Kristen Chester
Verified Expert in Project Management
Project Manager
Charlottesville, VA, United States
Toptal member since September 17, 2019
Kristen is a successful scrum master, agile coach, and technical problem solver with outstanding creative and critical thinking skills. She's passionate about agile transformation and leading and coaching high-performing teams. Kristen has demonstrated experience with agile software development across a wide range of industries and project types including content management, cloud migration, data and analytics, and mobile application development.
Project Highlights
Expertise
- Agile Coaching
- Agile Project Management
- Agile Software Development
- Certified ScrumMaster (CSM)
- Change Management
- Mobile App Development
- Scrum Master
- Software Development Lifecycle (SDLC)
Work Experience
SAFe Agile Coach and Atlassian Expert
Secretary of the US Air Force - CDMM
- Served as an Agile consultant and coach, providing training, transformation, and DevOps and workflow management consulting services.
- Designed an integrated requirement management system, providing a method for managing requirements that emphasizes flexibility and alignment with evolving priorities through adaptive acquisition and agile best practices.
- Designed a Jira project and portfolio management approach, leveraging best practices and effective automation, supported by Jira Service Management for intake and acquisition, along with documentation and knowledge management in Confluence.
- Supported usability of the Jira and Jira Service Management system by documenting processes, procedures, and quick start guides. Accelerated adoption through custom-tailored training on Jira, Jira Service Management, and Confluence.
- Served as an expert trainer, developing and delivering tailored concept and process training across this 150+-person organization.
Agile Coach
American Chemical Society
- Jumpstarted SAFe transformation, assessing teams, developing plans for achieving agile maturity, and creating a strong foundation in tooling, process, and knowledge to create sustainable change. Trained teams and mentored new scrum masters and RTEs.
- Enhanced collaboration by co-creating frameworks that bridged gaps between product, technology, and business functions, facilitating cross-functional agile practices and increasing delivery efficiency.
- Developed tailored training programs and reusable templates to support team agility, equipping teams with tools to adopt agile practices more effectively.
- Conducted team and organizational assessments and leveraged agile health metrics to measure progress and guide targeted coaching for continuous improvement.
- Served as a trusted partner to the DevOps team, providing guidance on the Jira setup and best practices and leveraging Confluence for documentation and knowledge management.
Scrum Master and Agile Coach
Anthem
- Fostered a culture of innovation and continuous improvement while coaching team members and stakeholders on Agile best practices.
- Managed administration, coaching, and leadership of multiple scrum teams using SAFe methodology.
- Facilitated team ceremonies, removed impediments, and helped the team organize their development and delivery of software products.
- Partnered with IT and business leaders to develop and implement a Lean-Agile Center of Excellence, focusing on scaling agile practices from the portfolio to the team level and integrating business and technology initiatives.
- Kept external stakeholders, management, and other interested parties aware of team progress and activities via ad hoc communication and formal reporting methods.
- Developed and delivered process and training materials for scrum masters, project managers, and team members on Agile project management processes and best practices.
- Established organization-wide project and program tracking and reporting processes.
- Coached enterprise-level scrum masters, release train engineers, product owners, and teams, elevating organizational capability and leading to a marked improvement in agile fluency and business value delivery.
- Spearheaded process and practice improvements that addressed systemic challenges, reducing delivery friction and accelerating time-to-value by aligning Agile, DevOps, and data science practices for innovation in AI/ML.
- Served as Jira expert and administrator, designing processes to support team efficiency while enabling transparency throughout the entire product lifecycle.
Agile Coach
Gartner - Transformation Office
- Created and delivered foundational training to a 55-person, globally distributed team on essential Agile concepts based on expert coaching and industry best practices.
- Partnered with scrum masters, product owners, and team leaders to fine-tune workflows and processes in Jira and develop core sprint planning and facilitation skills.
- Worked with business leaders to provide the core Agile knowledge, training, and support they need to continue to mentor and guide their teams' success.
