About this role
Custom Software Systems, Inc. (CSS) is seeking a Senior Scrum Master to serve as a servant leader for the Agile team, facilitating Scrum ceremonies, removing impediments, and coaching the team toward self-organization and high performance. This role is responsible for navigating resistance to Agile practices within the team, addressing team conflicts and dysfunctions, building psychological safety, and increasing cross-team collaboration. The Senior Scrum Master works closely with the Agile Coach and Product Owner to ensure the team operates effectively within Agile principles while delivering predictable value. This role operates independently with the team on day-to-day execution but adheres to the organization's Agile playbook, standards, and guidance from the Agile Program Manager. This role requires the ability to navigate organizational complexity, shield the team from external disruptions, and drive a culture of continuous improvement and accountability.
Responsibilities
• 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.
• 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.
Citizenship
· US Citizenship
Required Qualifications
• Minimum of ten (10) years of experience leading projects or key business initiatives.
• At least seven (7) years of hands-on experience as a Scrum Master serving multiple teams in complex, matrixed organizations.
• Two (2) years of IT portfolio and customer relationship management experience.
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.
• 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.
Education
• Bachelor’s Degree in Business, Computing Information Systems, Computer Science, or relevant technical discipline.
Certificates
• At least one of the following or its equivalent:
• PMP Certification, PMI-ACP, or Scaled Agile Framework or CSM (Certified Scrum Master).
Preferred Qualifications
• Government or highly regulated industry experience preferred.
Compensation & Benefits[1][2]
• Wage Range: $140,000 -170,000
• 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.