Senior Digital Scrum Master

They say you are the company you keep - and at Cracker Barrel, we take that seriously. At the Store Support Center, we're in the business of serving those who serve our guests. Whether you're designing solutions, telling our story, or setting our teams up for success, your work makes a difference every single day. Here, the work means more because we take pride in doing it together.

So, join our team and find your place, because here...we're all in good company.

• 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 work streams.
• 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, 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 Dev Ops, 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.

• 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 work streams.
• 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…