Vice President, Engineering

We are a very profitable and fast-growing healthcare startup—a small and mighty team of 200 helping people find and enroll in ACA health coverage. As the largest health insurance exchange for the ACA, enrolling more individuals than healthcare.gov and all our competitors, we have helped over 10 million people enroll in health coverage to date in 2024. We’re a mission-driven team that advocates for and cares deeply about the people we serve.

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

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

About The Role

We are looking for a hands-on VP of Engineering to join our dynamic team of over 25 engineers, two directors, and five engineering managers to take HealthSherpa’s software engineering and delivery to the next level.

You are an expert manager of engineers, managers, and directors and are comfortable working across the development stack and are passionate about improving both people and technology.

You believe in using data and analysis to form conclusions and refine thinking and are an expert in setting up practices that improve software delivery outcomes across the entire organization and multiple teams.

As part of the executive team, you will report to the VP of Product and Engineering. You will significantly impact the people, processes, and products at HealthSherpa, working with others across the company.

The base salary range is $257,000-$315,000 + bonus + equity + benefits. Within the range, work location and additional factors, including job-related experience, determine individual pay. Your recruiter can share more about the salary range for your preferred location during the hiring process.

You Will

• Take ownership of all software engineering, delivery, and operation for engineering in our ACA unit
• You will manage managers and directors, guiding and orchestrating their execution
• Establish and evolve lightweight processes using data-informed methods that are stage and scale-appropriate, ensuring technical quality, speed, and efficiency.
• Lead the engineering organization in building and delivering high-quality features in a rapid, organizationally scalable manner across the entire tech stack – frontend and backend
• Manage, coach, and improve the organization’s directors, engineering managers, and engineers by properly balancing competency, clarity, and control.
• Help shape and implement the technical vision, aligned with the product and vision, in close collaboration with other leaders
• Provide technical expertise to engineering activities

You Have

• You have 12+ years of software engineering experience and 7+ years of management experience, including 3+ years of managing directors
• Expert in full-stack engineering – front-end, back-end, operations, architecture, data models, infrastructure, and modern development practice
• Expert in raising the bar in organizations through training, standards, hiring, change management, processes, mentorship, and demonstration
• Expert in delivering engineering outcomes, whether that’s uptime or revenue

What We Offer (Full-time, Not Temporary/Not Seasonal)

• Remote-first company (US-based remote only)
• Great compensation package at a high-growth, profitable company
• Excellent benefits package that includes health, vision, and dental coverage for you, your spouse, and dependents
• HSA/FSA options with corresponding contribution limits
• Monthly grocery stipend and home internet reimbursement
• 401K w/ a match after a grace period
• Life and AD&D coverage
• Disability insurance (Short and Long Term)
• Parental leave
• Four (4) weeks of paid vacation in addition to paid holidays
• Home office budget for remote team members
• Mental health and other wellbeing support programs through a partner network

We welcome and 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!