Ricky Stewart | Technical Program & Technology Leader

Selected impact

Program metrics

20+

Engineering teams supported across simultaneous technology initiatives

$50M+

Program scope led as Lead Scrum Master, ~100 contributors

4,500

Employees served by a 40+ person Information Systems org

Project managers led across France, the U.S., and Bulgaria

80%

Milestone dates met after PMO standards were adopted

50%

Reduction in document creation time using AI tooling

Career roadmap

Reverse chronological

Director, IT & Information Systems

Most recent 74Software (Axway's parent company) Mar 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.
Adopted AI tooling across delivery workflows for meeting summarization, executive presentation drafting, and consolidating documents, resources, and email threads into BRD inputs, cutting document creation time by 50% while improving data accuracy.

Project Management Office Manager, IT/IS

Complete Axway Mar 2022 – Mar 2025

Built and scaled the enterprise IT PMO from the ground up, defining portfolio intake, governance, prioritization, delivery standards, review cadences, and executive reporting.
Standardized the entire PM workflow, authoring templates, checklists, and written guidance for project charters, BRDs and requirements gathering, RACI matrices, RAID logs, stakeholder registries, communication plans, reporting standards, retrospectives, and milestone roadmaps.
Drove the standard to 100% adoption through quarterly check-ins and hands-on coaching, moving delivery from ad-hoc execution with no shared standards to consistently planned projects with milestone dates met 80% of the time.
Established SharePoint as the system of record for meeting minutes, project artifacts, and milestone tracking, giving PMs and stakeholders a single source of truth.
Co-led the enterprise Wrike rollout with a peer director, defining the underlying workflows, project standards, and reporting structures; 100% of projects were tracked in Wrike by departure.
Led a distributed team of nine project managers across three countries (seven in France, one in the U.S., one in Bulgaria), aligning priorities, schedules, and communication across time zones and working cultures.
Supported integration of an acquired company (SBS) into the Axway landscape, managing escalations and navigating complex stakeholder relationships to keep integration work moving.
Led and developed program managers and Scrum Masters across four Scrum teams, managing resource tradeoffs, dependencies, sequencing, risks, and escalation paths.
Supported development and tracking of the Information Systems department budget, and tracked vendor spend against plan on a cross-functional project.

Senior Business Project Manager

Complete Axway Mar 2019 – Mar 2022

Partnered on the research, evaluation, and implementation of a new cloud ERP platform, taking over an initiative that had been stalled for years and driving it to a successful go-live in Q1 2022.
Tripled ticket output on the Salesforce team by moving them from a loose process to disciplined Agile delivery, with rigorous backlog grooming, story readiness, and genuine prioritization.
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, reducing renewal processing time by 25%.
Converted business objectives into structured requirements and coordinated program plans, stakeholder commitments, dependencies, and implementation milestones.

Project Manager / Scrum Master

Complete Infusionsoft (now Keap) Aug 2017 – Mar 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 Jan 2015 – Jun 2017

Served as Scrum Master for four engineering teams on a $50M+ program with ~100 contributors across Engineering and Product; the program was delivered on time.
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 Feb 2013 – Dec 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.

Building the PMO standard

Before & after

Before

Projects ran ad-hoc. No shared templates, no consistent requirements process, no single place to find project history. Timelines and milestones varied by whoever happened to be running the work.

After

A full documentation standard adopted by 100% of the PM organization, reinforced by quarterly check-ins. Milestone dates met 80% of the time, every project tracked in Wrike, and SharePoint serving as the system of record.

What I authored

Project charters BRD format & gathering guidelines RACI matrices RAID logs Stakeholder registries Communication plans Reporting standards Retrospectives & lessons learned Milestone roadmaps Workflow checklists

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 Budget support & vendor spend tracking Portfolio intake & prioritization

Data, Technology & Automation

Data-driven decision-making Product metrics & reporting AI-assisted delivery workflows Claude, Copilot, ChatGPT 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 Multinational team leadership M&A integration support Vendor & partner management

Toolkit & credentials

Platforms · affiliations · education

Tools & Platforms

Jira
Confluence
Wrike
SharePoint
MS Suite, incl. MS Project
Rally Agile Management
Claude, GitHub Copilot, ChatGPT

Affiliations

Scrum Alliance: Member CSPO, CSM
PMI Previous PMP & ACP

Education

Arizona State University B.S., Global Business Administration

What colleagues say

References

Paul Kielty

VP IT/IS, 74Software
(now retired)

“Rick built the IT/IS PMO Team and processes for a growing multinational company from scratch with great success.”

Full reference

“I had the great opportunity to work with Rick at 74Software for over 7 years. I know Rick both personally and professionally. He is a person of the highest integrity. I appreciate how Rick looks at problems as opportunities and addresses them systematically and logically. Rick built the IT/IS PMO Team and processes for a growing multinational company from scratch with great success. I highly recommend Rick for IT Leadership Roles.”

W Rob Ferguson, MBA

Program Manager, 74Software
Reported directly to Ricky

“It’s rare to work under someone who combines strategic clarity with genuine hands-on support for their team.”

Full reference

“I had the privilege of reporting to Rick during his time as Director, IT & Information Systems at 74Software and it’s rare to work under someone who combines strategic clarity with genuine hands-on support for their team.

“Rick led enterprise technology programs tied directly to company-wide strategic initiatives, and he had a real talent for cutting through complexity — whether that meant directing cross-functional teams through difficult, multi-layered IT and engineering initiatives, or building governance frameworks and PMO capabilities that made delivery timelines and accountability visible for the first time.

“Any organization would be fortunate to have him leading their technology and IT strategy. I enjoyed my time working for Rick immensely.”

Daniel Bankert

Senior Director, Global IS Business Applications, Axway
Now Global Sales Engineering, Matterport

“Ticket output roughly tripled.”

Full reference

“I worked with Ricky at Axway from 2019 to 2022, when I led global IS Business Applications and he was a project manager. We researched and implemented a new cloud ERP platform together, inheriting a project that had been stalled for years. By being agents of change we were able to successfully complete the project, resulting in a successful Go Live in Q1 2022.

“The clearest example of Ricky’s impact was the Salesforce team. Ricky moved them from a loose process to a real Agile methodology, with disciplined backlog grooming and genuinely prioritized work. Ticket output roughly tripled. This came from fanatical discipline and coaching, helping teams manage stories, shielding the team from churn, and holding everyone to the process long enough for it to stick.

“Ricky is direct, well organized, and someone I trusted with complicated cross-functional work. I would work with him again.”

Jeremy Wood

Founder, Outcome Focus
Co-Founder, Agent Buddy

“Exactly what organizations need from a technology or program leader today.”

Full reference

“I had the opportunity to work with Ricky at Glynlyon early in his career, and even then, the qualities that define strong technology leaders were obvious. He was a person of genuine character: positive, inquisitive, eager to learn, and never afraid to challenge the status quo when he saw a better way forward. What made Ricky especially effective was his ability to connect with nearly any personality while still encouraging people and processes to improve.

“I watched him continually read, study, and apply new ideas, not simply for his own development, but to help the teams around him perform better. That combination of curiosity, determination, integrity, and people-first leadership was rare then, and it is exactly what organizations need from a technology or program leader today. I would gladly work with Ricky again and recommend him without hesitation.”