and infrastructure to allow us to grow from millions enrolled to tens of millions, and from eight- to nine-figures of revenue. 

The VP of Ops will be responsible for the following teams/functions:
Agency Operations covers carrier relations, carrier audits, 1099 payments, and revenue analytics. This team is 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. 

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.

Support organization (including Agent / Broker support team as well as the Consumer Support team). There are about 50 support reps and this scales up 3-4x seasonally during Open Enrollment for 4 months, and we expect the base number to double every year.

IT, Security, and Facilities. These large and fluid teams need a home or office to work from, equipment to work work with, and they need the equipment to be secure.

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


About You
Reporting to the CEO, the ideal candidate will have experience scaling a growing organization. You will manage 4-5 direct reports and a larger team of 60-80 full-time employees across our Sacramento and San Francisco offices. You will require proficiency in operations, process optimization, analytics, management, support, and a working knowledge of IT 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 company operations, including IT and Facilities 
    • Oversee accounting and finance
    • Oversee compliance including managing fraud prevention unit (FPU), state reporting requirements, and maintaining insurance licenses
    • Oversee the entire support organization
    • Manage and grow the operations team
    • Anticipating & mitigating risk

Your Background

    • Demonstrated experience building and supporting diverse teams
    • 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
    • Experience with compliance and complex regulatory frameworks
    • Passionate about social impact and improving access to healthcare

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-figure revenue
    • 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. 
Physical requirements & work conditions

-Work is performed primarily in a standard office environment
-Physically able to reach, stretch, bend, walk, and navigate stairways

The physical demands and work environment characteristics described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Employees may, among other things, be required to undergo background investigations or security checks, or meet certain standards dictated by law, regulation or contracts, and as a prerequisite to employment candidates may be asked to consent to a due diligence/background investigation. As a condition to hiring and continued employment, we require all employees to meet those requirements that are necessary to fulfill their individual roles.