OCTO Program Manager Web Portfolio

Short Description: 
OCTO seeks a Master Program Manager to lead project management, reporting, and delivery oversight across the web team's portfolio, including the redesigned dc.gov site, other concurrent agency web efforts, and AI-powered search initiatives. 
 
Complete Description: 
 
The District’s web. team manages a portfolio of concurrent initiatives across more than 100 agency websites. The largest is the dc.gov redesign, which itself comprises multiple sub-projects including design implementation, content migration, agency-wide launch, and integration of AI—powered search. OCTO requires an experienced Master Program Manager who can bring structure, visibility, and accountability across this full portfolio, ensure each sub-project has a defined scope and milestone plan, and give OCTO leadership a clear, current picture of status across all active work.  
 
Key Duties:  

• Establish and maintain a portfolio-wide tracking system (RAID log, milestone schedules, dashboard) covering all active web team projects.   
• Run a recurring status reporting cadence to OCTO leadership across the full portfolio  
• Partner with OCTO SMEs to define project requirements and scope, including for initiatives that may require external vendor support  
• Advise on vendor/contractor scoping and deliverables, drawing on familiarity with SOW structure and government IT procurement norms   
• Track risks, issues, dependencies and action items across projects, escalating to OCTO leadership as needed  
• Report on project status, milestones, and delivery readiness across the portfolio, with the dc.gov relaunch as the flagship initiative   

Minimum Qualifications:  

• Demonstrated ability to translate technical and business requirements into actional project scope, working directly with subject matter experts  
• Experience supporting or informing scope of work development for external vendor contracts (SOWs, deliverables, acceptance criteria)  
• Experience managing a multi-project portfolio simultaneously, including establishing. PM tooling, reporting cadence, and prioritization across competing initiatives  
• Bachelor's degree in a related field, or equivalent experience  
• 11 years of program/project management experience, including large-scale website or CMS transition and migration projects  
• Experience managing multi-stakeholder government or enterprise projects  
• Working knowledge of Drupal CMS and website content migration practices  
• PMP certification preferred  
• Familiarity with AI/ML project delivery timelines and dependencies a plus, given active AI integration work within the portfolio   
• Strong communication, organizational, and stakeholder management skills  
• Prior experience supporting DC government or comparable public-sector clients preferred 

 
 

 
Candidate Skills Matrix: 
 
Following sections are to be filled by the candidate: 
 
Skills  | Required/Desired  | No. of Years  | How many years of experience candidate has?
Program/Project Management – multi-project portfolio oversight   | Required   | 11  | 
Requirements gathering & project scoping (working with SMEs)   | Required  | 8  | 
Drupal CMS – content migration and administration   | Required  | 6  | 
Stakeholder Management – multi-agency government environment   | Required   | 10  | 
Website Launch Planning & Change Management   | Highly desired  | 8  | 
Quality Assurance / Content Auditing   | Highly desired  | 11  | 
Government contract/vendor scoping support (SOWs, deliverables)   |  Highly desired  | 5  | 
AI/ML project delivery experience   | Desired  | 3  | 
Bachelor’s degree in IT or related field or equivalent experience   | Required   |   |  
Candidate must be able to qualify for a Master level role  | Required   | 16  |  
 
  
 
Background check:   
 

• Extensive criminal history background check will be required. We cannot submit candidates with recent histories (go back seven years) of extensive driving, drug, robbery or any other illegal activity. Any criminal activity on the background check will eliminate the candidate from consideration. If selected, please make certain that you inform all candidates that they will have to complete this criminal background check prior to starting. NATIONAL background checks are required; Federal background checks are NOT compliant under this contract. A national background check is a national criminal background check that pulls criminal records from State and County Courts in almost every US State.