CrackaJack Digital Solutions LLC

Role: Delivery Lead
Location: NYC (onsite) 
Duration: 12 month contract 

Position Overview:
The Delivery Lead is a key member of the Delivery team, responsible for owning the “who, what, where, when, and why” of both functional and technical details across Madison projects in their portfolio. This role requires engaging with key project members, effectively communicating both top-down and bottom-up, and managing critical processes including scope, risk, and issue management. The Delivery Lead also supports process reviews, audits of project documentation, and ensures timely delivery of SDLC-related artifacts.

Key Responsibilities:

• Project Planning:
  • Build comprehensive, end-to-end project plans from inception to completion.
  • Collaborate with peers and colleagues to develop project plans.
  • Capture business-facing milestones and critical path deliverables, tracking progress consistently.
• Project Estimation:
  • Partner with Engineering Leads and Product Managers to translate business requirements into technical stories and tasks.
  • Apply industry-standard estimation techniques (PDU, Story Points, Shirt Sizes, Complexity, etc.).
  • Execute effective capacity planning at both sprint and increment levels.
• Continuous Improvement:
  • Identify opportunities to enhance team delivery capabilities.
  • Apply lessons learned to tactical problem-solving and long-term strategic solutions.
  • Drive process improvements beyond Scrum retrospectives.
• Risk Management:
  • Proactively identify unanticipated risks and develop mitigation strategies.
  • Document and manage project issues, assessing impacts and communicating knock-on effects to relevant stakeholders.
• Project Execution:
  • Lead project teams, ensuring all SDLC tollgates and deliverables are met.
  • Track sprint execution using Jira Scrum Boards, Structure, EazyBI, and JQL queries.
  • Actively participate in change management processes and forums.
  • Collaborate across workstreams/pods to ensure successful delivery.
  • Manage scope, risks, and issues, escalating as needed, while assigning tasks to team members.
• Stakeholder Management:
  • Provide regular updates to senior leadership.
  • Manage change requests and scope creep using data-driven approaches.
  • Demonstrate strong upward and downward communication with project stakeholders.

Methodology:

• Fluent in both Agile and Waterfall methodologies, able to apply fit-for-purpose project management processes depending on project needs.
• Experience incorporating best practices from Waterfall, SAFe, or iterative frameworks as applicable.

Required Skills & Experience:

• Proven track record of delivering complex CRM and/or reporting projects.
• Clear leadership capability – able to take ownership of deliverables from ideation to deployment.
• Experience leading teams through feature estimation and SDLC ceremonies.
• Strong risk and issue management skills, with ability to resolve at the lowest level and escalate appropriately.
• Ability to collaborate across Madison, identifying dependencies and working with multiple teams.
• Prior experience in Financial Services software development projects.
• Successful delivery of complex, cross-workstream projects.
• Experience with agile or iterative development and familiarity with Waterfall/SAFe as needed.
• Proficient with Atlassian stack tools (Jira, Confluence, Structure, EazyBI) and Microsoft Suite.
• Experience with AWS and Kafka is preferred but not required.

Education:

• Bachelor’s degree in Computer Science, Information Technology, or related field (preferred).