Senior Director, Software Engineering

At Collective Health, we’re transforming how employers and their people engage with their health benefits by seamlessly integrating cutting-edge technology, compassionate service, and world-class user experience design.Role Overview Collective Health is transforming healthcare for millions who use our platform to understand, navigate, and pay for care. The Member Experience Engineering team builds every interface a member or Member Advocate interacts with: our web and mobile apps, plus the tools and AI powering our contact center. We are hiring a Senior Director of Member Experience Engineering to lead this organization. You will own the engineering strategy and execution across three connected domains: Member digital experience — the member web portal and mobile apps, including care navigation, secure messaging, benefits and claims views, and the notification systems that keep members informed. Member Advocate tooling — the internal application suite our advocates use to serve members, plus the platforms that make advocates faster and more accurate. Contact center experience (our biggest opportunity) — the AI, automation, and platform work that reduces call volume, deflects and resolves inquiries earlier, and makes every advocate interaction better. This includes our Contact-Center-as-a-Service (CCaaS) platform, Agent Assist, virtual assistants, IVR automation, and conversational analytics. The main focus of the role is using AI to lower the cost and raise the quality of member support — deflecting avoidable contacts, resolving inquiries in self-service, and giving advocates real-time, accurate answers when a human is the right channel. What you'll do Set the strategy for member experience engineering across web, mobile, advocate tooling, and the contact center — and translate it into a roadmap tied to measurable business outcomes (cost-to-serve, contact reduction, member and advocate satisfaction). Lead the AI agenda for the contact center. Drive the roadmap for Agent Assist , Smart Search, virtual assistants, IVR automation, and contact-deflection features. Push for real, defensible reductions in call demand and average handle time — not demos. Own the call-center technology platform, including our CCaaS migration and the integrations that connect telephony, chat, and digital channels into one member journey. Own conversational and contact analytics — topic tagging, quality monitoring at scale, and the reporting that tells us what members are calling about and which contacts we can prevent. Ensure this data actually steers the roadmap. Deliver the member-facing digital experience on web and mobile, meeting client and regulatory commitments (access controls, dependent access, SSO, privacy) on committed timelines. Own the advocate tooling suite — the internal applications that determine how efficiently and accurately advocates serve members. Partner deeply with our Customer Experience, Product and Design teams to build quality products for our members and member advocates Build and grow the team — hire, mentor, and develop engineering managers and senior engineers; set the bar for technical quality, security, and reliability in a HIPAA-regulated, PHI-handling environment. Report up and out. Communicate strategy, trade-offs, and results to executive leadership and represent engineering in cross-functional and client-facing forums. To be successful in this role, you'll need: 15+ years in software engineering with 5+ years leading engineering teams, including managing managers. Proven ownership of large-scale, member- or customer-facing web and mobile products. Contact center / customer support technology experience — hands-on familiarity with CCaaS platforms, telephony/IVR, agent-assist tooling, and support-operations metrics (contact volume, deflection rate, average handle time, first-contact resolution, cost-to-serve, quality/CSAT). Applied AI/ML fluency, especially using LLMs / GenAI to reduce support demand: knowledge of Retrieval-Augmentented Generation (RAG), intent detection, conversational analytics, and automated quality monitoring. You know how to evaluate accuracy, manage hallucination risk, and measure whether an AI investment actually moved the metric. Strong track record turning operational metrics into an engineering roadmap and defending trade-offs to executives. Excellent cross-functional leadership across product, operations, design, data/insights, and external vendors. Comfort operating in a regulated, data-sensitive domain (healthcare/HIPAA a strong plus) where security and privacy are non-negotiable. Nice to have: Healthcare, health-benefits, insurance, or other regulated-industry experience. Experience running a vendor selection and migration for a major contact-center or AI platform. Background scaling both customer-facing product engineering and internal operational tooling in the same org. Pay Transparency Statement This is a hybrid position based out of one of our offices: San Francisco, CA, Plano, TX, or Lehi, UT. Hybrid employees are expected to be in the office two days per week. #LI-hybrid The actual pay rate offered within the range will depend on factors including geographic location, qualifications, experience, and internal equity. In addition to the salary, you will be eligible for 1,000,000 stock options and benefits like health insurance, 401k, and paid time off. Learn more about our benefits at San Francisco, CA Pay Range$268,000—$335,000 USDLehi, UT Pay Range$214,400—$268,000 USDPlano, TX Pay Range$235,840—$294,800 USDWhy Join Us? Mission-driven culture that values innovation, collaboration, and a commitment to excellence in healthcare Impactful projects that shape the future of our organization Opportunities for professional development through internal mobility opportunities, mentorship programs, and courses tailored to your interests Flexible work arrangements and a supportive work-life balance We are an