Technical Program Delivery Manager Jobs in Madison, WI

Position Compensation Range: $113,000.00 - $194,000.00. Pay Rate Type: Salary. Compensation may vary based on the job level and your geographic work location. Relocation support is offered for eligible candidates.

As a Sr. Technical Program Manager in our Personal Lines organization, you will own end-to-end delivery for significant, cross-functional capabilities built on Guidewire, working at the intersection of Product, Pricing, Data & AI, and Digital & Customer Experience. You will be a senior individual contributor who thrives on complexity, earns credibility with engineers, and knows how to move organizations forward. You will be directly responsible for one or more high-priority portfolio initiatives, owning delivery from inception to production across multiple teams and systems. Your first assignment will be working on our Auto products, with opportunity for expansion into all our lines of business over time. You will report to the Senior Manager, Engineering. This flex office/home role requires a minimum of 10 days per month from either Madison, WI 53783 or Boston, MA 02110. Internal candidates are encouraged to apply. Depending on the candidate pool, this position may be filled at a lower level to maintain alignment with experience and qualifications. We will not consider candidates who require current or future sponsorship for this position.

• Initiate and lead new programs from scratch — driving scope definition, work breakdown, and system impact assessment across teams and domains.
• Own increment-based planning for initiatives, building iterative, cross-team program plans that reflect real dependencies and risks – not just a timeline.
• Serve as the technical bridge across all teams in a program, translating between engineering, product, and business to remove ambiguity and accelerate decisions.
• Actively participate in architecture and design discussions, identifying delivery risks embedded in technical decisions and ensuring solutions meet enterprise standards.
• Drive structured stakeholder communication and executive reporting – keeping the right people informed at the right level of detail, without creating noise.
• Maintain program-level risk, assumption, issue, and dependency tracking; drive resolution with appropriate urgency and visibility.
• Guide teams through plan deviations – diagnosing root causes, surfacing options, and maintaining delivery momentum without losing business alignment.
• Coordinate release readiness across engineering and quality teams, tracking against established quality gates, security checkpoints, and compliance requirements – escalating blockers and owning remediation.
• Monitor program-level delivery metrics (e.g., feature throughput, cycle time, predictability) to surface trends, inform prioritization, and support continuous improvement.
• Develop and maintain long-term capability roadmaps that stay connected to evolving business priorities and enterprise strategy.
• Help incorporate AI into workflows where it adds value and assess potential for process redesign where AI presents an opportunity to overhaul traditional ways of working.

• Demonstrated proficiency in Agile and SAFe delivery methodologies, including PI Planning facilitation and cross-team coordination.
• Demonstrated experience serving as the directly responsible individual for complex, multi-team technology initiatives.
• Solid understanding of SDLC best practices, including quality gates, release governance, and security/compliance checkpoints as they relate to program delivery.
• Exceptional written and verbal communication skills, with proven ability to translate technical complexity for both technical and business audiences.
• Demonstrated experience managing cross-functional dependencies, risks, and trade-offs in large, matrixed organizations.
• Demonstrated experience providing customer-driven solutions, support, or service.
• Travel Requirements up to 10%.

• 5+ years of TPM experience in a software engineering organization, with a track record of acting as the directly responsible individual for complex, multi-team technology programs end-to-end.
• Strong mid-level candidates with 3–5 years of relevant experience are welcome.
• Technical credibility. Ability to read a system design, participate meaningfully in architecture discussions, identify risk, and earn trust of senior engineers.
• Proficiency with scaled Agile delivery (SAFe experience is a plus; comfort with PI Planning, cross-team dependency management, and increment-based planning is expected).
• Familiarity with enterprise software ecosystems such as policy administration systems (e.g., Guidewire), insurance technology, or financial services platforms is a plus but not required.
• Technical design certification(s) (e.g., AWS, GCP, Cloud) and PMP and/or ACP are welcomed.
• Personal Lines Insurance background.

• Medical, dental, vision and wellbeing benefits.
• Competitive 401(k) contribution and a pension plan.
• Annual incentive.
• 9 paid holidays and a paid time off program (23 days accrued annually for full-time employees).
• Student loan repayment program.
• Paid-family leave.

We are an equal opportunity employer. We comply with all applicable federal, state, and local laws pertaining to non‑discrimination, non‑harassment, and equal opportunity. We also consider qualified applicants with criminal histories, consistent with applicable federal, state, and local law. American Family Insurance is committed to the full inclusion of all qualified individuals. If a reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please email AskHR@AmFam.com to request a reasonable accommodation.