Program Management Trainer and Mentor

Remote
Full Time
PMO
Senior Manager/Supervisor

At Goldschmitt and Associates LLC (G&A), we’re not just another company—we’re a catalyst for innovation and impact, and we’re inviting passionate, forward-thinking individuals to join us on this journey. Recognized multiple times on the Inc 5000 list of the fastest-growing companies, G&A is a leader in tech transformation and system modernization for some of the nation’s most important federal agencies.

Our culture is built on creativity and collaboration. We offer flexible schedules, telework options, and an environment where your ideas truly matter. At G&A, you won’t just clock in—you’ll be solving real-world challenges and working on projects that make a difference in the lives of millions.

Joining our team means becoming part of a vibrant, connected community where innovation thrives, your voice is heard, and your impact is felt. Whether you’re a tech enthusiast, a strategic thinker, or a problem-solver, at G&A, you’ll have the opportunity to level up your career while making a real-world impact.

If you’re ready to be part of a company that values purpose as much as progress, G&A is the place for you!

Summary
Goldschmitt & Associates is seeking a Program Management Trainer and Mentor, an exceptional senior enterprise leader to help Federal Student Aid fundamentally transform how technology and digital services are governed, prioritized, delivered, measured, and continuously improved. The role will operate at enterprise scale, advising FSA leadership, shaping the product operating model, influencing major systems integrators and delivery partners, and helping institutionalize a durable shift from project-centered execution to product-led, customer-responsive management. The successful leader must be equally credible with executives, product leaders, engineers, architects, operations teams, and large delivery organizations, and must be able to turn broad transformation goals into practical governance, decision rights, operating rhythms, measures, and behaviors that can endure across the agency.

Job Duties and Responsibilities

  • Serve as a senior enterprise advisor to FSA leadership on the transition from project-centered delivery to a sustainable, product-oriented operating model aligned to mission outcomes, borrower needs, operational priorities, and measurable value
  • Shape and help institutionalize agency-wide product governance, including product ownership, decision rights, intake, prioritization, roadmap practices, backlog management, lifecycle management, performance transparency, and accountability
  • Assess product management maturity across organizations and delivery teams, identify structural and capability gaps, and design targeted transformation strategies that can scale across a complex federal enterprise
  • Influence and align major systems integrators, contractors, technical teams, and business organizations around common product outcomes, operating principles, standards, and delivery expectations; challenge legacy processes when they impede product performance or customer outcomes
  • Coach senior leaders, product managers, product owners, engineering and delivery leaders, and cross-functional teams on product strategy, outcome-based delivery, prioritization, customer discovery, iterative capability delivery, and data-informed decision-making
  • Facilitate executive and cross-functional working sessions, Design Thinking workshops, product reviews, planning forums, and decision-making sessions that move teams from technical outputs toward user-centered outcomes and measurable service health
  • Establish integrated product and program management practices for planning, scheduling, reporting, risk management, dependency management, and backlog control in alignment with FSA priorities
  • Create practical mechanisms for coordinating upstream and downstream interfaces, technical dependencies, organizational handoffs, readiness conditions, and sequencing across FSA systems and participating organizations
  • Develop repeatable product frameworks, playbooks, templates, review cadences, communities of practice, office hours, and other knowledge-transfer mechanisms that enable FSA to sustain the transformation without long-term dependence on external coaching
  • Define and promote product outcome frameworks and KPIs that connect strategic objectives, stakeholder and user feedback, operational performance, and technology delivery
  • Synthesize stakeholder feedback, data, operational insights, and technical constraints into clear recommendations and decision support for FSA leadership and, when required, communications supporting senior federal stakeholders including OMB
  • Promote a culture of design thinking, experimentation, continuous learning, transparency, shared accountability, and customer-focused problem solving across business and technology organizations
Necessary Skills and Knowledge
  • Executive-level leadership experience in a large, complex technology, engineering, digital product, or enterprise transformation organization
  • Demonstrated success leading or materially shaping enterprise-scale transitions from project/program delivery toward product-based operating models, modern digital delivery, or comparable organizational transformation
  • Deep practical expertise across product strategy, product management, engineering delivery, portfolio prioritization, governance, operating models, and organizational change - not solely classroom training or agile facilitation
  • Experience influencing senior executives, technical leaders, business owners, and large delivery organizations across a matrixed environment where authority is distributed
  • Experience working with or overseeing major systems integrators, strategic technology partners, large vendors, or similarly complex multi-vendor delivery ecosystems
  • Ability to challenge entrenched processes constructively, build executive alignment, and convert strategic intent into actionable governance, operating mechanisms, and measurable outcomes
  • Strong understanding of iterative product delivery, agile methods, backlog and roadmap management, Design Thinking, customer discovery, outcome measurement, and data-driven feedback loops
  • Exceptional executive communication, facilitation, negotiation, and stakeholder-management skills, including the ability to communicate credibly with both senior leadership and deeply technical teams
  • Ability to understand complex engineering, architecture, data, security, operational, and integration considerations well enough to connect technical delivery decisions to enterprise product outcomes
Minimum Qualifications
  • Possess at least 15 years of relevant experience in Program Management and enterprise-level operations
  • Possess the ability to pass and maintain eligibility for a 6C Public Trust investigation
Preferred Qualifications
  • Previous experience as a Vice President, Head of Product, Head of Engineering, digital transformation executive, CTO-adjacent leader, or comparable senior enterprise technology leader
  • Leadership experience within a Fortune 100, major federal agency, large regulated enterprise, or similarly complex organization with substantial technology portfolios and multiple delivery partners
  • Experience driving transformation across federal programs or other highly governed environments
  • Experience building product management capability at organizational scale, including maturity models, governance frameworks, training programs, leadership coaching, and communities of practice
  • Experience presenting transformation strategy, operating metrics, or delivery performance to C-suite, agency, board, or other executive-level stakeholders

NOTE: This job description is not intended to be an exhaustive list of all duties, responsibilities or qualifications associated with the job. It is intended to describe the general nature and work responsibilities of the position. This job description and the duties of this position are subject to change, modification and addition as deemed necessary by the Company.

Goldschmitt and Associates offers the following benefits:

  • 401(k) with immediate vesting
  • Paid Federal Holidays
  • Tuition Reimbursement
  • Medical Insurance, including Vision and Dental Insurance
  • Employer-Paid Short-Term and Long-Term Disability
  • Employer Paid Life Insurance
  • Supplemental Life Insurance
  • FSA/HSA Programs
  • Commuter Benefits Program
  • Adoption Assistance Program
  • Employee Assistance Program (EAP)
  • Caregiver Support Program
  • Health Advocacy Program
  • Financial Wellbeing Support

Goldschmitt and Associates is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to sex, race, color, religion, national origin, disability, protected Veteran status, age, or any other characteristic protected by law.

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