Why Ryan?

Hybrid Work Options

Award-Winning Culture

Generous Personal Time Off (PTO) Benefits

14-Weeks of 100% Paid Leave for New Parents (Adoption Included)

Monthly Gym Membership Reimbursement OR Gym Equipment Reimbursement

Benefits Eligibility Effective Day One

401K with Employer Match

Tuition Reimbursement After One Year of Service

Fertility Assistance Program

Four-Week Company-Paid Sabbatical Eligibility After Five Years of Service

The Director, PMO will be responsible for leading and managing the Software Development Life Cycle (SDLC) for Ryan’s Platforms and SaaS product suite. This role oversees a portfolio of product development initiatives, ensuring alignment with business objectives, technology standards, and client needs. The position requires strong technical program/project management expertise, Agile leadership, and experience managing cross-functional teams in a fast-paced environment.

Duties and Responsibilities, as they align to Ryan’s Key Results

People

Create a positive team experience and working environment.

Manage Program/Project Management and Scrum standards.

Provide coaching and education to elevate program/project management knowledge, skills, tools, and techniques.

Client

Escalate and manage program/project issues and risks to stakeholders with clarity and professionalism.

Partner with cross-functional teams (Product, Engineering, QA, Compliance) to prioritize and organize completion of milestones.

Track progress and provide timely status reporting of dependencies, risks, and issues to initiative owners and leadership.

Design and deliver effective Change Management plans to communicate and educate end users.

Value

Oversee all scoping, planning, execution, and delivery activities for Platform and SaaS software products to ensure on-time, high-quality releases.

Drive continuous improvement of SDLC processes, Agile / Waterfall practices, templates/tools, and training.

Develop training and communication plans to support PMO and Scrum activities.

Perform other duties as assigned.

Education and Experience

Bachelor’s degree in Computer Science, Information Systems, or related field; MBA or advanced degree preferred.

10–15 years of program/project management experience, including 6+ years in leadership roles managing software development portfolios.

Proven success delivering complex, multi-product initiatives in an Agile & Waterfall environment.

Computer Skills

Proficient in Microsoft® Word, Excel, PowerPoint, Outlook, and Internet navigation.

Experience with Azure DevOps for Agile/Scrum management.

Essential Skills Required

Demonstrates senior executive engagement and influencing skills.

Ability to manage multiple concurrent software development projects in a cross-functional organization.

Strong understanding of SDLC and Agile/Scrum methodology.

Detail-oriented with strong organizational and communication skills.

Ability to coach teams and create structure around ambiguity.

Strong drive for results and continuous improvement.

Certificates and Licenses

PMP Certification preferred (not required).

Agile certifications (Scrum Master, SAFe) strongly preferred.

Valid driver’s license required.

Work Environment

Standard indoor working environment.

Long periods of sitting while working at a computer.

Occasional long periods of standing.

Regular interaction with employees and vendors both in person and via email and telephone.

Independent travel requirement: up to 20%.

Why This Role Matters

Ryan’s Platforms & Products are a cornerstone of our technology-driven tax solutions. This role ensures strategic alignment, operational excellence, and innovation in delivering software products that meet client needs and maintain market leadership.

Equal Opportunity Employer: disability/veteran