Head of Delivery (Software & AI Industry)

Offshorly

17h•Remote

About The Position

Offshorly is seeking a Head of Delivery to oversee the operational backbone of client work delivery. This role is central to the company's transition to a Client AI Solutions Team (CAST) model, focusing on quality standards, playbooks, team optimization, and mentoring. The Head of Delivery will define excellence in delivery, create repeatable systems, and act as an escalation point for delivery issues. This is a strategic and tactical role with significant autonomy, ideal for someone who thrives on bringing structure, solving problems, and driving progress. While client account ownership is secondary, experience in this area is a bonus.

Requirements

Minimum 5+ years in delivery management, project management, or digital operations.
Experience managing remote cross-functional digital teams (Developers, PMs, QA, Designers).
Strong understanding of Agile / hybrid delivery practices.
Comfort redesigning process rather than just running an existing one.
A mentoring track record, not just management.
Motivated by shaping delivery strategy alongside running it day to day.
Comfortable with autonomy, measured on outcomes rather than close oversight.
A proactive, can-do attitude to everyday problem solving.
Calm under pressure, proactive in finding solutions.

Nice To Haves

Experience with AI-native or AI-augmented delivery models.
Account management or client-facing experience.

Responsibilities

Own delivery quality and standards across all client projects and CAST units.
Lead onboarding for new clients to align expectations and success metrics.
Coordinate with delivery teams to align resources with client projects and business goals.
Track timelines and blockers, escalating risks to leadership.
Set and track business OKRs tied to delivery, productivity, and quality.
Mentor Project Managers and Team Leads, including performance reviews.
Build and evolve delivery playbooks for consistent AI orchestration.
Contribute to shaping delivery strategy as CAST matures, including client reporting and capacity forecasting.
Partner with AI Team leadership on playbook and orchestration rollout's impact on delivery standards.
Manage day-to-day delivery, including portfolio success, risk mitigation, and on-time delivery.
Oversee resource and capacity planning, prioritizing and coordinating resources across Project Managers.
Create, maintain, and version delivery playbooks and case studies.
Own the metrics for delivery improvement and present delivery metrics at Board reviews.
Identify and implement process improvements for better delivery.