Leo Estes

Director of IT Project Management

ad06av@r.postjobfree.com • 804-***-****

LinkedIn • Midlothian, VA

Summary

Seasoned and accomplished manager harnessing 15+ years of experience in driving multifaceted IT projects and fostering productive cross-functional collaborations. Recognized for translating visionary leadership into actionable strategies, efficiently liaising between diverse teams, and steering transformative initiatives to fruition. Adept at navigating transition challenges, optimizing decision-making processes, while consistently upholding the highest industry standards. Renowned for bolstering stakeholder engagement, reinforcing executive endorsements, and leading continuous advancements in team development, all underlined by a commitment to operational efficiency and excellence.

Technical Proficiencies

Project/Process Management & Frameworks:

Project Management & Collaboration Tools: JIRA, Clarity PPM, MS-Excel, MS-Project.

Agile Methodologies & Frameworks: Scaled Agile for Enterprise (SAFe), Scrum, IT Waterfall

Process Development, Process Management, Process Improvement

Cloud & Data Management:

Cloud Technologies & Operations: CloudOps, Azure, IaaS, PaaS.

Data Management & Transition: Server migrations, Data redundancy strategies, Data Migration Waves.

Security, Implementation & Governance:

Security & Network Protocols: L3 Firewall Configurations, Network Infrastructure.

Software & System Implementation: Comprehensive tool suite adoption, Aproove proof routing tool, National IT Remedy platform.

Governance & Policies: Cloud procedure operational policies, Federal Reserve policies, Service Level Agreements (SLAs), Risk Profiles.

Career Experience

Markel Corporation, Glen Allen, VA 2018 – 2023

CloudOps Operations Manager/Sr. Scrum Master (2019-2023)

Orchestrated transition of Markel's CloudOps team from project management to operational management. Directed specialized teams in Power Platform automation, AWS/Azure resource management, and QA tool distribution. Championed "All in on Agile" initiative, aligning all Cloud Team activities under a JIRA-based Agile Kanban framework. Developed strategic governance and operational policies for cloud processes and procedures.

Successfully transitioned Markel's CloudOps team post-implementation, streamlining operations, and eliminating process redundancies.

Spearheaded the establishment of Centers of Excellence in CloudOps, DevOps, and FinOps, resulting in standardized best practices across teams.

Pioneered the "All in on Agile" transformation, utilizing Agile Kanban, leading to a more efficient enhancement delivery schedule.

Reduced cloud-related issue response times through the implementation of formulated policies, processes and procedures.

Enhanced inter-team synchronization by representing CloudOps in the Markel IT PMO, optimizing support for Scaled Agile "Agile Release Trains."

Enterprise Cloud Project Manager 2018 – 2019

Spearheaded Markel's collaboration with IBM and Microsoft for Azure Cloud deployment. Facilitated establishment of markelcorp and Enterprise Dev/Test Azure tenants. Led configuration of markelcorp tenant with management groups for Markel North America and Markel International. Supervised Markel's adoption of both IaaS and PaaS service models. Managed infrastructure alignments, designating primary and secondary data locations.

Developed the processes and procedures to be used to secure Azure resources for use.

Collaborated with industry giants IBM and Microsoft to implement Azure Cloud, enhancing Markel's IT infrastructure.

Established Enterprise Dev/Test tenant as a dedicated sandbox, promoting innovation and fostering efficient resource planning.

Ensured strategic geographic data redundancy by designating specific primary and secondary data locations, optimizing data accessibility and reliability.

Apex Systems, Richmond, VA 2015 – 2018

Project Manager for RR Donnelly – DSG (2018 – 2018)

Oversaw migration to a new proof routing tool, which was part of the company's larger initiative to adopt a comprehensive tool suite, including a new Data Access Management tool and associated pipeline tools. Coordinated daily progress evaluations with Lead Developer and client Scrum Master. Partnered with client Product Owner to provide weekly project status updates. Served as primary conduit for remote enterprise project manager, streamlining communication and updates within JIRA environment. Guided design and creation of client-specific training materials for the Aproove proof routing tool. Evaluated and tested client-driven changes to Aproove tool's core functionalities.

Conducted rigorous unit and segment testing to identify critical limitations in Aproove software, demonstrating adeptness in quality assurance and strategic decision-making.

Forged an effective liaison role, markedly boosting communication efficiency between onsite and remote teams.

Merged varied data sources to craft a unified MS-Excel project task overview, heightening stakeholder transparency and optimizing decision-making processes.

Federal Reserve Bank of Richmond: National IT, Richmond, VA 2015 – 2017

Program Manager for Three Phase Migration Effort (New York Markets Infrastructure and Systems Transition) (2016 – 2017)

Organized structured three-phase migration strategy, encompassing Elaboration, Trial Period, and Transfer, to migrate Server Infrastructure and Production Support Operations from FRB New York to National IT. Led 3 project managers to handle distinct work streams, ranging from cataloguing server inventory to the development of Service Level Agreements (SLAs) and Risk Profiles. Developed a robust information-sharing framework, which entailed the inception of the Management Support Group (MSG) and Executive Advisory Group (EAG) to modernize communication and decision-making processes. Upheld rigorous adherence to Federal Reserve policies, ensuring periodic assessments with the Process Assurance Function (PAF). Oversaw intricate process during Trial Period, including facilitating daily progress discussions and managing the technicalities of system integrations and transitions. Strategically planned for the critical Transfer phase, with a particular emphasis on the seamless transition of Human Resources, Financial Assets, and Contracts. Initiated groundwork for 'New York Markets Future State' project, ensuring it aligned with National IT standards and infrastructural advancements.

