Senior 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 Scrum Master

Role Overview:
We are seeking a dynamic Senior Scrum Master to lead and facilitate Agile delivery in complex, multi-team programs driven by innovative technologies. This role requires a seasoned Agile professional who can simultaneously serve as a Scrum Master and collaborate closely with Product Owners, Leadership Stakeholders, and Release Train Engineers (RTEs) to ensure seamless execution across product increments. The ideal candidate will help nurture team maturity, remove impediments, and foster stakeholder alignment, ultimately driving meaningful outcomes in high-impact AI Enabled programs.

Key Responsibilities:

• Lead Scrum ceremonies (daily stand-ups, sprint planning, retrospectives, sprint reviews) across one or more Agile teams to ensure continuous delivery of high-quality work.
• Partner closely with Release Train Engineers and Product Owners to support program-level PI planning, backlog refinement, and dependency management.
• Serve as an Agile coach to teams, fostering self-organization, collaboration, and continuous process improvement.
• Remove impediments and obstacles that hinder team progress and escalate when necessary to maintain delivery velocity.
• Facilitate alignment and communication among cross-functional teams and stakeholders to ensure clear understanding of goals, priorities, and timelines.
• Support the adoption and scaling of Agile/SAFe frameworks by sharing best practices and driving discipline around Agile principles.
• Develop and implement repeatable delivery techniques to bolster both team and program predictability
• Manage dual responsibilities or collaborate effectively with those acting as both Scrum Master and RTE when needed.
• Track and communicate progress, risks, and issues to leadership and stakeholders promptly.
• Provide mentorship and guidance to junior Scrum Masters and Agile team members to build organizational Agile capability.

Qualifications:

• Proven experience as a Scrum Master in complex Agile environments, ideally with SAFe or scaled Agile frameworks.
• Excellent skills with story point development - partnering with PO, Program Leadership, Architects and Engineering leaders.
• Strong facilitation, communication, and conflict resolution skills.
• Experience supporting and/or performing Release Train Engineer duties is a plus.
• Ability to manage multiple teams and coordinate across geographic time zones.
• Demonstrated leadership in Agile coaching and driving cultural change.
• Background in technology or regulated industries (such as pharmaceutical or automotive) is preferred but not required.
• Certified Scrum Master (CSM), Advanced CSM (A-CSM) & Certified Scrum Professional (CSP), SAFe Scrum Master (SSM), or equivalent Agile certification.

This role offers an exciting opportunity to influence critical programs and grow Agile excellence within an innovative technology-driven environment.

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.