Antonia McCullough
Verified Expert in Project Management
Project Manager
New York City, NY, United States
Toptal member since November 28, 2022
Antonia transforms organizations into adaptable, high-performing teams through agile coaching and culture change. With 20+ years of experience, she specializes in embedding psychological safety, growth mindset, and sustainable agile practices that drive measurable results. Antonia partners with leaders at all levels to transition teams from "doing agile" to "being agile," creating frameworks and systems that foster lasting organizational transformation.
Project Highlights
Expertise
- Agile Coaching
- Business Strategy
- Complex Problem Solving
- Jira
- Jira Administrator
- Project Management
- User Feedback
- Zoom
Work Experience
Confluence and Jira Specialist
Yahoo! - Mail Engineering
- Interviewed project teams and stakeholders to assess workflows, project metrics, and organizational needs for Yahoo Mail’s Conference and event operations.
- Reviewed Jira projects and agile ways of working to develop strategies for transferring key documentation and metrics to Confluence for improved stakeholder access and transparency.
- Facilitated wireframing and design thinking sessions in Miro, collaborating with technical and business stakeholders to create updated Confluence pages optimized for usability and visual clarity.
- Recommended integration and documentation best practices, ensuring conference pages are aligned with Yahoo’s processes. Enhanced cross-team communication.
- Collected and synthesized user feedback through surveys, meetings, and ongoing conversations with teams, stakeholders, and sponsors to iteratively improve project deliverables and stakeholder satisfaction.
- Used AI to generate API scripts that improved communication between Jira and Confluence, automating updates, reducing manual errors, and strengthening alignment across product and engineering teams.
- Leveraged AI-assisted code generation to build scaffolding for Yahoo Mail wiki pages, accelerating documentation workflows and creating a structured, scalable knowledge base for cross-functional teams.
Senior Scrum Master
Ricoh Corporation - DSC - PortfolioSoftwareSolutions
- Oversaw a cross-functional team of developers, internal IT specialists, and product stakeholders, ensuring alignment and timely sprint execution.
- Fostered collaboration between matrixed stakeholder groups by facilitating transparency, demo readiness, and regular feedback loops.
- Navigated an unconventional project cadence, effectively managing “hurry up and wait” scenarios with strategic resource planning and communication.
- Managed project dependencies with a strong focus on time-to-market and workplace logistics, contributing to an on-schedule September 2024 MVP launch.
- Provided agile leadership and coaching to support continuous delivery, adaptability, and high engagement across diverse business units.
Agile Transformation Consultant
Pixely, Inc.
- Led agile transformation from rigid, siloed workflows to adaptive collaboration. Partnered with leadership to establish psychological safety, transparent communication, and sustainable practices, embedding continuous improvement.
- Designed a team charter framework for clear roles and decision-making. Created feedback loops surfacing blockers. Developed a growth mindset culture program with metrics. Established product roadmaps aligned with business goals.
- Increased team autonomy and decision velocity. Reduced cross-departmental bottlenecks. Built self-sustaining practices continuing post-engagement. Shifted culture from compliance to adaptive resilience.
- Used AI tools to streamline client engagement, automate workflow documentation, generate process playbooks, and accelerate organizational diagnostics for faster decisions and scalable transformation.
- Stepped into a mid-flight transformation, reduced delivery volatility, and moved the organization from reactive execution to disciplined, repeatable delivery.
- Established end-to-end program governance, integrated roadmaps, and dependency tracking across Scrum teams and a Kanban service team supporting enterprise platforms.
- Drove executive-level visibility through milestone tracking, risk management, and clear escalation paths, improving predictability and on-time delivery.
- Partnered with business and technical leaders to define readiness criteria for releases, including data quality, reporting, and stakeholder sign-off.
Agile Coach
McKinsey & Company
- Provided strategic leadership to large-scale Agile transformation initiatives, collaborating closely with cross-functional teams and executives.
- Guided teams to deliver on time and within budget by implementing Agile/Lean frameworks, achieving significant reductions in project delivery times.
- Developed coaching and team onboarding models, fostering self-organized teams and successful leaders.
- Conducted personalized coaching sessions, resulting in an increase in leadership understanding of agile principles and their role in transformations in less than a year.
- Facilitated workshops and retrospectives to enhance trust and collaboration, resulting in an improvement in team dynamics and a positive productivity boost.
- Collaborated with leadership and McKinsey's Global Agile Guild to drive agility across the enterprise, contributing to the development of the Agile Center of Excellence.
