Senior Digital Scrum Master

Role Description

Serve as Senior Scrum Master for multiple digital delivery teams or a portfolio of related digital initiatives, helping teams apply Agile, Scrum, Kanban, and pragmatic delivery practices consistently across complex workstreams.

• Lead sprint planning, backlog refinement, daily standups, sprint reviews, retrospectives, release planning, dependency planning, cross-team coordination sessions, and other delivery ceremonies needed to support predictable execution.
• Own delivery coordination across digital product, IT, marketing, operations, finance, legal, customer experience, QA, UX, architecture, infrastructure, security, analytics, support, and third-party partner teams.
• Partner closely with Product Owners and business stakeholders to improve backlog health, priority clarity, roadmap alignment, story readiness, acceptance criteria quality, sprint goal definition, and stakeholder expectations.
• Proactively identify, manage, escalate, and help resolve cross-functional impediments, risks, dependencies, sequencing conflicts, capacity constraints, decision gaps, and release impacts that affect team or portfolio delivery.
• Maintain transparent visibility into sprint commitments, planned versus actual progress, burndown, velocity, throughput, cycle time, carryover, aging work, blocker trends, release readiness, and delivery predictability.
• Use delivery metrics and team insights to facilitate practical continuous improvement, improve flow, reduce rework, increase predictability, and support data-informed planning and leadership communication.
• Drive Agile maturity across teams by strengthening estimation practices, sprint capacity planning, Definition of Ready, Definition of Done, intake discipline, retrospective follow-through, quality practices, and ownership of commitments.
• Facilitate alignment across teams and stakeholders to ensure decisions, risks, dependencies, milestones, tradeoffs, scope changes, release impacts, and business outcomes are clearly understood and documented.
• Support release readiness and operational handoff by coordinating sprint outcomes, UAT readiness, environment needs, test progress, defect prioritization, go/no-go inputs, release notes, support planning, and post-release follow-up.
• Protect team focus by managing distractions, clarifying priorities, reinforcing agreed intake and communication channels, and helping stakeholders balance urgent business needs with committed sprint and release goals.
• Mentor Product Owners, team members, delivery leads, and less experienced Scrum Masters on Agile principles, facilitation techniques, delivery metrics, team working agreements, and practical ways to improve execution.
• Support leadership communication by preparing concise status updates, delivery summaries, risk and issue updates, decision logs, dependency views, action tracking, and portfolio-level delivery insights.
• Maintain and improve delivery information in tools such as Jira, Confluence, Azure DevOps, Smartsheet, Microsoft 365, Teams, dashboards, or other approved project and Agile management tools.
• Support traditional project management activities when needed, including milestone planning, timeline coordination, dependency tracking, issue/risk management, status reporting, stakeholder follow-up, and leadership communication.
• Encourage a collaborative, accountable, data-informed, and outcome-focused delivery culture that supports high-quality digital execution, continuous learning, and customer-focused business outcomes.
• Understand and comply with all company privacy, security, accessibility, change management, and technology standards.

Qualifications

• Bachelor's degree in Information Technology, Computer Science, Business, Project Management, or a related discipline preferred; equivalent experience may be considered.
• 5+ years of experience as a Scrum Master, Agile Project Manager, Delivery Lead, Program Delivery Lead, or similar role supporting software, web, mobile, digital product, commerce, customer experience, or technology delivery teams.
• Experience independently supporting multiple Agile teams, complex cross-functional initiatives, or a portfolio of related digital delivery workstreams.
• Experience coordinating delivery across Product Owners, Business Analysts, UX, QA, developers, architects, infrastructure, security, operations, analytics, vendors, business stakeholders, and leadership.
• Experience managing cross-team dependencies, delivery risks, release readiness, UAT coordination, defect triage, stakeholder communication, and execution transparency in a digital or technology environment.
• Experience using Agile delivery tools such as Jira, Confluence, Azure DevOps, Smartsheet, Microsoft 365, dashboards, or comparable planning, documentation, workflow, and reporting platforms.
• Restaurant, retail, hospitality, loyalty, ecommerce, mobile app, CMS, or customer-facing digital platform experience preferred but not required.
• Experience with Agile at scale, portfolio delivery coordination, vendor delivery models, or enterprise technology transformation preferred.

Requirements

• Certified ScrumMaster (CSM), Professional Scrum Master (PSM), PMI-ACP, SAFe Scrum Master, SAFe Agilist, or equivalent Agile/Scrum certification preferred.
• Project Management Professional (PMP) or equivalent project management certification preferred.
• Additional training or certification in Agile coaching, Kanban, product delivery, ITIL, change management, digital delivery, or portfolio/program delivery practices is a plus.

Benefits

• Good Work Deserves Good Pay: Competitive Annual Salary | Annual Bonus Opportunities
• Support That Goes Beyond the Clock: Medical, Rx, Dental and Vision Benefits on Day 1 | Life Insurance and Disability Coverage | Paid Vacation/Employee Assistance Program
• Grow and Thrive Your Way: Business Resource Groups | Tuition Reimbursement | Professional Development
• Culture of Belonging: Support that starts on day one | Onboarding, training, and development to help you thrive | Recognition programs and employee events that bring us together
• Invest in Your Future: 401k Plan with Company Matching Contributions at 90 days | Employee Stock Purchase Program
• More Perks, Just Because: 35% Discount on Cracker Barrel Food and Retail items | Exclusive Biscuit Perks like discounts on home, travel, cell phones, and more!