Sr. Director, Architecture & Research

We are seeking a Senior Director of Architecture & Research to define and lead the architectural vision, cloud strategy, and applied innovation for our Health & Benefits technology ecosystem. This role is accountable for the technical foundations, operating model, and future direction of mission-critical SaaS platforms supporting Consumer Driven Health, Benefits Administration, HSA, COBRA, and Direct Billing.

Reporting to the VP of Architecture & Development, this leader will influence architectural outcomes across a global enterprise. The role demands deep technical authority, business fluency, and the ability to inspire large teams through clarity and credibility.

This role is accountable for the following strategic pillars:

Enterprise & Cloud Platform Architecture: Defining the end-to-end architecture of a large-scale, mission-critical SaaS platform, ensuring systems are highly available, secure, compliant, scalable, cost-efficient, and operable by design. This includes ownership of Azure cloud architecture, multi-region and Active-Active strategies, infrastructure automation, and platform engineering foundations that support reliability at enterprise scale.

DevOps, Platform Engineering & Operational Excellence: Establishing DevOps and platform engineering as a core operating model, enabling teams to build, test, deploy, and operate software safely and efficiently. This pillar covers CI/CD, Infrastructure as Code, automated resilience, observability, and release safety, with the goal of maximizing developer velocity while maintaining production stability.

World-Class User Experience (UX) Enablement: Ensuring architecture actively enables exceptional user experiences for members, employers, administrators, and operators. This includes designing platforms that support low latency, personalization, accessibility, consistency across products, and seamless AI-assisted experiences-recognizing that UX quality is a direct outcome of architectural and platform decisions.

API, Integration & Developer Ecosystem: Owning the strategy for API-first design, developer experience, and ecosystem integration. This includes building and governing a modern Developer Center, defining API standards and contracts, and enabling secure, scalable integrations with employers, carriers, payroll providers, financial institutions, and third-party partners.

Data Platforms & Intelligence Foundations: Leading the architecture of enterprise data platforms that power reporting, analytics, regulatory compliance, and AI. This includes operational and analytical data stores, data pipelines, governance, quality, and lineage-treating data as a strategic product that fuels insight and automation.

AI Platforms, Agentic AI & Intelligent Automation: Driving the vision and execution for AI-native platforms and agentic AI systems that augment and automate complex health and benefits workflows. This pillar includes governed AI platforms, model orchestration, human-in-the-loop controls, and the responsible application of AI to improve decision-making, efficiency, and customer experience.

Security, Privacy, Compliance & Trust: Embedding security-by-design, privacy-by-design, and compliance into every platform and architectural decision. This includes HIPAA, PCI-DSS, SOC 2 Type II, and emerging AI regulations, ensuring innovation never compromises trust.

Business Alignment & Industry Leadership: Serving as a strategic partner to Product, Engineering, Operations, and Executive leadership, translating technology decisions into business outcomes. Representing the company externally as a technical and industry leader, articulating platform maturity, reliability, and innovation to customers, partners, and peers.

• What "best-in-class SaaS" means for Health & Benefits

• How millions of users experience our products

• How developers build and extend our platforms

• How partners integrate and scale with us

• How data and AI drive smarter, faster decisions

• How trust, reliability, and innovation coexist at enterprise scale

1. Enterprise Architecture & Platform Strategy

• Own the end-to-end architectural vision across application platforms, APIs, data, integrations, cloud infrastructure, and developer tooling.

• Define platform-first and cloud-native architecture principles that promote reuse, composability, security, and delivery velocity.

• Establish reference architectures, standards, and guardrails that scale across hundreds of teams without creating friction.

• Ensure architecture decisions align tightly with business strategy, regulatory needs, and long-term growth.

2. Azure Cloud Architecture & Cloud Operating Model

• Define and own the Azure cloud architecture strategy, including:

  • Multi-region design

  • Network and identity architecture

  • Data residency and compliance considerations

  • Cost governance and FinOps alignment

• Lead the evolution toward cloud-native and platform-engineered solutions, leveraging Azure services (e.g., PaaS, containers, managed databases) where appropriate.

• Ensure cloud architectures support resilience, scalability, security, and rapid innovation.

• Partner with Infrastructure and Cloud Operations teams to continuously improve cloud maturity and operational efficiency.

3. DevOps, Platform Engineering & Automation

• Champion DevOps as an operating model, not just tooling.

• Drive adoption of CI/CD, Infrastructure as Code, automated testing, and policy-as-code across the engineering organization.

• Define architectural standards for deployment automation, environment consistency, and release safety.

