Portfolio Delivery Leader

RSM•Chicago, IL

2d•Hybrid

About The Position

The Portfolio Delivery Leader is accountable for collaboratively designing, aligning, and successfully delivering a prioritized portfolio roadmap. The role builds trust-based relationships with business stakeholders and partners with digital leaders to align technology investments with strategic objectives and measurable business value. It ensures teams, capabilities, and processes are in place to deliver high-impact, high-quality solutions, while advancing an integrated delivery model that strengthens business engagement, decision-making, and portfolio transparency. The role provides leadership and oversight for delivery using advanced technologies, including AI, and ensures teams apply current technology design practices, standards, and methodologies. It is accountable for team performance, delivery excellence, and continuous improvement, and leads client-facing product teams and in-house and third-party teams delivering custom solutions across cloud and hybrid platforms. The role also oversees advanced product, AI, and cloud platform development and governance, while maintaining a focus on reliability, scalability, security, data integrity, service quality, privacy, risk mitigation, disaster recovery, controls, and monitoring. This position leads portfolio and scaled Agile delivery across products, programs, Agile Release Trains, and shared capabilities. It manages prioritization, capacity, dependencies, portfolio flow, stakeholder expectations, delivery outcomes, and benefits realization, while developing leaders and coordinating employees, contractors, vendors, and globally distributed teams. The job follows RSM’s generally hybrid workstyle, with team members aligned to an RSM office and in-person work based on client and team needs.

Requirements

Bachelor of Science degree or equivalent experience in a software engineering, cloud, or technology leadership role.
At least 5 years of experience leading matrixed delivery teams, building strategic roadmaps, and aligning delivery with business needs.
Experience in solution development and governance.
At least 10 years of experience building enterprise-class on-premise, off-premise, and hybrid solutions.
At least 5 years of experience developing and maintaining policies, procedures, standards, and guidelines.
Deep experience leading technology products, platforms, programs, or transformation initiatives supporting a CPA Audit or Assurance organization.
Strong knowledge of audit methodology, practitioner workflows, independence, professional standards, regulatory expectations, and seasonal delivery demands.
Proven success owning end-to-end portfolio processes, including demand intake, evaluation, business-case development, prioritization, funding recommendations, delivery oversight, and benefits realization.
Experience establishing transparent portfolio intake, sequencing, capacity, and decision processes that balance practice quality, regulatory commitments, practitioner needs, strategic value, technology sustainability, enterprise risk, and organizational constraints.
Experience measuring adoption, workflow efficiency, standardization, delivery predictability, compliance, user satisfaction, and realized business benefits.
Experience leading delivery across multiple products, programs, Agile Release Trains, and shared capabilities within a Scaled Agile methodology.
Experience with strategic alignment, PI Planning, capacity allocation, dependency management, portfolio flow, and outcome measurement.
Technical depth to evaluate architecture, data, integration, cybersecurity, cloud, enterprise platforms, audit workflow automation, and AI implications; challenge assumptions; identify cross-product dependencies; and make informed portfolio tradeoffs.
Demonstrated success facilitating complex decisions, resolving competing priorities, and building and leading high-performing portfolio, program, product, or delivery teams.
Experience developing leaders, establishing accountability, and coordinating employees, contractors, vendors, and globally distributed teams.

Nice To Haves

Master of Science degree.
Experience supporting a large public accounting, CPA, professional services, or regulated Assurance organization.
Experience with digital audit platforms, engagement workflow solutions, audit evidence management, data ingestion and analytics, practitioner workflow automation, AI-enabled audit capabilities, or related Assurance technologies.
Demonstrated success driving practitioner adoption through business readiness, stakeholder engagement, communications, training coordination, release planning, feedback mechanisms, post-implementation support, and value measurement.
Experience applying SAFe Lean Portfolio Management practices, including portfolio Kanban, strategic themes, capacity allocation, epic prioritization, and outcome measurement across multiple Agile Release Trains and shared platform teams.
SAFe, product management, program management, technology, or portfolio-management credentials.
Experience coordinating vendors, implementation partners, managed services, or globally distributed delivery teams.

Responsibilities

Cultivate stakeholder relationships to shape portfolio roadmaps, prioritize initiatives by business value, and provide transparent visibility into delivery progress and effectiveness.
Lead high-performing, client-facing product teams in designing, implementing, supporting, and maintaining custom solutions integrated with internal and external systems.
Apply business knowledge across assigned lines of business and functional groups to align delivery with strategic goals.
Drive accountability for streamlining delivery workflows through AI, automation, and modern delivery tools.
Lead in-house and third-party teams in combining cloud and hybrid platform offerings into reliable, scalable, high-value solutions.
Establish and oversee processes that enable collaborative and reliable delivery of business and digital solutions.
Standardize Agile and SAFe practices and collaborate with Scrum Masters, Release Train Engineers, and Agile Coaches to uphold SAFe principles and maximize delivery velocity.
Improve Agile and SAFe practices to enhance delivery efficiency and team performance.
Oversee advanced product, AI, and cloud platform development and governance, manage stakeholder expectations, and advance business partnerships by focusing on business problems.
Identify leading practices for platform security, data integrity, service quality, scalability, privacy, risk mitigation, disaster recovery, controls, and monitoring.
Lead teams and ensure best practices, standards, and policies are followed during execution.
Lead process optimization efforts and provide regular performance oversight.
Lead portfolio intake, evaluation, business-case development, prioritization, funding recommendations, delivery oversight, and benefits realization across interdependent products and programs.
Establish portfolio sequencing, capacity, and decision processes and measure adoption, workflow efficiency, standardization, delivery predictability, compliance, user satisfaction, and business benefits.
Lead scaled Agile delivery across products, programs, Agile Release Trains, and shared capabilities, including strategic alignment, PI Planning, capacity allocation, dependency management, portfolio flow, and outcome measurement.
Facilitate complex decisions, resolve competing priorities, develop leaders, establish accountability, and coordinate employees, contractors, vendors, and globally distributed teams.