Lead Technology Portfolio Project Manager

American Family Insurance•Boston, MA

About The Position

The Lead Technology Portfolio Project Manager leads improvements to technology portfolio management processes and adoption, tailoring incremental enhancements to different levels of portfolio maturity. The role translates strategic priorities into integrated initiative plans, planning milestones, dependencies, governance needs, and leadership decisions. The position owns and continuously improves technology demand planning for discretionary work, including annual planning and quarterly demand refreshes. It supports initiative definition and planning by clarifying outcomes, scope, assumptions, milestones, risks, dependencies, and decision points, and guides teams on backlog planning, planning hygiene, dependency visibility, and readiness for execution. The role applies software development lifecycle knowledge to align portfolio processes with readiness, risk management, traceability, and predictable execution. It runs planning cadences and governance conversations, maintains decision logs and action tracking, supports escalation paths, and communicates insights and decision needs to executives. The position works across stakeholders to navigate competing priorities, funding or capacity constraints, and differing perspectives. The selected candidate will participate in New Employee Orientation during their first week, in person at the Madison, Wisconsin headquarters or another American Family core location; sessions may sometimes be virtual. The offer is contingent on applicable background checks and signing a non-disclosure agreement. Sponsorship will not be considered unless specified in the posting. Travel is up to 10%.

Requirements

Eight or more years of experience leading technology projects, programs, portfolio processes, and enterprise process improvements.
Experience working across large, matrixed technology organizations and engaging senior leaders.
Experience leading annual or quarterly planning, technology demand estimation, portfolio governance, or related investment-planning processes.
Experience applying SDLC, Agile, or SAFe practices to improve planning quality and delivery outcomes.
Strong understanding of portfolio intake, demand management, prioritization, investment traceability, portfolio health, governance, risk, dependency management, and executive reporting.
Solid understanding of software development lifecycle practices, stage gates, Agile / SAFe concepts, PI planning, backlog structures, readiness, and delivery health.
Ability to build and execute roadmaps, coordinate multiple critical efforts, manage RAID items, and create structure in ambiguous environments.
Comfort working directly with directors and vice presidents; ability to frame issues, present recommendations, and communicate decision needs clearly.
Demonstrated ability to lead groups to consensus, negotiate trade-offs, resolve ambiguity, and maintain progress across stakeholders without positional authority.
Proactive, curious, and pragmatic approach to identifying pain points, improving workflows, and supporting adoption through incremental change.
Excellent written, verbal, visual, and presentation skills, with ability to tailor details for executives, practitioners, and cross-functional partners.
Working proficiency with Jira, Confluence, enterprise planning tools such as Apptio Targetprocess, dashboards, and structured planning and reporting data.
Strong organization, attention to detail, adaptability, resilience, collaboration, independent judgment, and commitment to continuous learning.

Nice To Haves

Experience building practical operating cadences, decision forums, roadmaps, dashboards, or centers of practice is beneficial.

Responsibilities

Lead incremental technology portfolio process improvements and support adoption through communications, leader forums, training, feedback loops, and progress measures.
Translate strategic priorities into integrated initiative plans, milestones, dependencies, governance needs, and leadership decisions.
Own and continuously improve technology demand planning for discretionary work, including annual planning and quarterly demand refreshes.
Support initiative definition and planning by clarifying outcomes, scope, assumptions, milestones, risks, dependencies, and decision points.
Guide teams on backlog planning, planning hygiene, dependency visibility, and readiness for downstream execution.
Align stage-gate governance and portfolio processes with SDLC readiness, risk management, traceability, and predictable execution.
Run planning cadences and governance conversations; maintain decision logs, action tracking, and escalation paths.
Influence and negotiate across competing priorities, funding or capacity constraints, and differing stakeholder perspectives.
Build and execute roadmaps, coordinate critical efforts, manage RAID items, and create structure in ambiguous environments.