Senior Scrum Master

Custom Software Systems, Inc. (CSS) is seeking a Senior Scrum Master to serve as a servant leader and Agile coach, facilitating Scrum practices, removing impediments, and empowering teams to become self-organizing and accountable. The ideal candidate will have extensive experience leading Agile teams in complex environments, driving continuous improvement, managing stakeholder relationships, and supporting Agile transformation initiatives while ensuring consistent delivery of business value.

Responsibilities

• Team Self-Organization & Accountability: Build self-organizing, empowered teams that take ownership of commitments, foster accountability for sprint goals and delivery.
• Impediment Removal & Escalation: Identify and remove team-level impediments quickly, escalate organizational/systemic blockers to appropriate leadership, and maintain transparent impediment tracking and resolution.
• Continuous Improvement Culture: Facilitate meaningful retrospectives that drive action, implement improvements based on team feedback, and foster experimentation and learning mindset.
• Engaging and coaching product teams to help them recognize the effectiveness of self-organization and continuous improvement.
• Work closely with Product Owners to properly scope and plan current and future work.

Required Qualifications

• At least seven (7) years of hands-on experience as a Scrum Master serving multiple teams in complex, matrixed organizations.
• Minimum of ten (10) years of experience leading projects or key business initiatives.
• Two (2) years of IT portfolio and customer relationship management experience.
• Proven track record building self-organizing teams, navigating resistance to Agile adoption, and driving measurable improvements in team velocity and predictability.
• Demonstrated ability to address team conflicts, build psychological safety, and guide teams through cultural and mindset shifts.
• Strong facilitation, conflict resolution, change management, and stakeholder management skills.
• Experience working within established organizational playbooks while coaching teams to Agile maturity.
• Experience executing as a scrum master in an agile transformation.

Citizenship

·        US Citizenship

Knowledge, Skills & Abilities

• Knowledge of approaches discussed in the Agile space: Kanban and SAFe.
• Knowledge and/or experience with Agile techniques, including User Stories, Continuous Integration, Continuous Testing, Pairing, Automated Testing, Agile Games.
• Experience executing as a scrum master in an agile transformation.

Certificates

• Certified Scrum Master (CSM) or Professional Scrum Master (PSM II or higher) required; advanced certifications (e.g., Certified Scrum Professional, SAFe Scrum Master) preferred

Education

• Bachelor’s Degree in Business, Computing Information Systems, Computer Science, or relevant technical discipline.

Preferred Qualifications

• Government or highly regulated industry experience preferred.

Compensation & Benefits[1][2]

• Wage Range: Negotiable
• General Benefits: Custom Software Systems, Inc. offers our employees a competitive benefits package that may include:

• Health insurance plans
• Health Savings Account (HSA)
• Dental
• Vision
• Long-term disability
• Short-term disability
• Basic term life insurance
• Supplemental term life insurance for employees, spouses, and dependents
• Simple IRA
• Parking/Commuting expense reimbursement
• Training/Education

[1] Compensation range must be coordinated with and approved by the CSS Chief Operating Officer (COO).

[2] Compensation & Benefits information is required for all Maryland Employers effective October 1, 2024.