• Promote platform engineering practices that reduce cognitive load on product teams, enabling them to focus on customer value rather than infrastructure complexity.

• Ensure development teams leverage modern productivity tools (including AI-assisted development tools such as Cursor, Bolt, and Augment) in a secure and governed manner.

4. Extreme Reliability, Availability & Operational Excellence

• Lead the transition to multi-region Active-Active architectures designed for zero downtime and continuous operation.

• Architect self-healing systems with automated failover, elastic scaling, and intelligent recovery.

• Ensure platforms withstand extreme demand patterns, such as open enrollment surges and high-volume financial transactions.

• Partner with SRE and Operations teams to define SLOs, SLIs, observability standards, and incident management practices.

• Drive a culture of operational excellence and reliability engineering.

5. World-Class User Experience (UX) Enabled by Architecture

• Elevate user experience as a core architectural responsibility, recognizing that UX quality is inseparable from system design.

• Ensure backend and platform architectures enable:

  • Low-latency, responsive user interfaces

  • Real-time feedback and personalization

  • Consistent experiences across products and channels

• Partner with Product and Design leaders to align architectural decisions with customer trust, accessibility, and ease of use.

• Advocate for architectures that reduce friction for both end users and internal operators.

6. API Platforms, Developer Experience & Developer Center

• Own the API platform and developer experience (DX) strategy, treating developers-internal and external-as primary customers.

• Define standards for API design, governance, versioning, and lifecycle management.

• Lead the evolution of a Developer Center that includes:

  • Clear documentation and onboarding

  • SDKs, samples, and tooling

  • Sandbox and test environments

  • Reliability and performance guarantees

• Enable faster, safer partner integrations and ecosystem expansion.

7. Integrations & Ecosystem Architecture

• Define architectural patterns for integrations with external systems, including employers, carriers, payroll providers, banks, payment processors, and government agencies.

• Promote event-driven and API-based integration models that are resilient, observable, and scalable.

• Ensure integration architectures handle partner variability while preserving data integrity, security, and performance.

• Establish standards for contract testing, backward compatibility, and failure isolation.

8. Data Platforms & Analytics Architecture

• Lead the architectural vision for enterprise data platforms, supporting operational, analytical, and real-time use cases.

• Ensure data architecture enables:

  • Regulatory reporting and auditability

  • Advanced analytics and insights

  • AI/ML training, inference, and monitoring

• Guide the evolution of platforms leveraging SQL Server, Snowflake, MongoDB, and modern data pipelines.

• Establish strong data governance, lineage, quality, and access controls.

• Promote a data-as-a-product mindset across the organization.

9. AI Platforms, Agentic AI & Applied Intelligence

• Define and execute the AI platform strategy, moving from isolated experiments to scalable, governed AI capabilities.

• Champion AI-native and agentic AI architectures, enabling autonomous systems that:

  • Orchestrate complex benefits workflows

  • Make context-aware decisions within defined guardrails

  • Collaborate effectively with humans

• Establish architectural standards for model lifecycle management, orchestration, monitoring, and explainability.

• Ensure AI systems comply with privacy, security, and regulatory requirements while delivering measurable business outcomes.

10. Security, Privacy, Compliance & Responsible AI

• Embed security-by-design and privacy-by-design principles across all platforms.

• Ensure architectures comply with HIPAA, PCI-DSS, SOC 2 Type II, and evolving regulations.

• Define AI governance frameworks addressing ethical use, auditability, and data protection.

• Partner with Security, Legal, and Risk teams to proactively address threats and regulatory change.

11. Organizational Leadership & Technical Culture

• Lead, mentor, and develop senior architects, platform leaders, and principal engineers.

• Build a culture where architecture, cloud, and DevOps enable speed and quality, not bureaucracy.

• Set clear expectations for technical excellence, documentation, and decision-making.

• Inspire teams through strong communication, technical credibility, and clear vision.

12. Business Partnership & Executive Influence

• Act as a trusted technical advisor to Product, Engineering, Operations, and Executive leadership.

• Translate architecture, cloud, and DevOps decisions into business impact (growth, cost, risk, customer experience).

• Influence investment priorities and long-term platform evolution.

• Represent technology strategy confidently in executive and board-adjacent discussions.

13. External Thought Leadership & Industry Engagement

• Serve as a visible industry leader in architecture, cloud, DevOps, AI, and health technology.

• Represent the company in peer-level discussions with customers, partners, and vendors.

• Contribute to conferences, panels, publications, and industry forums.