Jira Expert Admin
Frazer Antalffy Integrated Consulting, LLC dba FAIC Group
- Worked with the program management team and business leaders to help them translate their business vision into a state-of-the-art Jira workflow and reporting system.
- Provided support with security configurations, workflows, groups, and project roles of Jira and Tempo to optimize the playbook and add clients.
- Developed an analysis of current practices and recommendations for company best practices. Documented new practices and provided training and support for Jira users.
Senior Project Manager
Avaya
- Led customer call center cloud migration efforts for multiple enterprise clients, including American Express, DirectTV, and The Washington Post.
- Created migration project plans and coordinated teams across multiple organizations to achieve success.
- Managed tracking, reporting, and planning for multiple large projects concurrently.
Scrum Master/Project Manager
Willowtree, Inc.
- Delivered the highest quality digital products for clients such as Regal Cinemas, Wyndham Hotels, and Pepsi.
- Collaborated with stakeholders to drive effective decision-making on complex issues of scope, design, architecture, and process.
- Defined and communicated release plans and rollout strategy and drove development towards these milestones and deadlines.
- Led multiple cross-functional Kanban and Scrum teams through the Agile planning and delivery process.
- Provided coaching and team leadership, fostering an environment of innovation and continuous improvement.
Scrum Master/Project Manager
Calero Software
- Provided end-to-end planning and implementation of large-scale, complex expense management and business analytics projects for clients, including USPS and large universities.
- Served as the team lead and coach to multiple cross-functional project teams.
- Kept multiple concurrent projects on schedule and within budget while managing risks and proactively informing stakeholders of project status and team performance.
- Facilitated assessment meetings with clients to understand business processes and stakeholder needs to define and document detailed functional and technical requirements for project deliverables.
- Coordinated the efforts of multiple teams and organizations through critical project transitions and production releases.
Agile Transformation Consultant/Scrum Master
Optimiser Energy (via Riversong Solutions)
- Established Agile project management processes and methodologies for a fast-growing software development company.
- Served as an agile coach and educator, guiding the team for high performance and effective project delivery.
- Served as the project manager and scrum master, providing team leadership, planning, and oversight for a diverse project portfolio.
- Managed vendor relationships and associated contracts.
Scrum Master/Senior Project Manager
MeadWestvaco
- Led and coached a project team new to Agile development to deliver a complex business analytics project for a major manufacturing company using the Scrum methodology.
- Educated the team on Agile best practices and established a process framework for future projects.
- Partnered with executive stakeholders and the business to define requirements, perform data analysis, and plan and report project progress against the milestone.
Agile Project Operations (PMO) Consultant
Unboxed Technology
- Drove the establishment of program, resource, and project management systems, procedures, and processes for a rapidly growing software and e-learning development company.
- Established project process and resource management systems and standards to support operational efficiency.
- Coached and mentored project management staff on best practices in an Agile environment.
- Led multiple project teams developing and delivering employee training courses for major US companies.
- Served as project manager for the initial scoping and development of the Unboxed learning management system product.
Senior Pinnacle Project Manager
Calero Software, Inc. (via Riversong Solutions)
- Managed and planned large-scale telecommunications expense management projects.
- Served as the primary project manager for the USPS (the United States Postal Service) implementation of telecommunications expense management financial software.
- Led a lean-Agile team, providing guidance and coaching to optimize productivity and customer success.
Project Manager
Silverchair Information Systems
- Managed multiple concurrent software development and content management projects for major medical journal publishers—from requirements definition through implementation, testing, release, and post-launch support and enhancement.
- Participated in training and coaching team members on Agile project management methodologies.
- Partnered with client teams on delivery of continuing education products.
Project History
Regal Cinemas Application (Android and iOS)
Managed several releases of application features, as well as design and delivery of an application rebrand.
Mead WestVaco Manufacturing Analytics and Agile Transformation
Led one of the first scrum teams at one of the nation's largest packaging manufacturers on production data analytics project.
Wyndham Hotels Mobile Check In
Managed the native app development, testing, and delivery of mobile check-in feature for a large international hotel chain.
