Technical Program & Technology Leader

Ricky Stewart IV

Technology Program Management Leader · Scaled Agile Expert · Enterprise IT Governance

Twelve-plus years turning enterprise complexity into shipped outcomes — building the IT PMO that gives Engineering, Product, and executives one shared picture of what's happening, what's at risk, and what's next.

Exploring Director / VP roles in Technology & Program Leadership

wrstewartiv@gmail.com / 602.770.6575 / linkedin.com/in/rickystewartiv

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Scottsdale, AZ · Remote & travel OK

Career roadmap

Reverse chronological

Director, IT & Information Systems

Most recent 74Software (Axway's parent company) Q1 2025 – Jul 2026

Led enterprise technology roadmap execution and company-wide initiatives across IT, Engineering, business operations, and executive stakeholders within a 40+ person IS organization supporting ~4,500 employees.
Established intake, prioritization, performance reporting, and escalation frameworks that improved portfolio visibility and enabled clearer capacity, risk, and value tradeoffs.
Tracked progress, dependencies, implementation readiness, risks, and stakeholder commitments across multiple technology initiatives, escalating decisions that required leadership attention.
Redesigned workflows and reduced manual handoffs to strengthen accountability, service delivery, and continuous improvement.

Project Management Office Manager, IT/IS

Complete Axway 2022 – 2025

Built and scaled the enterprise IT PMO — portfolio intake, governance, prioritization, delivery standards, review cadences, and executive reporting, from the ground up.
Led and developed program managers and Scrum Masters responsible for strategic initiatives and four Scrum teams, providing coaching and delivery leadership.
Managed resource tradeoffs, cross-program dependencies, sequencing, risks, and escalation paths to keep delivery aligned with business objectives and capacity.
Introduced Agile and hybrid delivery practices that improved backlog readiness, coordination, and delivery predictability across distributed teams.

Senior Business Project Manager

Complete Axway 2019 – 2022

Led a cross-functional legacy ERP decoupling initiative spanning R&D, IS Operations, Integrations, Security, Sales, and Finance — migrating four black-box product-key generation components to a standalone virtual server.
Eliminated security and fulfillment-continuity risk from unsupported technology while simplifying renewals from a two-system workflow into one.
Converted business objectives into structured requirements and coordinated program plans, stakeholder commitments, dependencies, and implementation milestones.

Project Manager / Scrum Master

Complete Infusionsoft (now Keap) 2017 – 2019

Drove Agile delivery for engineering teams building SaaS CRM and marketing automation products.
Aligned Product and Engineering stakeholders on roadmap priorities, release commitments, technical dependencies, and sequencing.
Maintained execution health through backlog refinement, sprint planning, reviews, retrospectives, and delivery metrics.

Project Manager / Scrum Master II

Complete Choice Hotels International 2015 – 2017

Served as Scrum Master for four engineering teams on a $50M+ program with ~100 contributors across Engineering and Product.
Improved sprint delivery through process optimization and coached teams and leadership on Agile practices.
Supported hiring and onboarding of new Scrum Masters, helping level up delivery capability org-wide.

Scrum Master

Complete Glynlyon 2013 – 2014

Facilitated Agile delivery for three engineering teams, including the primary feature team for the company's flagship product.
Managed coordination across distributed and offshore contributors, ensuring predictable sprint delivery.
Shielded teams from external disruptions, removing blockers so engineers could stay focused on delivery.

Agile & scaled delivery leadership

Scrum · Scaled Agile · transformation

Scaled Agile & Big Room Planning

Deep experience running Scaled Agile practices across multi-team environments, including facilitating PI planning and big room planning sessions that align release trains, dependencies, and cross-team commitments.

Scrum Master Training & Coaching

Trained and coached Scrum Masters and Agile practitioners, building internal capability so teams could run Scrum and Kanban well without leaning on a single expert.

Department-Wide Agile Transformation

Led full department transformations from traditional delivery to Agile methods — standing up Scrum and Kanban practices, governance, and cadences that stuck after the rollout ended.

Core competencies

By practice area

Agile & Scaled Delivery

Scaled Agile PI Planning / Big Room Planning Scrum Master coaching & training Agile transformation Scrum & Kanban delivery Multi-team release trains

Technical Program Management

Program strategy & roadmaps Cross-functional leadership Delivery planning & scheduling Risk & dependency management Executive reporting Portfolio intake & prioritization

Data, Technology & Automation

Data-driven decision-making Product metrics & reporting Business process automation APIs & systems integration Product architecture collaboration DevOps & continuous deployment

Leadership & Collaboration

Executive communication Stakeholder management Change management Team development & mentoring Influence without authority Vendor & partner management