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Director, Digital Products & Portfolio Management

Sasser Family Companies
life insurance, vision insurance, parental leave, paid holidays, sick time, tuition reimbursement, 401(k), remote work
United States, Illinois, Schaumburg
Apr 12, 2025

Recognized as one of Crain's "Best Places to Work in Chicago" as well as a 2023 "Great Places to Work", by the Great Place To Work Institute Inc., Sasser prides itself on supporting an employee-driven, opportunity-based culture that empowers, recognizes, and rewards its employees. From highly competitive benefits to exciting employee events to organic, grassroots philanthropy and volunteerism, Sasser is an awesome place to begin and grow your career. We are a fourth-generation, family-held transportation asset services and management company with roots dating to 1928. Sasser's six subsidiary units are leaders in providing commercial- and industrial-focused rail, automotive, containerized shipping, and aviation transportation equipment solutions including asset leasing, fleet administration management, asset repair and maintenance, and innovative technology services.

Sasser Family Companies includes subsidiaries Chicago Freight Car Leasing, Union Leasing, CF Rail Services, Express 4x4 Truck Rental, Xced Aviation Services, and Falcon Lease. To learn more about what makes Sasser special, visit www.sasser.com.

The Director, Digital Products & Portfolio Management (DPPM), is a senior leader in the Information Technology department responsible for overseeing Sasser's portfolio of products with the objective of ensuring they support cost-effective operations, provide strategic value, enable growth opportunities, and drive competitive advantages for each of our businesses. The role requires a broad set of skills to ensure impactful results, including talent development, strategic vision and planning, project and product management, influencing others, change leadership, and communication across all levels of the organization. . The DPPM works closely with the VP IT to ensure that cross-functional product teams deliver state-of-the art, high quality, secure and consistently available technology services and products that are readily adopted by and improve the experience of Sasser's personnel and customers.

The DPPM leads and oversees the product managers, ensuring they identify the emerging trends and business requirements to maintain product viability and competitiveness and cultivate and refine the internal backlog of required IT changes for all business units to execute and implement those changes successfully. The DPPM works closely with the VP IT, executive management, product teams, business unit leadership, and third-party providers to assess, prioritize, and lead business and technology changes needed to incrementally evolve and improve the product's ecosystem (i.e., people, processes and technology).

The DPPM propagates best practices, suggests practical applications of emerging technologies, provides strategic and tactical recommendations, and promote a consistent IT vision across product managers, product owners, business analysts, and development teams.

As a Director, Digital Products & Portfolio Management, Here's What You'll Do:



  • In conjunction with Product Managers and Owners, develop product roadmaps, including financial support for related investments.
  • Leverage foundational and enterprise-wide technology, data and security capabilities to promote speed to market and scalability of products.
  • Responsible for coordination, orchestration, and execution of product portfolios, initiatives, and programs to achieve or surpass desired business outcomes.
  • Focus on driving value and maximizing returns on investments while promoting the enablement of innovative ideas.
  • Ensure Product Managers develop near-term and long-term product roadmaps that appropriately leverage emerging technologies, including building financial budgets and forecasts to ensure products remain financially viable and meet established financial goals. In response to changing market conditions or priorities, recommends and implements actions, as required, to remain within budget or obtain necessary approvals for financially sound variances.
  • In conjunction with the VP IT, establish and maintain a best practice governance framework for the enterprise that enables speed, agility, and security that is consistent with Sasser's strategic objectives and customer requirements.
  • Direct and oversee governance activities supporting Sasser IT Governance structure, including business-unit level Process Leadership Committees (PLC), IT Steering Committee, and individual project team activities.
  • Effectively interface, collaborate, and synergize with product teams to best direct resources, rationalize project goalsetting, and increase leverage by prioritizing opportunities with high-impact and/or high-ROI potential.
  • Set standards for and direct the cultivation, validation, and optimization of a prioritized backlog of IT initiatives, changes, and opportunities in accordance with the current IT systems roadmap.
  • Lead products teams responsible for providing functional ownership of all business-unit and enterprise-level systems; partner with technical and business owners to ensure ongoing alignment of system development and maintenance in accordance with Product and IT roadmaps.
  • Lead hybrid business-IT teams tasked with distilling business requirements, designing technical solutions, developing recommendations and establishing initial time estimates and direction.
  • In partnership with Product Managers, business unit leadership and theVP IT, ideate the evolution of existing products and the launch of new products designed to drive top-line revenue growth, improve bottom-line financial results and/or enhance customer and employee experience.
  • Oversee Product Teams to ensure they deliver iterative value creation through minimally viable product scoping and the use of multi-stage adoption campaigns.
  • Establish Key Performance Indicators (KPIs) to support continuous improvement, including metrics for project progress, new feature releases, and enhanced IT functionality.
  • Review KPIs with Product Teams to ensure on-going relevance, identify opportunities and develop plans for improvement.
  • Create a standardized communication strategy to disseminate both formal and informal product communications to all stakeholders, both internal and external to Sasser.
  • Formalize and evangelize Agile methodology and SCRUM processes for adoption by all Product Teams.
  • Focus the efforts of all product team members to optimize the supporting processes and technology that enable business performance.
  • Work with Product Managers to optimize IT utilization/allocation of internal and external resources; facilitate reallocation or augmentation of resources on project basis, as needed.