Accomplished a comprehensive migration of Server Infrastructure and Production Support Operations, resulting in a cohesive and more efficient operational framework for National IT.

Revolutionized communication dynamics by institutionalizing the MSG and EAG, accelerating decision-making processes and expediting issue resolutions.

Spearheaded integration of National IT monitoring solutions across 461 distinct Market servers, ensuring enhanced system surveillance and prompt reactions.

Streamlined and fortified Incident and Change Management protocols by pivoting to the advanced National IT Remedy platform, culminating in a tangible surge in incident rectification rates.

Project Manager – New York Markets Discovery Effort 2015 – 2016

Led feasibility study for New York Markets Infrastructure transition from Federal Reserve Bank of New York to National IT. Identified key stakeholders in both organizations. Reviewed past transition attempts, recognizing challenges and pitfalls. Assessed and ranked potential strategies against set criteria. Presented top strategies to senior executives for decision-making.

Successfully navigated historical transition challenges, leading to an informed and viable strategy selection process.

Advocated and validated the strategic importance of the transition, securing unanimous executive endorsement.

Pioneered establishment of a powerful cross-functional team, which contributed to the streamlined and informed decision-making process.

Presented top three transition strategies to executives, achieving alignment on the optimal approach for both organizations.

Project Manager - New York Markets Network Transition 2015 – 2015

Managed a collaboration between the Federal Reserve Bank of New York Markets Group and National IT to streamline the Markets Network Infrastructure. Decoupled Markets Network Transition from Firewall Hardening effort, enabling targeted focus and agile execution. Headed design, procurement, and deployment of L3 firewalls in multiple environments including Production, QA, Test, and Development for the New York Markets Group. Handled change requests to optimize project timelines.

Impact Makers, Inc., Richmond, VA 2013 – 2014

AccelRx Production Support Readiness, Cigna (2014 - 2014)

Spearheaded establishment of a web-based Pharmacy benefit delivery system support team by implementing cross-functional collaboration. Secured out-of-budget allocations to meet 2014 project requirements. Partnered with Production Support vendors to formulate resource integration and capacitation plans. Assessed non-functional prerequisites vital for Production Support. Forged Extended Support agreements with external front-end vendors. Oversaw data migration sequences for streamlined Group and Eligibility data transitions for each of the 8-10 planned Data Migration Waves of client information.

Successfully enlisted ten pivotal production support specialists, achieving an equitable split of five onshore and five offshore personnel.

Introduced a novel Guided Support paradigm, fortifying competence and readiness of emergent team.

Assured operational efficiency of system by guaranteeing the punctual fulfilment of indispensable non-functional specifications.

Organized all-encompassing Extended Support strategy with third-party entities, fortifying system reliability and interoperability.

Core Ops Agile Roadmap Implementation, Cigna 2013 – 2014

Managed development of a Roadmap to Agile Maturity for Core Operations Agile Practice. Assessed existing practice processes and implemented changes using a modified Scaled Agile for Enterprise (SAFe) model. Strategized progressive releases to enhance team's maturity position. Scrutinized potential strategic partners for critical resource provisioning and specialized training.

Supervised integration of sixteen pivotal process Foundation Blocks, strengthening Agile practices.

Delivered five iterative releases, each advancing team process maturity by measurable increments.

Fostered key strategic partnerships, leading to enhanced resource capability and optimized training outcomes.

PM Best Practice Consultation, Cigna EQA 2013

Provided expert consultation and advice on how to build a project management best practice within the Cigna CQA group. This involved an analysis of what they had in place mapped against where they wanted to go, and then a plan to get them there.

Additional Experience

Implementation and Application Manager- Clarity PPM Tool, Capital One, Richmond, VA

Process Manager – Enhancements Process, Capital One, Richmond, VA

PMO Consultant – Project Support Office, Capital One, Richmond, VA

Portfolio Manager – Corporate Risk Governance, Capital One, Richmond, VA

Project Manager – HR Systems, Capital One, Richmond, VA

Education

Master of Science in Personnel and Human Resource Management

American University, Washington DC – Kogod School of Business

Bachelor of Arts in Theatre

Edinboro University of Pennsylvania – Department of Arts and Humanities, Edinboro, PA

Licenses & Certifications

ESI International

Associates Certificate in Project Management, George Washington University

Master’s Certificate in Project Management, George Washington University

Project Management International (PMI)

Project Management Professional (PMP): 2006 - 2009

The Scrum Alliance

Certified Scrum Master (CSM): 2012 – 2023

ITIL 4 Certified: 2018

Awards

Circle of Excellence Award – HR Data Warehouse

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