Carolina Calderaro
Chicago,IL
Summary
Professional with robust background in directing and managing large-scale projects and programs, consistently driving success through strategic planning and execution. Adept at implementing innovative solutions that enhance productivity and operational effectiveness. Known for fostering teamwork and adapting to evolving business needs, ensuring alignment with organizational goals.
Overview
18
18
years of professional experience
1
1
Certification
Work History
Director Technical Program & Project Management
Weight Watchers
08.2022 - Current
- Manages and coaches five Tech Project Managers across various locations.
- Leads large-scale, cross-functional projects, utilizing Agile and Waterfall techniques.
- Collaborates with C-level executives and cross-functional teams, across Engineering, Finance, Data Warehouse, Legal, Marketing and Product ensuring alignment on project goals and timelines.
- Successfully led the Project for WW Clinic - collaborating cross functionally with Tech, Product, Marketing, Finance & Legal teams to deliver the first merging project within the company.
- Took over a complex and severely delayed billing re-platform project and structured a plan for timely delivery resulting in over $2 MM cost savings.
Manager Agile Project Management
Weight Watchers
08.2021 - 08.2022
- Directed a distributed team of Scrum Masters while directly leading three development teams — CRM, Core Foundations, and Commerce — supporting critical platforms including customer management, backend microservices, and billing/pricing systems.
- Championed Agile transformation by refining Scrum and scaled Agile practices, driving consistency in sprint planning, retrospectives, and delivery metrics across teams.
- Partnered with Product, Engineering, and Architecture leaders to align priorities, balance technical debt with feature delivery, and improve release reliability for core systems.
- Fostered a culture of accountability and continuous improvement, resulting in faster delivery cycles, stronger cross-functional alignment, and measurable uplift in team performance and stakeholder satisfaction.
- Provided mentorship and coaching to Scrum Masters to mature Agile execution, enhance predictability, and embed data-driven decision-making into delivery practices.
Senior Scrum Master
Weight Watchers
03.2020 - 08.2021
- Led four distributed Agile development teams — CRM, Core Foundations, Commerce, and E-commerce — supporting critical systems spanning customer management, backend microservices, billing/pricing platforms, and the member e-commerce experience.
- Redefined team structure within the Commerce group by separating the Pricing Engine and E-commerce squads into distinct workstreams, enabling clearer ownership, focused backlogs, and significantly improved delivery velocity.
- Drove Agile best practices across teams through effective sprint planning, retrospectives, and stakeholder engagement, resulting in greater predictability, transparency, and throughput.
- Partnered with Product and Engineering leadership to align roadmaps, manage dependencies, and ensure seamless cross-platform integration between transactional and customer-facing systems.
Scrum Master
Weight Watchers
02.2019 - 03.2020
- Led three distributed Agile teams — CRM, Core Foundations, and Engagement/Gamification — delivering key capabilities across mobile and web platforms supporting millions of global members.
- Provided servant leadership to a group of 17 engineers across five countries, fostering collaboration, trust, and accountability in a partially remote, cross-functional environment.
- Applied Agile best practices with a pragmatic, people-first approach — tailoring ceremonies, communication rhythms, and delivery methods to the unique needs of each team.
- Partnered closely with Product and Engineering stakeholders to ensure backlog alignment, improve delivery cadence, and increase visibility into progress and priorities.
- Contributed to the foundation of WeightWatchers’ scaled Agile maturity, setting the stage for consistent delivery practices adopted across additional teams in subsequent phases of the transformation.
Project Manager / Scrum Master
J.Crew
07.2018 - 02.2019
- Rebuilt operational structure for a cross-functional engineering team supporting Digital Marketing and database management initiatives. Introduced Scrumban methodology (hybrid of Scrum and Kanban) to bring clarity, prioritize effectively, and drive accountability.
- Implemented Jira governance, defined workflows, and led daily standups, monthly planning, and retrospectives, increasing delivery predictability and reducing cycle time by 50%.
- Fostered a culture of collaboration and continuous improvement across technical and product workstreams, resulting in faster time-to-market and improved stakeholder satisfaction.
Project / Product Manager for SEO
StubHub
06.2017 - 06.2018
- Owned the SEO product roadmap and drove cross-functional prioritization across multiple engineering teams to deliver high-impact technical SEO enhancements without a dedicated dev squad.
- Leveraged Scrum and Agile principles to introduce structure and visibility into SEO initiatives, aligning efforts across Product and Engineering to accelerate delivery of critical optimization projects.
- Partnered with external marketing agencies to manage offsite SEO strategy and backlink profile, strengthening domain authority and organic search visibility.
