Senior Project Manager/Scrum Master

Company Overview

Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.

Our seasoned professionals deliver services based on Milestone's best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.

Job Overview

Senior Project Manager / Senior Scrum Master

Role Summary

We are seeking an experienced Senior Project Manager / Senior Scrum Master to lead delivery execution for a new product team implementing a modern, cloud-based forecasting platform to replace manual, spreadsheet-driven processes. This role combines senior project delivery ownership with senior agile leadership, requiring the ability to operate effectively at both the team and program levels.

The Sr. PM / Sr. SM will drive predictable delivery outcomes, manage cross-functional dependencies, coach Agile teams, and ensure strong stakeholder alignment during a time-bound engagement while long-term ownership roles are onboarded.

Key Responsibilities

Delivery Ownership

• Own end-to-end delivery, including scope, schedule, milestones, risks, issues, and dependencies
• Develop and maintain integrated delivery plans across multiple workstreams
• Manage cross-functional coordination across business, analytics, engineering, and vendor teams
• Proactively identify, escalate, and mitigate delivery risks and blockers
• Lead regular delivery and stakeholder forums, driving decisions and clear outcomes
• Provide transparent, executive-ready status reporting on progress, risks, and dependencies

Agile Leadership

• Serve as Scrum Master for one or more product teams, facilitating Agile ceremonies (sprint planning, daily stand-ups, reviews, retrospectives)
• Coach teams and stakeholders on Agile principles, roles, and best practices
• Partner with Product Owners to ensure healthy backlogs, clear priorities, and sprint-ready stories
• Identify and remove impediments to maintain delivery flow and team focus
• Foster a culture of continuous improvement, accountability, and high performance

Metrics, Predictability & Continuous Improvement

• Establish delivery visibility using Agile and delivery metrics (velocity, sprint health, predictability)
• Use retrospectives and data-driven insights to improve team effectiveness and delivery outcomes

Transition & Knowledge Transfer

• Ensure delivery artifacts, decisions, and key learnings are documented
• Support smooth transition and handover to incoming full-time PM and Scrum Master roles

Required Qualifications

• 10+ years of experience in enterprise technology delivery, including senior-level experience as both a Senior Project Manager / Senior Scrum Master
• Proven ability to manage complex, cross-functional initiatives with multiple stakeholders and vendors
• Strong hands-on experience facilitating Agile/Scrum teams in product-centric environments
• Expertise in delivery planning, dependency management, RAID management, and stakeholder communication
• Excellent facilitation, coaching, and communication skills

Preferred Qualifications

• Experience in data, analytics, forecasting, planning, or platform modernization initiatives
• Experience working with globally distributed teams
• Agile and/or project management certifications (e.g., Scrum Master, SAFe, PMP, PMI-ACP)

Compensation

Estimated Pay Range:

Exact compensation and offers of employment are dependent on circumstances of each case and will be determined based on job-related knowledge, skills, experience, licenses or certifications, and location.

Our Commitment to Diversity & Inclusion

At Milestone we strive to create a workplace that reflects the communities we serve and work with, where we all feel empowered to bring our full, authentic selves to work. We know creating a diverse and inclusive culture that champions equity and belonging is not only the right thing to do for our employees but is also critical to our continued success.

Milestone Technologies provides equal employment opportunity for all applicants and employees. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race, color, religion, gender, gender identity, marital status, age, disability, veteran status, sexual orientation, national origin, or any other category protected by applicable federal and state law, or local ordinance. Milestone also makes reasonable accommodations for disabled applicants and employees.

We welcome the unique background, culture, experiences, knowledge, innovation, self-expression and perspectives you can bring to our global community. Our recruitment team is looking forward to meeting you.