Director, Software Engineering; Sales App

Join us in creating a better way! At eHealth, our mission is to expertly guide consumers through their health insurance and related options when, where, and how they prefer. We’re creating a better way – one that’s transparent and trustworthy for both our consumers externally and our employees internally. Move your career forward while connecting countless people to the life‑changing, quality care they deserve.

Our diverse team of innovators supports one another in solving some of the toughest challenges. We’re always on the lookout for creative opportunities to do right by our customers, and each other. Together, we’re creating a better way to work, united by our common passion to make a difference. At eHealth, our mission is to expertly guide our customers through their health insurance needs by matching them with personalized, and affordable health insurance plans.

We connect our customers with quality, affordable health insurance through a proprietary marketplace offering Medicare Advantage, Medicare Supplement, individual, employer, and ancillary plans from 200 health insurance carriers nationwide. By doing so, our vision is to be the nation's leading and most trusted source of consumer purchasing of health insurance, ancillary products, and related options on our marketplace.

In this exceptional leadership opportunity, we are seeking a Director of Engineering to lead our Sales App engineering platform. Sales App business is one of the most important business‑line for eHealth and critical to the future of the company. Sales App engineering drives a large part of eHealth’s revenue. As we expand these business lines, this role will be crucial for developing core technologies, creating new experiences, building teams, and growing the engineering organization.

This role will partner closely with Product, Design, Marketing and Sales to bring the next‑generation vision to fruition. We offer a great deal of autonomy and flexibility to our teams. If you're a results‑oriented, technically confident leader who enjoys working with a lot of freedom, knows how to take full ownership, collaborate with cross‑functional teams and execute with quality, then this is the role you’ve been looking for.

The emergence of technologies like generative AI, natural language processing, and cloud‑based contact centers provides an exciting context for a fast‑growing company like eHealth. Our proprietary scripted sales and compliance software is “best in the business” and we are looking to build newer features with these new technologies extending eHealth’s significant competitive advantages. When integrated with the company’s online eCommerce platform and its unmatched capabilities in the industry — eHealth is driving toward an omni‑channel opportunity of enormous scale.

You will lead multiple engineering teams and have a significant impact within our company. You will have a dual mandate to modernize the Sales Application systems and bring in innovation leveraging AI.

• Lead the vision, strategy and execution of Sales App engineering in partnership with engineering and product leadership.
• Define a strategic engineering vision to build a highly scalable, resilient and secure system as we expand our product lines.
• Lead technical strategy and drive innovation to ensure eHealth’s platform continues to deliver best‑in‑class experience.
• Grow and expand your team by hiring great talent, mentoring team members and improving engineering quality, productivity and performance.
• Instill an inclusive team culture that is passionate, empathetic, and collaborative.
• Build operational excellence to achieve goals across multiple product lines.
• Demonstrate eHealth’s values in your behaviors, practices, and decisions.

• 10 years+ in Engineering with 6+ years in a significant leadership position.
• Strong leader who has managed, hired and grown engineering teams of 20+ team members across multiple geographic locations.
• A strong experience building consumer‑facing products, building high‑performing web experiences.
• Experience building highly scalable APIs and Micro‑services preferably in AWS.
• Experience delivering…