Director of Engineering, Eligibility & Revenue Systems

Omada Health is on a mission to bend the curve of chronic disease.

Job overview:

The Eligibility & Revenue Systems are the enterprise backbone that makes the employer and health plan business work: they ingest files, determine eligibility, power billing, and integrate incentives so customers can get members into care without friction. Together they cover Omada's part of the employer and health plan revenue cycle: file ingestion and partner integrations, eligibility, and claims and invoicing.

The role:

An experienced Director of Engineering is needed to lead multiple teams responsible for the Eligibility & Revenue Systems. These are the systems that lets Sales sell what can actually be delivered, make implementation predictable, and keep customers trusting Omada's operational backbone.

This is a senior leadership role for someone who understands that commercial and operations are the reason Omada works; the technology serves their commitments. The role owns the technical strategy and execution for the Eligibility & Revenue Systems, with clear OKRs, strong instrumentation, and disciplined planning to deliver consistently against reliability, scale, compliance, and partnership outcomes.

What you'll lead:

You will lead multiple engineering teams (and their managers) across the Eligibility & Revenue Systems, all serving the same set of users: internal operators and Commercial stakeholders.

The mandate is simple and hard: build and evolve the platform Commercial and operations partners trust, keep using, and can scale on year after year. Reliability, data integrity, contract fidelity, and SOX-aware auditability are not negotiable.

How you'll make an impact:

• Own the technical and execution strategy for the Eligibility & Revenue Systems: file ingestion, eligibility, billing, incentives, and the shared components that connect them.

• Partner closely with Commercial, Implementation, Finance, and other EPD leaders to keep the platform aligned with the sales pipeline, upcoming deals, and operational constraints.

• Define B2B Core OKRs and success metrics, and lead the teams to deliver against quarterly commitments with transparency and predictable execution.

• Ensure the platform scales each year: capacity, performance, and operability all improve as volumes and complexity grow.

• Raise the bar on architecture and shared components between B2B Core and other systems, reducing duplication and tightening interfaces.

• Hire and develop managers, plus Staff engineers and future leaders.

• Set a high bar for craft, performance, reliability, data integrity, and auditability. Commercial and customers notice the small things; getting the small things right is how trust is earned and kept.

• Build the relationship with Commercial so pipeline visibility and contract requirements show up as early inputs, not late surprises. Partner with Product on roadmap and assessing commercial opportunities.

• Work with Platform and other EPD domains on shared services, while owning reliability outcomes and operational excellence for everything B2B Core-facing.

• Ensure the Eligibility & Revenue Systems meet SOX and other relevant compliance requirements: controls are clear, changes are auditable, and financial flows are traceable end-to-end, in tight partnership with Finance and Security.

• Apply AI in the day job as a hard requirement: use AI and automation to improve engineering leverage, operational decision-making, workflow quality, and team effectiveness, while holding a high bar for trust and control.

This role is for you if you:

• Understand enterprise platforms that sit between Sales, implementation, and operations, and treat reliability and data integrity as product features.

• Are comfortable holding multiple team shapes at once: complicated subsystem, platform, and stream-aligned.

• Excel at influence and tight partnership with Product, Commercial, Implementation, Finance, and Platform. Teams align to a single narrative from pipeline insight through shipped change.

• Believe that great engineering reduces operational load, on-call fatigue, and customer escalations at the same time.

• Are comfortable in regulated, trust-heavy environments and treat privacy, security, SOX constraints, and contract fidelity as guardrails you design within from day 0.

• Turn ambiguous, multi-stakeholder goals into clear priorities and execution plans for teams.

• Have applied AI in the day job and can bring that same bar here: practical automation, better workflows, measured outcomes, and clear guardrails.

Required:

• 10+ years of experience in engineering leadership, including 3+ years managing managers.

• Experience leading multiple engineering teams in a trust-heavy, operator-facing domain, with a high bar for reliability and operator/customer trust.

• Proven ability to define success metrics and hold teams accountable to outcomes, not just output, in an Agile environment.

• Proven ability to lead quarterly planning and OKRs across multiple teams, including capacity planning, organizational design, dependency management, and data-driven course correction.

• Experience hiring, developing, and retaining high-performing engineering leaders, including standing up new teams or reshaping existing ones.

• Strong technical judgment in distributed systems, data pipelines, and integration architectures.

• Accountable for a healthy 24/7 on-call and reliability culture: reducing toil, improving incident response, and strengthening learning loops.

• Comfortable working with non-engineering operators and earning their trust on tooling and platform changes that affect their daily work.

• Experience leading business-critical platforms in regulated or audited environments (SOX, SOC-2, PCI, or similar), with the ability to own SOX responsibilities in partnership with Finance, Security, and Audit. You don't have to be a compliance specialist, but you know how to design systems and processes that pass scrutiny.

• Shipped AI- or automation-enabled improvements to user or operator workflows, and led teams to use AI to do their work better.

• Track record of predictable delivery: turning ambiguity into clear plans, managing dependencies, and hitting commitments without sacrificing quality.

• Background building tools for implementation, eligibility, billing, incentives, benefits, prior authorization, PBM integrations, or other operator-facing enterprise workflows.

• Experience integrating with Commercial and Finance as partners, including clear ownership boundaries for requirements, SLAs, and data contracts.

• Experience leading platform modernization or re-architecture in a complex, legacy-plus-new environment.

• Familiarity with Team Topologies vocabulary (stream-aligned, platform, enabling, complicated subsystem) and how to apply it.

• Hands-on technical background that helps with diving deep when needed.

Benefits:

• Competitive salary with generous annual cash bonus

• Equity grants

• Employee stock purchasing plan (ESPP)

• Remote first work from home culture

• Flexible Time Off to help you rest, recharge, and connect with loved ones

• Generous parental leave

• Health, dental, and vision insurance (and above market employer contributions)

• 401k retirement savings plan

• Lifestyle Spending Account (LSA)

• Mental Health Support Solutions

• ...and more!

It takes a village to change health care. As we build together toward our mission, we strive to embody the following values in our day-to-day work. We hope these hold meaning for you as well as you consider Omada!

• Cultivate Trust. We listen closely and we operate with kindness. We provide respectful and candid feedback to each other.

• Seek Context. We ask to understand and we build connections. We do our research up front to move faster down the road.

• Act Boldly. We innovate daily to solve problems, improve processes, and find new opportunities for our members and customers.

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