[Hiring] Senior Director, Agile Delivery & Technology PMO @DataSpring

Role Description

The Senior Director, Agile Delivery & Technology PMO (Member Data) will be responsible for owning technology delivery for DataSpring’s Member Data portfolio — how work is taken in, sequenced, staffed, and shipped across new product development, legacy platform replacement, and keep-the-lights-on operations. This role sets the standard for how technology delivery gets done at DataSpring, including how the organization uses enterprise-approved generative AI tools to strip manual effort out of program management.

This is a full-time, remote, exempt position and reports to the VP, Technology.

Specific Responsibilities

• Owns technology delivery for the Member Data portfolio, from intake and estimation through release, hypercare, and stabilization.
• Partners with the provider-side delivery leader to run Member Data and provider delivery as two halves of one practice, with shared agile standards, common Jira Cloud conventions, and one set of delivery metrics.
• Works with business operations and the enterprise PMO (ePMO) to improve the agile process across the organization, spanning ideation, prioritization, funding approval, development, and delivery.
• Establishes and matures agile ways of working, tailoring Scrum, Kanban, or scaled agile to each team rather than imposing a single framework.
• Directs new product development and legacy platform replacement programs, including parallel-running systems, data migration, and customer transition.
• Drives offshore development partners and vendors to committed outcomes on throughput, quality, and time-zone-aware delivery.
• Balances change-the-business delivery against keep-the-lights-on operations, making capacity allocation explicit and protecting planned work from unmanaged interruptions.
• Owns Jira Cloud as the delivery system of record — workflows, issue hierarchy, dashboards, automation, data hygiene — and leads evaluation, selection, and rollout of the broader delivery toolset.
• Defines and reports the delivery metrics leadership steers by, including predictability, throughput, cycle time, and portfolio health.
• Applies enterprise-approved generative AI to accelerate status synthesis, requirements analysis, documentation, and reporting, and coaches others to do the same.
• Leads and develops the delivery staff assigned to the Member Data portfolio, and coaches delivery practitioners across the technology organization.
• Drives cross-team dependencies, risks, and escalations to resolution, partnering with product management, engineering, architecture, security, and compliance.

Supervisory Responsibilities

• Manages the delivery staff assigned to the Member Data portfolio, with responsibility for team structure, resource alignment, performance, and development.
• Oversees offshore delivery partners and staff augmentation vendors, including statement-of-work scope, resource planning, performance management, and escalation.
• Participates in hiring and performance management for delivery staff, and mentors delivery practitioners across the technology organization.

Skills

• Applies agile frameworks pragmatically, knowing when to scale, when to simplify, and when a framework is getting in the way of delivery.
• Improves process across teams that do not report to this role, building buy-in rather than mandating compliance.
• Demonstrates advanced proficiency with Jira Cloud and can establish effective workflows, issue hierarchies, automation, dashboards, and governance standards.
• Runs portfolio management with rigor: capacity modeling, schedule and budget control, and reporting executives trust.
• Leads through influence across organizational boundaries and builds credibility with peers.
• Manages distributed and offshore teams, adapting communication, documentation, and ceremony design to bridge time zones.
• Uses enterprise-approved generative AI tools creatively and responsibly to remove manual effort from delivery and reporting.
• Evaluates tooling on the merits, building business cases and driving adoption after purchase.
• Reads technical detail well enough to challenge estimates, architecture trade-offs, and risk assessments without being the engineer.
• Coaches and develops people, gives direct feedback, and operates with composure during incidents and escalations.
• Communicates clearly at every altitude, from a sprint-level blocker to an executive roadmap briefing.

Experience

• 12+ years in technology delivery, program management, or engineering leadership.
• 5+ years of people management experience, including at least three years leading a delivery, agile, or PMO team.
• Experience improving agile practices across teams outside direct reporting authority.
• Full-lifecycle ownership of new product development and at least one legacy product replacement or platform modernization initiative including data migration and customer transition.
• Proven track record driving offshore or nearshore development teams and third-party vendors to committed outcomes.
• Hands-on Jira Cloud and Confluence administration in a multi-team environment; Jira Align or comparable scaled tooling a plus.
• Experience running keep-the-lights-on and production support alongside project delivery, with deliberate capacity allocation between the two.
• Experience leading enterprise tool selection and implementation, and partnering with an enterprise PMO, finance, or business operations function on intake and funding governance.
• Demonstrable use of generative AI tools, such as Claude, in a professional delivery or program management context.
• Experience presenting to and influencing executive leadership; healthcare, payer, provider, or other regulated-industry experience strongly preferred.

Education

• Bachelor’s degree in computer science, information systems, engineering, business, or a related field required; an equivalent combination of education and directly relevant experience considered.
• Master’s degree or MBA preferred.
• Agile certification strongly preferred: SAFe Program Consultant (SPC), SAFe Release Train Engineer (RTE), Certified Scrum Professional (CSP), or PMI Agile Certified Practitioner (PMI-ACP).
• Project Management Professional (PMP) certification preferred; Atlassian Jira administration certification (ACP-120 or equivalent) a plus.

Benefits

• Competitive compensation and a comprehensive benefits package for full-time employees.
• Medical, dental, and vision coverage.
• 401(k) with company contributions and matching.
• Paid parental leave.
• Tuition assistance.
• Generous paid time off.
• Commitment to investing in our people and supporting professional growth over time.

Equal Opportunity Employer

DataSpring is proud to be an equal opportunity employer and is committed to fostering a workplace where all individuals are valued, respected, and empowered. Employment decisions at DataSpring are made without regard to race, color, religion, sex, national origin or ancestry, age, marital status, disability, protected veteran status, personal appearance, sexual orientation, gender identity or expression, familial status, family responsibilities, matriculation, political affiliation, genetic information, source of income, place of residence, or any other characteristic protected by law. DataSpring does not tolerate unlawful discrimination or harassment of any kind.

Applicants have rights under the Family and Medical Leave Act (FMLA), Equal Employment Opportunity (EEO), and the Employee Polygraph Protection Act (EPPA). If you need a reasonable accommodation to apply for a posted position, please contact the DataSpring People & Culture team at [email protected] or 202-517-0436.