[Hiring] Delivery Lead @DreamHost, LLC

Role Description

The 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.

Responsibilities

• 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.
• 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.
• 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.

Qualifications

• 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
• Full health/vision/dental for the entire family at zero cost to team member.
• 3% Safe Harbor contributed to 401(k) plus up to 1% employer match.
• Opportunities for profit sharing and bonuses.
• Generous time-off (starting at 15 vacation days).
• 11 Paid holidays (Technical Support and Technical Operations use a floating holiday policy).
• Paid sick leave (80 hours accrued).
• Tuition reimbursement (50/50 up to a specific amount).
• Pet Insurance.
• Thrive Pass wellness allowance of $30 per month.
• Udemy online learning courses.
• Disability Insurance.
• Generous maternity/paternity leave.
• Discounted personal travel through corporate booking program Egencia.
• Laid-back atmosphere.
• Fun monthly company events.
• Free web hosting.