OverviewThe Delivery Lead operates at the program (cross-team) level, ensuring complex initiatives are planned, coordinated, and delivered successfully across teams and business functions. Working closely with Product Owners, Engineering Leads, and cross-functional stakeholders, the Delivery Lead is accountable for delivery quality from discovery through release, adoption, and post-delivery evaluation.
Success in this role requires technical fluency, systems thinking, sound judgment, and the ability to influence without direct authority while continuously improving how the organization delivers work.
ResponsibilitiesDelivery Leadership- Lead delivery of complex initiatives from discovery through release and adoption.
- Ensure initiatives are ready to execute by validating requirements, dependencies, technical considerations, operational impacts, and stakeholder alignment.
- Define and adapt delivery strategies, including sequencing, phasing, incremental delivery, and risk mitigation.
- Coordinate execution across Product, Engineering, Design, QA, Infrastructure, and business stakeholders.
- Maintain visibility into delivery health, proactively addressing risks, dependencies, blockers, and changing priorities.
- Coordinate organizational readiness for launches, ensuring operational teams are prepared to support successful adoption.
- Communicate delivery status, risks, tradeoffs, and recommendations to stakeholders throughout the initiative lifecycle.
Cross-Functional Leadership- Partner with Product Owners, Engineering Leads, and business stakeholders to improve planning, execution, and organizational outcomes.
- Facilitate alignment across teams while balancing scope, timeline, quality, dependencies, and business priorities.
- Challenge assumptions through thoughtful questioning and constructive facilitation.
- Surface risks, hidden dependencies, operational impacts, and alternative approaches before commitments are made.
- Drive timely decisions and appropriate escalation to maintain delivery momentum while protecting delivery quality.
Delivery Excellence- Coordinate post-launch reviews, usage metrics, and stakeholder feedback to evaluate delivery outcomes and inform future decisions.
- Leverage AI to improve documentation, reporting, workflow management, and other delivery activities while validating AI-generated outputs.
- Identify opportunities to improve delivery standards, governance, readiness practices, and team collaboration.
- Partner with the Delivery Systems Administrator to implement approved improvements to delivery tooling, reporting, workflows, and automation.
- Share lessons learned and contribute to the continuous evolution of the organization's delivery practices.
- Continuously deepen technical fluency and understanding of DreamHost's systems and delivery ecosystem.
Requirements- 5+ years of experience leading software delivery, project management, product operations, or similar cross-functional initiatives.
- Strong understanding of Agile methodologies, software development lifecycles, and modern engineering practices.
- Technical fluency with web technologies, APIs, cloud platforms, AI-assisted development, and modern software architecture.
- Experience coordinating work across Product, Engineering, Design, QA, Infrastructure, and business stakeholders.
- Proven ability to influence decisions, resolve conflict, and drive alignment without direct authority.
- Strong analytical skills with the ability to identify risks, dependencies, and delivery constraints early.
- Excellent communication, facilitation, negotiation, and stakeholder management skills.
- Experience leveraging AI tools to improve planning, documentation, reporting, and delivery workflows.
- Strong organizational skills with the ability to manage multiple concurrent initiatives.
Preferred- Bachelor's degree in Business, Information Technology, Computer Science, Engineering, or a related field, or equivalent experience.
- Experience leading program-level initiatives spanning multiple teams or organizational domains.
- Experience improving delivery governance, standards, or operating practices.
Compensation & Benefits- $100,000-$120,000 / yearly
