Head Of Delivery

WHAT THIS ROLE IS
The CEO answers to a group board and runs a small, senior team - Product & AI, Engineering, and other functional leads - each building something real and each carrying genuine execution risk. At this stage, the thing most likely to break the company isn't a bad decision. It's a good decision that quietly stops happening three weeks later because nobody was senior enough to notice and call it.
This role exists to make sure that never happens. It is a senior seat at the center of the company: you carry a real mandate from the CEO to know what every function has committed to, to judge which commitments are genuinely at risk, and to hold senior people to their word - using judgment and standing, not a reporting line. This is not a passive tracking role - you own the actual project and program plans for major cross-functional initiatives: the milestones, the dependencies, the critical path, and the risk register. Where a functional lead doesn't have a real plan, you build one with them. And you are judged on it: if a program you're running slips, that is your result to explain, not just a status you reported upward. This is a build role, not a maintenance role: you are designing the operating rhythm the company runs on, from nothing.
Concretely, this role owns four things:
Program ownership and planning: The actual project and program plans for major cross-functional initiatives - milestones, dependencies, critical path, and risk register - not just a tracker of other people's plans. You are accountable for whether these programs actually land, not just for reporting their status.
Execution intelligence: A single, board-grade picture of what every function has committed to, what's genuinely on track, and what's quietly at risk - before it becomes the CEO's problem to discover.
Judgment and escalation: The seniority to tell a functional lead their timeline doesn't add up, distinguish a real blocker from someone slow-walking, and put the right things in front of the CEO - early, and without drama.
Relentless follow-through: Nothing gets marked done until it's actually done. This is the person in the building who does not let things quietly die.
WHAT YOU'LL ACTUALLY DO
Program planning and ownership
• Build and own the actual project and program plans - milestones, dependencies, critical path - for major cross-functional initiatives, not just a tracker of other people's plans
• Carry the delivery outcome, not just the status report: when a program lands late, you're the one accounting for why, alongside whichever functional lead owned the work
• Identify resourcing and sequencing conflicts before they become fire drills, and bring the CEO a clear trade-off, not just a problem
• Own the risk register for active programs - surfacing schedule, scope, and resourcing risk proactively, before it's overdue
• Where a functional lead doesn't have a real plan, build one with them - this role sets planning discipline, it doesn't just audit for it
Execution visibility and operating rhythm
• Design and own the CEO's execution operating system - a live, board-grade view of every meaningful commitment across Product & AI, Engineering, and other functional leads
• Set and chair the review cadence that keeps senior stakeholders honest - built for accountability, not status theatre
• Convert scattered signal (Teams threads, half-finished docs, hallway conversations) into a clear, decision-ready picture for the CEO
Judgment and accountability
• Call slipping commitments before they're overdue, with enough judgment to know what's actually worth the CEO's attention
• Distinguish real blockers from avoidable delay, and hold senior functional leads to their commitments directly - your credibility does the work an org chart would do elsewhere
• Keep the definitive record of who owns what, so accountability never depends on memory, goodwill, or who spoke last
Follow-through
• Drive open items to genuine completion - not acknowledgment, not "in progress," done
• Build the operating cadence and lightweight systems that make this sustainable at scale, not something the CEO has to personally re-run every week
• Use AI tooling to make tracking, escalation, and reporting fast enough to be real-time - not a retrospective report on what already went wrong