- Coordinated cross-functional delivery with internal teams and vendors, managing dependencies and timelines across multiple concurrent initiatives.
- Led enterprise agile transformations, managing organizational conversion from traditional to agile frameworks through phased rollouts and change management.
Agile Project Manager and Coach
Verisk Analytics
- Transformed teams to self-organization using Agile best practices such as time-boxing, continuous integration, delivery, code and design reviews, product visioning, user story mapping, and technical debt reduction.
- Trained teams on agile fundamentals such as writing great user stories, prioritizing work based on business value, and mastering estimation by story points, development tasks, and ideal hours.
- Educated teams on the value of work in progress and using the marginal gains and Pareto principles to further timebox work and plan efficiently.
- Held training sessions solely for the product owners to help them understand their role on the teams and develop a release management structure for their product and its value streams (portfolios).
- Managed conversion and launch of seven applications in 12 months, coordinating teams and vendors through testing and cutover with zero incidents.
- Managed transition from legacy project management to agile delivery, including workflow conversion, training, and post-implementation support.
Agile Project Manager and Scrum Master
The New York Times
- Coached and mentored individuals and teams to discover and implement improved ways of collaborating and developing into high-performing, self-organized agile teams.
- Developed the CMS publishing and personalization teams to forecast roadmap, set team goals, and manage projects.
- Facilitated sprint ceremonies, such as planning, daily stand-ups, retrospectives, and other events as needed, ensuring the right people were in the proper conversation to solve problems effectively and develop solutions.
- Managed dependencies by working closely with teams outside CMS core and personalization to improve communications and set expectations for stakeholders on shared projects.
- Served on the Jira task force, testing new add-ons, aiding the Jira admins during the Jira upgrade, and continually educating users on how to use Jira and Confluence effectively. Recommended the use of a portfolio for product roadmaps.
- Supervised the NYT Architecture Review Board, a review board that acts as an architectural advisor to all teams and oversees the Request for Comments process for the NYT technology team.
- Led backlog refinement sessions, facilitated big planning meetings, and prioritized and forecasted roadmaps.
- Program managed AWS to Google Kubernetes migration, coordinating engineering and ops teams through multi-phase conversion with zero downtime.
Agile Coach and Scrum Master
Viacom International Media Networks
- Joined the team as a scrum master to identify, track and remove impediments to project success for the My Nick Jr. and My MTV mobile and Television Everywhere programs.
- Collaborated with global regions, such as North Europe, Asia, Latin America, Europe, the Middle East, and North Africa, for project localization and content delivery.
- Managed offshore development teams and third-party vendors during the R&D process for each global region.
- Served as senior SM to manage sprint and release planning or development cycles for multiple scrum teams in a scaled environment.
- Ensured planning of go-live and deployment activities within the MNJSuite program and managed their execution.
- Tracked and reviewed vital metrics as well as the budget for each program.
Senior Project Manager and Program Management
Macmillan Education
- Collaborated with management teams to deliver assigned programs within the digital systems education portfolio while holding big room planning sessions for quarterly priorities.
- Screened critical employees for the Digital Systems Education PMO, determined the resources required for projects within the DSE program, and allocated them accordingly.
- Created and initiated internal processes to improve program delivery within specific timeframes.
- Served as the department's Jira administrator, setting up Jira projects and wiki pages in Confluence and creating dashboards and portfolio roadmaps for reporting.
- Re-designed release management process, following SAFe practices, for the DSE technology team.
- Developed a weekly cross-functional meeting for the DSE, business, and product development teams to discuss upcoming releases and agile and scrum practice improvements.
- Worked with editorial and technical teams to develop new features and enhancements while maintaining current product quality.
- Managed the UI/UX teams in creating wireframes for new and existing projects. Assisted the engineers in documenting the project designs and making changes as per needs.
Senior Project Manager and Scrum Master
Usablenet
- Facilitated scrum events for project development grooming, sprint planning, retrospectives, and daily stand-ups.
- Managed the systems development lifecycle, from ideation to sprints to deployment.
- Coordinated and managed code releases while communicating with other management, engineers, product managers, owners, and support specialists on product issues.
- Tracked and communicated team velocity and sprint release progress.
Project Manager and Web Producer
Viacom | Nickelodeon
- Championed multi-million dollar online marketing campaigns for client portfolios such as Kraft, Hasbro, Mattel, Paramount Pictures, and AT&T.
- Negotiated Requests for Proposals (RFPs) to screen vendors and internal design teams hired to implement campaigns.
- Prepared project management plans for project stakeholders, which included costs, resources, project schedules with milestones, communication plans, vendor contracts, initial wireframes, and copy.
