Engineering Manager, Billing Systems

About the Role:

We are searching for an Engineering Manager to drive our B2B capabilities, including Billing, Incentives, and Performance Guarantees. This role requires technical acumen and strong leadership to advance our business objectives. In this role you will lead a distributed team that plays a vital role in new client implementations, enabling new partnerships, and expanding the scope and reach of Omada Health.

This is not a pure people manager role. You will bring genuine technical depth, help set architectural direction, and be the person your team looks to when there is no clear answer. You will also be expected to think ahead — to understand where this domain needs to go, make the bets, and connect strategy to the team's day-to-day. 

You will leverage your deep technical expertise in technologies like Ruby on Rails, Sidekiq, Redis, and Postgres to ensure system excellence, while also integrating AI advancements. Your leadership will be pivotal in fostering a culture of innovation and collaboration, encouraging diverse perspectives and driving the professional growth of your team as they contribute to our strategic goals.

What You Do:

• Lead and mentor a team of engineers, emphasizing technical excellence, productivity, and stakeholder satisfaction.
• Collaborate with cross-functional teams to align technical strategies with business goals, translating high-level vision into actionable objectives.
• Engage in direct technical contributions approximately 5–10% of your time to support system performance and scalability through activities like code reviews, architectural guidance, and hands-on debugging during critical incidents.
• Foster an inclusive culture that embraces diversity, promotes work-life balance, and nurtures professional development.
• Navigate complex projects within regulated industries, embedding security and compliance in everything you design.
• Define where the Billing domain needs to be in 12–24 months, translate that into team bets and priorities, and own that narrative
• Model and actively drive the use of AI-powered developer tools — agentic coding, AI-assisted code review, LLM-assisted debugging — as a core part of the team's SDLC.

Qualifications:

• 8+ years of software development experience, ideally within the Billing domain 
• 5+ years of management experience in engineering with a focus on delivering business-impactful solutions.
• Demonstrated ability to set technical strategy and connect it to team execution — not just managing delivery, but shaping direction.
• Active practitioner of AI-powered development tools and passionate about integrating AI into business solutions.
• You know how to build a roadmap, plan for capacity, evaluate trade-offs, and know how to negotiate with your stakeholders.
• Proven ability to attract, retain, and develop engineering talent.
• Excellent communication and collaboration skills with a strategic mindset.
• Strong cross-functional influence skills — you build trust with non-engineering stakeholders (RCM, Finance, Accounting, Compliance) and navigate ambiguous organizational dynamics without positional authority.
• Comfortable working in a highly regulated environment

Technologies We Use:

• Ruby on Rails, Sidekiq, Redis, Postgres
• Docker, Kubernetes, and modern frameworks
• Cursor, Claude Code, or any other AI-powered development tooling 

Benefits:

• Competitive salary with generous annual cash bonus
• Equity grants
• Remote first work from home culture
• Flexible Time Off to help you rest, recharge, and connect with loved ones