Here's What it Will Take to be Successful in This Role:



  • Minimum 10 years of relevant experience, with 5+ years in Product Management.
  • Bachelor Degree in Business, IT, or related field preferred
  • Experience in the financial services, leasing, asset management or logistics industries a plus.
  • Broad knowledge within the assigned business unit industry and/or IT.
  • Superior written and oral communication skills - the ability to communicate and interact effectively across all levels of the organization.
  • Strong aptitude and interest in evolving knowledge in related technical and business disciplines.
  • Can envision, articulate and create enthusiasm for new ideas, possibilities and practical steps to achieve them.
  • Ability to self-manage and engage with new problems proactively, with a sense of urgency and attention to detail.
  • A comprehensive understanding of business processes, procedures, financials, operations, and commercial strategy is essential.
  • Ability to manage, engage and drive the performance a culturally diverse population.
  • Balances the need for analysis with the need for action. Makes sound decisions without the benefit of full information and understands when / how to course correct. Ability to work well and productively, projecting a positive outlook to motivate and reassure others in a fast-paced, sometimes stressful environment.
  • Interpersonal skills to work in a team-orientated, collaborative environment.
  • Ability to create a culture focused on results, innovation, quality, lean practices, and accountability.
  • Deals with ambiguity; can effectively cope with and affect change; can comfortably handle risk and uncertainty.


Physical Demands

This job operates in a professional environment and routinely uses standard office equipment such as computers, phones, copy machines, filing cabinets, printers and fax machines.

Travel up to 10% maybe required.

Working Conditions

This position will be based out of our office in Oak Brook, Illinois. Until the Company moves to Oak Brook in early 2026, this will temporarily work out of the office in Schaumburg, Illinois. If fulltime, this role also offers remote work flexibility with 3 days in office, and 2 days remote. If part time, this role would need to be in office 2 days.

Compensation

The hiring range for this role is: $175,000 - $195,000 USD annual. This role is classified as exempt for purposes of all applicable wage and hour laws, which means that the individual hired is paid for the job and not by the hour, and will not be eligible for, and will not receive, overtime pay if working more than 40 hours in a workweek. This role will be paid on a semi-monthly basis.

Sasser is committed to fair and equitable compensation practices. Pay ranges are assigned to a job based on market data according to 3rd party salary benchmarking surveys. Actual base salary is dependent upon factors such as knowledge, skill level, and experience.

This role is also eligible for benefits. Sasser employees enjoy a competitive benefits program that:



  • Includes comprehensive medical, dental, and vision insurance plans, including HSA and FSA accounts with employer contributions toward HSA
  • Includes a 100% Company-paid disability and life insurance plans
  • Includes a 401K plan with company match PLUS additional end-of-year funding
  • Provides paid vacation time (tiered based on tenure), as well as personal time, sick days and summer half days for certain roles
  • Provides 10 paid holidays annually
  • Provides paid parental leave for new parents, as well as a monetary gift towards a 529 education account
  • Provides a confidential Employee Assistance Program
  • Provides training and tuition reimbursement
  • Provides community service opportunities, charity match opportunities, employee recognition programs, and many celebrations!


Note: Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

The Company provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.

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