- Worked with the ad sales group to implement online advertising campaigns and promotional sites.
Project Management | Branding and Customer Experience
Register.com
- Scheduled the brand marketing campaign calendar, which was used to track promotion release dates for the web, radio, TV, search engines, email, and direct mail. Coordinated with the internal teams to schedule release dates.
- Worked with the retail sales and marketing team to create and schedule the launch of product emails and additional digital marketing collateral.
- Organized and facilitated usability surveys and focus groups while working with the internal team and external agencies to create test designs.
- Maintained project plans, schedules, and task coordination for the design team.
- Copied the managed process and measured each project against the triple constraints.
- Planned brainstorming and kickoff meetings, managed the approval process, and closed out projects. Organized biweekly educational team meetings for the retail department.
Project Manager | Content Management
IBM
- Managed ibm.com commerce promotions and campaigns, creating schedules, budgets, and monitoring scope.
- Prepared Documents of Understanding (DOUs), which included project scope, process, and budget costs.
- Assisted in the creative process by sharing expertise on technical issues, content management, and developing web pages.
- Led special projects and promotions for the interactive marketing and affiliate marketing divisions.
- Received and processed requests for all new site builds and content changes for existing Enterprise '99 sites, which in 1999 totaled approximately 300 e-sites.
- Maintained site build and change request databases for Enterprise '99. Provided support to the technical lead and the operations team on issuing redirects for new builds, solving server issues and content problems, and updating the sites.
- Supervised the workflow of special projects and additional promotions posted to the site through the strategic marketing department, shop IBM, and gold service departments.
- Worked with brand clients to establish the best practices for their brand pages.
Project History
Agile Adoption and Organization Transformation
- 25% — Team Health and Agile Maturity Increase Within 6 Months
- 75% — Cycle Time Reduction for Epics Delivery and Completion (Features)
- 90% — Improved Stakeholder Visibility with New PO Cadence, Sprint Reviews, and Clear Delivery Insight
When I joined Party Rental, the tech team faced unclear priorities, reactive work, and no formal processes. I focused on bringing clarity, stability, and scalable structure through Agile. I introduced a full operating system, including team design, ceremonies, tooling, capacity planning, and transparent communication practices.
I began by assessing the team’s processes, tools, and delivery gaps, then analyzed patterns and maturity levels to design an Agile operating model. I implemented three Scrum teams and a Kanban service team, created team agreements, trained a new product owner, and introduced clear cadences, workflows, and release practices. Ongoing monthly and quarterly assessments improved flow, predictability, and collaboration across the department.
The shift to Agile brought clarity and predictability to the tech department. With new teams, a trained PO, and structured cadences, delivery improved, communication strengthened, and leadership gained meaningful visibility.
Macmillan Agile Transformation Digital Systems Education
Helped introduce Macmillan DSE to scaled Agile as the senior Agile project manager.
Introduced the initial ART (Agile Release Train) to help streamline the value stream across the department. Worked to establish change agents within to help champion the Agile and SAFe processes. Served as the department’s Jira administrator, setting up Jira projects and wiki pages in Confluence and creating dashboards and portfolio roadmaps for reporting.
Later, I managed the DSE release schedule, up to four monthly releases, over six separate product lines and eight different sprint teams. Re-designing the release management process, following SAFe practices, for the DSE technology team. From there, I developed a weekly cross-functional meeting for the DSE, business, and product development groups to discuss upcoming releases and review agile and scrum practice improvements. Finally, I created a multi-page wiki site on Confluence, detailing product and release information serving internal staff and business owners
McKinsey Connected Leaders Academy Management Accelerator
Completed McKinsey’s Connected Leaders Academy Management Accelerator in October 2020.
The project is designed for mid-career managers aspiring to take the challenging leap into senior leadership roles. This program focuses on enhancing leadership mindsets and behaviors, sharpening problem-solving for impact, and helping the organization set and execute a business strategy.
NYT Architecture Review Board
The first project manager on the NYT Architecture Review Board, a review board that acts as an architectural advisor of all teams and oversees the NYT technology team's Request for Comments (RFC) process.
Served on the review board for Architectural review of projects at NYT digital, such as cloud migration and personalization for the NYT Website. Reviewed RFCs, scheduled and facilitated conversations between the stakeholders regarding decision-making, and held vendor evaluation sessions once the project was approved.
McKinsey Connected Leaders Academy Management Accelerator (Moderator)
Full circle moment for me! I served as the moderator for the February 2023 Connect Leader Management Accelerator Cohort.
