> Markdown version of [/jobs/ext/234380-sr-principal-program-manager-ai-transformation](https://www.wearedevelopers.com/jobs/ext/234380-sr-principal-program-manager-ai-transformation). Every page supports `.md` or `Accept: text/markdown`. Links point to the HTML versions so they work for humans too. Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Sr. Principal Program Manager - AI Transformation - **Company:** Quad City Automotive Group, LLC - **Location:** Boston, MA, United States (Remote available) - **Experience:** Expert - **Salary:** $176,000.0 - $221,000.0 - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Data Analysis, Software as a Service, Human Resources Information System (HRIS), Enterprise Software Applications, Backend, Functional Dependencies, Workday HRIS, DocuSign, Workday - **Published:** May 30, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=cf1862748cc53057 ## About the Role Do you have experience in SaaS platforms?, * 15+ Years in Program Management * Proven track record of managing $20M+ portfolios within a global enterprise SaaS environment. * Matrixed Leadership: Expert experience working across Enterprise Application Engineering and Finance/Legal teams to deliver unified business solutions. * Methodology Mastery: Advanced proficiency in PMP/PgMP frameworks, focusing on Risk Management, Resource Leveling, and Value Realization. * Domain Experience: Must-have experience within HRIS and Legal environments. * Location: Candidates can be in any US time zone (limited to the US, but open to strong candidates from Latin America). Preferred Requirements: * Experience with Workday ERP, Workday HRIS, and Workday Adaptive. * Experience with DocuSign. * Experience with incentive/compensation systems, specifically CaptivateIQ. ## Description As a Sr. Principal Program Manager you will be the connective tissue between the functional business areas, their AI transformation and the enterprise tech teams developing automation and agentic solutions. This role is about architecting the shift from traditional roles to tech enabled automation and agentic AI workflows that redefine how our teams work. This role is responsible for the rigorous management of a multi-year roadmap that integrates corporate initiatives with a global Finance, HRIS, and Legal transformation. You will serve as the primary operational link between Finance, HRIS, and Legal business stakeholders. You will ensure that high-stakes workstreams are delivered on time, within budget, and aligned with corporate ROI targets, while maintaining a focus on a seamless, AI-augmented operational flow. What You'll Do * Lead the collaboration between the business areas and aligned enterprise tech team to ensure alignment between changing ways of working and tech/AI enabled automation and agentic solutions. * Collaborate with functional leaders and enterprise tech team on the roadmap and measurement of impact/benefits, adoption and enablement. * Navigate complex cross-functional dependencies to keep the engine moving-holding engineering, enterprise applications, and business teams accountable for hitting milestones and delivering measurable ROI on agentic initiatives. * Portfolio Governance & Roadmap Orchestration: Establish the standards for project intake, prioritization, and status reporting for the Finance, HRIS, and Legal infrastructure. Manage the "Golden Path" of initiatives that optimize the workflow journey. * AI Program Lifecycle: Oversee the programmatic rollout of AI-forward capabilities (e.g., automated legal review, automated financial workflows). Manage the pilot-to-production lifecycle and measurable business impact. * Dependency & Risk Mitigation: Proactively identify and manage critical path dependencies between Finance, HRIS, and Legal engines and the backend financial/contracting systems. Mediate resource contention across matrixed engineering and design teams. * Executive Steering & Communication: Chair high-level steering committees (SVP/C-Suite) to provide data-driven insights into portfolio health, budget variance, and risk-adjusted delivery timelines. ## Related Videos - [What if your HR software adapted to you, not the other way around?](https://www.wearedevelopers.com/videos/100259-what-if-your-hr-software-adapted-to-you-not-the-other-way-around) - [Destigmatizing the Workplace: Building Real Inclusion](https://www.wearedevelopers.com/videos/1492-destigmatizing-the-workplace-building-real-inclusion) - [Developing the Backend with Stefan Lingler, CTO at Shpock](https://www.wearedevelopers.com/videos/100360-developing-the-backend-with-stefan-lingler-cto-at-shpock) - [Empowering People in a Digital World: HR’s Next Big Chapter](https://www.wearedevelopers.com/videos/1813-empowering-people-in-a-digital-world-hr-s-next-big-chapter) - [The Future of Employee Wellbeing: Benefits, Trust & Performance](https://www.wearedevelopers.com/videos/1808-the-future-of-employee-wellbeing-benefits-trust-performance) - [Nest.js - TypeScript in the backend can also be clean](https://www.wearedevelopers.com/videos/1033-nest-js-typescript-in-the-backend-can-also-be-clean) ## Related Articles - [Highest Paying Tech Companies for Developers](https://www.wearedevelopers.com/magazine/220-highest-paying-tech-companies-for-developers) - [Dev Digest 121 - AI goes offline](https://www.wearedevelopers.com/magazine/456-dev-digest-121-ai-goes-offline) - [How to Turn Community Events Into a Powerful AI GTM Engine: The Daytona Playbook](https://www.wearedevelopers.com/magazine/732-how-to-turn-community-events-into-a-powerful-ai-gtm-engine-the-daytona-playbook) - [Coffee with Developers - Maria Apazoglou - Making AI understandable for all in production](https://www.wearedevelopers.com/magazine/475-coffee-with-developers-maria-apazoglou-making-ai-understandable-for-all-in-production) - [Navigating the AI Shift](https://www.wearedevelopers.com/magazine/629-navigating-the-ai-shift) - [Dev Digest 132 - Binging WADFlix?](https://www.wearedevelopers.com/magazine/473-dev-digest-132-binging-wadflix)