Senior Digital Scrum Master

This is a fully remote position, open to applicants in Tennessee.

📋 Description

• Act as the Senior Scrum Master for multiple digital delivery teams or a collection of interconnected digital initiatives.

• Oversee sprint planning, backlog refinement, daily standups, sprint reviews, retrospectives, release planning, dependency planning, and sessions for cross-team coordination.

• Manage delivery coordination across various functions including digital product, IT, marketing, operations, finance, legal, customer experience, QA, UX, architecture, infrastructure, security, analytics, support, and third-party partners.

• Collaborate with Product Owners and business stakeholders to enhance backlog health, clarify priorities, align roadmaps, ensure story readiness, define acceptance criteria, set sprint goals, and manage stakeholder expectations.

• Recognize, manage, escalate, and assist in resolving impediments, risks, dependencies, sequencing conflicts, capacity constraints, decision gaps, and impacts on releases.

• Keep track of sprint commitments, progress, burndown rates, velocity, throughput, cycle time, carryover, aging work, blocker trends, release readiness, and delivery predictability.

• Utilize delivery metrics and insights from teams to promote continuous improvement and facilitate data-driven planning and communication with leadership.

• Enhance Agile maturity by improving estimation, capacity planning, Definitions of Ready and Done, intake discipline, retrospective follow-through, quality practices, and ownership of commitments.

• Facilitate consensus on decisions, risks, dependencies, milestones, tradeoffs, scope alterations, release impacts, and business outcomes.

• Assist with release readiness and operational handoff, covering UAT readiness, environmental requirements, test progress, defect prioritization, go/no-go inputs, release notes, support planning, and post-release follow-up.

• Safeguard team focus by minimizing distractions, clarifying priorities, and reinforcing communication and intake channels.

• Mentor Product Owners, team members, delivery leads, and less experienced Scrum Masters.

• Prepare status updates, delivery summaries, risk and issue updates, decision logs, dependency views, action tracking, and insights at the portfolio level.

• Maintain delivery information using Jira, Confluence, Azure DevOps, Smartsheet, Microsoft 365, Teams, dashboards, and other approved tools.

• Support traditional project management tasks including milestone planning, timeline coordination, dependency tracking, issue/risk management, status reporting, stakeholder follow-up, and leadership communication.

• Foster a collaborative, accountable, data-driven, and outcome-focused delivery culture.

• Adhere to company standards for privacy, security, accessibility, change management, and technology.

⛳️ Requirements

• Preferred bachelor's degree in Information Technology, Computer Science, Business, Project Management, or a related field; equivalent experience will be considered.

• A minimum of 5 years’ experience as a Scrum Master, Agile Project Manager, Delivery Lead, Program Delivery Lead, or in a similar role supporting software, web, mobile, digital product, commerce, customer experience, or technology delivery teams.

• Demonstrated experience independently supporting multiple Agile teams, complex cross-functional initiatives, or a portfolio of linked digital delivery workstreams.

• Proven experience coordinating delivery among 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 ensuring execution transparency.

• Proficient in using Agile delivery tools such as Jira, Confluence, Azure DevOps, Smartsheet, Microsoft 365, dashboards, or similar platforms.

• Experience in restaurant, retail, hospitality, loyalty, e-commerce, mobile app, CMS, or customer-facing digital platforms is preferred but not mandatory.

• Previous experience with Agile at scale, coordinating portfolio delivery, vendor delivery models, or enterprise technology transformation is preferred.

• Preferred certifications include Certified ScrumMaster (CSM), Professional Scrum Master (PSM), PMI-ACP, SAFe Scrum Master, SAFe Agilist, or equivalent Agile/Scrum certification.

• Project Management Professional (PMP) or equivalent project management certification is preferred.

• Additional training or certification in Agile coaching, Kanban, product delivery, ITIL, change management, digital delivery, or portfolio/program delivery practices is a plus.

• Advanced knowledge of Agile, Scrum, Kanban, servant leadership, empirical planning, transparency, inspection, adaptation, flow optimization, and continuous improvement practices.

• Capability to lead productive ceremonies, cross-functional working sessions, dependency planning, decision discussions, retrospectives, conflict resolution, and stakeholder alignment conversations.

• Strong understanding of the software development lifecycle, digital product delivery, QA and testing practices, release readiness, DevOps concepts, production support, technology operations, and vendor coordination.

• Strong familiarity with Agile metrics and delivery reporting.

• Ability to convey complex delivery, technical, risk, dependency, sequencing, capacity, and priority information in a clear manner.

• Capacity to coach teams towards self-organization, accountability, focus, quality, collaboration, and enhanced delivery maturity.

• Excellent project and program coordination abilities.

• Strong analytical and problem-solving skills.

• Ability to influence without direct authority and build alignment among stakeholders.

• Proficiency with Microsoft 365, Teams, Jira, Confluence, Azure DevOps, Smartsheet, dashboards, and reporting tools.

• Exceptional verbal and written communication skills.

• High level of organization, follow-through, adaptability, professional judgment, and ability to work independently.

• Must be able to remain seated at a desk for extended periods during the workday.

• Must be able to engage in virtual and in-person meetings and facilitate team ceremonies and cross-functional working sessions.

🏝️ Benefits

• Competitive Annual Salary.

• Annual Bonus Opportunities.

• Medical, Rx, Dental, and Vision Benefits starting on Day 1.

• Life Insurance and Disability Coverage.

• Paid Vacation.

• Employee Assistance Program.

• Business Resource Groups.

• Tuition Reimbursement.

• Opportunities for Professional Development.

• Onboarding, training, and development programs.

• Recognition initiatives and employee events.

• 401k Plan with Company Matching Contributions after 90 days.

• Employee Stock Purchase Program.

• 35% Discount on Cracker Barrel Food and Retail items.

• Exclusive Biscuit Perks including discounts on home, travel, cell phones, and more!