The project is designed for mid-career managers aspiring to take the challenging leap into senior leadership roles. This program focuses on enhancing leadership mindsets and behaviors, sharpening problem-solving for impact, and helping the organization set and execute a business strategy.
Education
Bachelor's Degree in Communications
St. John's University - Jamaica, New York
Certifications
SAFe Agilist 5 Certification
Scaled Agile
Expert in Agile Coaching (ICE-AC)
Adventures with Agile
Enterprise Agile Coaching (ICP-ENT)
Adventures with Agile
Coaching Agile Transformations (ICP-CAT)
Adventures with Agile
Certified Scrum Professional (CSP)
Scrum Alliance
Project Management Professional (PMP)
Project Management Institute (PMI)
Skills
Tools
Jira, Zoom, Confluence, Project Management & Work Tracking Tools, Office 365, Microsoft PowerPoint, Slack, Miro, MURAL, Microsoft Project, Google Docs, Skype, InVision, Basecamp, Asana, Google Workspace, Atlassian
Paradigms
Agile, Scrum, Agile Software Development, Agile Product Management, Agile Project Management, Agile Leadership, Implementation Project Management, Kanban, Requirements Analysis, Azure DevOps, Design Thinking, Agile UX, Iterative Delivery
Platforms
SharePoint, Monday.com
Industry Expertise
Education Technology (Edtech)
Other
Microsoft Office, Jira Administrator, Scrum Master, Agile Coaching, Project Management, IT Project Management, Complex Problem Solving, User Feedback, Projects, Communication Strategy, Organization, Teamwork, Client Relationship Management, Relationship Building, Feedback Review, Psychology, Facilitation, Workshop Facilitation, Agile Transformation, Scaled Agile Framework (SAFe), Lean IT, Scrumban, Global Team Management, Offshore Team Management, IT Deployments, Agile Deployment, Release Management, Project Management Office (PMO), Scrum@Scale, Software Development Lifecycle (SDLC), Web Project Management, Product Management, Project Planning, Technical Project Management, Sprint Planning, Project Scheduling, Project Management Professional (PMP), Enterprise, User Stories, Project Timelines, Stakeholder Management, Project Tracking, Progress Reporting, Stakeholder Engagement, Communication, Planning, Objectives & Key Results (OKRs), Project Coordination, Workshops, Digital Project Management, Certified ScrumMaster (CSM), Sprint Ceremonies, Management Consulting, Business Transformation, Digital Strategy, Stakeholder Interviews, IT Projects, Vendor Management, Hybrid Project Management, Vendors & Suppliers, Client Management, Deployment, Product Strategy, PI Planning, Certified Project Manager, Reporting, Best Practices, Mentorship & Coaching, Product Owner, Websites, Scope of Work (SOW), Relationship Management, Digital Product Management, Backlog Management, Risk Management, Project Discovery, Project Delivery, Software Implementation, Content Management, Website Management, Program Management, App Integration, Executive Reporting, Scope Management, Documentation, Pitch Decks, Team Management, Business Planning, Branding, Implementation, Web Design, Website Design, Digital Transformation Program Management, Training & Training Content Development, Digital Transformation, Training Materials, Large-scale Projects, Project Planning & Execution, System Migration, Dependency Management, Team Coaching, Enterprise Project Management, Cross-functional Coordination, Jira Align, Google Apps, Business Strategy, Leadership, Microsoft, Marketing, Public Relations (PR), Graphics, Broadcasting, Communication Design, Public Speaking, Media, Writing & Editing, Diversity, Equity, & Inclusion (DEI), Web Marketing, Mobile Web, Mobile Web Design, Agile DevOps, Web UI Design, UX Wireframes, Google, Budgeting, Executive Presentations, Web Applications, User Experience (UX), Resource Management, Reports, Dashboards, Discovery Workshops, Discovery, PMO Development, Mobile App Development, Mobile Payments, eCommerce, Learning Management Systems (LMS), Software as a Service (SaaS), APIs, System Integration, Technical Program Management, Statement of Work, Business Analysis, User Interface (UI), Product Discovery, Web Development, Client Software, Website CMS, SEO Content, System Conversion, Portfolio Management, Data Integration, Data Warehousing, Motion AI, Artificial Intelligence (AI), Digital Brand Identity, Customer Relationship Management (CRM), Microsoft Teams, Advertising, Creativity, Journalism, Agile Product Delivery, Moderation, Facilities Management, Notion, Culture Management, Jira Administration, UI Design, IT
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