Coached team through complex testing and validation processes, and ensured successful and timely delivery.
Certifications
SAFe 6 Practice Consultant
Scaled Agile
SAFe 6 Program Consultant
Scaled Agile
Certified SAFe 5 Program Consultant (SPC)
Scaled Agile
SAFe Advanced Scrum Master
Scaled Agile
Certified Scrum Master
Scrum Alliance
Project Management Professional (PMP)
Project Management Institute (PMI)
Skills
Tools
Jira, Confluence, Atlassian Suite, Project Management & Work Tracking Tools, Google Workspace, Office 365, Miro, Atlassian, Adobe Analytics, Trello
Paradigms
Agile Project Management, Agile Delivery, Agile Leadership, Change Management, Agile, Scrum, Agile Software Development, Requirements Analysis, Agile Workflow, Implementation Project Management, Kanban, Lean Project Management, B2B, Key Performance Metrics, Agile UX, Management, Agile Product Management, UX Design, DevOps
Platforms
Android, iOS, Enterprise Resource Planning (ERP), WordPress
Industry Expertise
Healthcare, Insurance, Hospitality, Telecommunications, Lean Six Sigma
Other
Scrum Master, Native Mobile Apps, Mobile Apps, Mobile, Agile Product Delivery, Agile Transformation, Communication, Agile Sprints, Certified ScrumMaster (CSM), SAFe 4 Advanced Scrum Master, Customer Service Management (CSM), Agile Coaching, Agile Deployment, Software Project Management, Software Development Lifecycle (SDLC), Enterprise, Scaled Agile Framework (SAFe), Discovery Workshops, Project Discovery, Hybrid Project Management, Workshop Facilitation, Coaching, Certified Project Manager, User Stories, Story Mapping, Backlog Management, Backlog Grooming, Feature Backlog Prioritization, Minimum Viable Product (MVP), Planning, Sprints, Sprint Master, Sprint Planning, Sprint Ceremonies, Sprint Retrospectives, Implementation, Software Implementation, Status Updates, Project Management, Web Project Management, Website CMS, Project Timelines, Requirements, User Requirements, Business Requirements, Functional Requirements, Project Delivery, Product Delivery, Agile Release Training, Requirements & Specifications, Team Mentoring, Team Leadership, Remote Team Leadership, Cross-functional Team Leadership, Projects, IT Projects, IT Project Management, Product Discovery, Process Improvement Project Management, Teams, Agile Practices, Workflow, Software Development, Stakeholder Management, SAFe 6, Jira Service Management, Jira Automation, Quality Assurance (QA), Agile Program Management, Program Management, IT Program Management, Change Leadership, eCommerce, Project Management Professional (PMP), Web, Scrum Coaching, Lean Development, Lean IT, Product Management, Mobile App Development, Leadership, Project Planning, Project Estimation, Digital Project Management, Hybrid Frameworks, Jira Administrator, Jira Administration, Digital Innovation, Edtech Design, Teaching, Training, Training & Training Content Development, Dashboards, Google Apps, Business to Business (B2B), Enterprise SaaS, Enterprise Metrics, Key Performance Indicators (KPIs), Client Portals, Client Services, Client Management, Agile CRM, CRM Systems, Content Management, Product Roadmaps, Process Optimization, Business Process Optimization, Enterprise Systems, Data Migration, Data Management, Project Evaluation, Technical Project Management, Business, IT Operations Management (ITOM), Consulting, Operations, Product Ownership, User Experience (UX), User Interface (UI), Data Analytics, Supply Chain, Digital Platform Development, Integration, Version Control, Electronic Health Records (EHR), Risk Management, Research Analysis, Presentations, QA Automation, eCommerce Management, Engineering, Learning Management Systems (LMS), HTML, Startup Consulting, Business Analysis, Best Practices, SyteLine ERP, Product Requirements Documentation (PRD), Detail-oriented, Workflow Optimization, Data Analysis, SaaS, Scaled Professional Scrum (SPS)
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