Director Agile Delivery & Tools - Hybrid

Director Agile Delivery & Tools - Hybrid Location: Remote - USA At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Summary The Director, Agile Delivery, Methodology & Tools is an enterprise leader responsible for defining, governing, and continuously improving how work is planned, executed, and delivered across the organization. This role establishes standardized delivery methodologies, leads the Scrum Master and Agile Delivery practice, and owns the enterprise delivery tooling ecosystem that supports demand intake, planning, execution, and transparency across the portfolio. Job Responsibilities: Enterprise Delivery Standards & Ways of Working Define, maintain, and govern enterprise agile delivery standards, playbooks, and common ways of working aligned to business strategy and portfolio priorities. Establish fit for purpose delivery models (e.g., product, platform, project, hybrid) and ensure consistent application across teams and value streams. Ensure delivery standards scale across portfolios while allowing for intentional, governed exceptions where required. Agile Practice & People Leadership Lead the Scrum Master / Agile Delivery Lead practice, including role clarity, capability expectations, coaching models, and career progression. Set expectations for agile ceremonies, backlog quality, dependency management, and cross team coordination. Elevate delivery leadership capability through coaching, communities of practice, and continuous learning. Enterprise Tooling Strategy & Enablement (Tool Agnostic) Own the enterprise delivery tooling operating model, including standards, governance, data integrity, administration, and multi year roadmap—regardless of platform. Provide leadership across Azure DevOps (ADO), Jira, Jira Align, and comparable work management and planning platforms, ensuring consistent outcomes, reporting, and decision grade data. Define and govern common taxonomies, hierarchies, workflows, planning constructs, and reporting standards that work across tools and portfolios. Ensure tooling configurations align to delivery methodology, portfolio governance, and financial and capacity management needs not the other way around. Partner with Architecture, Engineering Enablement, and Enterprise Platforms to integrate delivery tools with demand intake, portfolio planning, CI/CD, financials, and capacity systems. Planning & Execution Enablement Enable and continuously improve Quarterly / PI Planning processes, including facilitation standards, readiness criteria, dependency visibility, and outcome quality. Ensure strong traceability from business demand → portfolio intent → team plans → execution outcomes across delivery tools. Partner with Portfolio and Business leaders to improve intake to delivery handoff quality, including definition of ready, sizing consistency, and prioritization discipline. Metrics, Transparency & Continuous Improvement Define and drive adoption of enterprise delivery metrics (e.g., flow, predictability, throughput, quality, dependency health), independent of tooling implementation. Establish inspect and adapt and continuous improvement routines using both quantitative delivery data and qualitative team insights. Provide executive level transparency into delivery performance, risks, systemic bottlenecks, and improvement opportunities using consistent, trusted data. AI Enabled Delivery & Modern Ways of Working Leverage AI enabled capabilities within delivery tools (e.g., forecasting, flow optimization, risk detection, automated insights) to improve planning accuracy and execution efficiency. Evaluate and pilot emerging delivery analytics, automation, and AI capabilities to modernize the enterprise delivery ecosystem. Ensure AI and automation are embedded responsibly, with strong data governance and change management. The above statement of duties is not intended to be all inclusive and other duties will be assigned from time to time. Job Requirements: Bachelor’s degree in information technology, computer science, software engineering, business, project management, or related field, or equivalent combination of education and/or related professional work experience. 12+ years of experience in agile delivery leadership, PMO / delivery transformation, or enterprise methodology roles. Proven success leading Scrum Master and Agile Delivery practices in scaled, multi team environments (e.g., SAFe, hybrid, product/platform models). Deep, hands on experience with Azure DevOps (ADO), Jira, Jira Align, or comparable enterprise delivery and planning platforms, including operating model design - not just tool usage. Demonstrated ability to translate delivery data into executive level insights and portfolio decisions. Strong partnership skills across portfolio management, architecture, product, and engineering leadership. Preferred: Experience in financial services, insurance, or other highly regulated environments. Direct involvement in enterprise portfolio management or operating model transformations. Familiarity with Lean Portfolio Management, COBIT, or ITIL concepts. Experience embedding AI, automation, and advanced analytics into delivery management. At this time, we're not considering applicants that need any type of immigration sponsorship (additional work authorization or permanent work authorization) now or in the future to work in the United States. This includes, but IS NOT LIMITED TO: F1-OPT, F1-CPT, H-1B, TN, L-1, J-1, etc #LI-SW If you’re ready to help make a difference, apply today.A resume is required to apply. TruStage may process applicant information using an Artificial Intelligence (AI) tool.This tool automatically generates a screening score based on how well applicant information matches the requirements and qualifications for the position. TruStage recruiters use the screening score as a guide to further evaluate candidates; the score is one component of an application review and does not automatically determine whether a candidate moves forward.Candidates may choose to opt out of this process. Compensation may vary based on the job level, your geographic work location, position incentive plan and exemption status. Base Salary Range: $167,000.00 - $310,600.00 At TruStage, we believe a sound, inclusive benefits program is of vital importance, along with a flexible workplace that allows for work-life balance, career growth and retirement assistance. In addition to your base pay, your position may be eligible for an annual incentive (bonus) plan.  Additional benefits available to eligible employees include medical, dental, vision, employee assistance program, life insurance, disability plans, parental leave, paid time off, 401k, and tuition reimbursement, just to name a few. Beyond pay and benefits, we also recognize that flexibility, including working in a place you prefer, is essential to caring for our employees.  We will continue to strive to offer flexibility and invest in technology and other tools that will make hybrid working normal rather than an exception, so that when “life happens,” you can focus on what’s most important. Accommodation request TruStage is a place where everyone can bring their best self and thrive. If you need application or interview process accommodations, please contact the accessibility department.