Head of Delivery (Tech & AI)

This is a remote position.

Remote Job (Philippines-based preferred)

Offshorly is a digital staff augmentation and delivery company with UK management and a Philippines-based team. We provide Developers, Designers, PMs, QA, and strategic delivery support to global clients. We are mid-shift from a traditional dev-led delivery model to CAST (Client AI Solutions Team), an AI-native, forward-deployed model built on shared playbooks and embedded creative/business and data/tech units, and this role sits at the center of that transition.

Role Overview

We are looking for a Head of Delivery to own the operational backbone of how Offshorly delivers work across a portfolio of global clients: quality standards, playbooks, team optimization, and mentoring across Project Managers and delivery teams. This is the person who defines what excellent delivery means at Offshorly and builds the systems and tool kit that make it repeatable. You'll also be the escalation point after Project Managers when delivery issues need to go further, solving problems fast and representing Offshorly with professionalism.

This is both a strategic and tactical role. You'll have real input into how the delivery model evolves as CAST matures. We're results-oriented here, so you'll have real autonomy in how you run delivery, not oversight for its own sake.

Ideal for someone who loves bringing structure, solving delivery blockers, and keeping people moving forward.

Client account ownership is a secondary, not primary, expectation for this role. Where a candidate can also carry account management and client success responsibilities, that is a genuine bonus. Where they cannot, the General Manager will cover that ground directly.

Key Responsibilities:

Operational Excellence and Team OKRs (Primary):

• Own delivery quality and standards across all client projects and CAST units, including leading onboarding for new clients so expectations and success metrics are aligned from day one.
  

• Coordinate with delivery teams to keep resources aligned across client projects and business goals; track timelines and blockers and escalate risk to leadership when needed.
  

• Set and track business OKRs tied to delivery, productivity, and quality from which team OKRs build on.
  

• Mentor Project Managers and Team Leads, including performance reviews.
  

• Build and evolve delivery playbooks so AI orchestration stays consistent as CAST progressively rolls out across delivery teams.
  

• Contribute to shaping delivery strategy as CAST matures, including client reporting and capacity forecasting for delivery pipelines.
  

• Partner with AI Team leadership on how playbook and orchestration rollout affects delivery standards, without owning AI Excellence reporting or team oversight directly (that sits elsewhere).
  

Account Management and Client Success (Secondary, bonus if covered):

• Internal alignment with PMs to stay across delivery status and client needs.
  

• External client management touchpoints (monthly and/or quarterly).
  

• Build working relationships with clients, partnering with leadership on the bigger picture.
  

What You'll Own:

Day-to-Day Delivery:

• Portfolio success: shared ownership with PMs of client expectations, risk mitigation, and on-time delivery; own delivery health checks across the portfolio.
  

• Resource and capacity planning: prioritize and coordinate resources across Project Managers, managing the impact of reallocation or resource changes.
  

Documentation and Planning:

• Playbook documentation: create, maintain, and version delivery playbooks and case studies, with support from PMs, as the operating model evolves.
  

• Performance tracking: own the metrics that show delivery is actually improving, and present your delivery metrics directly at quarterly Board reviews, full ownership of the numbers you're accountable for.
  

• Process improvement: find better ways to deliver, and to bring the team along on new ways of working.
  

What We're Looking For:

• 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, and comfort redesigning process rather than just running an existing one.
  

• A mentoring track record, not just management. This role builds people as much as it builds process.
  

• Someone 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.
  

• Bonus: experience with AI-native or AI-augmented delivery models.
  

• Bonus: account management or client-facing experience (this is not required, but genuinely valued).
  

What You'll Get:

• Ownership of how Offshorly delivers, at a moment where that model is actively being redefined.
  

• A genuine voice in shaping delivery strategy as the business evolves.
  

• Real autonomy to run delivery your way, we care about outcomes.
  

• A people-first culture that values growth, ownership, and contribution.
  

• Structured career support and advanced AI training.
  

• Bonuses and very competitive salary.
  

• Direct partnership with the executive leadership team on the next chapter of the business.