Principal Technical Program Manager Jobs in Miami, FL

Our Opportunity:

The HR Systems & Solutions team is seeking an experienced Senior Technical Program Manager (TPM) to join the Service Delivery Optimization (SDO) function. We are looking for someone who will lead complex, multi-functional programs that drive process improvement, optimize HR service delivery, and integrate technology solutions into scalable business operations.

You will work with leaders in HR, IT, Finance, and Operations to align service delivery needs with organizational approaches. You will ensure program governance, partner alignment, and operational excellence. The ideal candidate is a strategic yet hands-on leader with deep expertise in HR technology (Workday preferred), program management, and service delivery optimization.

This is a highly visible role requiring creativity, analytical skills, technical fluency, and the ability to influence across all levels of the organization. You will thrive in a fast-paced environment, manage ambiguity with confidence, and drive measurable outcomes that improve the Team Member and customer experience!

What you'll do:

• Service Delivery Optimization: Uphold Delivery Optimization standard as a center of quality, productivity, and reliability. 

  • Analyze processes and implement simplification, efficiency, and engagement improvements

  • Define and track metrics/dashboards to measure service performance and drive continuous improvement

  • Act as a role model in collaborator engagement, driving alignment and cultivating a strong network of leaders; Listen and understand what motivates stakeholders, partners and customers

• Project Management: Lead cross-team and/or multi-phase projects from design through implementation with a focus on security and scalability.

  • Define clear problem statements, program objectives, success criteria, and benchmarks that align with enterprise strategies

  • Govern program portfolios by identifying risks, managing dependencies, and ensuring timely delivery.

  • Deliver HR technology programs across all phases of planning, readiness, and launch

  • Lead documentation management across the lifecycle, ensuring all scope, timeline, and approach changes are captured

  • Maintain detailed project records and produce timely reports and presentations

  • Conduct risk and milestone assessments, creating mitigation plans for portfolio derailments.

  • Own delivery outcomes, ensuring technical service performance meets or exceeds expectations

• Communication: Lead the communication strategy across programs, providing executive-ready summaries of health, progress, risks, and issues.

  • Serve as the central point of communication and reporting for program health, risks, and milestones

  • Develop data-driven reports, dashboards, and recommendations to inform decision-making

  • Conduct research and analysis, develop and present recommendations to senior management to effectively drive overall program management and implementation activities

  • Adjust messaging for diverse audiences and communicate objectively on program status. Drive objectivity over subjectivity in the program status reporting process.

• Resource & Capacity Management: Monitor critical project pipeline volume and complexity, balancing active initiatives against team capacity.

  • Monitor equitable allocation of resources across OP1 priorities, business-as-usual (BAU), and ad-hoc initiatives

  • Track workload sustainability, backlog growth, and demand signals to identify risks of overextension

  • Provide capacity insights to leadership, enabling proactive resourcing decisions and long-term workforce planning

What You'll Need:

• Bachelor’s degree in Business, Information Technology, HR Systems or related field or equivalent experience

• 7+ years of relevant and successful program management experience leading highly complex projects in HR, IT, or enterprise technology initiatives

• Proven track record of delivering large-scale, cross-functional programs from strategy to execution

• Strong technical proficiency with HR systems (Workday, UKG Pro WFM preferred) and cloud-based platforms

• Expertise in program governance, risk management, process optimization, and capacity planning

• Excellent prioritization, organizational and facilitation skills

• Experience with Agile methodologies and the use of modern Cloud technologies and systems

• Proficiency in Jira, Confluence, Smartsheet, MS Project, Tableau, and Excel

• Extensive knowledge of the system development life cycle and solution strategies

• Exceptional critical thinking, communication, and executive presentation skills

• Demonstrated ability to influence and build consensus across business leaders

• Ability to thrive in a fast-paced, ambiguous environment with shifting priorities

• Ability to travel up to 25% as required for program delivery and engagement (minimal expected)

Bonus:

• PMP, Agile, or Six Sigma certifications.

• Background in HR transformation or large-scale enterprise operations

• Strong experience in resource modeling and portfolio demand management

• Advanced knowledge and experience with Workday (Core HCM, Benefits, Payroll, Compensation, Recruiting, etc.), UKG PRO WFM (time and labor management) Data Visualizations (Excel, Tableau) and HR technologies

• The specific salary offered to a candidate may be influenced by a variety of factors including but not limited to the candidate’s relevant experience, education, and work location. In addition, this position is eligible for 401k and a new hire and annual equity grant. C08+ positions may also be eligible for annual bonus.

We offer different types of insurance and benefits, such as medical/Rx, vision, dental, life, disability, hospital indemnity, critical illness, and accident. We offer parental leave, family services benefits, backup dependent care, flexible spending accounts, telemedicine, pet adoption reimbursement, employee assistance program, and many discounts including 10% off pet insurance and 20% off at Chewy.com. 

Exempt salary team members have unlimited PTO, subject to manager approval. Team members will receive six paid holidays per year. Team members may be eligible for paid sick and family leave in compliance with applicable state and local regulations. 

Chewy is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, gender, citizenship, marital status, religion, age, disability, gender identity, results of genetic testing, veteran status, as well as any other legally-protected characteristic. If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact CAAR@chewy.com.

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