Scrum Master
StubHub
10.2016 - 06.2017
- Led two Agile teams — Home & Browse (frontend) and UI Platform (backend) — driving delivery of high-impact customer acquisition and user experience initiatives across StubHub’s web ecosystem.
- Applied Scrum best practices to optimize sprint planning, backlog prioritization, and cross-functional alignment between product and engineering, ensuring seamless collaboration across customer-facing and platform layers.
- Acted as a servant leader and delivery gatekeeper, removing impediments and protecting team focus to maintain high velocity and quality across concurrent workstreams.
- Partnered with Product and Technical Leads to strengthen release predictability and ensure smooth end-to-end user experiences through coordinated frontend–backend delivery.
Project Manager / Scrum Master
Walmart Global eCommerce
07.2014 - 09.2016
- Led Tibco Integrations team at Walmart Canada.
- Managed off-shore contracts ensuring timely delivery and quality through effective vendor coordination.
- Co-led Walmart HLARG increasing Latino community participation.
Tech Planning Manager
Walmart eCommerce Brazil
06.2013 - 07.2014
- Managed Vendor Management Office and budget/cost control for the Technology Department based in Brazil which served as the development center for Latin America demands.
- Acted as LATAM focal point for Product Engineering demands improving communication efficiency across regions.
Financial Analyst
Walmart eCommerce Brazil
12.2012 - 06.2013
- Developed and spearheaded Walmart ecommerce Brazil’s first Vendor Management Office (VMO department).
Import Analyst
ABB Brazil
05.2012 - 12.2012
- Coordinated import processes and cost optimization reducing delivery time by 43% and costs by 30%.
- Negotiated with customs agents and freight forwarders achieving a 40% reduction in aging inventory and significant cost savings.
Account Assistant
G-Inter Transportes Internacionais Ltd.
01.2012 - 03.2012
- Negotiated cross charge payments with international partners improving payment processes.
Relationship Manager
Bank Bradesco S.A
01.2008 - 04.2009
- Promoted 20% growth in client base and 40% increase in portfolio investments.
Education
Bachelor - Business Management, Foreign Trade
Centro Universitário FIEO
01.2006
Project Management - Executing Complex Programs
Stanford Continuing Studies
01.2016
Skills
- Agile Project Management
- Scrum Mastery
- Cross-functional Team Leadership
- SEO
- Product Management
- Budget and Cost Control
- Vendor Management
- Multilingual Communication (Portuguese, English, Spanish)
Accomplishments
- Drove 50% faster delivery by introducing Scrumban methodology at J.Crew, bringing structure, visibility, and focus to a previously unorganized engineering team supporting Marketing and SEO initiatives.
- Redesigned Agile team structures at WeightWatchers, separating overlapping squads and streamlining delivery across global Commerce and E-commerce teams — increasing clarity, accountability, and velocity.
- Unified cross-functional alignment for SEO initiatives at StubHub by managing a decentralized development model and collaborating with multiple teams to prioritize technical SEO enhancements and grow organic visibility.
- Built high-performing distributed teams across 5+ countries, fostering collaboration, transparency, and ownership through people-centered leadership and adaptive Agile practices.
Certification
- CSM - Certified Scrum Master by Scrum Alliance (since 2015)
Languages
Spanish
Professional Working
Portuguese
Native or Bilingual
Timeline
Director Technical Program & Project Management
Weight Watchers
08.2022 - Current
Manager Agile Project Management
Weight Watchers
08.2021 - 08.2022
Senior Scrum Master
Weight Watchers
03.2020 - 08.2021
Scrum Master
Weight Watchers
02.2019 - 03.2020
Project Manager / Scrum Master
J.Crew
07.2018 - 02.2019
Project / Product Manager for SEO
StubHub
06.2017 - 06.2018
Scrum Master
StubHub
10.2016 - 06.2017
Project Manager / Scrum Master
Walmart Global eCommerce
07.2014 - 09.2016
Tech Planning Manager
Walmart eCommerce Brazil
06.2013 - 07.2014
Financial Analyst
Walmart eCommerce Brazil
12.2012 - 06.2013
Import Analyst
ABB Brazil
05.2012 - 12.2012
Account Assistant
G-Inter Transportes Internacionais Ltd.
01.2012 - 03.2012
Relationship Manager
Bank Bradesco S.A
01.2008 - 04.2009
Project Management - Executing Complex Programs
Stanford Continuing Studies
Bachelor - Business Management, Foreign Trade
Centro Universitário FIEO