• Monitor emerging trends that could reshape the competitive landscape.

• Senior Technical Leadership: 10+ years of experience in software engineering and architecture, including 5+ years leading architecture, platform, or senior engineering functions in large-scale technology organizations. Proven ability to influence architectural direction across hundreds of engineers without relying on direct reporting lines.

• Cloud & Platform Architecture (Azure): Deep experience designing and operating cloud-native platforms on Microsoft Azure, including multi-region architectures, identity and network design, data residency, and cost governance. Strong understanding of how cloud architecture choices impact reliability, scalability, security, and developer velocity.

• Distributed Systems & Reliability Engineering: Demonstrated success architecting highly available, resilient, and scalable distributed systems, including Active-Active designs, automated failover, and systems that support extreme load variability (e.g., seasonal spikes, high-volume transactions).

• DevOps, Automation & Platform Engineering: Strong background in DevOps as an operating model, including CI/CD, Infrastructure as Code, automated testing, and deployment safety. Experience enabling platform engineering practices that abstract infrastructure complexity and improve developer productivity.

• Data Platforms & Databases: Solid architectural experience designing and evolving enterprise data platforms, including:

  • Transactional and operational data stores (e.g., SQL Server, MongoDB)

  • Analytical and reporting platforms (e.g., Snowflake)

  • Data pipelines, governance, and data quality practices.

  • Ability to design data architectures that support regulatory reporting, analytics, and AI workloads.

• API-First & Integration Architecture: Proven experience defining API-first architectures and integration strategies that support internal teams, external partners, and third-party ecosystems. Strong understanding of API design, versioning, governance, and integration patterns (event-driven, synchronous/asynchronous).

• User Experience Awareness: Demonstrated ability to partner effectively with Product and Design leaders to ensure architecture enables great user experiences. Understanding of how latency, data models, workflow design, and platform constraints directly impact usability, accessibility, and customer trust.

• Security, Privacy & Compliance: Experience architecting systems in highly regulated environments, with working knowledge of HIPAA, PCI-DSS, SOC 2 Type II, and secure-by-design principles. Ability to embed security, privacy, and compliance into architectural decisions from the start.

• Communication & Executive Influence: Exceptional communication skills, with the ability to clearly articulate complex technical concepts to executive, business, and technical audiences. Proven track record of influencing senior leaders and aligning diverse stakeholders around a shared technical vision.

Preferred Experience & Differentiators

• AI Platforms & Agentic AI: Experience leading or architecting AI platforms and/or agentic AI systems, including AI-native architectures, model orchestration, governance, and human-in-the-loop controls. Familiarity with modern LLM ecosystems and applied AI in complex, regulated domains.

• Applied Innovation & R&D Leadership: Background leading research, innovation, or advanced engineering teams, with demonstrated ability to move from experimentation to production-scale impact.

• Health, Benefits, Insurance, or FinTech Domain Expertise: Prior experience in Health & Benefits, Insurance, or Financial Services environments, particularly those involving complex rules, payments, and regulatory oversight.

• Developer Experience & Tooling: Experience improving developer experience (DX) through strong APIs, documentation, tooling, and internal developer platforms or portals.

• Technical Thought Leadership: Evidence of technical thought leadership such as conference speaking, publications, open-source contributions, or patents.

• Transformation at Scale: Experience leading cloud, DevOps, or platform transformations in large, distributed organizations.

What We Value Most

• Architectural judgment over buzzwords

• Systems thinking over point solutions

• Business outcomes over technical novelty

• Inspiration and clarity over command-and-control leadership

• Azure cloud and DevOps operate as a highly automated, resilient, and cost-efficient platform enabling frequent and safe delivery at scale.

• Platforms consistently deliver near-zero downtime, strong performance, and built-in security and compliance that customers and regulators trust.

• Architectural decisions enable fast, intuitive, accessible, and reliable user experiences across all Health & Benefits products.

• Internal teams and external partners view our APIs, Developer Center, and tooling as best-in-class and easy to integrate with.

• External integrations are resilient, observable, and scalable, enabling rapid partner onboarding and ecosystem growth.

• Data platforms provide trusted, well-governed, high-quality data that powers analytics, reporting, and AI use cases.

• AI and agentic systems deliver measurable business value through intelligent automation and decision support.

• Teams innovate and ship new capabilities quickly without increasing operational, security, or compliance risk.

• Architectural standards and platforms are widely adopted and measurably accelerate delivery across the organization.

• Technology investments translate clearly into business growth, operational efficiency, reduced risk, and industry leadership