Richa Gupta

Senior Delivery & Technical Program Management Leader | AI & Digital Transformation at Scale

Gurugram, Haryana, India

About

With over 20+ years of experience spanning Expedia Group, OYO and TCS (17+ years) and executive development at IIM Kozhikode, I lead high complexity technology programs at the intersection of AI driven transformation, platform engineering and large scale global delivery across Shipping & Logistics, Travel, and Hospitality domains. I build delivery momentum where complexity is highest across Domains and geographies. My expertise spans the full program delivery life cycle from commercial solutioning and RFP through to global rollout and Production support. On the technical side, I bring hands-on depth in AI driven transformation , cloud platform delivery, distributed system architecture, Devops, SAFe at enterprise scale. Commercially, I have held direct P&L accountability across multi vendor, sub-contracted program ecosystems. At the team level, I actively invest in developing mid-to-senior engineers and program managers into delivery leaders.

Experience

  • Senior Technical Program Manager at Expedia Group
    May 2022 - Present · 4 yrs 3 mos

    Drove Strategic Platform Delivery across Traveler facing and internal technology ecosystem, owning end to end Program execution from Planning till Launch. Managing cross domain dependencies, resolving blocking issues and ensuring seamless execution across all contributing teams. Owned quarterly planning including OKR definition, capacity planning with Engineering Directors and Engineering Managers, Product Prioritization and stack ranking, Say/Do Metrics governance, trade-off decisions in collaboration with Product. Served as the primary communication owner across all program stakeholder. Actively collaborate with Engineering directors to secure resources, define scope and establish delivery milestones. Strong domain and solution understanding across dependent initiatives, applications and services. Actively collaborated in solution design discussions, dependency mapping across programs and continuous improvement of delivery success metrics.

  • Director Of Technology at OYO
    Dec 2021 - May 2022 · 6 mos

    Led Platform Programs across Booking, Post-Booking and Payments domains, reporting into the SVP with direct stakeholder communication to CTO and Chief of Staff. Responsible for monthly and quarterly planning, delivery execution, prioritisation and trade-off decisions and CXO level Program communication across business, Product and Technology stakeholders. Established myself as a critical program driver within the first month, managing cross functional dependencies and delivering outcome in a high-growth, fast-paced environment.

  • Tata Consultancy Services (17 yrs 6 mos)
    • Consultant, Program Manager
      Jan 2014 - Dec 2021 · 8 yrs

      Led a 200+ person implementation and support program on Azure Cloud for the world's largest shipping line - one of the most complex SAP TM transformations in the industry. Delivered first-of-its-kind instant booking confirmation platform in the shipping industry (Order Handling Platform), transforming customer experience. Executed Future Core Product program using SAFe with multiple Agile Release Trains running in parallel - a recognised success for both business outcomes and process excellence. Managed full commercial lifecycle: RFPs, proposals, contract management, sub-contracting, and P&L ownership. Set up fully automated, scalable DevOps pipelines on Azure. Mentored and grew mid-career professionals (8–15 years of experience) into leadership roles.

    • Senior Technical Project Manager
      Jul 2011 - Dec 2013 · 2 yrs 6 mos

      Managed full project lifecycle in onsite-offshore model - from inception through to rollout and support. Established transition and governance models; responsible for estimation, resource allocation, and utilisation. Facilitated all Scrum ceremonies and led Scrum of Scrums across multiple teams. Drove backlog health, impediment resolution, and continuous improvement practices.

    • Analyst, Designer, Developer
      Jul 2004 - Jun 2011 · 7 yrs

      Progressed from Java/J2EE developer to analyst and designer, delivering requirement gathering, solution design, and production support across enterprise applications.