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.  

What You'll Do - You'll Make the Moment

• 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.

Experience and Education

• 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.

Certifications

• 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.

Knowledge and Skills

• Advanced understanding of Agile, Scrum, Kanban, servant leadership, empirical planning, transparency, inspection, adaptation, flow optimization, and continuous improvement practices.
• Ability to lead productive ceremonies, cross-functional working sessions, dependency planning, decision discussions, retrospectives, conflict resolution, and stakeholder alignment conversations.
• Strong knowledge of software development lifecycle, digital product delivery, QA and testing practices, release readiness, DevOps concepts, production support, technology operations, and vendor coordination.
• Strong working knowledge of Agile metrics and delivery reporting, including burndown, velocity, capacity, cycle time, throughput, sprint predictability, carryover, aging work, blocker trends, release readiness, and delivery health indicators.
• Ability to communicate complex delivery, technical, risk, dependency, sequencing, capacity, and priority information clearly to development teams, business stakeholders, vendors, and leadership.
• Ability to coach teams toward self-organization, accountability, focus, quality, collaboration, and improved delivery maturity without relying on command-and-control management.
• Strong project and program coordination skills, including planning, prioritization, timeline management, action tracking, risk/issue management, dependency management, decision tracking, and stakeholder follow-up.
• Strong analytical and problem-solving skills with the ability to identify root causes, remove blockers, improve flow, resolve ambiguity, and drive practical process improvements across teams.
• Ability to influence without direct authority and build alignment across product, technology, business, operations, and vendor stakeholders.
• Ability to work effectively with Product Owners and leadership to improve backlog clarity, story readiness, acceptance criteria, sprint goal alignment, roadmap visibility, and stakeholder expectations.
• Proficiency with collaboration, documentation, and delivery tools such as Microsoft 365, Teams, Jira, Confluence, Azure DevOps, Smartsheet, dashboards, and reporting tools.
• Excellent verbal and written communication skills, including the ability to create concise status updates, meeting notes, risks, decisions, action items, executive summaries, and leadership-ready delivery updates.
• High level of organization, follow-through, adaptability, professional judgment, and ability to operate independently in a fast-paced digital environment with multiple priorities and stakeholders.

Environment and Working Conditions

• Must be able to sit at a desk for long periods during the work-day.
• Must be able to participate in virtual and in-person meetings, facilitate team ceremonies and cross-functional working sessions, and use standard office, collaboration, and project management tools.

Focus on You

We're all about making sure you're taken care of too. Here's what's in it for you:

• 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! 

A Little About Us

Since 1969, Cracker Barrel has been a place to gather around delicious food, abundant servings, unexpected finds, and a warm welcome. Over time, it's become even more - somewhere folks can reconnect and feel at home. With more than 70,000 team members nationwide, we take pride in our roots -- always serving up more than a meal.

See for yourself. Apply now.

Cracker Barrel is an equal opportunity employer.

Qualified applicants are considered for all positions without regard to race, color, religion, sex, sexual orientation, genetic information, national origin, age, marital status, medical condition, disability or any other class expressly protected by law.