13 days old

Digital Transformation: Program Lead

Los Angeles, California Work Remotely

Job Title:  Digital Transformation Program Lead

Division/Department:  Operations

Reporting Relationship:   COO

Status:  Exempt

The Digital Transformation (DT) Program Lead is responsible for the overall successful delivery of the DT Program’s integrated scope, schedule, and budget using best practices within the project management, technology, and financial industries & disciplines.

The ideal candidate will be a relentlessly inquisitive project management professional with 10+ years proven record of successfully managing staff & third-party vendors of different disciplines, executing multiple workstreams and projects, and producing results in a timely, professional and ethical manner. 

**If you would like to be considered for this role, please follow the application steps outlined at the end of this job description**


Primary individual responsible for the successful delivery of Digital Transformation program, currently scheduled for “go live” in April, 2022; tracking all aspects of the program’s tasks, contingencies, dependencies, risks, budget, schedule and quality;

  • Oversee the day-to-day relationship with data migration and software implementation vendors (e.g. oversight of task / milestone quality, engagement level of skilled staff and overarching, ongoing assessment meeting contractual obligations)
  • In partnership with data migration and software implementation vendor’s program managers; develop and manage overall project plan and reporting strategy between all organizations
  • Manage reporting and communication related to the digital transformation program within implementation and deployment environments; adjusting mode and messaging based on different audience groups
  • Working closely with business functional points of contact to identify, capture and prioritize requirements and identify gaps in an ongoing manner (e.g. change request management), providing ongoing status updates to key stakeholders regarding status of individual requirements over the course of the program
  • Ensures the quality of program / project deliverables and alignment to business objectives, using project management best practices for the following duties; 
  • Assess, and as needed, re-define and set-up program management governance, processes, and procedures
  • Develop detailed project and/or program plans, identifying and gaining buy-in for critical milestones, and agreed upon deliverables and quality standards
  • Ensure success by consistently deploying project management methodology, tools, and guidance throughout all tasks & behaviors 
  • Ensure with both internal and external stakeholders that there is a consistent approach to planning, design and implementation throughout the entire DT program, particularly in communication and documentation
  • Perform, as needed, detailed analysis to determine required resources and identify constraints related to DT Program (aka LOE leveling)
  • Ensure effective coordination and communication across multiple project/work stream teams, including internal SME’s and project resources
  • Communicate and escalate to the COO / program’s executive sponsor the overall program progress, timelines, risks, issues, budget information and scope changes
  • Communicate progress through a formal weekly dashboard / report / meeting; based on the needs of the different and specific audience groups
  • Contribute to preparing team and executive presentations
  • Regularly track and report on budget burn rate, scope alignment and overarching financial control (e.g. invoice processing)
  • Ensure project results align with customer objectives and contract deliverables
  • Prepare in-depth project plans with adequate supporting documentation to ensure successful implementation
  • Track project plans, milestones and deliverables status and assess any impacts changes will have on cost, resourcing and schedules.
  • Prepare parent/child-style, integrated Gantt charts to appropriately assess project & workstream status, dependencies and identify/manage critical paths.
  • Work with internal teams to develop & validate software release schedules throughout program life, establishing cadence and expectations for post launch software updates
  • Identify and successfully resolve conflicts/priorities within the program team members



  • Bachelor (4-year) degree, within a related major, such as information technology, business operations, computer science, or equivalent relevant work experience
  • Proven experience (min. 7 years) as a Program Manager for a cross organizational transformation; ideally proven ability to successfully execute a “turnaround”-style situation 
  • Holder of a Project Management Professional (PMP) Certification – ideally for 5+ years
  • Thorough understanding of project/program management techniques and methods 
  • Excellent knowledge of performance evaluation and change management principles 
  • Excellent knowledge of MS Office, Google G Suite/Workspace and other standard software tools used by project management professionals (e.g. Smartsheet, MS Project etc.)  
  • Exhibited outstanding leadership and organizational skills, ideally in both non-profit and for-profit environments  
  • Ability to navigate conflicting or overlapping obligations and timelines; prioritizing and escalating as appropriate with senior management
  • Excellent communication skills (written, verbal, non-verbal) 
  • Excellent problem-solving ability 



  • Holder of Information Technology Infrastructure Library (ITIL) certification
  • Strong background working within software development and lifecycle (SDLC) environment
  • Experience leading a data migration project 


  • Ability to maintain the highest level of discretion and confidentiality
  • The ability to interpret and/or discuss technical information and concepts with others that may not be familiar with technical jargon or concepts; performing the role of “liaison” between the business and the technology groups involved in the digital transformation program
  • Advanced proficiency of Microsoft Office tools
  • Advanced knowledge of Project Management-adjacent tools: e.g. JIRA, Basecamp, Trello, etc.
  • Ability to work with business functional points of contact to capture and prioritize requirements and identify gaps
  • Ability to design, document and implement processes and procedures
  • Exceptional communication, oral and written
  • Agile implementation methodology a plus
  • Business Acumen and self-motivation to understand processes in detail
  • Teamwork and leadership skills, proactive attitude
  • Flexibility to sometimes work evenings and weekends with little or no advance notice should a program related issue arise


  • 401(k)
  • 401(k) matching
  • Dental insurance
  • Health insurance
  • Flexible Spending Account
  • Life insurance
  • Paid time off
  • Vision insurance


Please email your responses to the below questions to Allie Walker @ awalker@singerlewak.com. 

A. Answer the following four questions (minimum of three sentences each): 

1. What skills or previous experience do you think makes you a great candidate for this role? 

2. What one work activity would you say you enjoy doing the most (e.g. interacting with people, streamlining a process, working through a problem with team mates) - in other words, what "gets you into the zone"? 

3.  Which of your traits do you feel best equips you for being a leader?

4. What responsibility/skill in this Digital Transformation Program Lead role description would you say you have the least experience with - and what sort of support do you think would help you get up to speed as quickly as possible?   

B. Provide any working time limitations/considerations you would like to have included in the interview process (e.g., volunteering responsibilities, early / late start preferences).  

C. Provide two professional references: name, contact info (phone number or email) and relationship description (e.g. boss at the job from 3 years ago). 

Salary Details


Market competitive, dependent on skills and experience. 



Posted: 2021-04-27 Expires: 2021-06-11

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Digital Transformation: Program Lead

Los Angeles, California

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