Gurusewak Kalra

• Lead product engineering for Spring Insights, the enterprise customer-value platform employers use to measure financial value, clinical outcomes, and engagement from their mental health benefits. Leadership scope has included up to two teams totaling approximately 11 engineers across frontend, backend, data, and quality, with responsibility for roadmap execution, technical direction, hiring, performance, and career development.
• Lead the continued expansion of Spring Insights from a reporting portal into a customer-value and growth platform spanning savings and ROI analytics, multi-year health-plan savings projections, clinical outcomes, executive reporting, campaign performance, and expansion intelligence, supporting customer renewal and expansion conversations. Achieved 85% customer satisfaction and delivered 10 of 10 targeted reporting and operational improvements through organizational change and capacity constraints.
• Own hiring, onboarding, performance management, promotion readiness, succession planning, and career development across engineering levels. Coach senior engineers from individual execution toward technical direction, design ownership, documentation, mentorship, and cross-functional influence.
• Shifted teams from ticket-oriented delivery toward outcome ownership using structured shaping, technical spikes to reduce risk before commitment, earlier alignment on scope and dependencies, and post-launch measurement against the intended customer result.
• Led delivery of AI-enabled support and knowledge experiences covering retrieval over curated knowledge, intent classification, intelligent routing, automated creation of structured work, and summarization. Built each with permission-aware access, human escalation paths, and deterministic fallbacks.
• Strengthened reliability and release confidence across customer-facing workflows through automated regression coverage of critical flows, synthetic production monitoring, observability, permission-aware access controls, and targeted technical-debt reduction.
• Led product-team AI-assisted development pilots across discovery, requirements, technical design, implementation, testing, code review, and documentation. Defined cycle time, review speed, rework, defect rate, and maintainability as the success measures rather than tool adoption.
• Led updates to engineering IC and manager career ladders to define leveled, evidence-based AI-fluency expectations, and helped design an AI-native interview model pairing AI-enabled and AI-disabled evaluation to assess problem framing, verification, and tradeoff reasoning over recall.
• Influenced shared AI architecture to help product teams build reusable, production-ready capabilities instead of one-off integrations, including agent orchestration, retrieval-augmented generation, MCP-aligned capability contracts, domain semantics, controlled handoffs, evaluation, and observability.

• Led engineering across enterprise customer platforms, member experience, growth, internationalization, accessibility, scheduling, payments, and Sales enablement.
• Led development of a Snowflake-powered customer insights engine that surfaced employee engagement, enrollment, and utilization data inside the enterprise admin portal, establishing the analytics foundation for the current customer-value platform.
• Partnered with Customer Success and Revenue Operations on a ranked expansion-lead system connecting product usage signals, Snowflake pipelines, and Salesforce workflows, plus guided quote-to-buy flows for specialty-care and tobacco-cessation upsells. Generated $1.8M in qualified expansion opportunities in one quarter, with $1.2M converted into closed opportunities.
• Launched customer self-service and engagement capabilities with Marketing, including a resource library, monthly summary reporting, campaign opt-in, and automated lifecycle communications, reducing customer-support email volume 32% while increasing new monthly active users from unique customers 28% and freeing Customer Success to focus on strategic accounts.
• Led development of an in-house video-conferencing experience that contributed to securing a $20M enterprise contract.
• Led international expansion of the product experience to 19+ countries, directing six engineers and two quality engineers across localization and regional compliance requirements.
• Directed development of a configurable Sales demonstration platform, applying generative AI and image generation to produce curated, customer-specific demo experiences that improved internal Sales satisfaction from 2.6 to 4.6.
• Delivered an accessibility-compliance initiative within a fixed three-month deadline, coordinating Engineering, Product, Design, and Legal.
• Led delivery of member-facing revenue and access capabilities covering direct coaching scheduling, dependent and minor enrollment, session cost transparency, and payment-integrated no-show and late-cancellation billing. Established automated regression coverage of critical flows and synthetic monitoring that improved release confidence.

Tech: Ruby on Rails, React, Next.js, TypeScript, Python, PostgreSQL, Snowflake, dbt, GraphQL, AWS, CircleCI, Datadog, Salesforce, Iterable, Looker, Stripe, OpenAI, Cypress

• Led architecture and implementation across global customer-support, content, localization, analytics, and knowledge-management systems.
• Automated content localization for 70+ customer-support sites across nine languages using source-control commits and translation-platform webhooks for continuous sync, replacing manual translation and publishing workflows and reducing translation cost and time-to-publish.
• Rebuilt the authoring-to-publishing pipeline by integrating the XML authoring tool with the CMS and AI-powered support platform, automating metadata generation, SEO, URL creation, and mapping of content to React components, reducing multi-platform manual uploads, publishing errors, and operational overhead.
• Consolidated content from CRM and authoring sources into a centralized knowledge platform supporting 17 products, with auto-populating search and dynamic components that ranked articles by category, tag, and live search behavior.

Tech: Java, React, Redux, Brightspot CMS, Bold360 AI, PostgreSQL, AWS, Snowflake, Salesforce, Zendesk, Tealium, Optimizely, Google Analytics

• Designed and built a unified account-management platform covering plans, profiles, connected accounts, user roles, billing, and payment methods across multiple products.
• Led redesign of the quote-to-buy purchasing journey, reducing checkout friction and improving conversion across self-service plans.
• Led multi-channel customer-support experiences including chatbot, Call-Me, and Web-to-Call that contributed to improving Net Promoter Score from 5.5 to 7.8 within six months, raising digital engagement from 85% to 93%, and generating more than $5M in operational savings.
• Owned full lifecycle delivery across architecture, implementation, testing, deployment, monitoring, and experimentation. Provided technical leadership through design and code review, debugging support, and coordination of onshore and offshore teams.

• Built customer-facing and internal applications with Angular, Node.js, Express, MongoDB, and AWS, and supported Citrix as a consulting engineer on self-service and customer-support platforms.
• Designed an internal administration portal covering customer contracts, contractor tracking, project oversight, and timesheets. Rebuilt the company marketing site during a rebrand.