Job Description
Job Description
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
Education
· Bachelor’s Degree in Business, Computing Information Systems, Computer Science, or relevant technical discipline.
Preferred Qualifications
· Government or highly regulated industry experience
· Advanced certifications (e.g., Certified Scrum Professional, SAFe Scrum Master)
Compensation & Benefits[1][2]
· Wage Range: Negotiable
· General Benefits: Custom Software Systems, Inc. offers our employees a competitive benefits package that may include:
ü Health insurance plans
ü Health Savings Account (HSA)
ü Dental
ü Vision
ü Long-term disability
ü Short-term disability
ü Basic term life insurance
ü Supplemental term life insurance for employees, spouses, and dependents
ü Simple IRA
ü Parking/Commuting expense reimbursement
ü 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.
Company DescriptionCompany Background:
Headquartered in Leesburg, Virginia, Custom Software Systems, Inc. (CSS) is a Woman-Owned (WOSB) and HUBZone certified small business. Built on a foundation of trusted client partnerships, CSS has fostered a stakeholder-centric yet disciplined approach to IT solutions development. This ensures our ability to consistently meet or exceed our customers' expectations.
Benefits:
CSS is a very employee oriented company knowing that well trained, professional associates are what make our company great. We offer a competitive benefits package that includes: paid holidays and paid time off; medical insurance that includes vision; dental insurance; company paid long and short-term disability and life insurance; a Simple IRA plan (similar to 401k); parking and commuter reimbursement. We also work with our employees on training and professional certification plans that benefit the employee, the client and CSS - a win-win-win strategy.
Equal Opportunity Employer:
CSS provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. CSS complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including, but not limited to, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.
CSS expressly prohibits any form of unlawful employee harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of CSS employees to perform their expected job duties is absolutely not tolerated.
Company Description
Company Background:\r\nHeadquartered in Leesburg, Virginia, Custom Software Systems, Inc. (CSS) is a Woman-Owned (WOSB) and HUBZone certified small business. Built on a foundation of trusted client partnerships, CSS has fostered a stakeholder-centric yet disciplined approach to IT solutions development. This ensures our ability to consistently meet or exceed our customers' expectations. \r\n\r\nBenefits:\r\nCSS is a very employee oriented company knowing that well trained, professional associates are what make our company great. We offer a competitive benefits package that includes: paid holidays and paid time off; medical insurance that includes vision; dental insurance; company paid long and short-term disability and life insurance; a Simple IRA plan (similar to 401k); parking and commuter reimbursement. We also work with our employees on training and professional certification plans that benefit the employee, the client and CSS - a win-win-win strategy.\r\n\r\nEqual Opportunity Employer:\r\nCSS provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. CSS complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including, but not limited to, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.\r\n\r\nCSS expressly prohibits any form of unlawful employee harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of CSS employees to perform their expected job duties is absolutely not tolerated.